
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.

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.

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!!

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.

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.

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.

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!

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.

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.

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.

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.

"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 : ↓ ↓

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
House rentals with a pool

Luxurious five-bedroom villa with modern comforts

Luxory/Championsgate/private Pool/2 gulf courses

Disney Orlando vacation home with private pool 2

Gorgeous 12bdr/11.5 bath/Theater/Sleeps 30/Game Rm

Spectacular 8Bd 5.5Bth 4K Movie Theater Pool & Spa

Brand New 12br/33 ppl-Pool/Arcade/Theatre

New! Eights Mansion Themed House w/pool by Disney

Amazing 6BR Disney - Universal - Encore Resort 460
Condo rentals with a pool

Perfect for Two Families • Sleeps 8 • Top Location

Stylish Condo 20 mins to Disney/King Bed

A luxurious living just 15 min/Disney!

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Waterfront Condo minutes to Disney & Universal

Modern Lake view Condo 1 mile from Disney

Chic Disney Resort Condo • Pool Access Near Parks

Cozy Condo at Secret Lake near Disney
Other vacation rentals with a pool

Paradise Lake Lodge

Luxury 4BR Villa Golf View /Theater/Huge Pool&Spa

Modern Vacation Home Near Disney SL4962

Paradise Suite

Dreamy 5 Bed w/ Game Room, Pool & Themed Bedrooms!

The Denmark

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

Modern Luxury Kissimmee Retreat
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $212 CAD | $221 CAD | $236 CAD | $210 CAD | $184 CAD | $196 CAD | $206 CAD | $181 CAD | $168 CAD | $177 CAD | $199 CAD | $235 CAD |
| Avg. temp | 16 °C | 18 °C | 20 °C | 22 °C | 25 °C | 27 °C | 28 °C | 28 °C | 27 °C | 24 °C | 20 °C | 17 °C |
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
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Key West Vacation rentals
- Tampa Bay Vacation rentals
- Mansion rentals Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a home theater Kissimmee
- Lake house rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with an accessible height bed Kissimmee
- Cottage rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with beach access Kissimmee
- Private suite rentals Kissimmee
- Beach house rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Villa rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a sauna Kissimmee
- Apartment rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with outdoor seating Kissimmee
- Cabin rentals Kissimmee
- Vacation home rentals Kissimmee
- Guesthouse rentals Kissimmee
- Tiny house rentals Kissimmee
- Rentals with breakfast Kissimmee
- Hotel rooms Kissimmee
- House rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Rentals with a hot tub Kissimmee
- Condo rentals Kissimmee
- Rentals with a kayak Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with pools Osceola County
- Rentals with pools Florida
- Rentals with pools United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- University of Central Florida
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club







