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Vacation rentals in Wildwood

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Quick stats about vacation rentals in Wildwood

  • Total vacation rentals

    Explore 1,110 vacation rentals in Wildwood

  • Nightly prices starting at

    Wildwood vacation rentals start at G$6,266 GYD per night before taxes and fees

  • Verified guest reviews

    Over 18,070 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,040 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 460 rentals that welcome pets

  • Vacation rentals with a pool

    470 properties feature pools

  • Rentals with dedicated workspaces

    690 properties have a dedicated workspace

  • Wi-Fi availability

    1,110 of Wildwood vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Wildwood rentals

  • 4.9 Average rating

    Wildwood stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Wildwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.
Home in Lady Lake
4.96 out of 5 average rating, 353 reviews

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

LocationFamilyKitchen

Top guest favorite
An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.
Place to stay in The Villages
5.0 out of 5 average rating, 127 reviews

Safari themed private addition with pool/hot tub.

This special Guest house addition is Central to everything in The Villages! Making it easy to plan your visit. In The Village of Osceola Hills @ Soaring Eagle Preserve. Just North of Rt 44. A short golf cart or car ride to Brownwood Square & Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Play over 50 golf courses at a minimal fee, & free rec centers! We have an easy 4 seater Golf-cart rental , & request free Guest passes!

ValueLocationComfort

Top guest favorite
A spacious living area is presented, featuring a light-colored sofa paired with white accent tables. A ceiling fan above enhances airflow, and modern kitchen appliances are visible in the background. Natural light floods the space, highlighting the hardwood flooring and simple decorative touches.
Home in The Villages
5.0 out of 5 average rating, 42 reviews

Bay Breeze Villa Free Golf Cart Close to Eastport

Welcome to Bay Breeze Villa, where modern comfort meets coastal charm. This brand-new 2-bedroom, 2-bath patio villa seamlessly blends style and functionality with sleek finishes and an inviting atmosphere perfect for relaxing or entertaining. Located in a vibrant community, close to top-rated restaurants, beautiful golf courses, and nightly entertainment. Embrace the relaxed yet active lifestyle you’ve been dreaming of – Bay Breeze Villa is the perfect place to call your home away from home.

LocationValueHospitality

Top guest favorite
A spacious living room features a large sectional sofa facing a mounted television. Natural light filters through sheer curtains, highlighting a decorative area rug. A round coffee table sits in the center, with a wooden console against the wall, adding functional charm to the space.
Home in The Villages
4.88 out of 5 average rating, 58 reviews

Olivia's Oasis

Enjoy a peaceful retreat in this cozy, fenced home featuring 2 bedrooms, 2 bathrooms, a full kitchen, garage, living room, office space, and a lanai. Conveniently located close to Orlando's theme parks and beautiful beaches, plus all the amazing amenities The Villages has to offer: pools, golf, and more! Golf cart included. Whether you're looking to relax in a quiet area or explore nearby attractions, our home is perfect for a memorable stay. Book now for an unforgettable experience!

ValueLocationKitchen

Top guest favorite
An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.
Villa in The Villages
4.86 out of 5 average rating, 277 reviews

Perfect "get-away" home for a couple or family!

Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. Golf cart included in price for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

ValueFamilyDecor

Top guest favorite
An extended lanai features a dining table surrounded by cushioned chairs, with views of a heated saltwater pool and lush greenery beyond. Comfortable seating arrangements are designed for relaxation, while ceiling fans provide a gentle breeze throughout the open space.
Home in The Villages
4.98 out of 5 average rating, 115 reviews

New Luxury Home-Pool-Waterfront View-3 King Suites

Enjoy this unique, tranquil getaway in a new 2023 home less than 3 miles from Sawgrass Grove (nightly entertainment, restaurants), and only a few blocks from Mickylee Pitch and Putt, Jubilee Putting Course, and the new Franklin Recreation Center. Ezell, Homestead, and Citrus Grove Rec Centers are all under 3 miles away. Back yard with lanai, pool with fountain, pond, and trees is a RARE find in The Villages! 3 king bedroom suites! Golf cart (4 seats) available for an additional fee.

FamilyLocationAccuracy

Top guest favorite
Home in Wildwood
5.0 out of 5 average rating, 42 reviews

Newest Hotspot in The Villages Eastport/Middleton”

Welcome to Eastport! The Villages’ most exciting new lifestyle destination — Eastport! Whether you're visiting for a weekend getaway or an extended stay, this beautifully furnished 2-bedroom, 2-bath Patio Villa w/golf cart puts you in the heart of everything The Villages has to offer — golf, pickleball, shopping, dining, entertainment, recreation, and serene nature. From the moment you arrive, you’ll see why Eastport is the new standard for luxury, leisure, and active adult living.

ValueFamilyComfort

Top guest favorite
A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.
Home in The Villages
5.0 out of 5 average rating, 59 reviews

Pirates & Parrots - The Villages - Golf Cart &Pool

GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a saltwater pool and a hot tub. 77 inch TV with sound system, and 2 car garage/golf cart . Outdoor bar with big screen TV with seating area and a second seating area outside the bird cage. TV’s in both bedrooms. Great out door living! Minutes to everything via golf car: Brownwood 12 Sumter 16 Sawgrass 19. 4 champ golf and 7 exec golf courses 5-10. Publix, Walmart 5 minutes Golf Car 2022 Yamaha included! No smoking!!

ValueLocationComfort

Top guest favorite
Home in Wildwood
5.0 out of 5 average rating, 10 reviews

Sawgrass & Eastport Town Square Golf Community

This spacious, clean, and well-appointed designer home is less than a five-minute golf cart ride from Sawgrass Grove where you can enjoy live nightly entertainment! It's also minutes away from the Clifton Cove 18 Hole Putting Course, McGrady's Restaurant & Pub the Sawgrass Indoor Market, and the Ezell Regional Recreation Center. You can dance or relax with a beverage under the lighted canopies, with live music every evening at the Sawgrass Grove boxcar stage. .

LocationComfortLong stay

Top guest favorite
An aerial view showcases a spacious property surrounded by lush greenery. The home features a neat driveway and is complemented by several nearby buildings, including a recreation center with a pool. Sunlight highlights the rooftops and well-maintained lawns.
Home in The Villages
5.0 out of 5 average rating, 113 reviews

Pool and fun right out back

Bring the family to this beautiful place with lots of room for fun. With the Waterlily Rec Center right out back you can walk to the family pool in just a few steps. Pickle ball, exercise equipment, corn hole, bocce ball, shuffleboard and a walking/biking path is all right out the back door. A four-seater golf cart is included. One minute to the Waterlily golf cart bridge and eight minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

FamilyLocationQuiet

Top guest favorite
A living room is showcased with two blue sofas facing a glass coffee table. Soft lighting is provided by two table lamps and a large TV is positioned on a dark wood console. Colorful wall art adds brightness to the space, complemented by a dining area in the background.
Home in Wildwood
5.0 out of 5 average rating, 31 reviews

Private home in The Villages

Welcome to your perfect get-away in The Village of St. John’s. The cozy 3/2 villa is bright, fully equipped and comfortably furnished and includes guest passes. Enjoy the convenience of nearby shopping, dining and entertainment at Brownwood Paddock Square. Stroll on the walking trail which leads along Lake Okahumpka to the Recreation Center. Whether you’re here for excitement or relaxation, this is the perfect base for your stay in The Villages.

LocationFamilyQuiet

Top guest favorite
Home in Wildwood
5.0 out of 5 average rating, 11 reviews

Stylish Villages Getaway

Welcome to your modern luxury escape in The Villages. Perfect for snowbirds, couples, or families, this brand-new home is designed for comfort and convenience. Enjoy high-end furnishings, elegant interiors, and access to resort-style community amenities. Make the most of your stay with a premium 6-passenger golf cart, electric bikes, and endless entertainment. Stay active, relax, and create unforgettable memories.

FamilyLocationHospitality

Popular amenities for Wildwood vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Stay near Wildwood's top sights

Lake Sumter Landing

124 locals recommend

Sharon L. Morse Performing Arts Center

21 locals recommend

The Villages Golf Cars

13 locals recommend

Rohan Regional Recreation Center

5 locals recommend

Volusia Executive Golf Course

4 locals recommend

Marsh View Pitch & Putt Executive Golf Course

4 locals recommend

Other great vacation rentals in Wildwood

Guest favorite
Home in The Villages
5.0 out of 5 average rating, 6 reviews

Htd Pool & Attached Hot Tub. Rare corner propty

LocationFamilyHospitality

Top guest favorite
Home in The Villages
5.0 out of 5 average rating, 13 reviews

Seashell Villa~Pet Friendly~Golf Cart

LocationSleep qualityCondition

Top guest favorite
Home in The Villages
5.0 out of 5 average rating, 18 reviews

Vibrant Villa-Sumter Landing! NEW Golf Cart, KING

LocationFamilyPool

Top guest favorite
Home in The Villages
5.0 out of 5 average rating, 13 reviews

The Creative Cottage! Premium Amenities!

LocationFamilyAccuracy

Guest favorite
A private heated pool is framed by a spacious lanai with a sleek, white deck. The pool features a shimmering blue surface and tiled border. Surrounding walls provide privacy while natural light pours in from above, creating a bright and inviting space.
Home in Wildwood
4.91 out of 5 average rating, 99 reviews

New, private pool getaway in The Villages, FL

ValueFamilyHospitality

Top guest favorite
Two goats are seen in a lush green field, one featuring a predominantly black coat with white markings, while the other is white with black patches. The surrounding grass is tall, contributing to the farm setting.
Ranch in Wildwood
5.0 out of 5 average rating, 28 reviews

Owl Cove Ranch Sunset Barn Apartment

LocationFamilyAccuracy

Top guest favorite
A stylish villa exterior is presented with a gray facade and a welcoming porch area. A well-maintained lawn features a white picket fence and newly planted shrubs. A golf cart is parked on the driveway, ready for use, while the surroundings depict a tranquil neighborhood setting.
Home in Wildwood
4.97 out of 5 average rating, 94 reviews

Newer Villa in The Villages near Brownwood

LocationFamilyHospitality

Top guest favorite
A heated pool is enclosed within a screened patio, featuring gentle water features and surrounded by lush greenery. Two wooden adirondack chairs and a small side table are positioned nearby, inviting relaxation in this outdoor space.
Home in The Villages
4.9 out of 5 average rating, 21 reviews

The Villages | Heated Pool | Walk to Sawgrass!

FamilyLocationGrill

When is the best time to visit Wildwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$36,551 GYDG$41,773 GYDG$40,729 GYDG$30,076 GYDG$24,228 GYDG$24,228 GYDG$21,304 GYDG$20,886 GYDG$21,304 GYDG$23,811 GYDG$27,361 GYDG$30,076 GYD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Frequently Asked Questions

  • What are the best places to stay in Wildwood?

    Vacation rentals in neighborhoods near parks or the city center are often recommended for convenient access to dining and attractions. Areas around nature preserves provide quieter settings and opportunities for outdoor exploration.

  • What are the best things to do in Wildwood with kids?

    Kids can enjoy playgrounds, mini golf, and interactive activities at local parks. Family friendly fairs, fishing spots, and outdoor markets are frequently suggested for memorable outings.

  • What are some of the best things to do in Wildwood?

    Explore city parks, browse local antique shops, or join a community festival in Wildwood. Nature preserves and regional art galleries provide outdoor and cultural experiences, appealing to a range of interests.

  • How is the weather in Wildwood?

    Wildwood has warm, humid summers reaching up to 92°F (33°C), with frequent rain, and mild winters from 49–72°F (10–22°C). Spring and autumn bring comfortable temperatures and moderate rainfall, making outdoor activities popular.

  • When is the best time to visit Wildwood?

    Late winter through spring is often recommended for milder temperatures from 49–79°F (10–26°C) and lower humidity. Fall also brings pleasant weather, with local festivals and community events adding to the experience.

  • What are the best places to visit in Wildwood?

    Popular places to visit in Wildwood include city parks, historic sites, and local markets. Nature preserves and galleries showcasing regional artists are often recommended for a deeper look into the community.

  • What are some hiking trails in Wildwood?

    Wildwood has nature trails in area parks and preserves, often featuring shaded paths among pine forests and lakes. Exploring these local trails is frequently suggested for birdwatching and relaxation.

  • What are some family activities we can do in Wildwood?

    Families in Wildwood can explore community parks, playgrounds, and picnic areas. Nature trails, mini golf, and seasonal events are often recommended for group fun.

  • What are some of the best day trip ideas from Wildwood?

    Day trips from Wildwood frequently suggest exploring nearby nature parks, visiting lakes for boating, or discovering historic downtowns in surrounding communities. Regional art galleries and local farms are also favorites for an immersive experience.

  • Are there any pet friendly accommodations available in Wildwood?

    Wildwood has several pet friendly accommodations, including vacation homes and rentals with fenced yards. Parks and walking trails around the city make it easy to spend time outdoors with pets.

  • What are some local tips for visiting Wildwood?

    Local tips include visiting farmers markets early for the freshest produce and exploring parks during cooler morning hours. Many recommend joining community events to experience Wildwood’s friendly spirit.

  • What is Wildwood known for?

    Wildwood is known for its welcoming atmosphere, historic roots, and access to open spaces. The city has community traditions, local markets, and a connection to outdoor recreation.

  • What are the best hidden gems to explore in Wildwood?

    Wildwood has small antique shops, quiet parks, and local markets that highlight the area’s community spirit. Exploring nearby nature preserves and lakes is often recommended for those wanting less crowded spaces.

  • What are the best foods to try in Wildwood?

    Wildwood has classic Southern dishes, barbecue, and fresh produce from local farms. Visitors often seek out homemade pies, fried chicken, and regional specialties such as catfish.

  • What should I bring for a trip to Wildwood?

    Pack lightweight clothing for warm days, a hat, sunscreen, and sturdy walking shoes. For outdoor activities, bring a reusable water bottle and bug spray, especially in summer months.

  • What is the nightlife in Wildwood like?

    Wildwood’s nightlife centers on casual venues, family owned restaurants, and local bars. Some spots feature live music or karaoke nights, with a relaxed, community-oriented atmosphere.

  • What are the most popular events or festivals in Wildwood?

    Wildwood often features local fairs and community celebrations throughout the year, with seasonal events around spring and fall drawing crowds. County fairs and cultural festivals are frequently suggested for live music, crafts, and food experiences.

  • Are there family friendly vacation rentals in Wildwood?

    Wildwood has many family friendly vacation rentals, including homes with spacious layouts, backyards, and amenities like kitchens and laundry. Neighborhoods around community parks are frequently suggested for families seeking quieter settings and recreational spaces.

Destinations to explore