Vacation rentals with a pool in Kissimmee

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kissimmee

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

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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
4.88 out of 5 average rating, 270 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.

Top guest favourite
A themed kitchenette features a bamboo bar with high seating and colorful pendant lighting. The walls are adorned with tribal art and shelves hold various artifacts. Kitchen appliances, including a refrigerator and counter space, reflect a blend of modern convenience and cultural decor.
Cottage in Kissimmee
4.99 out of 5 average rating, 198 reviews

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

Guest favourite
A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.
Home in Buenaventura Lakes
4.93 out of 5 average rating, 136 reviews

Villa Resort Club

VILLA LUJOSA - BARRIO SÚPER HERMOSO POOL HEATER HOUSE - Diviértete con toda la familia en este alojamiento con estilo moderno , te encantará el área de picnic frente de la casa , el área de juegos y piscina con calentador , un espacioso lugar de hierba artificial para jugar tus niños y en una zona muy trankila cerca de los parques de Disney y del aereopuerto MCO . TE ENCANTARÁ LA CASA Local utility or county personnel may access exterior areas for maintenance without prior notice.

Top guest favourite
The exterior of the house is displayed, featuring a well-maintained lawn with manicured shrubs and a palm tree. The light-colored structure is complemented by large windows, and decorative stones are arranged artistically in the landscape. A clear blue sky enhances the inviting appearance.
Home in Buenaventura Lakes
4.95 out of 5 average rating, 113 reviews

Your All in One Home, 17 mins from Disney World

Welcome to JeremyAnthonyHouse, a place that was created with so much love and care thinking of you. The house has everything you might need during your stay, it does not matter if it is for one night or an entire month; from bathroom amenities, free Netflix, Wifi, YouTube, in house laundry and dryer to kids' toys, security system. In addition, it has a private pool, easy access to expressways and theme parks. Very close to Disney springs and The Medieval Times Castle is a must see.

Top guest favourite
An outdoor area features a private pool surrounded by a safety fence. A gas grill is positioned nearby. Comfortable seating is arranged under a protective screen, set against a backdrop of clear skies. The adjacent indoor space showcases modern furnishings and vibrant decor.
Townhouse in Kissimmee
4.92 out of 5 average rating, 102 reviews

2697 Resort 4BR House Waterpark by Disney Orlando

Minutes from Disney, stylish & peaceful Townhouse, with 4 bedrooms and 3 full bathrooms, fully equipped kitchen for up to 8 guests, located in the family friendly Storey Lake Resort. Enjoy our private pool with optional water heater. The open floor plan blends Kitchen, Dining and Living room. Close to outlet malls & retail stores. Great Resort amenities: Heated Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Lake, Kayak, Tiki Bar, Ice Cream Shop & more.

Top guest favourite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 151 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Superhost
Apartment in Kissimmee
4.81 out of 5 average rating, 493 reviews

Spacious 2BR Apt in Resort 10 min from Disney

Featuring comfortable, family-friendly amenities, this property provides relaxation in a peaceful, wooded setting while being close to all the major area theme parks. Enjoy the outdoor swimming pool or stay active at the fitness center and tennis courts. Families will appreciate the playground and children's pool. Additional conveniences such as a bar, free Wi-Fi, and free parking ensure this property is your home away from home near Orlando's famous theme parks.

Top guest favourite
A modern living area features a comfortable sofa in neutral tones alongside two vibrant orange chairs. A round glass coffee table is positioned in front of the sofa, while a large television is mounted on a wooden accent wall. Floor-to-ceiling windows allow natural light to fill the space.
Home in Kissimmee
4.97 out of 5 average rating, 119 reviews

Modern 4bdr Storey Lake w/themed rooms near disney

Have fun with the whole family at this stylish place: themed bedrooms and a peaceful feeling. With Disney just 5 miles away and Universal Studios 15-20 minutes away, the resort offers endless fun. Storey Lake Resort also has many nearby shopping malls and dining options. From its resort-style pool, splash pad, and watersides to its clubhouse, poolside bars, fitness center, and lake-based activities, Storey Lake is the happy ending to your vacation rental search.

Top guest favourite
An expansive pool area is surrounded by lounge chairs and palm trees, featuring a large beach-entry pool sparkling under blue skies. Nearby, a vibrant kids' water play area features a large pirate ship structure. A spacious living area is designed with light furnishings and a large TV, while a children's bedroom showcases Disney-themed twin beds with playful decor.
Townhouse in Davenport
4.99 out of 5 average rating, 134 reviews

3bd/2.5b Close to Disney °Luxury Paradise Living

Welcome To our beautiful, peaceful piece of paradise. A family friendly home! Enjoy the beautiful views, luxury decor, fine foods near you, and all this home has to offer! This home is all about creating loving memories. This beautiful home is newly built has 3 bedrooms 2.5 bathrooms, over 2,000 sqft, all new furniture, and super fast internet speed. The resort has a large beach-entry pool, kids water park, beach volleyball, mini-golf, arcade, and gym.

Top guest favourite
A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.
Home in Kissimmee
4.95 out of 5 average rating, 210 reviews

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

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
4.95 out of 5 average rating, 242 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 : ↓ ↓

Guest favourite
Villa in Kissimmee
4.89 out of 5 average rating, 119 reviews

Retreat w/ Pvt Pool + Club Access | Disney 15min

Experience comfort, style, and resort living in this beautiful 5-bedroom, 5.5-bathroom vacation home just 15 minutes from Disney. Enjoy elegant living spaces, Smart TVs throughout the home, an Xbox One, and a private screened pool area with patio furniture and a BBQ grill — perfect for relaxing after a fun day in Orlando. The open-concept kitchen and spacious dining area are ideal for gathering with family and friends.

Popular amenities for Kissimmee rentals with a pool

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Quick stats about vacation rentals with a pool in Kissimmee

  • Total vacation rentals

    Explore 6,460 vacation rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee vacation rentals start at $27 CAD per night before taxes and fees

  • Verified guest reviews

    Over 243,320 verified reviews to help you choose

  • Family-friendly vacation rentals

    5,500 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 1,020 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,560 properties have a dedicated workspace

  • Wifi availability

    6,400 of Kissimmee vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Kissimmee rentals

  • 4.7 Average rating

    Kissimmee stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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