Villa vacation rentals in Winter Garden

A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.

4.86 out of 5 average rating, 198 reviews

Near Disney Gated LakeView Pvt Heated Pool

LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

4.99 out of 5 average rating, 137 reviews

A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.

Villa in Osceola County

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

A private pool is surrounded by a screened enclosure, reflecting the bright blue sky. Two lounge chairs are positioned near the pool, with light-colored walls and large glass doors providing views of the backyard. A clock is mounted on the wall, indicating the time.

4.91 out of 5 average rating, 111 reviews

Lakeside Villa, Sunny Pool Deck, 10Min From Disney

At this peaceful and centrally-located place you will wake up with a lake view, a private pool, and beautiful spacious clean space. You will be in a gated community complete with community pool and playground. This home facing south so you can sun bathing all day. You'll be minutes away from majors theme parks. Such as; Walt Disney World, Universal Studios/Islands of Adventure, Sea World, Legoland/Cypress Gardens, Discovery Cove, Cape Canaveral, and more. This can be you home away from home.

4.93 out of 5 average rating, 99 reviews

Villa in Clermont

Cute N Cozy Villa near Disney, pool, Wi-Fi

Welcome to our Cute N Cozy villa, located in the beautiful Vacation Village community in Clermont, FL! This clean and beautifully updated 2 bed/2 bath, family friendly villa sleeps 6 and has all you need for an enjoyable getaway. Community amenities include an Olympic size heated pool, tennis/pickle ball courts, basketball, shuffle board, playgrounds, and lake access to Lake Louisa. Located approximately 25 minutes to Walt Disney World and conveniently located to other major theme parks.

A private pool deck is enclosed with mesh, providing a clear view of the surrounding greenery. Two comfortable loungers are arranged beside the inviting swimming pool, adorned with orange striped towels. The peaceful outdoor space is well-lit by natural sunlight.

4.87 out of 5 average rating, 126 reviews

Sunny Family Retreat ~ Peaceful Pool ~ Game Room

Unwind in this sunny 4 Bedroom 3 Bath house nestled in a serene family-friendly neighborhood. This prime location allows quick access to nearby restaurants and shops while being just a short drive away from Disney World, Universal, Legoland, and more. The lively pool deck and entertaining game room offer various relaxing and fun amenities. ✔ 4 Comfortable Bedrooms ✔ 3 Large Bathrooms ✔ Fully Equipped Kitchen ✔ Swimming Pool ✔ Game Room ✔ Six TVs w/ Roku ✔ Sun Loungers Learn more below!

A screened-in patio area features a private pool surrounded by comfortable lounge chairs. The inviting water reflects the colors of the sunset sky, and a small dining table is visible nearby. The home is designed for relaxation and outdoor enjoyment.

4.9 out of 5 average rating, 190 reviews

Beautiful 4 Bedroom Pool Villa Near Disney World

This sunny single story home has 4 beautiful bedrooms (2 master suites) and 3 full bathrooms with its own private screened pool. It is an ideal accommodation for 2 families to share, or one large family. This villa is located in the gated community, a small peaceful community set away from any main road traffic. The home is situated approximately 15 minutes from the Walt Disney World, and is conveniently located from all major Orlando attractions, nearby restaurants and shopping.

A private pool area is enclosed by a protective screen, showcasing clear turquoise water. Lush palm trees are visible in the background, providing a tropical ambiance, while the surrounding patio features lounge chairs for relaxation. A spacious outdoor environment invites leisure and enjoyment.

4.78 out of 5 average rating, 240 reviews

Feel the Magic: 9 min Disney • Pool • Pet • Relax

✨ Looking for comfort, privacy, and fun near Disney? Our pet-friendly home is ready to welcome your family — including your furry friend — for amazing days under the Florida sun. Magic Kings House invites you to create magical moments with your loved ones, offering comfort and exclusivity at Windsor Palms, the resort most loved by guests. Every detail has been carefully prepared to make your vacation easy, relaxing, and filled with wonderful memories. 🌴🐶☀️

A private pool area is surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.

4.91 out of 5 average rating, 252 reviews

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

A private screened patio features a heated swimming pool and a Jacuzzi surrounded by a spacious deck. Outdoor seating is provided, with a dining table and lounge chairs positioned for relaxation. Sunlight glimmers on the water, creating a serene atmosphere.

4.92 out of 5 average rating, 126 reviews

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi

Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

4.98 out of 5 average rating, 114 reviews

Vacation home near Disney w/ private pool

Welcome to a warm and welcoming Kissimmee villa designed for relaxed group stays and easy access to top attractions, with plenty to enjoy right at home: - Sleeps 14 | 5 bedrooms | 8 beds | 5 baths - Private pool & hot tub with patio seating - Harry Potter-themed game room w/ arcade & foosball - Fully equipped kitchen & open living area - Fast Wi-Fi, TVs & in-unit washer/dryer - Storey Lake resort access w/ pools, lazy river & gym

A private swimming pool is enclosed by a screened lanai, providing a clear view of the serene lake beyond. Two reclined loungers line the edge, positioned for relaxation under the sun. A spa area is visible next to the pool, enhancing the tranquil environment.

4.91 out of 5 average rating, 116 reviews

Hot tub, gameroom near Disney

I am chuffed to bits to host your family! The villa is a 15-minute drive to Disney and 25 to Universal. There are five golf clubs locally and plenty more things to do—why not check out one of Florida’s beaches or shop at Downtown Disney? There is so much to see in Orlando. If you choose to stay in, take advantage of the private swimming pool, spa, and spacious, family-friendly home with a fully equipped kitchen and game room.

4.99 out of 5 average rating, 103 reviews

Amazing Villa near DisneyWorld FREE heated-pool

Have fun with the whole family at this stylish place. Our home has everything you will need for you and your guest to have a great experience. This home is a short drive from Walt Disney World and Orlando Attractions!! Don’t wait book with us now and give you and your family the vacation you all deserve. We can’t wait to welcome you . BBQ ( free to use ) Heated pool (free) Dogs friendly! Extra fee $120 per stay

Popular amenities for Winter Garden villa rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Private villa rentals

Superhost

A private pool area is enclosed with a screen, featuring a clear blue pool surrounded by lounge chairs. A dining table is positioned nearby, with green landscaping visible in the background. The expansive sky above is bright and clear, enhancing the outdoor leisure space.

4.67 out of 5 average rating, 150 reviews

Villa w/ Pvt Pool & BBQ + Resort | 10 min Disney

The image showcases a private outdoor pool with a screened enclosure, surrounded by lush greenery. A cozy children's bedroom features themed bedding with characters from popular movies. A spacious master bedroom is highlighted with a view of the pool through large glass doors. An overhead shot reveals the entire property set within a landscaped community.

4.97 out of 5 average rating, 116 reviews

Private South Pool & Nature View | 10m to Disney

4.97 out of 5 average rating, 36 reviews

The outdoor pool area is framed by a screened enclosure, reflecting the warm lights above. The pool water shimmers softly, and a colorful beach ball rests on the surface. A glimpse of the inviting interior, including white furniture, is visible through the large windows.

Villa in Clermont

Luxury home | Lakeside Landing

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

4.94 out of 5 average rating, 100 reviews

Luxury Villa! /Game Room/ Pool Heater

5 out of 5 average rating, 31 reviews

WaterView 4 miles to Disney 3Br 2Ba Pool Home

The pool deck features a spacious swimming pool surrounded by a screened enclosure. Four sun loungers are positioned nearby, accompanied by a cantilevered umbrella for shade. The tranquil conservation area is visible in the background, providing a peaceful setting.

4.98 out of 5 average rating, 53 reviews

Beautiful 4 bedrooms with South/West facing pool

The open living area features high ceilings, large windows, and a cozy seating arrangement with a sofa and armchairs. Decorative wall art and plants enhance the design, while an elegant dining space and modern kitchen are visible in the background.

4.98 out of 5 average rating, 93 reviews

The Balmoral Manor: Luxurious & Bright 5BR Oasis

A private pool area is visible, featuring a clear blue pool surrounded by spacious lounge chairs. The pool deck is screened-in for comfort, with a dining area in the background under a ceiling fan, creating a serene setting for relaxation.

4.94 out of 5 average rating, 16 reviews

Disney Family Retreat w/screened-in patio & pool

Luxury villa rentals

A spacious themed room is depicted, featuring an imaginative design with a dark, cosmic ceiling. The room includes a large blue slide and a staircase, adjacent to cozy bean bag chairs for seating. Colorful space-themed murals enhance the playful atmosphere.

4.98 out of 5 average rating, 122 reviews

4mi to Disney | Games | Private Pool

A spacious dining area features a long glass table surrounded by white chairs, set for a large meal with blue and gold accents. A striking blue wall with geometric gold patterns creates a modern backdrop, while contemporary light fixtures illuminate the space.

4.94 out of 5 average rating, 116 reviews

Blue Paradise 15BR 11BA, Sleeps 36, Theater/GameRm

A vibrant themed room showcases a blue slide and bunk beds, enhancing playfulness. Adjacent, a cozy bedroom features rich curtains and themed decor. A home theater room displays a large projector screen and comfortable seating. The private pool area is highlighted with seating, a projector, and colorful inflatables.

4.98 out of 5 average rating, 125 reviews

Poolside Movies | 3Min.Walk to Waterpark| Game Roo

An interactive stage area is presented, featuring musical instruments including an electronic drum set and keyboard. A large mural of a guitar and palm trees creates a vibrant backdrop. The space is equipped with seating and surrounded by a lush green carpet.

4.97 out of 5 average rating, 116 reviews

Luxury Villa/15min2parks/Lakeview/Vgames/Theater

4.97 out of 5 average rating, 112 reviews

A private pool is framed by a stone patio, with lounge chairs positioned nearby for relaxation. Lush greenery and palm trees surround the area, creating a serene outdoor environment. A spa is positioned next to the pool, providing an inviting space for relaxation.

Villa in Four Corners

The Golden Bear Villa | Private Pool & Theater

A game room features striking themed decor, with large flat-screen TVs and seating. The private pool area showcases a serene swimming pool surrounded by a screen enclosure, highlighted by comfortable lounge furniture. A cozy outdoor seating area is visible, offering a relaxing view.

4.95 out of 5 average rating, 171 reviews

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

A Star Wars-themed game room is featured, complete with multiple screens displaying iconic scenes. An air hockey table and foosball setup are visible, alongside gaming chairs arranged for comfortable seating. The room is brightly lit, emphasizing the vibrant decor that adds to the entertainment atmosphere.

4.96 out of 5 average rating, 188 reviews

Sleeps 24✦Free Pool Heat✦15 min to Disney✦Hot Tub

4.92 out of 5 average rating, 127 reviews

Storey Lake•9BR•Fire Pit•Pool•Hot Tub•Game•EV

Villa rentals with a pool

The private pool area is enclosed with a screen for safety and features a resort-style pool with an adjacent spa. Sun loungers are positioned nearby, surrounded by tall shrubs for added privacy while enjoying outdoor relaxation.

4.85 out of 5 average rating, 59 reviews

Magical✨️4b/3b Private Pool/Game Room Disney Area

The exterior of a Mediterranean-style villa is shown, featuring a spacious front yard with landscaped greenery. A brick driveway leads to a two-car garage. Golf course views are visible in the background, highlighting the peaceful surroundings of the property.

4.94 out of 5 average rating, 68 reviews

Executive Disney Home on Highlands Reserve

4.9 out of 5 average rating, 72 reviews

4 Miles to Disney - Pretty In Pink

A private theater is presented with six reclining seats, arranged in rows facing a large 155-inch screen. The room is accented by dark walls and illuminated with blue lighting, enhancing the cinematic atmosphere. Movie posters adorn the walls, contributing to the entertainment theme.

4.95 out of 5 average rating, 55 reviews

Disney Fun Time 8BD 4K Movie Theater Jacuzzi Pool

A single-story residence features a neat brick driveway leading to a two-car garage. Lush green landscaping includes palm trees and colorful plants, enhancing the curb appeal. The front porch is inviting, with symmetrical windows framing the entrance under a gently sloped roof.

4.93 out of 5 average rating, 74 reviews

Luxury 4 Bedrooms, 3.5 Bathrooms with pool.

4.81 out of 5 average rating, 27 reviews

Luxury Townhouse Near Disney | 3BR

4.87 out of 5 average rating, 85 reviews

A fenced pool area features a crystal-clear heated pool surrounded by a screened enclosure. Several loungers are positioned around the pool, with lush greenery visible in the background and a bright blue sky enhancing the outdoor space.

Villa in Clermont

Beautiful 3bed 2bath house with pool near Disney

A private pool and hot tub are surrounded by a screened enclosure, showcasing crystal-clear water. Comfortable lounge chairs are positioned along the edge of the pool deck, with large glass doors offering views of the adjoining living spaces. The sky displays soft colors of twilight.