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Holiday rentals with a pool in Osceola County

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Top-rated rentals with a pool in Osceola County

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.
Apartment in Kissimmee
4.97 out of 5 average rating, 196 reviews

303_To Infinity & the Ocean Breeze Apartment

Welcome to your ultimate family getaway near Disney! This spacious 3-bedroom apartment is perfectly located just minutes from the magic of Disney. Designed with families in mind, it features two beautifully themed kids’ bedrooms—a Toy Story adventure and a Moana-inspired tropical escape—guaranteed to delight the little ones. Enjoy full access to an amazing waterpark, included free of charge, making every day feel like a vacation. Whether you're unwinding after a day at the parks or splashing th

Top guest favourite
A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.
Home in Kissimmee
4.98 out of 5 average rating, 105 reviews

Mickey's Lakefront Villa at Sunset Lakes

Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

Top guest favourite
The exterior of the barn showcases a rustic wooden facade beneath a metal roof. A porch with seating options invites relaxation, while the neatly maintained yard features green grass and landscaping. A driveway leads to a side garage, enhancing the property's charm and accessibility.
Barn in St. Cloud
4.97 out of 5 average rating, 164 reviews

Rustic Barn Retreat

Experience the rustic elegance of this beautifully remodeled 1,800 sq. ft. barn nestled on a serene 17-acre property. Unwind in the private heated hot tub and soak up the peaceful surroundings. The prime location offers convenient access to major attractions—just a 35-45 min drive west will take you to Disney, Universal, SeaWorld, and gator parks, while a 45-60 min drive east leads you to the breathtaking Atlantic beaches and the Space Coast. Plus, the property is only 40 min from the airport

Guest favourite
Two lounge chairs are positioned beside a heated pool, overlooking a serene lake. A pink flamingo pool float rests nearby. The outdoor area includes a large umbrella for shade, creating a peaceful space for relaxation.
Home in Kissimmee
4.89 out of 5 average rating, 101 reviews

Dreamy Waterside Villa | Heated Pool & Near Disney

Experience a quiet waterfront villa, this stunning property offers breathtaking views, luxurious amenities, and prime location for your getaway. Relax by the pool enjoying the unwind lake view, With spacious interiors, modern furnishings, and impeccable attention to detail. Whether you're seeking relaxation or adventure, is your perfect vacation home. Book your stay at our stunning home and create unforgettable memories with your loved ones. NO PARTIES/NO SMOKE $50 pet fee $35 pool heater fee

Top guest favourite
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
4.99 out of 5 average rating, 130 reviews

*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.

Top guest favourite
A living area features a modern television displaying a virtual fireplace, paired with elegant wall art and a decorative plant. Below, a pool area is illuminated with soft purple lighting against a backdrop of warm string lights, creating a relaxed atmosphere.
Home in Kissimmee
4.97 out of 5 average rating, 114 reviews

Perfect Getaway. Private Pool.Kissimmee/Orlando

This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Superhost
The Captain's Lounge features shiplap walls and vintage maritime decor, with luxurious crimson and gold velvet upholstery. An oversized treasure chest serves as a coffee table, while an entertainment center boasts a 65" HDTV. A vibrant view of the adjacent lake is available from the patio.
Home in Osceola County
4.9 out of 5 average rating, 125 reviews

Pirate & Princess: Themed/Disney/Resort

Wishes come true at The Pirate & Princess 5BR/6BA immersive vacation home, 6 miles from Disney. Seeking enchanted adventure? Sprinkle pixie dust, second star to the right, to… Reunion Resort! Gated golf resort; pools/dining/gym. Treasure Island, Peter Pan, Tinker Bell, Captain’s Lounge, Little Mermaid & Moana; Disney-inspired rooms, professionally designed! Private Pool/Spa/BBQ/Chef’s Kitchen/Office/Laundry/WiFi/In-Law Apt./Sunset Lake Views. Family-friendly gem to delight kids! Sleeps 15.

Guest favourite
An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.
Apartment in Osceola County
4.89 out of 5 average rating, 105 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Top guest favourite
A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.
Home in Kissimmee
4.95 out of 5 average rating, 127 reviews

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Amazing Brand New Modern Luxurious Home at Encore Resort @ Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much Much More Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

Top guest favourite
An outdoor view shows a private pool, where a person is enjoying the water with a serene water view beyond. Inside, an illusion room presents colorful decorations and a lively atmosphere. A cozy bedroom showcases a spacious bed adorned with soft linens. A game room is visible, featuring engaging entertainment options.
Home in Kissimmee
4.99 out of 5 average rating, 138 reviews

[20% OFF] Illusion Home •Waterfront Private Pool

❤ Illusion room with character outfits ❤ Private pool with water view ❤ 15 min to Disney ❤ 25 min to Universal, SeaWorld, Convention Center, 2 min to Walmart ❤ Game room with board games & kids toys ❤ 100" movie theater screen ❤ Free Netflix ❤ Fully equipped kitchen ❤ Sleeps 12 ppl ❤ 2 king beds, 2 cribs, 1 Queen memory foam sofa bed, 6 twins ❤ Newly renovated home ❤ Fully stocked home ❤ Alice in Wonderland®-themed home ‼️ No parties, No smoking, 4 dogs max $75/pet

Top guest favourite
A screened patio area features a sparkling saltwater pool with a gentle waterfall. Comfortable loungers and dining furniture are arranged around the pool, providing ample space for relaxation. Lush plants add natural touches, while the surrounding view includes nearby homes and green lawn areas.
Home in Kissimmee
4.95 out of 5 average rating, 104 reviews

Home w/ Heated Pool, Near Disney & Universal

Relax in this peaceful lakeview home just 15–20 minutes from the Orlando International Airport and top attractions like Disney, Universal, and SeaWorld. Perfect for families, this fully equipped 3-bedroom home features a private heated pool, outdoor living space, full kitchen, washer/dryer, and more. Enjoy nearby shopping centers, outlet malls, and a variety of restaurants. No smoking or parties allowed—just comfort, convenience, and fun for the whole family.

Guest favourite
The exterior of a two-story yellow cottage is shown, featuring large windows and a fenced private pool. Sunlight reflects off the water, and lush greenery surrounds the pool area, enhancing the inviting atmosphere. Balconies are visible on the upper level, overlooking the pool.
Home in Kissimmee
4.96 out of 5 average rating, 227 reviews

"Vista Lago"Hotel Amenities/lake view,private pool

HOTEL AMENITIES , Reach out to the host if you find similar cottage for cheaper prices for possible price match ( not guaranteed) WHY THIS SPECIFIC COTTAGE IN MARGARITAVILLE ??? ( In the next description we will clarify the difference between this cottage which is rented as a 3 Bedroom Elite Cottage and other different cottages in Margaritaville so you have a clear view to choose the best cottage that fits your needs : ↓ ↓

Popular amenities for Osceola County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
A serene backyard pool area is enclosed by a screened lanai, featuring two lounge chairs adorned with vibrant blue and green cushions. Lush greenery and trees are visible beyond the pool, enhancing the peaceful view. The clear water reflects the cloud-dotted sky.
Home in Kissimmee
4.96 out of 5 average rating, 171 reviews

4 bedroom, south facing pool 3 miles to Disney

Guest favourite
An inviting pool area is framed by a screened enclosure, revealing beautiful water views at sunset. Soft lighting enhances the relaxing atmosphere, with lounge seating positioned nearby for comfort. The tranquil setting is ideal for unwinding and enjoying outdoor moments by the pool.
Home in Kissimmee
4.96 out of 5 average rating, 324 reviews

Game Room/HeatedPool/Piano Upscale Waterfront Home

Superhost
A screened-in patio features a private swimming pool and hot tub, surrounded by a tranquil lake view. String lights create a soft illumination against a colorful sunset sky, enhancing the peaceful outdoor setting.
Home in Kissimmee
4.88 out of 5 average rating, 148 reviews

10 min Disney | Lakeview Hot Tub, BBQ | Game Room

Top guest favourite
The recreation area is designed with vibrant blue lighting and themed decor. It features a pool table, arcade games, and a commercial air hockey table. The walls are adorned with popular character themes, including Super Mario and Avengers, creating an engaging and playful atmosphere.
Home in Kissimmee
4.98 out of 5 average rating, 98 reviews

Dream Vacation w/Avengers, Star Wars, & Mario Kart

Superhost
A cozy living area is highlighted by a decorative wall, a TV mounted above a light-colored cabinet, and a plush seating arrangement. A fire pit with glowing embers is visible, providing a warm ambiance. A game table with two chairs and a pool table is present, alongside a screened pool area showcasing a sunset view.
Home in Kissimmee
4.88 out of 5 average rating, 206 reviews

Waterfront retreat,KING Bed,Heated Pool & Fire Pit

Top guest favourite
A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.
Home in Kissimmee
4.99 out of 5 average rating, 147 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

Top guest favourite
The image features a collage of vibrant themed bedrooms and a modern kitchen area. One room showcases a playful bunk bed against a backdrop reminiscent of a train station, while another has colorful Disney-themed décor. A spacious living area boasts light-colored furniture and a contemporary kitchen with stainless steel appliances.
Home in Kissimmee
4.97 out of 5 average rating, 107 reviews

3BD/3BA Themed House Near Disney

Guest favourite
The exterior of the home features a fresh white brick façade with contrasting dark shutters on the windows. A circular driveway is lined with vibrant landscaping, including flowering plants and greenery. The property is well maintained, with a clear view of the entrance and a sunny blue sky overhead.
Home in Haines City
4.9 out of 5 average rating, 134 reviews

Villa Blanca

Apartment rentals with a pool

Top guest favourite
A picturesque view of the resort-style pool area is presented, featuring several palm trees and lounge chairs around the sparkling water. Colorful slides and a splash park are visible, with pathways leading to different activities amidst landscaped greenery.
Apartment in Kissimmee
4.91 out of 5 average rating, 173 reviews

P-Gated Resort-5 miles to Disney-2 FREE Water Park

Top guest favourite
A cozy bedroom showcases a spacious bed adorned with decorative pillows. On either side, wooden nightstands hold table lamps. Above the bed, a shelf displays framed artwork and a plant, adding a touch of greenery to the neutral wall.
Apartment in Kissimmee
4.99 out of 5 average rating, 194 reviews

Bright, Airy Home near Disney and Attractions

Top guest favourite
A view from the balcony showcases a large, inviting pool surrounded by palm trees and lounge chairs. The pool area is highlighted by decorative landscaping and is set against a backdrop of a multi-story building, reflecting the vibrant atmosphere of the resort.
Apartment in Kissimmee
4.94 out of 5 average rating, 160 reviews

A1 POOL VIEW-By Disney/Universal/Balcony view

Superhost
A spacious bedroom is adorned with a blue accent wall featuring a starry pattern. A large, plush bed covered in a soft blue throw and white linens is centrally placed. A framed picture is mounted above the bed, and a small plant adds a touch of greenery.
Apartment in Kissimmee
4.9 out of 5 average rating, 245 reviews

Disney Oasis by the lake

Guest favourite
A cozy sleeping area features a spacious bed dressed in crisp linens, accompanied by two bedside tables topped with lamps. A wall-mounted television offers access to various streaming services. Light-colored walls and a vibrant orange accent wall enhance the inviting atmosphere.
Apartment in Kissimmee
4.77 out of 5 average rating, 270 reviews

King Bed Small Studio Disney World Universal

Top guest favourite
A patio area is presented under a covered porch, featuring a round table set for two with a white tablecloth and colorful cups. Two comfortable chairs with blue cushions are positioned around the table. A scenic view of a lake with greenery can be seen in the background.
Apartment in Kissimmee
4.83 out of 5 average rating, 141 reviews

Stunning view, near Disney.

Top guest favourite
A refreshing swimming pool features a large water slide in vibrant green and blue. Palm trees provide shade around the area. Several lounge chairs are positioned beside the pool, inviting relaxation while enjoying the sunny landscape.
Apartment in Kissimmee
4.96 out of 5 average rating, 150 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

Top guest favourite
A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.
Apartment in Kissimmee
4.91 out of 5 average rating, 132 reviews

Modern Condo with Lake View Near Disney 3151

Home rentals with a private pool

The modern home exterior features a combination of light-colored walls and a stone facade. A landscaped front yard includes neatly trimmed grass and a palm tree. A paved walkway leads to a front entrance, and large windows provide ample natural light.
Home in Four Corners

630sst- the Retreat at Championsgate

A spacious living area is highlighted by a large wall-mounted TV above a modern electric fireplace. The white sectional sofa, accented with colorful pillows, faces a sleek coffee table on a patterned rug. Natural light floods in through large windows draped with light curtains.
Villa in Four Corners
4.14 out of 5 average rating, 7 reviews

Disney's Championsgate: Private Pool & Arcade Fun!

The exterior of the home features a two-story structure with a light beige facade and a tiled roof. Lush landscaping, including palm trees and shrubs, enhances the entrance, while a spacious driveway leads to a two-car garage.
Home in Davenport

Beautiful 9 Br Pool Home In the Solterra Resort!

Villa in Kissimmee
4.78 out of 5 average rating, 256 reviews

Visit Disney World from a Sunny Home with a Pool

A serene view from the patio showcases a private pool reflecting the colorful sky at sunset. The screened enclosure offers unobstructed sightlines to the lush greenery beyond, while the calm water enhances the tranquil atmosphere of the setting.
Home in Haines City

New! 209mcv - Balmoral Resort

Home in Four Corners

840dsd-The Retreat at Championsgate

Four themed bedrooms are displayed, featuring vibrant colors and unique decor. Two bedrooms contain spacious beds with playful beddings, while a game room is visible, showcasing air hockey and colorful wall art, adding to the immersive atmosphere for all guests.
Townhouse in Kissimmee

4323sl-Storey Lake Resort

A refreshing swimming pool is framed by neat paver stones, surrounded by manicured greenery and palm trees. A spa is attached to the pool, with two lounge chairs positioned for sunbathing under the expansive blue sky dotted with clouds.
Villa in Kissimmee

New! Brand New Encore Resort 5 Bed Resort Home

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