Vacation rentals in Wildwood, FL with a pool

Discover vacation rentals, homes, and villas in Wildwood, FL for an upcoming trip, whether for leisure or work. Every home is curated and professionally managed, offering more space, comfort, and flexibility for your trip. Along with premium amenities like 24/7 local support and high-speed Wi-Fi, many homes are equipped with features to suit different travel styles, group sizes, and budgets. However you're looking to experience your stay, Homes & Villas by Marriott has your next vacation home waiting. Marriott Bonvoy members can earn and redeem points on every stay.

4 Homes with Pools in Wildwood

Private Pool & Lake Views: Family Home in Oxford

The Villages, FL, US
3 Bedrooms 10 Guests
Aug 24 - 29
$333 night

Spend your next Florida family getaway with a stay at this beautiful 2-story house with a lake view and a large swimming pool! This 3-bedroom, 3-bath Oxford vacation rental features a private backyard, furnished screened porch, and just a short walk from Lake Miona which includes a playground, beach, and boat ramp! Explore shops and restaurants around nearby Lake Sumter Landing, check out kayaking at Lake Griffin State Park, or plan a day trip to Disney or Universal Studios while in town! -- THE PROPERTY -- Fireplace | Screened Porch | 2 Mi to Lake Sumter Landing | Water Views Bedroom 1: California King Bed | Bedroom 2: 2 Twin Beds | Bedroom 3: 2 Twin Beds | Living Room: 2 King Air Mattresses INDOOR LIVING: Smart TVs, board games, books, dining table, walk-in closet, en-suite bathroom, walk-in showers, garden tubs, ceiling fans OUTDOOR LIVING: Private pool, spacious deck, patio seating, outdoor dining, rocking chairs, basketball goal, fire pit KITCHEN: Refrigerator, drip coffee maker, stove/oven, microwave, dishwasher, toaster oven, kitchen island, dishware & flatware, cooking basics GENERAL: Self check-in, free WiFi, central heating & A/C, washer & dryer, laundry detergent, iron/board, towels/linens, trash bags/paper towels, complimentary toiletries, hair dryer FAQ: Pet fee (paid pre-trip) ACCESSIBILITY: 2-story house, 2 steps required to enter, interior stairs required to reach all bedrooms on 2nd floor PARKING: Carport (3 vehicles), driveway (8 vehicles), RV parking allowed (electrical hookups on-site) -- THE LOCATION -- NEARBY ATTRACTIONS: Lake Sumter Landing (2 miles), Spanish Springs Town Square (6 miles), Brownwood Paddock Square (7 miles), Venetian Gardens (14 miles) OUTDOOR FUN: Lake Miona Park & Boat Ramp (0.3 miles), Lake Miona Park (0.3 miles), Lake Griffin State Park (10 miles), Eaton's Beach at Lake Weir (12 miles) HIT THE LINKS: Lopez Legacy Golf & Country Club (6 miles), Hacienda Hills Golf & Country Club (6 miles) FLORIDA DAY TRIPS: Universal Studios (57 miles), Disney World (58 miles), Downtown Orlando (58 miles) AIRPORTS: Leesburg International Airport (18 miles), Orlando International Airport (65 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 - Pet friendly w/ $150 fee (+ fees & taxes) - No events, parties, or large gatherings - Must be at least 25 years old to book - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: While this 2-story house only requires 2 steps to enter, an interior staircase is required to reach all of the home’s bedrooms on the 2nd floor - NOTE: This property sleeps 6 guests in 5 beds, with room for 10 total by using the air mattresses

Glendale Poolside Retreat

The Villages, FL, US
3 Bedrooms 6 Guests
Aug 24 - 29
$219 night

IMPORTANT !!! JAN-MAR only full month bookings / no partial bookings allowed Other times of the year - Minimum two-week stays. 🌟 Glendale Poolside Retreat in the Village of Charlotte 🌟 Discover the perfect blend of luxury and relaxation at Glendale Poolside Retreat, an elegant 3-bedroom, 2-bathroom designer home in the desirable Village of Charlotte. Just a short stroll to the Captiva Family Pool and Recreation Center, this beautifully furnished residence offers a private pool and is ideally located close to Brownwood Paddock Square and just a quick ride to Lake Sumter Landing. 🏡 Sophisticated Living & Stunning Design Step inside and experience the grandeur of this beautifully designed home. The open floor plan seamlessly connects the living, dining, and kitchen areas, providing an inviting space for relaxation or entertaining. The home features tile floors, soaring ceilings, and sophisticated finishes that create an atmosphere of timeless charm. The master suite includes a luxurious king bed and a private bathroom, while the guest rooms offer a queen bed in one and two twin beds in the other. Each bedroom is designed for comfort and style, ensuring a restful stay. 🌞 Private Poolside Oasis Step outside through the glassed-in lanai to find your private poolside escape enclosed within a spacious birdcage. Whether you’re lounging poolside or hosting a BBQ, this tropical oasis is perfect for making the most of the Florida sunshine. With lush surroundings and ample seating, your outdoor space invites relaxation and fun in equal measure. Solar system for temperature controls - no heat pump 🌴 Explore The Villages! As a guest at Glendale Poolside Retreat, you’ll enjoy all the incredible amenities of The Villages, Florida’s premier 55+ active adult community. For a small fee, obtain a Villages Temporary Resident ID and access over 40 executive golf courses, resort-style pools, and recreation centers that offer everything from tennis and pickleball to fitness classes. Choose from family pools, lap pools, and adult-only pools to suit your mood. 🚶‍♀️ Prime Location: Convenience at Your Doorstep Located just minutes from Brownwood Paddock Square, where you can enjoy live music, dining, and shopping, and a quick ride to Lake Sumter Landing, this home offers the perfect balance of peaceful living and access to entertainment. With Captiva Recreation Center just around the corner and other centers close by, you’ll always have something fun to do. This stunning home in the Village of Charlotte offers a private pool, luxurious accommodations, and easy access to all the excitement of The Villages. Experience the best of both worlds with convenience, comfort, and relaxation at your fingertips. Solar system for temperature controls - no heat pump

Allenwood Pool Home at The Villages

The Villages, Florida, US
3 Bedrooms 6 Guests
Aug 24 - 29
$174 night

Allenwood Pool House | Private Heated Pool • Outdoor Kitchen • Golf Cart • Near Lake Sumter Landing Escape to Allenwood Pool House, a beautifully appointed designer home in the desirable Village of Amelia, where resort-style outdoor living meets one of the most convenient central locations in The Villages. Featuring a private pool, outdoor kitchen, dedicated workspace, and complimentary golf cart, this home is perfect for golf vacations, extended stays, snowbirds, or simply enjoying everything The Villages has to offer. The Home This beautifully designed 3-bedroom, 2-bath home comfortably accommodates up to six guests with an open floor plan that creates the perfect gathering space for family and friends. Sleeping Arrangements Primary Suite: King bed, Smart TV, private ensuite bathroom with walk-in shower Guest Bedroom 1: Queen bed with Smart TV Guest Bedroom 2: King bed with Smart TV Guest bathroom with full bathtub Every bedroom includes its own television, and the spacious living room also features a large Smart TV for relaxing after a day exploring The Villages. Chef’s Kitchen Whether you’re preparing breakfast before golf or hosting dinner with friends, the kitchen is fully equipped with everything you’ll need. Features include: Granite countertops Large center island Gas stove Upgraded stainless steel appliances Fully stocked cookware, dishes, utensils, and small appliances Coffee maker Pantry storage Dining options include: Dining table seating for 6 Breakfast nook seating for 4 Kitchen island with bar seating Outdoor Living The backyard is designed to make every day feel like a vacation. Enjoy: Private swimming pool Optional pool heat (additional fee) Outdoor kitchen Covered lanai Comfortable outdoor seating Private patio terrace Whether you’re enjoying your morning coffee, grilling dinner, or relaxing by the pool after a round of golf, this outdoor space is one of the home’s highlights. Dedicated Workspace Need a quiet place to work? The den features: Desk Comfortable office chair Quiet space for remote work, reading, or conference calls Included Amenities Complimentary high-speed Wi-Fi Smart TVs in the living room and every bedroom Full-size washer and dryer Fully equipped kitchen Linens and towels provided Two-car garage Complimentary 2-passenger gas golf cart Explore The Villages The Village of Amelia is one of the most sought-after central neighborhoods in The Villages, offering easy golf cart access to shopping, recreation, golf, and entertainment. Lake Sumter Landing Approximately 4 miles | About 10–15 minutes by golf cart Lake Sumter Landing is one of The Villages’ three iconic town squares and features: Free nightly live entertainment Waterfront restaurants Boutique shopping Happy hours Coffee shops Ice cream Seasonal events Movie theater Brownwood Paddock Square Approximately 8 miles | About 20–25 minutes by golf cart or 15 minutes by car Brownwood offers: Free nightly live music Restaurants Shopping Farmers markets Seasonal festivals Dancing Entertainment throughout the year Recreation Nearby With Temporary Resident IDs, guests may enjoy access to The Villages’ outstanding recreation system, including neighborhood and regional recreation centers, pools, pickleball, tennis, bocce, shuffleboard, clubs, and organized activities. Amelia Neighborhood Recreation Center Approximately 2 minutes away Features include: Adult pool Shuffleboard Bocce Horseshoes Social activities Pavilion Colony Cottage Regional Recreation Center Approximately 10 minutes away Offers: Sports pool Pickleball Tennis Billiards Meeting rooms Daily activities Fitness classes Lake Miona Regional Recreation Center Approximately 10 minutes away Features: Sports pool Pickleball Tennis Fitness activities Arts & crafts Clubs Indoor recreation Golf Golf enthusiasts will love the location. Numerous Executive Golf Courses and Championship Golf Courses are just minutes away by golf cart, giving you endless opportunities to play throughout your stay. Shopping & Dining Within just a few minutes you’ll find: Publix Fresh Market Walmart Target Walgreens CVS Pharmacy Banking Medical facilities Countless restaurants Golf cart-accessible shopping and dining Temporary Resident IDs Guests staying with AJ Home Rentals may purchase Temporary Resident IDs (approximately $50 per household, payable directly to The Villages when picking up the IDs). Temporary Resident IDs allow eligible guests to enjoy many of the community’s outstanding amenities, including recreation centers, pools, executive golf (trail fees may apply), organized activities, and more. Please note that Temporary Resident IDs are not Guest Passes and are issued by The Villages based on eligibility and availability. Golf Cart A complimentary 2-passenger gas golf cart is provided for your convenience. Guests who wish to use the golf cart must complete AJ Home Rentals’ Golf Cart Waiver before arrival. The golf cart is provided as a complimentary amenity. While we make every effort to ensure it is available, unforeseen maintenance, repairs, recalls, weather, or other circumstances may occasionally prevent its use. No refunds or credits will be issued for golf cart interruptions. Pet Policy We welcome well-behaved dogs upon prior approval. Dogs require advance approval. Breed, age, weight, and house-training information may be requested. Additional pet fees may apply. Cats are not permitted. Whether you’re planning a golf getaway, an extended seasonal stay, or a relaxing Florida vacation, Allenwood Pool House offers the perfect blend of comfort, convenience, and resort-style living in the heart of The Villages. From the private pool and outdoor kitchen to the golf cart and unbeatable location near Lake Sumter Landing and Brownwood, everything is here for an unforgettable stay.

Tropical Private Fenney Escape

Wildwood, FL, US
3 Bedrooms 6 Guests
Sep 13 - 18
$195 night

IMPORTANT !!! JAN-MAR only full month bookings / no partial bookings allowed 🌟 Welcome to Tropical Private Fenney Escape: Your Exclusive Oasis in The Villages! Discover the ultimate getaway at Tropical Private Fenney Escape, a stunning and spacious home in the heart of the sought-after Villages of Fenney. This luxurious 3-bedroom, 2-bathroom residence is perfect for those seeking both comfort and adventure, offering a private pool, lush garden views, and easy access to some of the best amenities The Villages has to offer. ✨ Relax in Style & Comfort Step inside this beautifully designed home, where natural tones and calming whites create a serene atmosphere. The open-concept living area is perfect for entertaining, with a fully equipped kitchen that includes all the tools you need for cooking, baking, and hosting. The bar area adds a touch of fun for evening gatherings, while TVs in every room ensure entertainment at your fingertips. The master bedroom features a luxurious king-sized bed and an en-suite bathroom for ultimate relaxation. The two additional guest rooms each have comfortable queen beds, providing restful retreats for family or friends. Step outside to your private pool, where you can unwind in total privacy. The enclosed lanai offers the perfect space for dining or lounging, surrounded by the lush greenery of the garden. 🏌️‍♂️ Fun & Adventure in The Villages Located in the vibrant Villages of Fenney, this home is minutes away from all the fun and excitement. Enjoy a meal at the Fenney Grill or explore the nearby Everglades Recreation Center, offering everything from pickleball courts to a lap pool for swimming or water volleyball. For those who love adventure, the area even features archery ranges and scenic nature trails. Golf enthusiasts will love the proximity to top executive golf courses, perfect for a leisurely round. After a day of activities, head back to Tropical Private Fenney Escape to relax and unwind in your peaceful retreat. 🚗 Convenience & Comfort This home comes with a spacious 3-car garage, providing ample room for cars, golf carts, or any fun toys you bring along. With plenty of storage and a fully equipped kitchen, you’ll feel right at home whether you’re cooking, hosting, or just relaxing by the pool. ⛳ Explore The Villages With your Villages Temporary Resident ID (available for a $50 fee), you’ll have access to over 40 executive golf courses, recreation centers, pools, and more. Whether you’re exploring the golf cart paths, enjoying live music, or dining at Sawgrass Market Square, there’s always something to do in The Villages. Make Tropical Private Fenney Escape your next home away from home and experience all that The Villages has to offer—luxury, adventure, and relaxation await!

Vacation Rentals in Wildwood by Amenities & Features

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Vacation Rentals Near Wildwood

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