Holiday rentals in Wildwood
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Top-rated holiday rentals in Wildwood
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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. No garage access.
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.
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.
Newer Villa in The Villages near Brownwood
Kick back and relax in this calm, stylish new villa in the Villages. It is within walking or a 3 minute golf cart ride to Brownwood Town Center where there are dining, shopping and nightly music. It is also near Lake Okahumpka Recreation Center where you can fish or kayak. This area has beautiful nature trails for walking or biking with separate golf cart paths. There is a neighborhood pool and other amenities nearby. It also comes with a complementary golf cart for your convenience.
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.
Fabulous Courtyard Villa close to Sumter Landing
This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.
Seashell Villa~Pet Friendly~Golf Cart
Welcome to the Seashell Villa, your cozy coastal getaway! The thoughtfully decorated space brings accents of the beach to each room. Great 2 bedroom, 2 bath villa just steps from Sawgrass Grove, Ezell rec center, the new Eastport and all the great things the Villages has to offer. Included in this rental is a golf cart and a BBQ grill. We welcome small dogs under 35lbs. PLEASE NOTE: We require a signed rental agreement and a copy of your ID to finalize your reservation.
Serendipity Lake private dock, canoes & kayaks
FL is in a drought, water levels are 8ft + lower than normal. You can still enjoy fishing and kayaking on our direct waterway. Watch the sunrise and sunset over the water on a private dock. This is a place you will want to come back to time and time again. We do provide kayaks and canoes to enjoy the lakes. Plenty of room for outdoor games and activities. Pet friendly. Just a short drive to downtown Inverness and 30 minutes to Crystal River. Simply perfect!
Private Villa + Golf Car by Lake Sumter Square
Welcome to our cozy 3-bedroom, 2-bath courtyard villa in the Village of Virginia Trace, just 4 minutes from Lake Sumter Square. Enjoy the convenience of nearby shopping, dining, and entertainment. The private, fenced yard with a fire pit and grill is perfect for outdoor living. The rental includes an electric atomic golf cart for easy exploring. Inside, the villa is bright and comfortable, with a king bed in the primary room and queen beds in the other two.
Villages-Private Heated Pool-Central Location
Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses
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!
Captain's Cottage - 3/2 w/ POOL & Golf Cart
This open-concept, 3 Bed, 2 Bath in The Village of Shady Brook, has a private, screened-in pool! It is located 4 miles from SAWGRASS GROVE SQUARE where you will have shopping, dining and nightly entertainment. Executive/championship GOLF COURSES and REC CENTERS at your fingertips. No need to go far while staying in this newly built home! 4-seat electric golf cart available starting May 15'26.
Popular amenities for Wildwood holiday rentals
Other great holiday rentals in Wildwood
Balcony Oasis Home
Prime Village Location! - Brownwood! 2 Golf Carts!
Pool Access: Sleek Home in The Villages w/ Lanai
Willie’s Place w/Golf Cart, Hot Tub & Dog Friendly
Free Golf Cart and Bikes ! With Rental !
The Villages, Citrus Grove home away from home
Villages Home w/ Pool and Golf Cart
Uniquely decorated home with private backyard
When is the best time to visit Wildwood?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $224 SGD | $256 SGD | $249 SGD | $166 SGD | $147 SGD | $138 SGD | $130 SGD | $128 SGD | $130 SGD | $146 SGD | $167 SGD | $184 SGD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°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 $38 SGD 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!
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