
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.

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291
Unable to book this house? Don't worry! Feel free to check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE Disney is just a short 8-mile drive away Tired of visiting the parks every day? Step inside this beautiful thematic 2,169 sqft house with a private pool, spa, BBQ, Star Wars themed movie theater, and a Mario Kart game room complete with arcades, pool table and foosball table all designed for family enjoyment! Make your vacation truly unforgettable!

Captivating home 12 minutes from Disney world Fl
Amazing home, located in the upscale community of reunion resort. Nearly all the bedrooms in the homes are master suites with beautiful, private bathrooms. Adults as well as our little guests are the ones who really get spoiled with our popular Superheroes themed bedrooms and princess themed room. Let's not forget our amazing game room/theater room. This home is ideal for a family vacation with 5 luxury bedrooms, multiple entertainment options, an amazing pool/jacuzzi overlooking the golf course

Casa Bella Mediterranean Style near Disney
Welcome to this beautifully 4-bedroom, 3-bath pool home located in the desirable Westside Tuscany community — a peaceful Mediterranean-style enclave just minutes from Walt Disney World and Orlando’s world-class attractions. Step inside to a bright and spacious open living area with large windows and sliding doors that lead directly to your private screened pool, where you can relax and enjoy peaceful wooded views after a fun day at the parks. Enjoy your own private Florida retreat! Book now!

Waterfront next to Resort by Disney Game &Theater
Lakefront Luxury Everything is Completely remodeled 5 bdrms\5 bthrms luxury villa – Located in the gated Paradise Palms Resort,which is just around the corner from Disney. Only a few steps away from the Clubhouse amenities & nature path,this home offers privacy & lake\nature views from the sun soaked south facing color changing pool\spa.Enjoy , New home theater, two 1st floor master bdrms & 2 bthrms + another master & immersive themed rooms on 2nd floor. AC Arcade TV gameroom & billiards Loft

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE
AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

Magical 5-Bedroom Villa Near Universal's Wizarding
Ensure an enchanted holiday in Orlando. Inspired by everyone’s favorite castle, this magical home provides an immersive experience with 5 bedrooms, common room with large screen TV with Netflix & Nintendo Switch, dining hall, fully equipped kitchen, swimming pool, patio with grill and laundry room. Located in a quiet residential community, 10 miles to the Wizarding World of Harry Potter, 6 miles to Disney, 5 miles from Celebration, 4 miles from Old Town and 18 miles from downtown Orlando.

Family Fun in Near Disney Star Wars, Pool, BBQ
This beautifully designed townhouse is centrally located and will provide everything you need to create wonderful memories with your family. There is a free heated private pool and BBQ grill in the patio, large screen TVs, a fully stocked kitchen and Star Wars / Mickey theme rooms. The resort amenities include a pool with a tiki bar, pirate boats and a lazy river, as well as kids' playgrounds and a gym! This magical place is ideally located close to all the main parks and attractions!!

Sanctuary w/ Game Room + Pool | Walk to Clubhouse
Welcome to an unforgettable Orlando getaway! This fabulous 6-bedroom villa in Windsor at Westside is just minutes from Disney and top attractions. Perfect for families and large groups, it features a private east-facing pool with Bbq grill, fun themed bedrooms, and a game room for all ages. Only a 6-minute walk to the clubhouse, where you’ll enjoy a resort-style pool, jacuzzi, splash area, lazy river, and more. Comfort, fun, and convenience all in one place!

Modern Condo with Lake View Near Disney 3151
STOREY LAKE RESORT A premier vacation community just 8 miles from Disney and minutes from Universal & SeaWorld, this community is surrounded by restaurants, shops, and top malls. Only 30 minutes from Orlando Airport, it offers easy access to everything you need. Book your stay for 7 days or more and unlock an exclusive 5% discount ! Stay 30+ nights and save 10% (Discount will apply on selected stays) Reserve now! we would love to be your host!

2 BR Harmony House at Regal Oaks Resort
Come get away to our modern, super-clean, self-contained garden oasis town house in the Regal Oaks Resort - close to grocery stores and take out food - minutes walk from Old Town Kissimmee and a short drive from Disney's ESPN - World of Sports and Town Center Celebration. We are 15 minutes drive from Epic - Universal and Disney parks. Our private screened in hot tub is the perfect place to relax in the Florida sun or under our sun shade.

Pet-Friendly Pool Home Near Orlando
Welcome to your perfect Orlando retreat! This beautiful and spacious home offers a blend of modern comfort, stylish design, and exceptional amenities — all just minutes from the top parks and attractions. Enjoy a private screened-in pool, elegant interiors, and thoughtfully designed spaces ideal for families, groups, or long stays. Every detail has been curated to provide comfort, relaxation, and an unforgettable vacation experience.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Themed 10-Bedroom | Sleeps 26 w/ Pool & Game Room!

Magical 6BR at Encore Resort next to Disney - 453

Pool & Spa Oasis/Golf Retreat/Near Disney/3BR Home

Luxury Villa with Private Pool Near Disney World

Villa Resort Club

Near clubhouse new Storey Lake 15 guests pool&spa

9BD - Storey Lake - Newly Themed - Theatre, Games

*NEW* Super Amazing Vacation Getaway
Condo rentals with a pool

Cozy space 5/10 universal & epic

Waterfront Condo minutes to Disney & Universal

1-104 Legacy Dunes, Pool View, Close to Disney

Chic Disney Resort Condo • Pool Access Near Parks

207_ Sparkle Apartment Close to Disney Free Waterp

3171-107 Resort Lake View Disney Universal Orlando

Cozy Apartment Close to All Disney' Parks

Cozy ❤️ Beach Style Condo near Disney & Universal
Other vacation rentals with a pool

Best Location! Best Location!Villa in Kissimmee

Storey Lake! Best Resort/4 Beds/3 Baths/10 ppl/BBQ

Amazing 4BD Pool & Spa Home In Margaritaville

Luxury Townhouse Near Disney | 3BR

Blue Oasis - Peaceful Lake-View Pool

10 Min from Disney | Luxury & Modern | No Carpet

VillaLumine•PrvtPool•Heater•Aesthetic•NearDisney

Peaceful Modern Oasis Backing to Nature Preserve
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $215 CAD | $225 CAD | $240 CAD | $214 CAD | $187 CAD | $200 CAD | $209 CAD | $184 CAD | $170 CAD | $180 CAD | $202 CAD | $239 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 $28 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
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- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- 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
- Camping World Stadium
- Reunion Resort Golf Courses - Palmer & Watson
- Aquatica
- University of Central Florida
- ICON Park
- Disney's Hollywood Studios
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ESPN Wide World of Sports







