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Holiday houses in Wildwood

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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 $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 18,070 verified reviews to help you choose

  • Family-friendly holiday rentals

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

  • Pet-friendly accommodation

    Find 460 rentals that welcome pets

  • Holiday 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 holiday 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 holiday rentals in Wildwood

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

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Guest favourite
A modern living area features a yellow leather sectional sofa and a round coffee table. A dining area with a dark wood table and chairs is visible, along with a large flat-screen TV. Natural light filters through the window coverings, creating a warm ambiance.
Home in The Villages
4.95 out of 5 average rating, 22 reviews

Peaceful Oasis in Fenney

Entire home with an Office Two (of the 3) bedrooms are furnished for Guest comfort 1) Master bedroom with king bed 2) Office with printer 5 night minimum @ listed price Sleeps up to 3 people. Modern, luxurious furnishings make you feel right at home. Golf, pickle ball, live music, free activities Fast Internet & YouTubeTV Fully equipped kitchen Complimentary Coffee & Tea Filtered water system Please NON-smokers ONLY welcome NO pets Not suited for children Reduced fee for 28+ nights

Top Guest favourite
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, 43 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😀

Guest favourite
A private outdoor area features a heated pool and spa, surrounded by screen enclosure. Comfortable seating is arranged beside the pool, complemented by an outdoor dining setup. The space is designed for relaxation with a stylish stone paver patio and clear blue skies above.
Home in Wildwood
4.93 out of 5 average rating, 15 reviews

Pool and Spa Luxury Retreat

Escape to this charming 3BR/2BA home in The Villages, FL! Enjoy a private heated pool & spa, perfect for relaxation. Walk to the nearby recreation center or take a short 1-mile ride to Eastport. This home includes a 4-person golf cart, making it easy to explore all The Villages has to offer. Comfortably furnished with modern amenities, it’s ideal for a peaceful retreat or an active getaway. Book now for the perfect blend of convenience and leisure! Heating of the pool and spa included in rate.

Top Guest favourite
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 favourite
A charming home exterior showcases a light blue facade and a white picket fence, surrounded by vibrant landscaping. A two-car garage is positioned prominently, with decorative plants adding interest. The clear blue sky provides a bright backdrop, accentuating the inviting appearance of the house.
Home in Wildwood
4.97 out of 5 average rating, 38 reviews

Brownwood Square - Villages Home

Indulge in a stylish retreat at this centrally located home, just minutes from the vibrant Brownwood Square in the sought-after Village of DeLuna. Immerse yourself in the full Villages experience with a community pool, recreation center, and included golf cart—perfect for exploring. Enjoy nearby shopping, dining, live music, nightlife, sports, and more. Explore Central Florida or take a short drive to the Gulf Coast, Atlantic Ocean, Disney, or Orlando’s vibrant attractions—all within an hour!

Top Guest favourite
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 favourite
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 favourite
The exterior of the home is visible, showcasing a well-maintained landscaping with neatly trimmed bushes and grass. A spacious driveway leads to a two-car garage, while porch lights illuminate the entrance. The roof is gabled, and large windows complement the inviting facade.
Home in The Villages
4.98 out of 5 average rating, 53 reviews

Entire 3-BR W/Cart - Between Brownwood & Sumter

Welcome to the Village of Pinellas where you'll be wowed by the beautiful landscapes, luxurious Palms and within walking distance (or golf cart ride) to the Pinellas shopping Plaza. This Modern 3 bed-2 bath open concept home is waiting for you. Enjoy the many golf courses, pools, nightly entertainment close by Brownwood & Lake Sumter or your fully stocked kitchen for a relaxing evening at home in the screened-in lanai. Sit on the covered front porch while enjoying your favorite drink!

Top Guest favourite
Home in The Villages
4.96 out of 5 average rating, 102 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 favourite
Home in The Villages
5.0 out of 5 average rating, 20 reviews

Eastport Emerald Escape 2BR Luxury in Well Point

Escape to The Eastport Emerald 🌴, a luxurious 2-bed, 2-bath villa in The Villages' Village of Well Point. This bright, open-concept home is ideal for snowbirds, vacationers, and extended stays, featuring 1GB fiber Wi-Fi, a chef's kitchen with gas range, and a private screened lanai. Enjoy self check-in with smart lock 🔑, community pools 🏊, lake access, and waterfront walking paths. Just a golf cart ride ⛳️ to Eastport Square and Sawgrass Grove.

Top Guest favourite
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 favourite
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.

Popular amenities for Wildwood holiday rentals

KitchenWifiPoolFree parking on premisesAir 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

12 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 holiday rentals in Wildwood

Guest favourite
The exterior of a modern single-story home is showcased at twilight, featuring a neatly landscaped front yard with tropical plants. A cozy seating area is visible by the entrance, and a two-car garage complements the home’s facade under a colorful sunset sky.
Home in The Villages
4.83 out of 5 average rating, 12 reviews

King-Sized Comfort

Guest favourite
The welcoming living area features a spacious sectional sofa paired with a comfortable armchair. A natural wood coffee table is centered on an area rug, while a flat-screen TV is mounted on the wall. Large windows allow natural light to fill the space, enhancing the inviting atmosphere.
Home in The Villages
4.97 out of 5 average rating, 29 reviews

Welcome to the Sawgrass/Eastport Area The Villages

Guest favourite
Home in Wildwood
5.0 out of 5 average rating, 7 reviews

Into The Mystic - 3/2 Dog Friendly w/ Golf Cart

Top Guest favourite
Home in Wildwood
5.0 out of 5 average rating, 10 reviews

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

Top Guest favourite
The kitchen features modern stainless steel appliances and a large island with seating for four. The quartz countertops complement the rich cabinetry and vibrant blue wall. Pendant lights provide illumination, enhancing the sleek design of the space.
Home in The Villages
5.0 out of 5 average rating, 24 reviews

Designer Home in The Villages, FL.

Top Guest favourite
An outdoor view of the home's exterior is presented, featuring a silver golf cart parked on a concrete driveway. The well-maintained front yard includes a white picket fence and landscaped areas with shrubs. A spacious garage is visible in the background under a clear blue sky.
Home in The Villages
4.93 out of 5 average rating, 70 reviews

Stunning Villa 2B/2B With Golf Cart

Top Guest favourite
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, 20 reviews

The Villages | Heated Pool | Walk to Sawgrass!

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

Uniquely decorated home with private backyard

When is the best time to visit Wildwood?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$298 NZD$340 NZD$332 NZD$245 NZD$197 NZD$197 NZD$174 NZD$170 NZD$174 NZD$194 NZD$223 NZD$245 NZD
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