Holiday rentals in Wildwood

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Top-rated holiday rentals in Wildwood

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

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Top guest favourite
Cottage in Coleman
4.97 out of 5 average rating, 199 reviews

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to a peaceful private farm cottage just minutes from Villages. Enjoy a romantic, cozy retreat with a private fenced courtyard, mini farm charm, and thoughtful comforts throughout. Pets are welcome with no surprise fees. Easy self check-in and simple checkout make your stay stress-free. Close to Brownwood, dining, shopping, and I-75. Extra parking may be available for boats, trailers, or larger vehicles with advance notice. Traveling with family or friends? Ask about nearby sister rentals.

Top guest favourite
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 out of 5 average rating, 97 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 golf cart is included for golfing and access to the rest of The Villages. 1 minute to the Waterlily golf cart bridge and 8 minutes to Brownwood Square. Or Edna’s on the Green is just a few minutes away.

Top guest favourite
A modern Patio Villa is depicted in a well-maintained neighborhood, featuring a gray and white exterior with a slanted roof. A blue golf cart is parked on the driveway, surrounded by neatly trimmed grass and small shrubs.
Home in The Villages
4.98 out of 5 average rating, 49 reviews

Latitude Adjustment

Change your latitude in this beautiful two bedroom, two bathroom Patio Villa in The Villages. Located in the Village of Newell, this spacious and modern home has everything you need to make your stay relaxing and fun, including a golf cart! Enjoy a cup of coffee from the Keureg after your morning stroll on one of the nearby nature trails. Pools, pickleball and golf are all five minutes by golf cart, along with dining and entertainment at Sawgrass Grove and twelve minutes to the new Eastport!

Superhost
A single-story home is depicted, featuring a well-maintained front yard with lush greenery and decorative plants. The exterior is painted in light colors, while dark roof shingles provide a modern touch. A multi-car driveway leads to a garage with a contemporary door.
Home in Wildwood
4.79 out of 5 average rating, 19 reviews

Cozy Retreat right next to EastPort

Welcome to The Villages Retreat, a charming house nestled in the heart of Moultrie Creek Village! This delightful property boasts three bedrooms, providing ample space for a comfortable stay, perfect for families or groups visiting to watch their grandkids sports games, or to celebrate their graduation! This Home is Centrally Located and is within 5 minutes from locations such as: The Villages Charter Highschool and it's stadiums, The Tracy Performing Arts Center, and East Port Town Square.

Guest favourite
Home in The Villages
5 out of 5 average rating, 12 reviews

Luxury Villages Stay • Golf Cart • Near Brownwood

Welcome to your Villages retreat! Step into comfort and style in this beautifully decorated, designer home fully furnished with everything you need for a relaxing stay. From cozy bedding to modern furniture. Located in the sought-after Village of Osceola Hills, end of Moyer Blvd just south of Route 44, this spacious 3-bedroom, 3-bathroom home (2021 sq. ft.) features a 2-car garage and comes with a golf cart. You're just minutes away from Brownwood (3 miles) and Sawgrass Grove (2 miles).

Top guest favourite
The exterior of a single-story villa is displayed, featuring a neatly landscaped front yard with greenery and a small garden bed. A parked golf cart is visible next to the driveway, while a two-car garage is positioned at the front of the house.
Home in Wildwood
4.93 out of 5 average rating, 73 reviews

Villa in The Villages Great Location

Kick back and relax in this calm, stylish villa in The Villages. It is in the village of McClure (Fenney area). It is a super clean villa with newer furnishings. The villa comes with a golf cart as a courtesy to enjoy. It is close to Everglades Recreation Center Magnolia Shopping Center, family pools, sports pools, executive golf courses and many other activities. The neighborhood pool is within walking distance to this home! The home is fully furnished and has a fully equipped kitchen.

Top guest favourite
Home in Wildwood
5 out of 5 average rating, 22 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.

Top guest favourite
Home in The Villages
4.95 out of 5 average rating, 39 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

Enjoy this beautiful 2/2 home in De Luna. With quick access to the turnpike and I-75 to enjoy everything in and around the Villages. This Ruby model villa is close to Brownwood and Ednas’ on the Green & soon to be East Port. It comfortably fit 4 people in two queen beds. The living room can fit two on the pull out sectional. The front screen porch is a wonderful place to wave to your neighbors while you have your morning coffee or just the place to relax before going to bed.

Top guest favourite
Home in Wildwood
5 out of 5 average rating, 43 reviews

Opal Oasis in The Villages

Want a newer vacation home close to Sawgrass Grove where free nightly entertainment is available, several pools, recreation centers, biking paths and the town square of Eastport? Look no further. Check out this fully furnished home! The outdoor living is relaxing and tropical as we have an outside patio behind the palms. It will make you feel like the only person on the street! The home is within a 12 minute drive to the Villages High school/ Middleton and 18 minutes to Leesburg

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

Luxury Pool Home with a View in The Villages, FL

Enjoy your own private sports pool, spa, and climate-controlled lanai as well as all of the amenities that The Villages has to offer. Free executive golf courses, water volleyball, and water aerobics for stays of 30+ days. Pickleball, tennis, billiards, shuffleboard, bocce ball, outdoor exercise equipment and nightly entertainment for all guests. Get to Brownwood town square in approximately 10 minutes. This home is located on a pond with a natural preserve beyond the pond.

Top guest favourite
Home in The Villages
4.96 out of 5 average rating, 93 reviews

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

Your NEW home includes a very comfortable KING BED. With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house 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!!

Top guest favourite
A serene pool area is enclosed by a mesh screen, featuring clear blue water and a decorative fountain. A stone statue adorns the poolside, alongside a woven basket filled with towels. Lush greenery and a calm lake are visible in the background.
Home in Wildwood
4.97 out of 5 average rating, 149 reviews

Fenney Waterview Retreat w/Pool in The Villages

If you are looking for a Tranquil escape, then this is the right home for you. Sit by the pool and overlook the sun dance upon the sparkling water as you sip on your drink or read a great book. This Ultra Clean 3 bed/3 bath home has all of the comforts you'll be looking for. There's plenty of space for you and friends or family as everyone has their own space in the home.

Popular amenities for Wildwood holiday rentals

When is the best time to visit Wildwood?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£119£129£122£96£85£80£75£74£75£84£96£106
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.

Quick stats about holiday rentals in Wildwood

  • Total holiday rentals

    Explore 1,110 holiday rentals in Wildwood

  • Nightly prices starting at

    Wildwood holiday rentals start at £22 per night before taxes and fees

  • Verified guest reviews

    Over 17,620 verified reviews to help you choose

  • Family-friendly holiday rentals

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

  • Pet-friendly holiday rentals

    Find 460 rentals that welcome pets

  • Holiday rentals with a pool

    460 properties feature pools

  • Rentals with dedicated workspaces

    710 properties have a dedicated workspace

  • Wifi availability

    1,110 of Wildwood holiday rentals include wifi 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!

Destinations to explore

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