Family friendly vacation rentals in Orleans, MA

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! ®

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! ®

This property is professionally managed by Pretty Picky Properties Brand New Luxury Home with Heated Pool, Walk to Rock Harbor Sleeps 10 Linens Included, Beds Made Rents Friday to Friday in Peak Summer Off-Season Weekends and Partial Weeks Available Ideally situated on the bay side of Orleans, this brand-new property features a 35’ x 18’ salt water heated pool, with a built-in spa and auto close cover. It is complemented by a large hardscape patio with plenty of lounge space. You can walk a mere 0.4 miles to scenic Rock Harbor for boat charters, seafood and the best sunsets on Cape Cod! There’s also a beach for swimming! Back at the house your group of up to 10 will be delighted with luxury living tastefully furnished throughout. Start with the custom chef’s kitchen, fully outfitted with top-line everything – from the high-end appliances to the 10-foot-long granite topped island with bar seating. The adjacent café dining table offers comfortable casual seating which walks out to the patio and pool. There is more formal dining for eight in the separate dining room as well. The kitchen flows into the adjoining sunroom which is bathed in cheery sunlight, thanks to the large windows, and vaulted, handsome bead-boarded ceiling with skylight. This level is also home to the primary bedroom suite with its generous king size bed and large private, radiant heat bath with a twin sink vanity and oversized step-in glass shower. Also located on the main level: a half bath, the laundry/pantry and mudroom. Upstairs are three generously sized en suite bedrooms: One has a king bed, the next has a queen bed. The final bedroom has a queen plus 2 twin beds. Comfy sleeping for up to 10. This luxury home has high-speed Wi-Fi, multiple smart TVs, and central air conditioning. Please enter in 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%. Please note: pool and hot tub are open Memorial Day - Columbus Day. 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! ®

15517 - Endless Summer: Private pool 3 mins to Skaket Beach! Imagine long afternoons by the pool, evenings spent playing games with family and friends, cocktails in the upstairs bar and game room, and plenty of room for everyone to spread out and relax. With 3,500 square feet of living space, four bedrooms, and a sprawling private backyard, Endless Summer is the perfect home base for your Cape Cod getaway.<br><br>The outdoor space is the true highlight of this home, featuring a private pool, spacious patio with plenty of seating, gas grill, outdoor shower, and a large lawn for corn hole, yard games, or simply soaking up the sunshine. When you’re ready for the beach, Skaket Beach is just a three-minute drive away. You’ll also be minutes from Nauset Beach, Rock Harbor, Hog Island Brewery, Rock Harbor Grill, Orleans Bowling Center, and other local favorites, making it easy to enjoy everything from beach days and fresh seafood to breweries and family-friendly entertainment.<br><br>Inside, the first floor features a fully equipped kitchen, comfortable living room, a king primary suite with an updated en suite bath, a second bedroom with a twin bed, and an additional half bath. Upstairs, you’ll find two more bedrooms—one with two queen beds and another with a full bed and twin bunk beds—plus a spacious lounge and game room above the garage complete with a built-in bar. Central A/C, WiFi, cable TV, and a washer and dryer provide all the comforts of home.<br><br>Whether you’re challenging the family to a ping pong tournament, gathering around the board games after dinner, or unwinding by the pool under the stars, Endless Summer is the kind of place where lasting vacation memories are made. Reserve your Orleans getaway today and experience the very best of Cape Cod.<br><br>Home Details:<br>-No Pets (fines remitted)<br>-Sleeps 10<br>-2 Floors<br>Bedrooms<br>-Total 4<br>-1st Floor Bedroom: King Bed w/ en suite Full Bathroom<br>-1st Floor Bedroom: Twin Bed<br>-2nd Floor Bedroom: 2 Queen Beds<br>-2nd Floor Bedroom: 1 Full Bed and 1 Bunk Bed (2 Twins)<br>Bathrooms<br>-Total 2.5<br>-1st Floor: Half Bathroom<br>-1st Floor: Full Bathroom w/ Shower (en suite King Bedroom)<br>-2nd Floor: Full Bathroom w/ Shower/Tub combo<br>Other Amenities<br>-Central A/C + Split A/C in game room<br>-TV<br>-WiFi<br>-Washer/Dryer<br>-Bar/Game Room<br>-Outdoor shower<br>-Private Unheated Pool (Pool Open from Memorial Day to Labor Day - may be longer but not guaranteed)<br>-Large private yard<br>-Gas grill<br>-Minutes from Skaket Beach<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>-Parking for 4 cars maximum<br>C0425922240