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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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Guest favourite
A shaded lounging area features comfortable seating and a glass-top table, set with refreshments. In the background, a large pool glistens under the sun, surrounded by palm trees and various seating options, including cabanas and sun loungers.
Townhouse in Kissimmee
4.84 out of 5 average rating, 214 reviews

Orlando Disney ºoº 3BD in Resort | Kissimmee

Modern Townhouse in Resort w/ preserve area and Amazing Clubhouse. (NO resort fees!) | 1 min | Old Town Kissimmee | 3 min | Publix®, McDonald's®, Wendy's®, Miller's Ale House® and more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | DISNEY® AREA (All Theme Parks) | 9 min | Premium Outlet® | 11 min | Disney Springs | 11 min | ESPN® Sports | 13 min | Convention Center | 15 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 70 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Top Guest favourite
The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.
Home in Kissimmee
4.87 out of 5 average rating, 263 reviews

3 bedroom Villa in Kissimmee

The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

Guest favourite
A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.
Condo in Kissimmee
4.86 out of 5 average rating, 133 reviews

Stylish Condo 20 mins to Disney/King Bed

Escape to our lovely vacation villa, nestled in the vibrant heart of Orlando's premier golfing destination. Just a 7-mile drive from Disney attractions and 30 minutes from Orlando International Airport. Discover the awe-inspiring Reunion Resort, offering an array of delights. Indulge in delectable dining experiences, take a dip in sparkling pools, savor refreshing drinks at poolside bars and grill. Embark on an extraordinary getaway that exceeds all expectations. Book your stay with us today!

Guest favourite
An open living area features a modern design with a spacious layout. A comfortable sofa with accent pillows and a coffee table is set in front of a large window. The adjacent kitchen is equipped with sleek cabinetry and modern appliances, complemented by a dining space visible in the background.
Apartment in Kissimmee
4.93 out of 5 average rating, 107 reviews

3180-207 Resort Pool View Disney Universal Orlando

Brand New Bohemian & Chic 2bedroom /2bath fully equipped apartment . Pool View for up to 6 guests. Located in the family friendly Storey Lake Resort minutes from Disney. The open floor plan blends kitchen, dining, living room with 70"TV & Relax Room. Master suite has a King bed & 65"TV. Second bedroom has a Queen & Twin bed w/ Smart TV. Close to outlet malls & retail stores. FREE Water Park & Amenities: POOLS, KIDS SPLASH ZONE, WATER SLIDES, LAZY RIVER, GYM, TIKI-BAR, ICE CREAM SHOP & More.

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, 138 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.

Guest favourite
A modern keypad lock is installed on a door, featuring illuminated numbers for easy access. Blurred in the background, a vibrant green plant adds a touch of nature to the entryway, enhancing the welcoming ambiance of the space.
Guest suite in Kissimmee
4.93 out of 5 average rating, 191 reviews

It's too much like a elegant mini-hotel (7)

It's too much like a elegant mini hotel with rich artistic atmosphere！ All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

Superhost
A screened-in pool area is illuminated by string lights, offering a serene view of the lake at sunrise. The inviting pool features floating noodles, and the surrounding space is bordered by greenery, enhancing the tranquil atmosphere.
Home in Kissimmee
4.85 out of 5 average rating, 216 reviews

Disney & Universal Retreat| Heated Pool | Fire Pit

Sit back and relax in this stylish home with all the amenities you need for a fun family getaway. This home has a spacious layout with 3 bedrooms and 2 baths. We have thought of everything so you don't have to-toiletries,washer/dryer, and wifi. Enjoy your morning coffee in the screened in pool area with a beautiful sunrise and lake view or sip a glass of wine while floating in the pool. Just minutes to Theme Parks and major highways, this is the dream home you have been waiting for!

Guest favourite
Townhouse in Kissimmee
4.87 out of 5 average rating, 371 reviews

Be Our Guest !

Whether you’re seeking a romantic getaway or a family vacation time, our house offers you the perfect blend of comfort, style, and fun. Book with us today and enjoy your stay. Centrally located, just a short drive from theme parks and attractions, only 4 miles from Disney Explore the local restaurants, where you can savor the flavors of multicultural food. Nearby shopping centers and malls, Wal-Mart, Publix, Aldi supermarkets. Dollar Tree convenience store across the street.

Guest favourite
A sleeping area is equipped with a spacious bed adorned with navy and white accents. Neutral wall colors complement decorative framed wall art. A bedside table and lamp are positioned beside the bed, with a welcoming pillow displayed prominently. The entry to a well-lit kitchen is visible in the background.
Cottage in Kissimmee
4.92 out of 5 average rating, 427 reviews

Bungalow cottage close to Disney Universal, for 4!

A full cottage for 4! The perfect place. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check our unit. We also have three other cottages on property, the Bitty Belle, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other

Guest favourite
A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.
Condo in Kissimmee
4.9 out of 5 average rating, 184 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Less than 1 mile from Walmart, Target, and restaurants, your family will have everything they need. Water Park, gym, and all amenities FREE. Free parking, 24/7 security in this gated resort and with an automatic check-in with direct access code and elevator available

Guest favourite
The open living area features a round dining table with four chairs, a wall-mounted TV, and a comfortable sofa. Natural light enters through sliding glass doors leading to a scenic outdoor view. A rustic wood accent wall adds texture to the space.
Condo in Four Corners
4.88 out of 5 average rating, 174 reviews

"Ocean's Gate" - 2BD/2BA condo near Disney

Welcome to our beautiful ground-level condo! With the prime location at ChampionsGate Resort near Disney World and major parks, this 2BD/2BA condo unit is designed for your best accommodation. Spread out in 1,558 Sq. Ft., the unit offers a fully equipped kitchen, a cozy living room, a working station, and comfortable bedrooms. With access to the Clubhouse and resort amenities, you’ll spend amazing days in our home!

Top Guest favourite
Home in Kissimmee
4.92 out of 5 average rating, 131 reviews

Entire Modern Home near Disney • Pool & Game Room

Make memories at our beautifully renovated home in Kissimmee — close to Disney, Universal, and everything Orlando has to offer. Relax in your private pool, enjoy 3 comfortable bedrooms and 2 full baths, and check in easily with keyless entry. Nestled in the safe, gated community of Cumbrian Lakes, it’s the perfect spot for families and friends to unwind together.

Popular amenities for Osceola County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top Guest favourite
A two-story home with a light brown exterior is set within a lush green landscape. A spacious driveway leads to a white garage with a large door. The property is enclosed by a white privacy fence, creating a secluded outdoor environment.
Home in Kissimmee
4.93 out of 5 average rating, 171 reviews

South Facing Pool Home! 5 Miles from Disney

Top Guest favourite
The spacious living area features a light-filled environment with comfortable seating arrangements, including a sofa and armchair. A coffee table sits in the center, accompanied by a decorative bowl of sunflowers. A large television is positioned against a wall, complemented by neutral-toned decor.
Home in Kissimmee
4.9 out of 5 average rating, 107 reviews

4BD 2BA Kissimmee Pool House near Disney

Top Guest favourite
A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.
Home in Kissimmee
4.95 out of 5 average rating, 88 reviews

Paradise Suite

Top Guest favourite
An enclosed in-ground swimming pool is featured, surrounded by a screened lanai. Various lounge chairs and umbrellas provide seating options. The pool is clear and inviting, with a decking area that offers space for relaxation.
Home in Kissimmee
4.92 out of 5 average rating, 159 reviews

Disney New Neighbor

Top Guest favourite
A cozy hanging egg chair provides a relaxing spot next to the heated saltwater pool. A blue lounge chair and a shaded umbrella offer additional seating options. Lush greenery adds a refreshing touch to the outdoor area.
Home in Kissimmee
4.97 out of 5 average rating, 98 reviews

Modern Villa with Saltwater Pool & Themed Rooms

Top Guest favourite
A sunny pool deck features a private pool surrounded by a screened enclosure. Four chaise lounge chairs are positioned near the pool, alongside a covered area with a table and chairs for outdoor dining.
Home in Kissimmee
4.96 out of 5 average rating, 162 reviews

Large House | Near Disney | Private Pool | 6 beds

Top Guest favourite
An outdoor area with a screened enclosure showcases a private pool surrounded by a well-maintained yard. Lounge chairs are positioned near the water, and pathway stones lead to the pool, illuminated by soft lights above. The evening sky adds a serene backdrop.
Home in Kissimmee
4.97 out of 5 average rating, 123 reviews

Kissimmee/20 min to Disney/Private Heated Pool

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, 154 reviews

Heated Pool 15 Minutes to Disney PS5 l Switch

Condo rentals with a pool

Top Guest favourite
A comfortable living area features a cozy gray sofa and loveseat arranged around a wooden coffee table, with decorative pillows adding a touch of style. Natural light fills the space through sliding glass doors that lead to a screened balcony with outdoor seating.
Condo in Kissimmee
4.93 out of 5 average rating, 132 reviews

Disney Dream Condo & Pool

Guest favourite
A spacious living area is designed with light grey sofas and a glass coffee table, surrounded by greenery. Large windows with wooden blinds allow natural light to fill the room, while a ceiling fan enhances airflow. Soft, neutral tones create a relaxing atmosphere.
Condo in Kissimmee
4.88 out of 5 average rating, 163 reviews

Near Disney/Universal Lovely 2bedroom/2bath Condo

Top Guest favourite
A sparkling pool is framed by lush palm trees and lounge chairs, inviting guests to relax. The cheerful two-story building in the background features vibrant blue-green accents and large windows, complementing the clear sky above.
Condo in Kissimmee
4.93 out of 5 average rating, 122 reviews

Modern, spacious, and relaxing!

Guest favourite
A spacious living area is highlighted by large windows that allow natural light to fill the room. A dark sectional sofa and a coffee table are present, while a wall-mounted TV provides entertainment options. Decorative elements and plants add a touch of greenery.
Condo in Kissimmee
4.91 out of 5 average rating, 506 reviews

Newly Renovated 3/2 close to Disney parks

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.
Condo in Kissimmee
4.96 out of 5 average rating, 158 reviews

Luxurious Spot 10 Mins Away to Most Attractions!!!

Superhost
An open living space is presented, featuring a gray sofa and a patterned chair. A small television is placed on a stand. A kitchen area is visible, showcasing modern appliances. Light enters through large windows, illuminating the area and enhancing the plush area rug.
Condo in Kissimmee
4.79 out of 5 average rating, 247 reviews

**LOCATION**Clean/sanitized 1BR apt next to Disney

Top Guest favourite
An aerial view captures the expansive resort-style pool area, featuring tropical landscaping and winding water features. Sun loungers and cabanas line the poolside, while a lazy river and splash park invite guests to relax and enjoy. The serene water is bordered by a scenic lake.
Condo in Kissimmee
4.94 out of 5 average rating, 169 reviews

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

Superhost
The exterior of the Westgate Vacation Villas showcases an elegantly designed building with multiple levels. Soft lighting from street lamps illuminates the entrance. Rows of golf carts are parked in front, surrounded by manicured landscaping and palm trees under a clear blue sky.
Condo in Kissimmee
4.87 out of 5 average rating, 210 reviews

Westgate Vacation Villas - 1 Bedroom

Other holiday rentals with a pool

Guest favourite
A modern living area showcases a mix of comfortable seating, including a plush blue couch and a tan sofa, arranged around a stylish, round ottoman. A large television is mounted above a lighted console, and natural light filters through the nearby window, enhancing the warm decor.
Apartment in Osceola County
4.92 out of 5 average rating, 25 reviews

Luxury Serenity | Reunion Living Near Disney

Top Guest favourite
A dining area with a rectangular table set for six features simple decor and a centerpiece. A cozy living space is visible with a sofa, chairs, and a TV. Light streams in through large windows, accentuating the open layout and inviting atmosphere.
Townhouse in Osceola County
4.99 out of 5 average rating, 95 reviews

Amazing townhouse near Orlando theme parks

Guest favourite
A private screened-in pool is surrounded by a clear enclosure, offering unobstructed views of a serene lake and lush greenery. Sunlight reflects off the water, enhancing the tranquil atmosphere. Comfortable lounge chairs are positioned nearby for relaxation.
Home in Kissimmee
4.95 out of 5 average rating, 56 reviews

Serene 4BR Pool Home Near Disney

Top Guest favourite
An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.
Home in Kissimmee
5 out of 5 average rating, 58 reviews

Luxury Home w/ Pool & 6 Beds near Disney

Guest favourite
A spacious living area showcases large windows that invite natural light, complemented by comfortable seating. A private pool is visible outdoors, surrounded by a screened enclosure. The bedroom features a king bed and calming decor, while another area displays two twin beds in bright, inviting colors.
Home in Kissimmee
5 out of 5 average rating, 36 reviews

Fun in Paradise: Pool Villa near Attractions!

Guest favourite
A large resort-style pool is viewed in the foreground, surrounded by a spacious deck featuring lounge chairs. A clubhouse sits in the background, with palm trees lining the perimeter under a clear blue sky scattered with clouds.
Condo in Four Corners
4.93 out of 5 average rating, 40 reviews

2BD Champions Gate Magical Near Disney (CG 1177)

Guest favourite
A patio area features two wicker chairs and a glass-top table, overlooking a lush green golf course. The scene captures an expansive view of the manicured landscape, with well-maintained grass and trees in the distance under a cloudy sky.
Apartment in Kissimmee
4.88 out of 5 average rating, 81 reviews

Golf Course View/Free Parking/Pool /Gated/Disney

Top Guest favourite
A spacious living area is highlighted by large windows framed with white curtains. A comfortable sofa adorned with decorative pillows faces a sleek glass coffee table, while a modern armchair complements the stylish decor. A dark, patterned rug adds warmth to the light-flooded space.
Home in Kissimmee
4.97 out of 5 average rating, 30 reviews

*Modern condo on resort. No fees 15-Min to Disney*

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