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Vacation rentals in Wildwood

Find and book unique accommodations on Airbnb

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 well-maintained exterior of a single-story home is presented, featuring a light yellow facade and a welcoming front porch. Lush greenery and palm trees are positioned along the pathway, with a manicured lawn and trimmed shrubbery enhancing the curb appeal.

Home in The Villages

4.96 out of 5 average rating, 134 reviews

2/2 custom pool home with 4 person gas golf cart

Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

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, 320 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.

Top guest favorite

The exterior of the home showcases a welcoming facade with a screened porch and lighted entry. A driveway leads to the front, bordered by lush greenery and decorative stones. The sky is painted in warm hues during sunset, enhancing the inviting atmosphere.

Villa in The Villages

5 out of 5 average rating, 12 reviews

Seaside Charm in The Villages

Welcome to your beach-inspired retreat in The Villages! This newly renovated home features calming blue decor in a central location. Just 10 minutes to Lake Sumter Landing, 13 minutes to Brownwood, and 19 minutes to Spanish Springs, enjoy easy access to dining, shopping, and entertainment. Dive into nearby pools, explore over 50 golf courses, and soak up the Florida sun. This home is your ideal getaway for relaxation and fun! Book your stay today & experience all that The Villages has to offer!

Top guest favorite

A single-story home features a simple façade with a covered entryway and a spacious driveway. Lush green grass borders the driveway, complemented by small landscaping elements. The neighborhood displays well-maintained properties on either side, under a clear blue sky.

Home in The Villages

4.96 out of 5 average rating, 53 reviews

The Sunshine Retreat with Golf Car

Come and enjoy this beautiful 2 Bed/2 Bath Patio Villa Home. We have made it very relaxing and welcoming for your stay. You will enjoy just a 3 minute golf car ride to Sawgrass, 15 minute golf car ride to new Eastport and a 20 min ride to Brownwood. It’s only a 5 minute walk to the pool and Aviary rec center is about a 5 minute golf car ride away. Golf Car included with home. Renter assumes all liability and will be responsible for any damage or injury caused by the use of the golf car.

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

4.99 out of 5 average rating, 81 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.

A red golf cart is parked on a concrete driveway in front of a light-colored villa. The cart features a canopy with a patterned design and spacious seating for passengers. The attached garage is visible in the background, along with some landscaping.

Home in The Villages

5 out of 5 average rating, 13 reviews

Courtyard Villa in The Villages

Beautiful 2 bedroom, 2 bath Courtyard Villa in the heart of The Villages, FL. Home is fully furnished with a king size bed in primary bedroom, queen in the second, and 3 TV’s. The yard features lanai with extended birdcage and is fully fenced in for pets. Golf cart also available for use. Numerous golf courses, rec centers, and both family pool and senior pools close by. 10 minutes to both Lake Sumter Landing and Brownwood Town Centers with lots of shopping and nightly entertainment.

Top guest favorite

A single-story vacation home is presented with a light exterior and a neatly maintained front yard. A white picket fence encloses colorful landscaping, while a spacious driveway leads to a two-car garage. Clear skies enhance the inviting curb appeal of the property.

Home in Wildwood

5 out of 5 average rating, 23 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 future 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! We are also within 12 minute drive to the Villages High school/ Middleton and 18 minutes to Leesburg

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 out of 5 average rating, 31 reviews

Pirates & Parrots - The Villages - w/Golf Car !

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

A friendly sheep stands next to a large planter pot within a landscaped area. Surrounding greenery provides a natural backdrop. The sheep's white coat contrasts softly with the earthy tones of the ground and pot, highlighting the homestead atmosphere.

Cottage in Coleman

4.96 out of 5 average rating, 162 reviews

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

Top guest favorite

The exterior of the home displays a well-manicured front yard with decorative plants and a white picket fence. A paved driveway leads to a two-car garage featuring a symmetrical design, accompanied by a clear blue sky above.

Home in The Villages

4.95 out of 5 average rating, 84 reviews

Golf Cart, King Bed, Small Dogs, and 52+ Pools!

Your NEW home includes a very comfortable KING BED, complimentary GOLF CART, and golf clubs. 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!!

The A-frame cabin features a striking black exterior with large windows that reflect the surrounding greenery. A spacious wooden deck is highlighted, equipped with a picnic table. Lush trees frame the cabin, creating a serene and inviting outdoor setting.

4.96 out of 5 average rating, 205 reviews

Cozy A-Frame Retreat w/ hot tub!

Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!

Top guest favorite

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

4.96 out of 5 average rating, 135 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.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Wildwood vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Wildwood

A private in-ground pool is enclosed by a screen patio, featuring a textured stone deck. Comfortable lounge chairs line the poolside, with a railing leading into the water. Lush greenery surrounds the area, offering a sense of tranquility and seclusion.

Home in The Villages

4.96 out of 5 average rating, 45 reviews

Beautifully Furnished 3/2 with In-ground Pool

Top guest favorite

The exterior of a single-story villa is highlighted, featuring a yellow facade with a two-car driveway and a well-maintained landscape. Lush green shrubs and palm trees are observed, alongside colorful planters that add vibrancy to the entrance.

Home in The Villages

4.93 out of 5 average rating, 81 reviews

Villa la Bella

Home in Sumterville

5 out of 5 average rating, 3 reviews

Spacious 3BR in The Villages | King Bed, Golf Cart

Top guest favorite

A heated pool is featured with a smooth, curvaceous shape and clear water reflecting surrounding shadows. Access is provided by steps leading into the water. The pool area is enclosed by a screen, allowing views of the lush green yard and nearby homes.

Home in The Villages

5 out of 5 average rating, 41 reviews

Pool Home Great Location 3/2 & 2 Golf Carts

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 out of 5 average rating, 18 reviews

Bay Breeze Villa

Top guest favorite

Home in The Villages

4.95 out of 5 average rating, 19 reviews

The Sandpiper Villa

Top guest favorite

A screened-in patio area showcases two hanging chairs with cozy cushioning, accompanied by a low coffee table. A lush green artificial lawn enhances the space, while a ceiling fan provides airflow. Beyond the screens, outdoor seating is visible under a shaded canopy.

Home in The Villages

5 out of 5 average rating, 24 reviews

Private Villa + Golf Car by Lake Sumter Square

Top guest favorite

A comfortable living area features a white sofa, two brown armchairs, and a round coffee table atop a patterned rug. Wall-mounted shelves are filled with plants and decorative items, while light streams through a nearby window, illuminating the neutral-toned walls and ceiling.

Home in The Villages

5 out of 5 average rating, 48 reviews

Beautiful cottage w/ ample indoor & outdoor space

Quick stats about vacation rentals in Wildwood

Total rentals
990 properties
Total number of reviews
15K reviews
Family-friendly rentals
880 properties are a good fit for families
Pet-friendly rentals
390 properties allow pets
Rentals with a pool
390 properties have a pool
Rentals with dedicated workspaces
580 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Wildwood?
Yes! Work meets play with ease at over 580 vacation rentals in Wildwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Wildwood?
Four-legged friends are welcome in Wildwood. Choose from more than 390 vacation rentals for guests traveling with pets.
Are there Wildwood vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 390 vacation homes with pools in Wildwood, available on Airbnb. Make a splash and soak up the sun in style!
Do villa rentals in Wildwood have a bbq area?
Absolutely! We offer over 30 villa rentals with a bbq area in Wildwood. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Wildwood have a gym?
Absolutely! We offer over 10 villa rentals with a gym in Wildwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Wildwood have air conditioning?
Absolutely! We offer over 840 house rentals with air conditioning in Wildwood. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in villa rentals in Wildwood?
Experience the best of Wildwood with our villa rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Wildwood have wifi?
Absolutely! We offer over 830 house rentals with wifi in Wildwood. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly villa rentals in Wildwood?
Wildwood has more than 100 family-friendly villa rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Villa Rentals in Wildwood?
Enhance your stay in our Villa Rentals with the most popular amenities: over 100 homes with air conditioning, over 100 homes with wifi, over 30 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

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