Family friendly vacation rentals in Truro, MA

12226 - Aqua Oasis: Beautiful backyard, pool, deeded beach rights! Tucked away in Truro, with neighborhood association access to Tru Haven Beach, this vacation home promises an idyllic escape. Situated within a quaint neighborhood, this beach gem is a mere 2-minute drive or a leisurely 15-minute stroll from your doorstep, with the convenience of a drop-off area too (please note, parking is not available) and a private staircase leading you to the sandy shores. <br><br>Designed with unique flair by the renowned architect Alan Dodge, this home exudes personality and character. Thoughtful touches and eclectic Truro-style furnishings create a space that feels both unique and welcoming - perfect for accommodating multi-generational families. The first floor features a king bedroom with an en suite bathroom, while upstairs offers two queen bedrooms (one with an en suit bathroom), a bedroom with two twin beds, and an additional full bathroom. <br><br>While here, relish in the pleasures of a private pool where your family will share priceless memories they will replay while daydreaming of future stays (please, no dogs in the pool area). The expansive patio invites you to fire up the grill and take in the salt air with peek-a-boo views of Cape Cod Bay and Provincetown. As the sun begins to dip below the horizon, savor your favorite cocktails on the second-floor deck accessible from two bedrooms, offering even more breathtaking water vistas.<br><br>For those quintessential evening activities, our designated sand area boasts a fire pit, perfect for marshmallow roasting, with ample seating for everyone to sit back and relax.<br><br>When the culinary delights of Cape Cod beckon, you’re in for a treat. The Box Lunch is your go-to spot for scrumptious beach sandwiches, while Truro Vineyards, a short jaunt from your home, offers the perfect afternoon of wine tasting. These Cape Cod staples are both conveniently less than a mile away!<br><br>Escape to a one-of-a-kind vacation retreat, where Truro’s beauty and charm come to life. Your adventure begins here.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 8<br>-2 Floors<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 King Bed w/ en suite Bathroom<br>-2nd Floor Bedroom: 1 Queen Bed w/ en suite Bathroom <br>-2nd Floor Bedroom: 1 Queen Bed <br>-2nd Floor Bedroom: 2 Twin Beds<br>Bathrooms<br>-Total 3.5<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom w/ Shower and Soaking Tub (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower<br>Other Amenities <br>-Private Heated Pool (Only guaranteed to be open Memorial Day - Labor Day)<br>-Outdoor Shower<br>-Central AC<br>-Electric Fireplace available for guest use<br>-WiFi<br>-TV<br>-Washer/Dryer<br>-Propane Grill <br>-Please note outdoor amenities are available seasonally<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0455953000

13377 - Wind Down : Tranquil Woodland Escape in Wellfleet! Located on a quiet road, this mid-century modern gem in Wellfleet beckons you to unwind amidst nature’s embrace. Imagine waking up in one of the four cozy bedrooms, all conveniently located on the first floor, with the gentle rustle of leaves as your morning soundtrack. With two full bathrooms boasting shower/tub combos, you’ll find comfort and convenience at every turn.<br><br>The heart of this home is its open-plan kitchen and dining area, which flows effortlessly onto a spacious deck. Here, surrounded by the serene woods, you can bask in tranquility or engage in lively family activities. The game room in the basement promises hours of entertainment with arcade games, foosball, and a plush seating area perfect for movie nights on the Smart TV.<br><br>Beyond the peaceful confines of this woodland retreat, Wellfleet offers a bounty of natural wonders. A short drive takes you to the pristine sands of Bound Brook Island Beach or the scenic trails of Great Island. After a day of exploration, treat yourself to waterfront dining at Mac’s on the Pier or savor local flavors at Moby Dick’s.<br><br>Whether you’re grilling on the BBQ or enjoying a quiet moment on the patio, this home offers a unique blend of mid-century style and modern comforts. With a washer and dryer, free parking, and thoughtful amenities like split A/C and heat, every detail is designed for a seamless stay.<br><br>Don’t miss the chance to create cherished memories in this enchanting woodland haven. Book your stay today and let the magic of Wellfleet captivate you!<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Sleeps 12<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 1 Queen Bed<br>-1st Floor Bedroom: 2 Bunk Beds (Queen over Queen Bunk Beds)<br>Bathrooms<br>-Total 2<br>-1st Floor: Full Bathroom w/ Tub/Shower Combo<br>-1st Floor: Full Bathroom w/ Tub/Shower Combo<br>Other Amenities <br>-Central AC via Mini-Splits<br>-WiFi<br>-Smart TV<br>-Streaming Service<br>-Washer/Dryer <br>-Propane Grill<br>-Fire Pit (wood)<br>-Outdoor Shower<br>-Indoor Fireplaces are not for guest use(fines remitted) <br>-Please note outdoor amenities are available seasonally<br>-2 of the 3 garage bays are available for storage but not for cars. Please use the driveway to park vehicles.<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>-Parking for 3 cars maximum<br>-C0525193180<br>

13337 - Cape Cabana: Gorgeous Outdoor areas with Heated Pool & Hot Tub! Experience a resort-like vacation this summer at our Coastal Castle-- located in Wellfleet amidst the Cape Cod National Seashore. Our home is packed with so many luxury amenities, you’ll barely want to leave the house! <br><br>Spend the day poolside lounging in a chaise or floating in the Salt Water Pool and spend the nights chilling in the rec room (Pool, Ping-Pong, Card Table, and More!), serving up drinks in the wet bar, or relaxing in the hot tub. Expand your horizons and take a walk to the secluded Dyer Pond or take a drive to Great Pond for a quick dip in the freshwater. <br><br>Follow the wooden boardwalk through the front garden and use the front door to enter into the main living area of our home. Unpack the groceries in the main kitchen, and store your extra Spiked Seltzers in the Wet Bar Fridge on the ground level. Roll-up a few wraps to serve with a side of Cape Cod Potato chips (stop by the Eastham Superette for supplies on your way into town) in the newly renovated kitchen--clean, spacious, and brimming with top-of-the-line Stainless appliances. Enjoy a quick bite in the small breakfast nook with a Marble Tabletop or a more formal dinner with the whole group in the dining room. Looking to have a low key night? Head downstairs to share a few drinks at the Wet Bar, play a game of poker, or challenge the group to a pool or ping-pong tournament (losers get the next round!) When things start heating up, head outside to get some ocean-fresh air and center yourself under a starry Cape Cod night. <br><br>At the end of the night disperse your separate ways between 7 Suite-Style bedrooms-- each with its own attached Full Bathroom! Starting on the 2nd Floor, the Master bedroom sits all the way to the right and features a stunning water view, Jacuzzi tub overlooking the beautiful backyard and woodland beyond, built-in storage console, TV, and King bed. The room next door also shares the same pool view has a TV and holds 2 Queen Beds. The 3rd bedroom in the back left corner has a private balcony, lounge area/sofa bed, and a Queen bed. Across the hall at the front of the home is the final bedroom on this floor-- complete with an abundance of built-in storage space, bonus room with desk and bunk beds (perfect for a young family of 4!), TV, and a King bed. Travel downstairs to the solo bedroom on the 1st Floor. This room overlooks the back pool and patio through a large sliding glass door, has lots of natural light, a soaking tub, TV, and a King Bed. Climb down one more flight of stairs to the basement to reach the 6th and final bedroom-- designed with a lavish Walk-In Closet, sitting area, private slider for quick access to the patio, TV, and King Bed. <br><br>Split systems (like Central A/C will keep our home dry and comfortable-- throughout your entire stay. Other amenities include 2 Garage Parking Spots, WiFi, cable TV, a gas grill, an outdoor shower, and sheets and bath towels provided for each guest. <br><br>Lastly, if you do feel like venturing out, there are plenty of great options to choose from! Take a day trip to Provincetown and climb the Pilgrim Monument or shop along Commercial street, head to Truro Vineyards for some local wine tasting, spend the day tailgating on the beach and listening to live music at the Beachcomber (just 5 minutes away), catch a live show or movie at the Wellfleet Harbor Actors Theater, or eat the most delicious local fried seafood at PJ’s. Do it right and send it this summer from our exclusive Wellfleet Pool Club!<br><br>Home Details:<br>No Pets(Fines Remitted)<br>-Sleeps 16<br>-3 Floors<br>Bedrooms<br>-Total 7<br>-1st Floor Bedroom: 1 King Bed w/ en suite Full Bathroom<br>-2nd Floor Bedroom Master Bedroom: 1 King Bed w/ en suite Full Bathroom<br>-2nd Floor Bedroom: 1 King Bed w/ en suite Full Bathroom<br>-2nd Floor Bedroom: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor Bedroom: 2 Queen Beds w/ en suite Full Bathroom<br>-2nd Floor Bedroom: 1 Bunk Bed (2 Twins)<br>-Ground Floor Bedroom: 1 King Bed w/ en suite Full Bathroom<br>Bathrooms<br>-Total 6 Full Baths, 2 Half Baths<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom w/ Shower and Tub (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower and Jacuzzi Tub (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower and Tub (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower (en suite 2 Queens Bedroom)<br>-Ground Floor: Half Bathroom<br>-Ground Floor: Full Bathroom w/ Shower (en suite King Bedroom)<br>Other Amenities <br>-Split Systems (like Central A/C)<br>-Smart TV w/ Streaming<br>-WiFi<br>-Game Room (Ping-Pong, Pool, and Card Tables)<br>-Washer/Dryer (1st and 2nd Floor Sets)<br>-Decks/Balconies with Furniture<br>-Patio with Furniture<br>-Gas Grill <br>-Outdoor Shower<br>-Heated Saltwater Private Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Hot Tub (Hot Tub Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Walk to Dyer Pond<br>-2 Car Garage (w/ an Electric Car Charging Station)<br>-NO pets (fines remitted)<br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0403113180

- C0298845300 - Free WiFi - 1,926 Sq Ft A serene seaside getaway awaits you in North Truro! Ideal for families or groups, this 4-bedroom, 2.5-bath vacation rental features a large deck with breathtaking views, 2 kitchens, and proximity to the beach! Don't miss whale watching at Provincetown Whale Watching or shopping at the Whalers Wharf, just 5 miles away. When you're not soaking up the sun, grab a brew at Provincetown Brewing Co! -- THE PROPERTY -- SLEEPING ARRANGEMENTS: - Bedroom 1: Queen Bed - Bedroom 2: Queen Bed - Bedroom 3: 2 Twin Beds - Bedroom 4: Full Bed HOME FEATURES: - Smart TVs - Dining table & bar seating - Ceiling fans KITCHEN: - Refrigerator, stove/oven, dishwasher - Coffee maker, microwave - Dishware & flatware GENERAL: - Washer & dryer - Towels/linens - Central heat, window & mini-split A/C units ACCESSIBILITY: - 1 step to access FAQ: - Pet fee (paid pre-trip) - 3 exterior security camera (facing out) PARKING: - Detached garage (3 vehicles) - Driveway (6 vehicles) - RV/trailer parking -- THE LOCATION -- - 5 miles to Provincetown Whale Watching - 7 miles to Provincetown Municipal Airport - 114 miles to Boston Logan International Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $60 fee (+ fees & taxes, max 2 dogs) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires 1 step to access - NOTE: Your safety matters. This property features 3 exterior security cameras. Camera 1 is a Ring doorbell device with an exterior security camera facing the front outdoor entry. Camera 2 is on the west side of the house facing the driveway. Camera 3 is on the east side of the home facing the garage. The cameras are outward facing and do not look into interior spaces. The cameras record video and sound when activated by motion

Exquisite in East Orleans, Heated Pool, Fire pit, Gym! Linens Included, Beds Made Pets Considered Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Pool & Hot Tub open from Memorial Day to Columbus Day Welcome to The Breakaway, a stunning vacation home nestled in the picturesque Tonset Area of Orleans, Massachusetts. This luxurious property offers a perfect blend of comfort and elegance, making it an ideal retreat for families or groups seeking a memorable getaway. With 5 spacious bedrooms and 5.5 bathrooms, this home comfortably accommodates up to 14 guests, ensuring everyone has their own space to relax and unwind. As you step inside, you’ll be greeted by a beautifully designed interior featuring a gas fireplace that adds warmth and charm to the living area. The central air conditioning throughout the home ensures a cool and comfortable atmosphere, even on the warmest summer days. The fully equipped kitchen is a chef’s dream, complete with modern appliances, ample counter space, and a dining area perfect for family meals. The outdoor space is truly a highlight, boasting a heated private pool and a hot tub, perfect for soaking up the sun or enjoying a relaxing evening under the stars. The fenced yard provides a safe space for children and pets to play, while the outdoor seating areas and fire pit create an inviting atmosphere for gatherings. For those looking to stay active, the property features a gym and a game room equipped with a pool table and entertainment options, ensuring fun for all ages. Each bedroom is thoughtfully appointed, with the master suites offering TVs and sound systems for added convenience. Located just a short walk from the beach and near various attractions, including local Breweries and outdoor adventures, The Breakaway is the perfect base for exploring all that Cape Cod has to offer. Don’t miss out on this exceptional property—book your stay today and create unforgettable memories! Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

13380 - Salt and Sun: Game Room, Walk to Two Landings! Step into Salt and Sun, your private escape in Wellfleet. Down a peaceful drive, this classic Cape home welcomes you with echoing character—think wide planks, playful shiplap, and robust ceiling beams that speak to its seafaring legacy, now thoughtfully paired with modern comforts like air conditioning. With six bedrooms across the ground floor, first floor, and second floor. Salt and Sun accommodates up to twelve guests with open arms. The main floor features a versatile queen bedroom and primary living spaces ideal for gatherings, while upstairs, a king suite and three more inviting bedrooms promise restful nights. Three and a half bathrooms, including a main-level powder room and ground-level full bath, ensure ease for your whole group. A family/playroom and kid-friendly ground floor with an additional Queen bed and foosball table mean there’s room for everyone to unwind. Outside, lush lawns and a hammock invite lazy afternoons in the private backyard, while an outdoor shower awaits after days exploring the nearby landings. Great for launching kayaks and enjoying views of boats passing by, Pleasant Point Landing and Paine Hollow Landing offer adventure and serene views. Tucked among whispering woods yet open to a large grassy yard, the home offers seclusion without sacrificing convenience. Explore Wellfleet’s famed galleries, catch a sunset at Mayo Beach or peruse the local farmer’s market, all mere minutes away. Evenings are best spent grilling or playing beneath a canopy of Cape Cod stars. Longing for a storied getaway where families connect, and each day ends with salt in your hair and sun on your skin? Make Salt and Sun your next Cape Cod tradition—book this unforgettable Wellfleet retreat today. Home Details: -Dogs Welcomed (w/fee of $40/night per dog) -Sleeps 12 Bedrooms -Total 6 -Ground Floor Bedroom: 1 Queen Bed -1st Floor Bedroom: 1 Queen Murphy Bed -2nd Floor Bedroom: 1 King Bed (w/ ensuite bathroom) -2nd Floor Bedroom: 1 Queen Bed -2nd Floor Bedroom: 1 Queen Bed -2nd Floor Bedroom: 2 Twin Beds Bathrooms -Total 3.5 -Ground Floor: Full Bath, Shower -1st Floor: ½ Bath -2nd Floor: Tub/Shower Combo -2nd Floor: Shower (ensuite) Other Amenities -Central AC, Split System AC, Window Units, and Floor Unit -WiFi -TV -Washer/Dryer -Propane Grill -Outdoor Shower -Indoor Fireplaces are not for guest use (fines remitted) -Please note outdoor amenities are available seasonally -Sheets and Bath Towels Provided with Beds made Upon Arrival -Cleaned with Hospital Grade Disinfectant -Parking for 4 cars maximum -C0408343180

This property is professionally managed by Pretty Picky Properties. Private Orleans resort with water views, heated pool & spa 4 beds/4 full, 2 half baths, sleeps 14 Rents Friday to Friday during peak season Linens included Pool & Hot Tub open from Memorial Day to Columbus Day Your multi-generational or multi-family summer vacation has found its home. Enjoy panoramic views of Nauset Inlet and the Atlantic Ocean beyond from this beautifully remodeled Orleans home. The owners have added a heated salt water pool, hot tub, gas fire pit and outdoor grilling area, all with splendid views. Walk less than 3 minutes to your beach and launch the owner provided kayaks to explore Nauset Inlet or Town Cove. Inside, on the main level, the vaulted ceilings and open floor plan create a grand sense of light and space. You will find a chef inspired kitchen with high-end, stainless steel appliances including a wine refrigerator and gas stove. The kitchen is equipped to entertain and cook for a crowd. There are mesmerizing views from the large dining room table and the living room, which walk out to the large deck and pool area. This home offers sleeping for up to 14 guests in four bedrooms, each with a private bath plus two half-baths. The main level features a generous primary bedroom suite with a king size bed, beautiful views of the water and a luxurious en-suite bath. There is a jetted tub, over-sized shower, dual vanities and a walk in closet. Upstairs are two bedrooms, each with a private bath and private balconies overlooking the water. The first bedroom provides a king size bed plus a day bed, perfect for the family with a small child. The other bedroom features another king size bed and private bath. Above the garage in the west wing of the home you’ll find a giant bunk room, a wonderful space for the kids. There are 3 twin-over full size bunk beds and two twin size beds plus a private bath, TV, Xbox and charging stations. And it’s away from the rest of the home so children can have their own space and do their own thing. The completely refinished lower level is the media/game room. Enjoy the full bar and Foosball table, pool table, gaming table, plus large screen TV and comfy lounge seating. It’s a perfect spot to relax in case the weather doesn’t cooperate. And of course the home is equipped with all the modern amenities you’d expect: central air conditioning, Wi-Fi, charging stations, cable TV, and a washer and dryer. Each room provides high-end linens and towels, no need to bring your own. This property provides the accommodations you need to bring the whole family and enjoy your own private mini-resort. Whether it’s spending the day at the pool, on the beach, out on the water on the kayaks or playing corn-hole in the yard, the entire family can find something to enjoy. And once the day is done, marvel at the beautiful starry nights while dining al fresco on the deck. Bask in the glow from the cheery fire pit. Or slip into the soothing hot tub and gaze out over Nauset Inlet and ocean views. Please note: pool and hot tub are open Memorial Day - Columbus Day. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. This property offers a three night minimum stay during select weeks in May – June & Sept, Oct. & November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is Professionally Managed by Pretty Picky Properties. 5850 sq. ft. of Luxurious Summer Living, Heated Pool. 5 Minute Drive to Nauset Beach Sleeps 11 Rents Friday to Friday during peak season Linens Included, Beds Made Pool open from Memorial Day to Columbus Day The location is ideal: less than a 5-minute drive to world famous Nauset Beach and less than five minutes to Orleans Center with all its appealing shops, restaurants, galleries and Cape Cod League Baseball. Of course, now with a beautiful new heated saltwater pool in your back yard, you probably won’t go anywhere as often as you might otherwise! Around the pool is a generous pool patio that includes a huge umbrella-shaded loveseat, padded outdoor furniture, a gas fire-pit with Adirondack chairs and poolside loungers! This big, bright, magnificent contemporary home is located in the upscale Tonset neighborhood of Orleans. You will find plenty of room inside and out for your group of up to 12. Inside there is more than 5800 square feet of living space where your group can spread out and enjoy the perfect summer vacation. The expansive, private deck and spacious yard provides a great place to enjoy summer outdoor living, Cape Cod style. Here you’ll find the gas grill, umbrella shaded dining table, fire pit and enclosed outdoor shower. Inside, the thoughtful floor plan and tasteful décor elevate your vacation experience. There are five bedrooms in all; two master suites on the main level and three bedrooms upstairs. The first master bedroom has a king bed and walks out to the mahogany rear deck. There is a spacious, luxurious en suite bathroom featuring a jetted tub, separate step-in shower and a dual vanity sink. In addition, there is a sitting room off the master. The other master bedroom on the main level is outfitted with a queen bed and has a private full bath and access to the deck. The main level study also has a sleep sofa that converts to a full size double. Also on the main level you’ll find the generously sized chef’s kitchen, equipped with topline stainless steel appliances and amenities including, the Subzero® fridge, Viking® range and granite counters. The kitchen is light, bright and cheery, thanks to vaulted ceilings and plenty of windows. It opens to the dining and living areas so everyone can socialize during meal prep. The large flat screen TV is viewable from the kitchen as well. There is a breakfast counter with three seats for quick meals, kids’ snacks or kitchen kibitzers. Upstairs there are three bedrooms, one of which is outfitted with a Full bed and two Twin beds. It has its own private bath. Another bedroom on this level offers a queen bed and has a full private bath en suite. The final bedroom has two twin beds. There is also another pleasant lounge area on the upper level. The house has five full baths plus one half bath. The home is centrally air conditioned, has high speed Wi-Fi, smart TV with cable, and a Sonos® sound System. Recreational added value here comes in the form of a game room with a ping pong table in addition to kayaks provided for guest use. Once you experience this property and location, you’ll want to return for years to come, creating priceless memories of your family summer vacations on the Cape! Please enter your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 As is customary in vacation rentals there are additional fees to the rates listed. Those fees include $145 reservation fee and an $80 non-refundable Accidental Damage Protection (ADP) fee. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Please note: the pool is open Memorial Day - Columbus Day. This property offers a three-night minimum stay during select weeks in May – June and September – October. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

13356 - Bluefish Burrow: Private Pool and Close to Marconi Beach! The woods of Wellfleet are waiting for your next vacation. With your own private pool, access to the Cape Cod Rail Trail, a separate guest home and Marconi and Lecount Hollow Beach just a short bike ride away, you’ll be happy as a clam at the Bluefish Burrow. Pulling onto this secluded property, your eyes will gaze across the sprawling property, where both a main home and detached guest house welcome you to this sleeps 12 estate. Stepping up to the main home, you’ll walk over the covered front porch and enter this stunning two story home. You’ll immediately notice this home’s beautiful kitchen, with wooden countertops, center island, gorgeous painted wood floors and an elegant glass door pantry, as well as a dining table at the rear of the room. The home’s back deck is accessed off of the kitchen, where you can enjoy meals under the stars or afternoon drinks before heading to the beach. <br><br>Back inside, you will find endless entertainment options in the home’s living room, located towards the back of the home. The living room houses a large wall-mounted TV, board game options, a comfortable sectional and dining table awaiting mid-game drinks with chips and dip. Also located on the first floor is the home’s primary bedroom, a cozy room to the right of the front entryway, complete with king size bed and easy access to the home’s first bathroom. <br><br>Head upstairs via the beautiful main staircase, where the remaining two bedrooms preside. The second bedroom has a king bed and seating area, while the third and final bedroom has a bunk bed with trundle, as well as two additional twin beds. Straight ahead from the staircase is the second bathroom, with a large soaking tub and stand up shower.<br><br>Stroll across the gorgeous yard to the home’s guest house, where you can escape the main household for a little extra privacy. Entering into this two story home, you’re greeted by a stylish living room with wood stove, wall-mounted TV and comfy couch.Natural light pours in from both the exterior doors and windows surrounding the living room and kitchen. The open-concept living room and kitchen is separated by a dining table, providing the perfect place to sit down for a mid-day meal. Cook up some grub while you overlook the backyard and the Cape Cod Rail Trail, watching bikers heading to more Cape adventures. Upstairs is a bedroom with a king size bed and a unique ceiling fan keeping you cool all summer long, as well as a full en suite bathroom.<br><br>The allure of these homes aren’t constrained to the indoors. Enjoy all this home has to offer with a brand new swimming pool, a multi-tiered yard with plenty of room for your pup to run around, and easy access to the Cape Cod Rail Trail, one of the most beautiful bike trails in the country. Using the map shown, walk or bike to Lecount Hollow Beach and avoid any stress parking might bring! <br><br>Other amenities include a washer and dryer, numerous outdoor seating areas, a fire pit and an outdoor shower. Escape to the Outer Cape and spend your vacation like a true Wellfleetian, at the Bluefish Burrow. <br><br>Home Details:<br>-Dogs Welcomed (w/fee of $40/night per dog)<br>-Signature Home<br>-Sleeps 12<br>-Main House with Guest House<br>-3000 sq ft. Total<br>-Main House: 2 Floors (1st Floor + 2nd Floor)<br>-Guest House: 2 Floors (1st Floor + 2nd Floor)<br>-4 Bedrooms Total<br>-4.5 Bathrooms Total<br>-Bedroom #1: 1 King Bed, 1st Floor<br>-Bedroom #2: 1 Full/Full Bunk Bed w/ Twin Trundle + 2 Twin Beds (2 Full Beds + 3 Twin Beds Total), 2nd Floor<br>-Bedroom #3: 1 King Bed, 2nd Floor<br>-Bedroom #4: 1 King Bed (Guest House), 2nd Floor<br>-3.5 Bathrooms<br>-Bathroom #1: Full Bath w/ Shower, 1st Floor<br>-Bathroom #2: Full Bath w/ Jacuzzi Tub and Shower, 2nd Floor<br>-Bathroom #3: Full Bath w/ Shower (Guest House), 2nd Floor<br>-Bathroom #5: Half Bath (Guest House), 1st Floor<br>-Fully Equipped Kitchen<br>-A/C units in bedrooms <br>-Smart Lock/Self Check-In<br>-WiFi<br>-Smart TV w/ Cable<br>-Washer/Dryer (1st floor)<br>-Patio<br>-Deck<br>-Gas Grill<br>-Fire Pit<br>-Outdoor Shower<br>-Private Yard<br>-Private Heated In-Ground Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Abuts Cape Cod Bike Tail<br>-Just a few minute bike ride to Marconi Beach and Lecount Hollow Beach<br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0421903180

This home is professionally managed by Pretty Picky Properties Grand Villa Overlooks Nauset Beach & the Atlantic, Heated Pool, Hot Tub & Gas Fire-pit! Rents Friday to Friday Off-season partial weeks available. Sleeps 14 Linens Included/Beds Made Pool and hot tub are open Memorial Day - Columbus Day Your group of up to 14 will vacation in style at this superb ocean side manor house at famous Nauset Beach in East Orleans. The stunning location provides panoramic views of the beach and ocean from both levels of the house. And you have a very short walk to the beach. The property also features a 36’x18’ heated pool, hot tub and gas fire pit!! The spacious, social, fully loaded kitchen anchors the main level and includes a breakfast bar with high boy seating for four. A few steps away, the large dining room easily seats 10 and can accommodate more. Relax in the exquisite living room with lounge seating and a large flat screen TV. This home has Sonos sound system off the back deck and in the lower level living space. It is centrally air conditioned and has hi-speed Wi-Fi and cable TV. A large, covered patio is just off the living room, with a dining table and chairs, plenty of lounge seating and views of the Atlantic. A separate lounge/bar room offers a wet bar with fridge, another TV, and bar seating for three. Walk out from there to a beautiful, hexagonal screened porch which leads to the pool deck. There is one bedroom on the main level, a roomy primary suite with a King size bed and full bath en suite with a walk in shower. The main level also includes a half bath and quiet den/study to serve as your work station, if necessary. On the upper level, you’ll first encounter another lounge area, which walks out to the upper deck that presents 180-degree breathtaking views of Nauset Beach and ocean. Comfy lounge seating here too, including a king-size super comfy sleeper sofa. On this level, you’ll find four more bedrooms. There’s a second, oversized primary suite, with a king size bed plus twin day bed with a twin trundle below. There is a full bath en suite, of course. Another bedroom suite features a King size bed and private full bath. Bedrooms #4 and #5 can be closed off to create a two-bedroom suite. Both bedrooms feature a queen size bed with a standard twin bed and twin trundle bed. The two bedrooms share a full bath between, Jack & Jill style. The lower level of the home houses an extraordinary full home theater with a projector, 10-foot screen and luxurious lounge seats with cup holders for up to 12, plus giant bean bag seating for more. What an amazing place should the weather not cooperate or for your evening entertainment. Also on this level: a workout room, a ping pong table, and a half bath. There are four full and two half baths in all. The yard and grounds provide plenty of space for kids to play safely. There is also a gas grill and horseshoe pits to keep everyone entertained. Consider planning your summer vacation at this truly remarkable property in one of Cape Cod’s most coveted locations. Please enter in your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

All of your worries will disappear the moment you step inside this charming 3-bedroom, 3.5-bath Cape Cod condo! Boasting 3 full floors and 1,700 square feet of living space, this Provincetown vacation rental is the perfect Northeast getaway for groups. Soak up the sun at Herring Cove Beach, take a short drive to the Race Point Lighthouse, or explore local eateries on Commercial Street. After the day’s activities, whip up a delicious meal on the gas grill or simply relax on the private patio. -- THE PROPERTY -- C0058582420 | Free WiFi (High-Speed) | Lounge & Dine Outdoors Bedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed OUTDOOR LIVING: Furnished patio, dining area, gas grill INDOOR LIVING: Smart TV, DVD player, dining area, ceiling fans, books KITCHEN: Cooking basics, refrigerator, microwave, stove/oven, dishwasher, dishware & flatware, coffee maker, ice maker, toaster, water filter, stainless steel appliances, granite countertops GENERAL: Towels/linens, window A/C unit, in-unit washer/dryer, hair dryer, iron/board, trash bags/paper towels FAQ: Stairs required to enter & addt’l stairs to reach all beds, limited cell service PARKING: Designated parking spot (1 vehicle) -- THE LOCATION -- BY THE WATER: MacMillan Pier (0.5 miles), Provincetown Marina (0.6 miles), Moment Sailing Adventures (0.6 miles), Herring Cove Beach (2 miles), Long Point Beach (2 miles) EATS + DRINKS: Strangers & Saints (0.2 miles), Provincetown Brewing Co. (0.2 miles), Pepe's Wharf Restaurant (0.3 miles), Harbour Lounge (0.3 miles), The Lobster Pot (0.4 miles), The Mews Restaurant & Cafe (0.4 miles) LOCAL HIGHLIGHTS: Provincetown Whale Watching (0.4 miles), Pilgrim Monument and Provincetown Museum (0.6 miles), Commercial Street (1 mile), Wood End Lighthouse (2 miles), Pilgrims' First Landing Park (2 miles), Race Point Lighthouse (5 miles), Expedition Whydah (45 miles), Plymouth (77 miles) AIRPORT: Provincetown Municipal Airport (3 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking or vaping of any kind - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to enter and additional stairs to reach all bedrooms - NOTE: The property does have cell phone service but it may be spotty due to the rural location Licence number: C0058582420;BOH-21-1179;BOH-21-1179;C0058582420;BOH-21-1179;BOH-21-1179;BOH-21-1179

This home is professionally managed by Pretty Picky Properties Luxury Brewster Estate – Pool, Hot Tub, Steps to Bike Trail "Brewster Barefoot Bliss" 3447-BMH Rents Saturday to Saturday in Peak Season Linens Included, Beds Made Six bedrooms, Seven Full Baths Sleeps Twelve Pets Considered **Additional separate two bedroom cottage available to rent next door, total occupancy of sixteen possible** Discover the perfect blend of classic Cape Cod charm and modern luxury at this stunning six bedroom vacation home in Brewster. With four private bedroom suites and space to sleep 12 guests, this expansive retreat is designed for relaxation and adventure alike for groups of any size. Location Nature lovers will appreciate the home’s prime location—adjacent to the popular Cape Cod Rail Trail bike path and just across the street from Nickerson State Park. Spend your days exploring the park’s scenic trails or take a short stroll (under a mile) to Crosby Landing Beach, considered Brewster’s best by many. You can be in downtown in Orleans in about two miles via the bike path. Outside Living Space No doubt most of your lounging and living will be done out on the spacious pool patio with a covered cabana area, gorgeous outdoor kitchen, a large dining table and chairs, a full bathroom and, of course, the heated pool. There’s also a hot tub and gas fire pit, ideal for gathering under the stars. You can whip up a feast in the cabana’s completely outfitted outdoor kitchen. The large, manicured yard is bordered by a tasteful variety of flowering plantings and makes a perfect place to throw a Frisbee ® or whack a Whiffleball ® And here’s an unusual extra amenity: your own private hockey rink! The special synthetic surface accommodates both roller blades and ice skates. Inside Living Space This home seamlessly blends classic coastal elegance with modern finishes, offering stylish and comfortable living spaces. The main level consists of a spacious and elegant kitchen, complete with everything you’ll need to prepare any meal and entertain any group. There’s seating for 12+ at the main dining table and adjacent round table plus there’s additional counter seating at the immense kitchen island. This part of the main level includes a wet bar, pantry and parlor. Fitness enthusiasts will appreciate the fully equipped gym. Then there’s the “Great Room,” which is nothing short of awe inspiring. Original to the structure, this room with soaring ceilings exudes old world charm in stunning fashion. The wood paneled walls are from a French chateau, the circular stairs from a British ship. Sleeping Accommodations The main level rounds out with two bedrooms, one with a queen, the other with a pair of twins, plus a full bath and a half bath. There are three, count ’em, three sets of stairs to the second level bedrooms. The first is off the small parlor and features a vintage narrow staircase to a queen bedroom with a private full bath. The second, more modern staircase leads to a second level area with two queen-bedroom suites, each with a private full bath. The final upstairs area is the most recent renovation and is essentially a self-contained apartment with a living area, kitchenette, king bedroom and a luxurious bathroom with a step-in shower, soaking tub and dual vanity. For a summary of bedrooms and bed configurations, use the Room Details tab above. Amenities This home has high speed WiFi, a Sonos® Sound System and central air conditioning. For a complete list of amenities, please click on the Amenities tab above. The owners reside in a smaller home on the grounds. so you can be sure that any issues that may arise will be quickly addressed. But you won’t see them unless you need them. Book now and experience the best of Brewster in this extraordinary vacation retreat. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for vacation rental on Cape Cod. It’s your vacation. Get Picky! ®

Al Fresco Dining | Walk to MacMillan Pier | 2 Mi to Herring Cove Beach Provincetown style meets ultimate comfort at this well-appointed vacation rental. Fire up the gas grill for a sunset dinner on your private patio or sip coffee from the breezy balcony. From the condo, make the short walk to the vibrant Commercial Street galleries, shops, and world-class dining, or stroll MacMillan Beach. Your ideal Cape Cod escape starts here — secure your stay today! -- THE PROPERTY -- Lodging Certificate Number: C0011562420 SLEEPING ARRANGEMENTS - Bedroom 1: 1 queen bed - Bedroom 2: 1 queen bed MAIN FEATURES - Flat-screen cable TV, electric fireplace - Mahogany hardwood floors, spiral staircase - Coastal decor KITCHEN - Granite countertops, high-end stainless steel appliances - Bosch gas stove, oven - Drip coffee maker - Microwave, toaster - Cooking basics, spices, dishware & flatware GENERAL - Free WiFi - Washer, dryer - Central heating & A/C - Linens/towels, hair dryer ACCESSIBILITY - 2-story condo, 2 steps for entry - Bedrooms & full bathroom on 2nd floor PARKING - Designated spot (1 vehicle) -- THE LOCATION -- - Experience the eclectic soul of Provincetown just steps from your front door - Walk to Provincetown Art Association and Museum & Pilgrim Monument & Provincetown Museum - Walk to MacMillan Pier Ferry Terminal - 1 mile to Beech Forest Trailhead - 4 miles to Race Point Lighthouse - 47 miles to Cape Cod Gateway Airport -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - No pets allowed - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in ADDITIONAL INFORMATION - This 2-story condo requires 2 steps for entry. The bedrooms are on the 2nd floor Licence number: C0011562420

This property is professionally managed by Pretty Picky Properties Luxurious Estate by the Bay in Brewster: Sleeps 20 with Expansive New Pool, Walk to Beach, Walk to Town Rents Saturday to Saturday in Peak Summer Off-Season Weekends and Partial Weeks Available Choose this vacation headquarters and give your group of up to 20 the best of all options. A main house plus separate guest house on nearly an acre and a half of level yard for play space. A stunning new 20’ X 60’ heated saltwater pool with large stone patio. A three-minute walk to Brewster’s Breakwater Beach. And an eight-minute walk to the iconic Brewster Store and Main Street/Route 6A, where you’ll discover some excellent restaurant choices. The main house, just completed in 2020, offers elegance without pretense, centered on its spacious, thoughtfully outfitted chef’s kitchen. Here you’ll appreciate the large center island with high boy seating, beautiful granite and tile, as well as abundant counter space bathed in natural light. The kitchen opens to a TV lounge, which walks out to the expansive patio and pool. There is also a good-sized dining room here, as well as a handy half bath and laundry. The main house has sleeping for up to 12 in five bedrooms, two of which are king masters, one on the main level, the other upstairs. Each master has its own private full bath en suite. The separate guest house offers single level living and sleeps up to eight in three bedrooms with a full bath. You have a full eat-in kitchen here, as well as a TV lounge. Your outdoor summer living is optimized on the oversized patio which envelops the big pool. There’s also a hot tub, a large gas grill, a fire pit and an enclosed outdoor shower. Each house is centrally air conditioned, has cable TV, a SONOS Sound system and high speed Wi-Fi. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

Private, Spacious, Pristine with Heated Pool 7-Night minimum for June, July & August Linens Included, Beds Made Rents Friday to Friday in Peak Summer Pool open from Memorial Day to Columbus Day Welcome to Orleans Oasis, a stunning vacation home nestled in the picturesque neighborhood of Pleasant Bay in South Orleans. This spacious house offers a perfect blend of luxury and comfort, making it an ideal retreat for families or groups seeking a memorable getaway. With a generous 3,450 square feet of living space, this property comfortably accommodates up to 10 guests across its four beautifully appointed bedrooms and three bathrooms. As you step inside, you’ll be greeted by an inviting ambiance that features updated interiors and modern amenities. The main level boasts a master bedroom with a king-sized bed, while the second floor offers three additional bedrooms, including another king suite, a room with a double bed and twin singles, and a cozy queen bedroom. Each room is designed for relaxation and comfort, ensuring a restful night’s sleep. The heart of the home is the expansive living area, perfect for gathering with loved ones. Enjoy the convenience of a fully equipped kitchen, complete with a kitchen island, dining table, and modern appliances, including a dishwasher and microwave. The living room is ideal for unwinding, featuring comfortable seating and entertainment options such as a television and games. The lower level unfinished space is home to the ping pong table. Step outside to discover your private oasis. The outdoor space features a heated pool, perfect for a refreshing dip, and a wood fire pit for cozy evenings under the stars. The patio provide ample space for outdoor dining and relaxation, making it easy to soak up the sun or enjoy al fresco meals. For those seeking adventure, the property is conveniently located near a variety of attractions, including beautiful beaches, golf courses, and opportunities for fishing, hiking, and whale watching. Whether you’re looking to explore the local area or simply relax by the pool, Orleans Oasis is the perfect home base for your Cape Cod vacation. Don’t miss out on the chance to experience this exceptional property. Book your stay at Orleans Oasis today and create unforgettable memories with family and friends! Please enter your travel dates in top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14471 - Salt Water Sabbatical: Heated Saltwater Pool Hot Tub! In the woods of Eastham, a stunning oasis awaits. With your own heated in-ground saltwater swimming pool and hot tub, you’ll be soaking up the sun and salt water at the Salt Water Sabbatical. <br><br>The backyard is designed for long summer days and memorable evenings, featuring a private heated saltwater pool, hot tub, spacious stone patio, outdoor dining area, propane grill, fire pit, and outdoor shower. Whether you’re enjoying a morning swim, unwinding in the hot tub after the beach, or gathering around the fire pit under the stars, there’s no shortage of ways to enjoy your time outdoors.<br><br>When you’re ready to explore, you’ll be just minutes from both the Cape Cod Bay beaches and the Cape Cod National Seashore, making it easy to experience both the calm tidal flats and the Atlantic shoreline. Spend the day swimming, beachcombing, or watching the sunset before returning home to your own private oasis.<br><br>Inside, the bright, open layout is designed with comfort in mind. The first floor features a spacious living room with a Smart TV and home theater sound system, a beautifully appointed kitchen with a large center island, a half bath, laundry, and a queen primary suite with an en suite full bathroom. Upstairs, you’ll find three additional bedrooms—two with queen beds and one with two twin beds—along with two full bathrooms, providing plenty of space for everyone to spread out.<br><br>Whether your perfect vacation includes pool days, beach adventures, or simply enjoying the peaceful surroundings, Salt Water Sabbatical offers everything you need for an unforgettable Eastham escape. Book your stay today and experience the best of the Outer Cape.<br><br>Home Details:<br>-No Pets (Fines Remitted)<br>-Sleeps 8<br>-2 Floors (1st + 2nd Floor)<br>-2,400 Sq. Ft. <br>Bedrooms<br>-Total 4<br>-1st Floor: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor: 1 Queen Bed w/ en suite Full Bathroom<br>-2nd Floor: 1 Queen Bed w/ Jack and Jill Full Bathroom<br>-2nd Floor: 2 Twin Beds w/ Jack and Jill Full Bathroom<br>Bathrooms<br>-Total 3.5<br>-1st Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo (en suite Queen Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo (Jack and Jill style)<br>-1st Floor: Half Bathroom<br>Other Amenities<br>-Central A/C<br>-WiFi<br>-Smart TV <br>-Washer and Dryer (1st Floor)<br>-Propane Grill<br>-Fire Pit<br>-Patio with Outdoor Dining and Lounging<br>-Outdoor Shower<br>-Private Heated Saltwater Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Hot Tub<br>-NO Pets (fines remitted) <br>-Sheets and Bath Towels Provided with Beds made Upon Arrival<br>-Cleaned with Hospital Grade Disinfectant<br>C0404030860

This property is professionally managed by Pretty Picky Properties New Custom Built Luxury Home, Heated Pool, Close to Bay Beaches “Stony Brook Sanctuary” 95-B Rents Saturday to Saturday during peak season Linens Included, Beds Made Sleeps 10 Location In 2022, the owners turned a vacant wooded lot into a tasteful luxury home. The lot is just under two acres and offers plenty of privacy and ample outdoor yard space. When you’re ready for the beach, you won’t have to go far. It’s less than a five-minute drive to Sea Street Beach and the intriguing Brewster Flats. It’s also about a 25-minute walk along an appealing path through the scenic marshlands leading to the beaches on Cape Cod Bay. You have your choice of several sandy beaches along the Bay in East Dennis, including the exceptional Corporation and Mayflower Beaches. You can also drive a few more minutes to Paine’s Creek Beach in Brewster for some of Cape Cod’s most beautiful sunsets. You’re also near excellent dining at several highly rated restaurants scattered along Main Street (Route 6A). Check out the Brewster Fish House, Scargo Café and the Sesuit Harbor Café, to name just a few favorites. Outside Living Space The centerpiece, of course, is the extra long heated pool, ideal for swimming laps as well as for splashing around with the kids. The superb outdoor living space behind the house features a large patio with an umbrella shaded oversized picnic table. The kids will make good use of the playscape/swing set as well! You’ll also take advantage of the enclosed outdoor shower and handy gas grill. Fire up the grill and serve dinner outside. Off the front side of the house you’ll enjoy a generous screened porch with comfy seating and a full-scale wood burning fireplace. Inside Living Space This home has 3,700 sq ft of interior living space, not counting the large screened porch and the finished lower level. You’ll be impressed by the combination of taste and quality the owners have brought to bear on all three levels of the house for your vacation enjoyment. And in case you have any office work to be done, the home has two offices equipped with high speed Wi-Fi. The extraordinary kitchen features a large center island with counter seating for five. The new, top of the line appliances are a pleasure to use, including the induction range. There is also a custom wood topped wet bar island in the kitchen with a wine fridge included. Immediately adjacent is the dining area with seating for eight, which can be expanded to 12, at a table lovingly crafted from reclaimed 17th century red pine. And just off that, the living room is light and bright with comfortable lounge seating and a gas fireplace. The finished lower level offers a comfy TV lounge, a recreation room with a regulation size pool table and another full bath. In all, the house has 5.5 baths. Sleeping Accommodations Start with the primary bedroom on the main level. It has a king size bed and a full private bath and a large TV. On the second level there are four more bedrooms. Two have queen size beds. One has a bunk bed with a full-size double under a twin on top. Finally, the fifth bedroom has a king size bed plus a sleep sofa with a fold out twin. It also has an adjacent full bath. For more information on bedrooms and baths, please click on the Room Details tab above. Amenities This amenity-rich home has two laundries, central air conditioning, high speed Wi-Fi, a Sonos® Sound System, cable/smart TV and much more. For a complete list of amenities please click on the Amenities tab above. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $245.00 In addition, there are state and local taxes applied to all reservations of l 31 days or less that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties Magnificent Mansion, Privacy, Pool, Water Views in Brewster Come for July 4th! Arrive on Thursday July 2 or Friday July 3rd and enjoy the holiday! Sleeps 22 in 10 Bedrooms, 9.5 Baths Linens and Bed Making Included The newly constructed Quivett Compound is the perfect summer retreat for your discerning group of up to 22. The property is secluded on seven-plus acres and set far back from the historic Old King’s Highway in beautiful West Brewster by the bay, the property serves up sweeping views of Quivett Creek and Cape Cod Bay beyond. Launch an owner-provided kayak or canoe and explore the creek. Watch the kids frolic in the in-ground heated pool, which provides continuous entertainment when they come off the nearby bay side beaches in both Brewster and Dennis. You’ll spend a lot of time on the expansive shaded deck or outdoor patio with its built-in gas grill, fire pit and large dining table. Set up the net provided and organize a volley ball or badminton tournament. You certainly have plenty of space to do it! Inside, you’ll roam through 6,300 square feet of modern luxury, exquisitely designed and superbly furnished and appointed. The main level common living space includes an immense living room with two seating areas, one with a large flat screen, wall mounted TV. There is also a separate TV lounge with wet bar upstairs. The kitchen is big, bright and totally social. It is equipped with everything you could ask for, including two dishwashers, a beverage center and a Keurig coffee maker. The adjacent dining room offers a great place to gather inside, although you’ll likely choose to eat outside most summer days on the deck and patio. The lower level has a very cool game room, ready for action with a pool table, ping pong table, air hockey, video games and more. Then, it’s show time in the home theater, with its huge movie screen and comfy recliner chair seating. The laundry lives on this level, as well, with not one but two new washers and dryers. The ten bedrooms break down as follows: six kings, three queens, one full size double and two twins. The 9.5 baths sort out this way: one half bath on the main level, six bedrooms with en suite baths plus two full baths on the lower level. Finally, there is a room above the detached garage withe a King bed and a full bath. Of course, the home is centrally air conditioned and has high-speed Wi-Fi and Cable TV. **Please note that the bedroom and bathroom over the garage is fully winterized from 11/1 - 5/1 each year. As a result the property only has 9 bedrooms and 7.5 baths from November through April sleeping a maximum of 20 guests*** *** Pool is open and heated from Memorial Day (late May) through Columbus Day (early October)*** ****The Quivett Creek Compound does consider small events (with a maximum of 50 attendees including guests staying at the property) on site on a case by case basis in May, June, September and October. There are no events allowed in July and August. Please contact us for more details.**** Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14429 - Herring Brook Haven: 2025 Remodel! Walk to Pond, 2 Min Drive to Beach! If you thought a trip to this spacious retreat couldn’t get any better, over $300,000 of interior and exterior renovations were completed in 2025 and are ready to welcome guests! These include a brand new kitchen, the addition of 2 full bathrooms, renovation of the 2 existing bathrooms, brand new decking, interior and exterior painting, trim upgrades, and a revamped mini-split AC system. Escape to the quintessential Cape Cod retreat where every member of the family is invited to bask in the beauty of land and sea. Nestled within the tranquil embrace of Eastham, this expansive family home promises a week of relaxation and adventure, whether you’re lounging by the pristine shores of Herring Pond or exploring the scenic trails of the National Seashore.<br><br>Situated just a stone’s throw from the crystalline waters of Herring Pond, one of Cape Cod’s deepest and most pristine ponds, outdoor enthusiasts will delight in the array of recreational opportunities at their fingertips. <br><br>If you can pull yourself away from the comfort of the newly upgraded home, grab your bike and set off on an exhilarating journey along the rail-trail or meander through the quiet back roads, soaking in the natural splendor of the surrounding landscape.<br><br>Set upon a sprawling lot enveloped in privacy, this remarkable vacation home offers three levels of spacious living, ensuring ample room for everyone to spread out and unwind. Ascend to the top level (2nd floor), where a welcoming open-concept layout awaits, boasting a spacious kitchen (newly renovated), dining area, living space bathed in natural light, and half bathroom. Step out onto the expansive deck (newly re-constructed), where panoramic views of the enchanting natural landscape and glimpses of the famous First Encounter marshlands await. There is also a game room located above the garage and accessible via the exterior stairs/deck.<br><br>Back on the first floor, retreat to one of the three spacious bedrooms, each thoughtfully appointed to ensure a restful night’s sleep. Discover a queen bedroom with an en suite full bath room, a bedroom with two twin beds, and another room with a bunk bed (twin over full). There level also includes an additional full bathroom. Descend to the professionally finished basement, where a private laundry room awaits alongside two separate sleeping areas, furnished with a queen bed and a twin bed and a newly constructed bathroom. <br><br>From scenic vistas to ample space for gatherings, this fantastic vacation home offers the perfect blend of comfort, convenience, and coastal charm for an unforgettable Eastham getaway.<br><br>Home Details:<br>-Dogs Welcomed (w/fee of $45/night per dog)<br>-3 Floors: 1st Floor, 2nd Floor, Ground Floor<br>-Sleeps 8<br>Bedrooms<br>-Total: 4<br>-1st Floor Master Bedroom: 1 Queen Bed w/ en suite full bathroom<br>-1st Floor Bedroom: 2 Twin Beds<br>-1st Floor Bedroom: 1 Bunk bed (1 Twin Bed and 1 Full Bed)<br>-Ground Floor Bedroom: 1 Queen Bed and 1 Twin Bed (Semi-Private Sleep Area)<br>Bathrooms<br>-Total: 3.5<br>-1st Floor: Full Bathroom w/ Shower<br>-1st Floor: Full Bathroom w/ Shower (en suite Queen Bedroom) <br>-2nd Floor Half Bathroom<br>-Ground Floor: Full Bathroom w/ Shower/Tub combo<br>Other Amenities:<br>-Split A/C <br>-Cable TV<br>-WiFi<br>-Washer/Dryer in basement<br>-Tub<br>-Outdoor shower<br>-Private yard<br>-Gas grill<br>-Game Room<br>-Please note outdoor amenities are available seasonally <br>-There is parking for a maximum of 6 cars<br>-1-minute walking distance to the pond!<br>-Sheets and bath towels provided with beds made upon arrival<br>-Cleaned with hospital grade disinfectant<br>C0414890860

This home is professionally managed by Pretty Picky Properties Orleans: New Construction, Pool, Hot Tub, Close to What Counts Sleeps 10 Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pool open from Memorial Day to Columbus Day Welcome to Stillwater, a stunning luxury home nestled in the picturesque Arey’s Pond area of Orleans, Massachusetts. This newely constructed property offers an exquisite retreat for families and friends, accommodating up to 10 guests with its four spacious bedrooms and 4.5 bathrooms. Enjoy breathtaking views of the private heated pool and hot tub, perfect for relaxation and entertainment. Step inside this beautifully designed house, where modern elegance meets comfort. The main level features a luxurious primary bedroom with a king-sized bed, while the second level boasts two guest bedrooms, each with a queen-sized bed, and an additional primary bedroom with another king-sized bed. Each bedroom is thoughtfully appointed to ensure a restful night’s sleep. The heart of the home is the fully equipped kitchen, complete with a dishwasher, refrigerator, and an espresso maker, making it a chef’s dream. Gather around the dining area or enjoy meals al fresco in the outdoor eating area. The living space is designed for relaxation, featuring a cozy private living room and a game room with a pool table and ping pong table for endless fun. Step outside to your private oasis, where you can soak in the heated pool or unwind in the hot tub. The outdoor space also includes a gas grill and fire pit, perfect for evening gatherings under the stars. Safety features such as smoke detectors, fire extinguisher, and a carbon monoxide detector ensure peace of mind during your stay. For those looking to explore, the property is conveniently located near beautiful beaches, golf courses, and local attractions such as Nauset, Beach, Skaket Beach, and a small freshwaster beach on Crystal Lake. Whether you’re seeking adventure or relaxation, Stillwater is the perfect destination. Don’t miss out on this luxurious getaway—book your stay at Stillwater today and create unforgettable memories! This home has high speed Wi-Fi, smart TV’s, a SONOS sound system and central air air conditioning. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is Professionally Managed by Pretty Picky Properties Luxurious Orleans Estate with Pool, Cabana, Game Room, and Stunning Finishes Sleeps 14 6 Bedrooms, 6.5 Baths Rents Friday to Friday in Peak Summer Linens Included, Beds Made Pets Considered Pool is open from Memorial Day to Columbus Day Welcome to your dream vacation home in Orleans! This custom-built, newly constructed property offers the perfect blend of luxury and comfort, designed to make your Cape Cod getaway unforgettable. Main House Highlights 5 Spacious Bedrooms: Each bedroom features a private en-suite bathroom, ensuring comfort and privacy for all guests. There’s one king bedroom on the main level, the primary bedroom suite is upstairs with a king size bed, the other two rooms have a king and queen respectively. The lower-level bedroom is the kid lair with 2 sets of queen over queen bunks. Vaulted Ceilings: The open concept living, dining, and kitchen areas are bathed in natural light and exude sophistication with soaring ceilings and high-end finishes. Gourmet Kitchen: Fully equipped with top-of-the-line appliances, perfect for preparing meals and entertaining. Luxurious and custom décor throughout: no expense was spared in outfitting the home with décor and furniture rarely seen in a vacation rental property. Outdoor Oasis Heated Saltwater Gunite Pool: Take a refreshing dip or lounge poolside in style. Hot Tub: room for 6 to enjoy! Pool House with Cabana Bar: Enjoy cocktails by the pool with a full cabana bar, a bathroom, and an additional bedroom for added convenience and flexibility. Entertainment Galore Game Room: The massive game room is a paradise for kids and adults alike, featuring Pop-A-Shot basketball, ping pong, air hockey, and more. High-End Furnishings: Every room is thoughtfully decorated with custom, high-quality furnishings to elevate your stay. 5-minute drive to Orleans Center and Nauset Beach: shopping and dining or head to one of the best beaches on the Cape. Whether you’re lounging by the pool, hosting a family game night, or enjoying the luxurious finishes of this one-of-a-kind property, this Orleans retreat is the perfect base for your Cape Cod vacation. Book now and experience the pinnacle of coastal living! Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

This property is professionally managed by Pretty Picky Properties. "Second Wind" - An Orleans Estate with large heated pool, spa, on Town Cove Sleeps up to 24 in three dwellings Linens and bed making included Pets Considered up to 25 lbs. Weddings not permitted on property Pool is open Memorial Day - Columbus Day This Orleans Estate is located in the heart of Orleans Village on picturesque Town Cove. Bring the whole family and leave the cars in the driveway for the week. You’ll spend countless hours around the pool and spa at the Main House. There’s plenty of room for everyone to gather around the fire pit and cook out poolside at the outdoor kitchen. You can walk to everything in Orleans Center, including some of the best restaurants in town, village shops and of course, ice cream. There are four ice cream shops within walking distance! The mid-century homes have been recently updated with all the modern conveniences while retaining much of the original charm. The large 1.3 acre lot is waterfront on Town Cove and has a heated pool and spa (open Memorial Day - Columbus Day). The large lot provides plenty of recreation space on the gently sloping lawn. Hold your own version of the Whiffle Ball World Series. Town Cove is a great place to drop an owner-provided kayak or SUP and explore the in-land waterways of Nauset Cove and Nauset Marsh. Bring your boat and use the adjacent town boat ramp to motor your way to Nauset Beach by boat! The Main House underwent a full remodel in 2023, you have an updated kitchen with granite counters and new appliances, including a huge side-by-side refrigerator and two dishwashers. There are two dining areas along the back of the house so that large groups can dine together. There is also an enclosed porch overlooking the lawn, pool and cove beyond. The house is great for bringing family together but you have enough space to spread out as well. There are 3 large seating areas in the Main and Carriage Houses that are great spots to watch a ball game or for the kids to watch their shows/movies. The Main House has 5 bedrooms, 5 full baths and 1 half bath. You’ll find one of three primary suites on the main level of the Main House with a king size bed, sitting area and beautiful ensuite bath. There is also a powder room on the main level and living room with separate card-table room. Upstairs in the Main House, there are 3 bedrooms: the second primary suite with a king bed and a private full bath, the third primary suite features a king size bed and ensuite bath, and the third bedroom has a queen size bed with a twin bunk above. There is a full bath for guests of this room in the hallway with a tub/shower combination. In the lower level, you’ll find an extra sleeping area with 2 twin beds for overflow sleeping. Plus a wonderful new media room, laundry room and there is a full bath down here as well plus an outdoor shower not far away. Next door in the Carriage House, you’ll find a second full kitchen, a dining area, a powder room, a primary suite with king size bed and a private full bath on the main level. Upstairs in the Carriage House, you’ll encounter a loft space with a TV and cozy couch. There is a full bath and a bedroom with a queen sized bed plus 2 twins. The third structure, the Guest House has been fully remodeled – brand new kitchen with stainless steel appliances and granite counters. On the main level is a queen bedroom with full bath while upstairs you have a kid’s room with a bunk bed (full under a twin) and another twin with trundle bed with an en suite bath. The primary suite upstairs features a king size bed and stunning views of Town Cove with a wonderful en suite bath. The shower feels like an outdoor shower! In addition, the Guest House has an outdoor shower and 6-person hot tub overlooking the Cove. All three homes have AC, WIFI and cable TV. If you feel like leaving your own private resort, good news – two world famous beaches are less than 5 minutes’ drive away, Nauset Beach on the Atlantic or Skaket Beach on Cape Cod Bay. There is nothing that is overlooked at this ideal vacation property for larger groups. Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%. This property offers a three night minimum stay during select weeks in May – June and September – November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived. Be sure to search this site for your best selection of prime vacation homes available for summer rental on Cape Cod. It’s your vacation. Get Picky! ®

14447 - The Dive In: Beautiful Spacious Family Retreat w/ Pool! Look no further than this beautiful spot for your next Cape Cod getaway, the house is spacious, clean and has everything you need to enjoy a great vacation! The star feature is its huge fenced-in yard with gorgeous private pool, tall pine trees, and large deck for enjoying grilling out while the kids run around and play. You’ll also enjoy two separate living/relaxing spaces that each have their own TV, so two separate groups can enjoy watching whatever they like. The kitchen is modern and well equipped, which will make whipping up meals for a crowd a cinch. Your days can be spent relaxing at the beach, taking a Seal Tour in Chatham, Whale Watch in Provincetown, wine tasting at Truro Vineyards, and more —the mid and Outer Cape have so much to offer! Return home after a day of fun to take an outdoor shower, jump in the pool and unwind with friends and family under the stars from the comfort of your own backyard. Other amenities include WiFi, cable TV, gas grill, central A/C, and washer/dryer. Fresh sheets and bath towels are provided free of charge. <br> <br> Home Details:<br> -Sleeps 8<br><br>-2 Floors<br><br>-2nd Floor Bedroom #1: 1 King Bed<br><br>-2nd Floor Bedroom #2: 1 Full Bed<br><br>-2nd Floor Bedroom #3: 1 Full Bed<br><br>-2nd Floor Bedroom #4: 1 King Bed, 1 Twin Bed w/ Trundle<br><br>-2nd Floor Common Area: 2 Twin Beds<br><br>-Central AC <br><br>-Cable TV<br><br>-WiFi<br><br>-Washer/Dryer <br><br>-Private Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br><br>-Outdoor Shower<br><br>-Gas Grill<br><br>-NO DOGS! (heavy fines remitted)<br><br>-Sheets and Bath Towels Provided with Beds Made Upon Arrival<br><br>-Cleaned with Hospital Grade Disinfectant<br>C0405890860

This property is professionally managed by Pretty Picky Properties Brand New Luxury Home in Orleans, Heated Pool, Steps to Town and Bike Trail Sleeps 10 in 4 bedrooms plus a bonus room Rents from Friday to Friday in Peak Season Linens included, beds made Pool is open Memorial Day to Columbus Day Welcome to “Liberty” a newly constructed home near downtown Orleans and convenient to Skaket and Nauset Beaches. This luxurious home features all new furnishings and décor, a heated saltwater pool and over 4,000 square feet of living area over three levels. The main level features soaring paneled ceilings in the main living area. The state-of-the-art kitchen is adjacent with a sizable island. The dining room is also in this area for easy prep and service of meals. There’s a cozy sunroom off the back of the main level as well for additional lounging and relaxation space. The primary bedroom is just off the kitchen and features a king-size bed, TV and a luxurious private bath. Upstairs, there are two bedrooms, one with a king-size bed and one with 2 full beds. There’s a shared bath up here with a shower/tub combo. The 4th bedroom is up a separate flight of stairs and has a king-size bed plus a private bathroom. The Lower level is expansive and has a movie room area, wet bar, full bath and easy access to the pool deck. There is also a king bed on the lower level for additional sleeping. The pool area has ample lounging area and of course a warm saltwater pool for use. Head out on foot or by bike and in moments you’ll be in downtown Orleans for dining, coffee, and shopping. The bike trail intersection is 0.4 miles from the house. Or maybe it’s a beach day! Skaket Beach on the bay is 1.5 miles or maybe the rolling waves of Nauset Beach is your fancy! Head 4 miles east for the open Atlantic. Vacation at Liberty! This luxury home has high-speed Wi-Fi, multiple smart TVs, and central air conditioning. Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $ 245.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%. Be sure to search the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. ​​​​​​​ It’s your vacation. Get Picky! ®