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$6,246 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 modern home with a welcoming facade features a dual garage and a front entrance illuminated by a stylish light fixture. Large windows reflect the evening light, while a manicured lawn with minimal landscaping is visible in the foreground.
Home in The Villages
5.0 out of 5 average rating, 42 reviews

3/2 Designer Home W/ Golf Cart

Make this home your Villager get away! This is a designer home fully furnished with everything you will need for your vacation. This home is perfectly located minutes away from Sawgrass where you can enjoy live music every night. 🎶 The home is only an 18 minute drive from Brownwood which is a crowd favorite town-center. Home comes with a 4 seater golf cart perfect for adventuring to the pickleball courts, golf courses, pools & so much more! Come enjoy the sunshine in the beautiful Villages😀

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, 40 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.

Top guest favorite
Home in The Villages
5.0 out of 5 average rating, 17 reviews

Pool House Near Eastport and Middleton

Relax at this peaceful new home in The Villages. Only minutes to Eastport, Sawgrass and Middleton. Enjoy the beautiful outdoor area and heated pool (heated for additional $20/day) with plenty of space and seating. There are TVs in the living bedrooms and the lanai to watch from the pool or comfortable outdoor seating. There’s a king bed in the master and queens in each of the guest bedrooms. Your stay includes a gas 4-seater Yamaha golf cart and probably a 2nd cart. That one’s not promised.

Top guest favorite
A screened-in patio features a refreshing private pool surrounded by lush landscaping. Two chaise lounges are positioned beside the water, while a float rests in the pool. A fountain adds a tranquil element to the relaxing outdoor space.
Home in The Villages
4.97 out of 5 average rating, 97 reviews

Casa Santin Luxury in The Villages w/Private Pool

A refined Florida Luxury home designed for effortless indoor-outdoor living, Casa Santin blends modern coastal style with relaxed comfort—creating the perfect escape for your next getaway. Your Private Oasis. The highlight of Casa Santin is the stunning screened lanai and private pool—your own resort-style sanctuary. Start your mornings with coffee in the sunshine, spend afternoons poolside, and unwind in the evenings with a western sunset, a glass of wine under the soft glow of the lanai.

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, 112 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.

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, 56 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!!

Top guest favorite
Home in The Villages
4.96 out of 5 average rating, 101 reviews

King Bed, Golf Cart, Small Dogs & Water Filter!

Your NEW home includes a very comfortable KING BED and GOLF CART!! With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house NOVA WATER filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!! 2 SMALL DOGS OK.

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.

Guest favorite
Home in Wildwood
5.0 out of 5 average rating, 9 reviews

New Home! Wildwood Area

Welcome to your perfect Florida getaway! This cozy and comfortable home in Wildwood offers the ideal place to relax while staying just minutes from The Villages, local restaurants, shopping, and beautiful outdoor attractions. 5 miles away from Brownwood Paddock Square. Whether you’re visiting family, exploring Central Florida, or enjoying the vibrant lifestyle of The Villages, this home provides a peaceful and convenient stay.

Superhost
Home in The Villages
4.85 out of 5 average rating, 13 reviews

The Sunseekers Eco-Villa

Located inside the sought-after village of Hawkins, near the community pool with golf courses, restaurants, recreation centers, shops, and more just an easy golf car ride away. The screened-in lanai opens to the backyard with a BBQ provided for grilling your favorite meal. A perfect relaxing retreat after a busy day of activity and exploration. All natural cleaning products and sustainability considered each step of the way.

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

Top guest favorite
Home in Wildwood
5.0 out of 5 average rating, 9 reviews

Spotless 3BR Home w/ Golf Cart, Near Brownwood Sq

Relax at Pleasantville, a newly furnished home in The Village of McClure! Golf cart included for easy trips to Sawgrass Grove, Brownwood Square, Magnolia Plaza, and top golf courses. Enjoy pools, pickleball, walking trails, and more at nearby rec centers. Just 5 mins from Eastport’s golf academy & Sunset Island. Quiet, scenic, and perfect for fun, relaxation, and adventure—only 1 hour from MCO and Disney parks!

Popular amenities for Wildwood vacation rentals

When is the best time to visit Wildwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$36,434 GYDG$41,638 GYDG$40,597 GYDG$27,065 GYDG$23,942 GYDG$22,485 GYDG$21,236 GYDG$20,819 GYDG$21,236 GYDG$23,734 GYDG$27,273 GYDG$29,980 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