Wildwood vacation rentals

4.96 out of 5 average rating, 311 reviews

A sparkling blue pool is the focal point of the outdoor area, surrounded by a spacious patio. A wooden pergola offers shaded seating alongside lush greenery and a koi pond, creating a serene environment. Black patio chairs are visible near the pool's edge.

Home in Lady Lake

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.

5 out of 5 average rating, 14 reviews

Entire Home with an Office in Fenney

My home is furnished for the ultimate in guest comfort and working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, printer, TV Furnishings are modern & luxurious, making you feel right at home. Fast Internet & YouTube TV Fully stocked kitchen Coffee & tea is complimentary Filtered home water system Please NON-smokers ONLY welcome NO pets Not suited for children Fees reduced for 28+ days, ask for details

A well-organized office space features a large white wardrobe while two additional white cabinets are positioned against the walls. A comfortable desk with a computer setup is present, accompanied by a black ergonomic chair. Soft, neutral carpet covers the floor, and natural light filters through the window.

4.96 out of 5 average rating, 23 reviews

Perfect Home in The Villages!

This delightful two-bedroom, two-bathroom home is the perfect place to enjoy all the beauty and amenities that this vibrant 55+ community has to offer. Nestled in the esteemed Village of DeLuna, you'll enjoy the perfect balance of tranquility and convenience. The open-concept design connects the living, dining, and kitchen areas, providing an ideal setting for entertaining or simply enjoying the spaciousness of your home. Minutes from Brownwood Square and activities at Everglades Rec Center.

Aerial view of a recreational area surrounded by lush greenery, featuring a centrally located pool area with lounge chairs. Pathways meander through the landscape, leading to a natural pond. Several buildings with sloped roofs are positioned around the pool, enhancing the scenic environment.

4.95 out of 5 average rating, 20 reviews

Cheerful King Bed Home in the Villages

Welcome to your perfect getaway in The Villages! This charming 2-bedroom, 2-bathroom home is ideally located for you to enjoy all the best amenities the area has to offer. Fenney Pitch and Putt is nearby, offering a fun and relaxing experience. The Sugar Cane Recreation Center, with its beautiful walking trail & adult pool is perfect for leisurely days under the sun. Also nearby is the popular Fenney Grill, with a resort style family pool, you can enjoy delicious meals and refreshing drinks.

5 out of 5 average rating, 16 reviews

An outdoor seating area features a round table set with glasses, alongside a bottle of red wine. Light turquoise chairs create a relaxed atmosphere, complemented by a wall art piece depicting a serene beach scene. Clear blue skies and green foliage are visible in the background.

Home in Wildwood

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!

4.97 out of 5 average rating, 151 reviews

Cottage in Coleman

Peaceful Cottage Mini Farm/Garden Near Villages

Perfect Getaway! Enjoy our clean, peaceful, chic tiny farmhouse located on our 1.5 acre homestead. This is the perfect location as we are 5 minutes from I75 and Florida Turnpike. We are 10 minutes from LIVE Music, Restaurants and more in the Brownwood Town Square. We offer free parking for 2 vehicles and welcome well behaved dogs. (Please let me know if you are bringing your furry friend) Looking forward to hosting you! 1 h. from Orlando/Disney & Tampa/Busch Gardens 25 m. Leesburg Hospital

A single-story home is positioned on a well-manicured lawn, with vibrant landscaping and a concrete driveway. The porch is highlighted by a welcoming blue door and outdoor seating. Soft lighting from the lamp illuminates the entry. A colorful sunset fills the sky in the background.

5 out of 5 average rating, 11 reviews

The Villages, Citrus Grove home away from home

Create great memories at this centrally-located home, with an open floor plan with vaulted ceilings. The kitchen is well equipped and the living room has a queen size sleeper sofa and a smart TV (internet/WIFI). The master bedroom has a king size bed, walk in closet, smart TV, master bathroom and a work area with a desk and printer. The guest bedroom has a queen size bed, large closet and smart TV. Both bedrooms have black out curtains and hair dryers, and linens. Grill/2 bikes incl.

A screened-in patio is visible, featuring a single wooden chair positioned against the wall. The view includes a green lawn beyond the patio, with nearby houses framed by the screen. The area is well-lit with natural light filtered through the screen enclosure.

4.85 out of 5 average rating, 47 reviews

Beautiful home in the heart of The Villages.

Located in the village of Buttonwood, this cozy, fully furnished home is about 5 mins away from Lake Sumter Landing,which is perfect for great food and happy hour. This home is spacious, sunny, and comes full equipped with a TV with cable, Wi-Fi, and a golf cart. The master bedroom has a private bathroom walk in closet, as well as a king -sized bed. Washer & dryer included! The house boasts tall ceilings, and a large furnished patio, perfect for lounging and grilling. Includes a BBQ grill!

A golf cart is parked on a concrete driveway in front of a single-story home. The home's exterior is light-colored with a front porch and surrounded by neatly maintained landscaping. A clear blue sky provides a bright backdrop.

5 out of 5 average rating, 54 reviews

Enjoy The Villages and relax in our cozy home!

Enjoy your stay in our home while experiencing The Villages Lifestyle! The Villages is an active 55+ community where you can enjoy doing as much or as little as you desire. Spanning over 32sq miles, you can enjoy golf (we have over 50 courses), swimming, pickleball and many other activities. There is shopping, dining, and Live Entertainment 365 days a year at 3 different town squares + Sawgrass Market. Explore all that the Villages has to offer while using our complimentary golf cart.

A gray golf cart is parked on a paved surface, featuring two tan seats and a canopy overhead for shade. Surrounding the cart, well-maintained greenery and flowering plants are visible, enhancing the overall appeal of the outdoor area. The sky is bright and partly cloudy.

5 out of 5 average rating, 13 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.

4.94 out of 5 average rating, 71 reviews

Golf Cart, King Bed, Small Dogs, and Water System!

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!!

4.99 out of 5 average rating, 116 reviews

VIEW-T-FUL! w/Golf cart

Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

Vacation rentals for every style

Get the amount of space that is right for you

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Cottages

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Popular amenities for Wildwood vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Wildwood

4.94 out of 5 average rating, 118 reviews

Townhouse in Kissimmee

Meriggiare! Perfect for Disney Vacation! FREE WiFi

A charming exterior features a decorative black mailbox mounted on a pole beside a pathway. The house's entrance is enhanced by a welcoming porch with seating and palm trees, while a neatly landscaped area showcases decorative stonework.

4.82 out of 5 average rating, 17 reviews

Location, Location! Hot Tub!

4.94 out of 5 average rating, 189 reviews

A dining area features several wooden tables and comfortable black chairs. Set for breakfast, the tables display white dishware and glassware. A bar area with stools is visible in the background, along with shelves containing various beverages.

Townhouse in Kissimmee

Beautiful family home near all attractions.

5 out of 5 average rating, 7 reviews

A spacious screened-in pool area is showcased, featuring a crystal clear pool surrounded by paved flooring. Comfortable lounge chairs are positioned near the water’s edge, with views of the private beach and dock beyond, framed by lush greenery and bright blue skies.

Home in Ocklawaha

As good as it gets! Lakefront - with a pool!

4.95 out of 5 average rating, 21 reviews

An outdoor dining area is visible under a covered patio, featuring a spacious table with chairs. A private pool is showcased nearby, surrounded by a screened enclosure. Sunlight filters through the area, illuminating the pool and outdoor seating.

Home in Ocala

Family Vacation house with Pool

5 out of 5 average rating, 21 reviews

A stone patio features a fire pit surrounded by seating areas. Adjoining the space is a gazebo overlooking the water, set against a backdrop of greenery. The area is designed for relaxation and socializing, with a clear view of the landscape beyond.

Home in Crescent City

Lake Cabin! Private Dock, Tennis Court & Pool

4.81 out of 5 average rating, 70 reviews

The entrance features a dark green front door with a paneled design, complemented by a small window above it. The door is framed by light green walls, and a neatly maintained shrub is positioned on either side of the doorway.

Townhouse in Kissimmee

Entire Townhouse -Kissimmee, 4 Bedrooms 3 Bath