Holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool
Home in Kissimmee
4.88 out of 5 average rating, 112 reviewsNo Airbnb Fee! Thematic Rooms Pvt Pool °o° Area #2
Home in Kissimmee
4.82 out of 5 average rating, 251 reviewsNew Home Next To Disney!
Home in Kissimmee
4.91 out of 5 average rating, 295 reviewsFamily Home minutes from Disney!
Home in Kissimmee
4.94 out of 5 average rating, 173 reviewsTito's Beachy Townhouse, 1.5 miles from Disney
Home in Kissimmee
4.97 out of 5 average rating, 102 reviewsCozy Cove on the Lake
Home in Kissimmee
4.82 out of 5 average rating, 121 reviewsNice house, private community, with pool
Home in Kissimmee
4.82 out of 5 average rating, 104 reviewsPool House in Kissimmee
Home in Kissimmee
4.8 out of 5 average rating, 171 reviews4 Bedroom House Heated Pool 20 min From All Parks
Apartment rentals with a pool
Apartment in Kissimmee
4.8 out of 5 average rating, 117 reviewsStunning view, near Disney. 2 pools
Apartment in Kissimmee
4.95 out of 5 average rating, 113 reviewsCheery 2BR Condo w/zero entry pool near Disney
Apartment in Kissimmee
4.99 out of 5 average rating, 156 reviewsBright, Airy Home near Disney and Attractions
Apartment in Kissimmee
4.96 out of 5 average rating, 156 reviewsWelcome to our Son Shine condo ....
Apartment in Kissimmee
4.91 out of 5 average rating, 266 reviewsBeautiful Beach Style Condo minutes from Disney
Apartment in Kissimmee
4.79 out of 5 average rating, 154 reviewsMickey's Retreat
Apartment in Kissimmee
4.93 out of 5 average rating, 192 reviewsFancy renovated 3/2 Apt close to Parks w amenities
Apartment in Kissimmee
4.9 out of 5 average rating, 181 reviewsPerfect Condo | Pool & Tiki Bar | 15 min. Disney
Home rentals with a private pool
Townhouse in Kissimmee
4.88 out of 5 average rating, 128 reviewsStellar Five Bedroom Townhome Under Ten Minutes to Disney
Villa in Kissimmee
5.0 out of 5 average rating, 13 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Home in Davenport
4.97 out of 5 average rating, 98 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Villa in Kissimmee
4.79 out of 5 average rating, 225 reviewsVisit Disney World from a Sunny Home with a Pool
Home in Davenport
4.75 out of 5 average rating, 4 reviewsLuxurious 8br Palms Villa Pool Home-Champions Gate
Villa in Davenport
4.67 out of 5 average rating, 6 reviewsAmazing Dream Solterra Villa -Disney/club/pool/spa
Townhouse in Davenport
4.64 out of 5 average rating, 121 reviewsModern Oasis Villa W/ Private Pool & Pool Table
Home in Kissimmee
Vacation Resort Home Right Outside of Disney World
Quick stats about holiday rentals with a pool in Kissimmee
Total rentals
6.6K properties
Rentals with dedicated workspaces
3.2K properties have a dedicated workspace
Pet-friendly rentals
920 properties allow pets
Family-friendly rentals
5.9K properties are a good fit for families
Total number of reviews
188K reviews
Nightly prices starting at
€ 18 before taxes and fees
Destinations to explore
- St Petersburg Holiday rentals
- Anna Maria Island Holiday rentals
- Sarasota Holiday rentals
- Tampa Holiday rentals
- Key West Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Orlando Holiday rentals
- Rentals with pools United States
- Rentals with pools Orlando
- Rentals with breakfast Kissimmee
- Resort rentals Kissimmee
- Rentals with a firepit Kissimmee
- Townhouse rentals Kissimmee
- Rentals with a kayak Kissimmee
- Cottage rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with an EV charger Kissimmee
- Waterfront rentals Kissimmee
- Flat rentals Kissimmee
- Rentals with a cinema Kissimmee
- Rentals with a sauna Kissimmee
- Beachfront rentals Kissimmee
- Villa rentals Kissimmee
- Cabin rentals Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Wheelchair-accessible rentals Kissimmee
- Hotel rentals Kissimmee
- Family-friendly rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with beach access Kissimmee
- Apartment rentals Kissimmee
- Pet-friendly rentals Kissimmee
- Monthly Rentals Kissimmee
- Rentals with an accessible-height bed Kissimmee
- Private suite rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Rentals with a fireplace Kissimmee
- Tiny house rentals Kissimmee
- Rentals with an accessible-height toilet Kissimmee
- Guest house rentals Kissimmee
- Rentals with lake access Kissimmee
- House rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with pools Florida
- Rentals with pools Florida
- Rentals with pools Tampa
- Rentals with pools Osceola County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom