Compare Vacation Rentals with Pools in Kissimmee, FL

15321 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Kissimmee, FL vacation rentals
Choose vacation accommodation with a pool
Price per night
Accommodation type
Rating

Choose from Top-Rated Vacation Rentals with Swimming Pools in Kissimmee, FL

Summer Sparkle Home - Kissimmee, FL
9.6 48 reviews
Kissimmee, FL
08/20 – 08/25
$289/nighttotal: $1445 (5 )

Summer Sparkle Home

4 10
house, Kissimmee
This Kissimmee house offers a private swimming pool and hot tub, ideal for a relaxing getaway and located just 10 miles from Disney's Hollywood Studios and 8.9 miles from Disney Springs.
Spanning 2100 square feet, this family-friendly home features 4 bedrooms, 4 bathrooms, a fully equipped kitchen with a dishwasher and microwave, air conditioning, complimentary WiFi, and private parking.
Luxury Villa At Storey Lake Resort 6 Rooms Pool - Kissimmee, FL
9.7 158 reviews
Kissimmee, FL
11/06 – 11/08
$447/nighttotal: $894 (2 )

Luxury Villa At Storey Lake Resort 6 Rooms Pool

1 14
house, Kissimmee
Just 2 minutes from Target and 5 minutes from Walmart, this house offers a prime location in Kissimmee, situated within the Storey Lake Resort and only 15 miles from Disney.
This spacious 6-bedroom, 5-bathroom house accommodates up to 16 guests and features a private swimming pool and jacuzzi, alongside exclusive access to resort amenities like a lazy river, water slides, and a fitness center.
Jc Disney Home! Cozy House Near Disney - Kissimmee, FL
9.8 67 reviews
Kissimmee, FL
06/19 – 06/22
$195/nighttotal: $585 (3 )

Jc Disney Home! Cozy House Near Disney

1 4
apartment, Kissimmee
This apartment in Kissimmee is located within the secure, gated Lake Berkley resort, offering convenient access to major theme parks, just a 19-minute drive to Disney World, 23 minutes to Sea World, and 25 minutes to Universal Studios.
Enjoy a spacious 3-bedroom, 2-bathroom apartment perfect for up to 6 guests, featuring a fully stocked kitchen, a comfortable living room with flat-screen TV, and access to resort amenities including two swimming pools, a kids' pool, sports courts, and a playground, all complemented by a private heated pool for your getaway.
Great Lovely Family Apartment Close Disney - Kissimmee, FL
8.6 55 reviews
Kissimmee, FL
07/18 – 08/01
$185/nighttotal: $2590 (14 )

Great Lovely Family Apartment Close Disney

3 4
apartment, Kissimmee
Located in Kissimmee, this apartment offers convenient access to attractions, situated just over 7 miles from Gatorland and within a 7.9-mile radius of Disney Springs and Disney's Wide World of Sports.
Enjoy this 1290 square foot apartment with 3 bedrooms and 2 bathrooms, perfect for up to 11 guests, featuring an outdoor swimming pool, fitness center, tennis court, and a private balcony with a barbecue, ideal for a getaway with a pool.
Dluxx Townhouse With Splash Pool At Le Reve 1144 - Kissimmee, FL
9.1 256 reviews
Kissimmee, FL
07/24 – 08/03
$197/nighttotal: $1970 (10 )

Dluxx Townhouse With Splash Pool At Le Reve 1144

4 2
house, Kissimmee
Located in Kissimmee's Le Reve district, this townhouse is conveniently situated 6.5 miles from Gatorland and 8.8 miles from Disney Springs.
This family-friendly house with a pool offers a private splash pool, access to an indoor pool, a fitness center, and a fully equipped kitchen with a dishwasher.
15 Bd 16.5 Ba Sonoma Resort 4071 Sb - Kissimmee, FL
Kissimmee, FL
10/19 – 11/01
$1519/nighttotal: $19747 (13 )

15 Bd 16.5 Ba Sonoma Resort 4071 Sb

15 36
house, Kissimmee
This spacious 15-bedroom house in Kissimmee offers a private swimming pool, perfect for your next getaway, and is located just 10 miles from SeaWorld Orlando and Disney Springs, with Gatorland 4.8 miles away.
Boasting 150 square feet of floor area, this air-conditioned accommodation accommodates up to 79 guests with a fully equipped kitchen, complimentary WiFi, and a fitness center for your convenience.
Terra Verde Vacation Rentals - Kissimmee, FL
8.9 34 reviews
Kissimmee, FL
12/23 – 01/05
$262/nighttotal: $3406 (13 )

Terra Verde Vacation Rentals

3 4
house, Kissimmee
Located in Kissimmee, this house is 7.7 miles from Gatorland and 10 miles from Disney Springs and Disney's Wide World of Sports.
This family-friendly house features 1280 square feet of living space, three bedrooms, three bathrooms with a hot tub, a kitchen with a dishwasher, microwave, and oven, and offers an outdoor swimming pool with a pool bar, a spa center, and a fitness center, perfect for a getaway with a pool.
Boho Resort Villa | Pool, Spa & Disney Area - Kissimmee, FL
9.8 261 reviews
Kissimmee, FL
08/02 – 08/04
$202/nighttotal: $404 (2 )

Boho Resort Villa | Pool, Spa & Disney Area

1 6
house, Kissimmee
Just 15 minutes from Walt Disney World, this boho-inspired townhome in Kissimmee offers a fantastic family getaway with a community swimming pool.
This family-friendly townhome accommodates up to 7 guests and features a fully equipped kitchen, in-unit laundry, free Wi-Fi, and two parking spaces, all perfect for a relaxing stay with a pool.
Last Minute Disney! Private Pool, Game Room & Themed Bedrooms. Book Now! #38884 - Kissimmee, FL
Kissimmee, FL
10/19 – 11/01
$1263/nighttotal: $16419 (13 )

Last Minute Disney! Private Pool, Game Room & Themed Bedrooms. Book Now! #38884

15 36
house, Kissimmee
Conveniently located in Kissimmee, this house is just 7 miles from Disney World, 10 miles from Animal Kingdom and SeaWorld, and 14 miles from Universal Studios.
This spacious 15-bedroom house accommodates up to 38 guests and features a private screened-in swimming pool, a themed games room, and access to resort amenities, offering an ideal getaway with a pool for large families.
Luxury 5br/5ba Villa With Spacious Outdoor Patio Near Disney & Universal Parks - Kissimmee, FL
9.8 149 reviews
Kissimmee, FL
07/01 – 07/05
$531/nighttotal: $2124 (4 )

Luxury 5br/5ba Villa With Spacious Outdoor Patio Near Disney & Universal Parks

5 12
apartment, Kissimmee
This 5-bedroom, 5-bathroom apartment in Kissimmee offers a prime location, just 15 minutes from Walt Disney World and close to SeaWorld and Universal Studios.
Enjoy ample space for up to 16 guests in this 3000 sq ft apartment featuring a swimming pool, jacuzzi, spa, and fitness center, with a no-chore checkout policy for ultimate relaxation.
Storey Lake Townhome | Private Pool | Disney - Kissimmee, FL
9.8 69 reviews
Kissimmee, FL
07/04 – 07/08
$289/nighttotal: $1156 (4 )

Storey Lake Townhome | Private Pool | Disney

1 4
house, Kissimmee
Conveniently located in Kissimmee's Storey Lake Resort, this house is just a short drive from Walt Disney World and other major attractions.
This spacious house accommodates up to 11 guests and features a private swimming pool with a screened enclosure, perfect for family fun and relaxation, alongside access to resort amenities like a lazy river and fitness center.
Hideaway Dream Home - Kissimmee, FL
9.7 24 reviews
Kissimmee, FL
07/07 – 07/12
$423/nighttotal: $2115 (5 )

Hideaway Dream Home

6 10
house, Kissimmee
This spacious 2850 square foot house in Kissimmee is located just 7.8 miles from Gatorland and approximately 10 miles from Disney's Boardwalk, Disney's Hollywood Studios, Disney Springs, and Disney's Wide World of Sports.
Enjoy your stay with a private swimming pool, a relaxing hot tub, complimentary Wi-Fi, and free private parking, all within easy reach of Orlando International Airport.

Find a Luxury Vacation Rental with a Private Pool in Kissimmee, FL

Amazing 8br /Private Pool  & Hot Tub 2547 - Kissimmee, FL
9.6 29 reviews
Kissimmee, FL
07/31 – 08/03
$417/nighttotal: $1251 (3 )

Amazing 8br /Private Pool & Hot Tub 2547

1 16
apartment, Kissimmee
Located in the Veranda Palms gated community, this apartment is just 4 miles from Disney World and 5 miles from I-4, providing easy access to Universal Studios, SeaWorld, and Premium Shopping Outlets.
This family-friendly apartment offers 8 bedrooms and accommodates 17 guests, featuring a private swimming pool, hot tub, and a full kitchen with a fridge, microwave, and dishwasher.

Best Family-Friendly Vacation Rentals with Pools in Kissimmee, FL

Among the 15321 accommodations in Kissimmee, FL, here are the 8 best family friendly rentals

The Galactic Getaway, 3bed, 2bath Apartment, Free Parking, Heated Pool - Kissimmee, FL
9.8 15 reviews
Kissimmee, FL
07/03 – 07/06
$193/nighttotal: $579 (3 )

The Galactic Getaway, 3bed, 2bath Apartment, Free Parking, Heated Pool

3 4
apartment, Kissimmee
Located in Kissimmee, this apartment is 6.8 miles from Disney Springs and 7.3 miles from Gatorland.
This family-friendly apartment offers 1190 square feet of living space with 3 bedrooms and 2 bathrooms, perfect for up to 8 guests, and features a heated swimming pool, a hot tub, a fitness center, and complimentary private parking.
72+ 5 Star Reviews Villa@storey Lake Mins 2 Disney - Kissimmee, FL
9.8 76 reviews
Kissimmee, FL
07/02 – 07/06
$931/nighttotal: $3724 (4 )

72+ 5 Star Reviews Villa@storey Lake Mins 2 Disney

1 13
house, Kissimmee
Located in the Storey Lakes Resort area of Kissimmee, this 9-bedroom villa offers unobstructed lake views and is conveniently situated approximately 7 miles from Disney and 12 miles from Universal Studios.
This spacious villa sleeps 20 guests and features a private screened-in swimming pool, a hot tub, a dedicated cinema, and a Star Wars game room, with full access to resort amenities including a water park and fitness center.
Charming , 2 Bedroom , 1 Bath - Kissimmee, FL
9.8 21 reviews
Kissimmee, FL
07/15 – 07/19
$141/nighttotal: $564 (4 )

Charming , 2 Bedroom , 1 Bath

2 2
apartment, Kissimmee
This 600 sq ft apartment in Kissimmee is conveniently located near Walt Disney World® Resort, theme parks, and golf courses like Mystic Dunes Golf Club.
Enjoy your stay at this family-friendly apartment with a swimming pool, offering a private outdoor living area and a fully equipped kitchen for up to 4 guests.
Wb4301 Storey Lake Condo  5 Bed 4 Bath  Private Pool & Free Waterpark - Kissimmee, FL
9.4 118 reviews
Kissimmee, FL
06/19 – 06/22
$279/nighttotal: $837 (3 )

Wb4301 Storey Lake Condo 5 Bed 4 Bath Private Pool & Free Waterpark

5 10
apartment, Kissimmee
This apartment in Kissimmee's Storey Lake Resort is less than 1 mile from Walt Disney World Resort and Disney Springs, offering a prime location for exploring nearby attractions.
Enjoy resort amenities including a lazy river, two swimming pools, and a fitness center, all within this spacious 2130 square foot apartment that accommodates up to 13 guests.
Newly Updated Family Fun Resort, Close To Disney! - Kissimmee, FL
9.7 153 reviews
Kissimmee, FL
07/08 – 07/22
$151/nighttotal: $2114 (14 )

Newly Updated Family Fun Resort, Close To Disney!

1 3
house, Kissimmee
Located in the gated Terra Verde Resort in Kissimmee, this townhouse is just minutes from major theme parks and attractions.
This family-friendly house with a swimming pool offers a private 6-person hot tub, a newly updated kitchen, and access to extensive resort amenities, accommodating up to 6 guests.
Pool House In Kissimmee - Kissimmee, FL
9.7 142 reviews
Kissimmee, FL
12/24 – 01/05
$168/nighttotal: $2016 (12 )

Pool House In Kissimmee

1 6
apartment, Kissimmee
Perfectly situated in Kissimmee, this apartment is just a 20-minute drive from world-renowned theme parks including Walt Disney World, Universal Studios, Aquatica, and SeaWorld.
This family-friendly apartment offers a private swimming pool and accommodates up to 9 guests with 4 bedrooms and 2 bathrooms, plus a BBQ area and high-speed WiFi.
Stylish Disney Escape | Private Pool And Jacuzzi! - Kissimmee, FL
9.4 63 reviews
Kissimmee, FL
09/13 – 09/18
$245/nighttotal: $1225 (5 )

Stylish Disney Escape | Private Pool And Jacuzzi!

1 4
house, Kissimmee
Located in Kissimmee, this house is just minutes from Walt Disney World and Universal Studios, offering prime access within the Bella Vida Resort.
Enjoy a private screened-in swimming pool with optional heat, alongside a fully equipped kitchen and access to resort amenities including a fitness center and jacuzzi.
Cozivill - Kissimmee, FL
8.5 40 reviews
Kissimmee, FL
08/02 – 08/03
$199/nightfor 1 night

Cozivill

3 2
apartment, Kissimmee
Located in Kissimmee, this apartment is just over 7 miles from Disney Springs and 7.6 miles from Disney's Wide World of Sports.
This spacious 3-bedroom apartment sleeps 11 guests and features a fully equipped kitchen, a swimming pool, a hot tub, and a fitness center, offering a perfect getaway with a pool.

Popular destinations

Explore Our Top Pet-Friendly Vacation Rentals with a Pool in Kissimmee, FL

Among the 15321 accommodations in Kissimmee, FL, here are the 8 best pet friendly rentals

Luxury Villa: Pool, Cinema, Bbq & Near Disney - Kissimmee, FL
9.5 34 reviews
Kissimmee, FL
07/13 – 07/17
$580/nighttotal: $2320 (4 )

Luxury Villa: Pool, Cinema, Bbq & Near Disney

1 15
apartment, Kissimmee
Located in the esteemed Sonoma Resort in Kissimmee, this apartment offers a prestigious address just 5 to 6 miles from Walt Disney World Resort, SeaWorld, and Universal Studios.
This pet-friendly, family-friendly apartment accommodates up to 24 guests with 10 bedrooms and 8.5 bathrooms, featuring a private cinema, game console, and a private swimming pool with optional heating for an ultimate getaway.
Near Disney 3 Bdrm Villa With Pools And Clubhouse! - Kissimmee, FL
9.5 58 reviews
Kissimmee, FL
12/24 – 01/05
$143/nighttotal: $1716 (12 )

Near Disney 3 Bdrm Villa With Pools And Clubhouse!

1 6
house, Kissimmee
This 3-bedroom, 2-bathroom villa is located within the secure Venetian Bay community in Kissimmee, offering resort-like amenities and quick access to major theme park attractions, dining, and shopping, just minutes away.
Enjoy a spacious open floorplan and the convenience of a private swimming pool, alongside access to community pools, a gym, game room, and theater, making this house perfect for families and groups of up to 6 guests.
Stay At Hogwarts Harry Potter's Home, Free Parking, Pets Allowed - Kissimmee, FL
9.5 36 reviews
Kissimmee, FL
08/02 – 08/03
$436/nightfor 1 night

Stay At Hogwarts Harry Potter's Home, Free Parking, Pets Allowed

4 2
house, Kissimmee
This unique Harry Potter-themed house in Kissimmee offers an unforgettable experience, located just 8 miles from Gatorland and 7.5 miles from Orlando International Airport.
Explore this pet-friendly 10,000 square foot house with 4 bedrooms and 3 bathrooms, featuring a fireplace, an on-site water park, and complimentary parking, perfect for accommodating up to 17 guests and ideal for families seeking a getaway with a pool.
6br Family Home W Pool Near Disney - Kissimmee, FL
10 1 review
Kissimmee, FL
11/06 – 11/08
$474/nighttotal: $948 (2 )

6br Family Home W Pool Near Disney

6 16
house, Kissimmee
Conveniently located approximately 7-8 miles from Walt Disney World attractions like Hollywood Studios and Disney's Boardwalk, this 6-bedroom house in Kissimmee offers a perfect getaway with a pool for your next vacation.
This spacious 3600 square foot home features a private swimming pool, air conditioning, complimentary WiFi, and a fully equipped kitchen, ideal for accommodating up to 39 guests with an outdoor dining area for enjoying the Florida climate.
Charming Pond View Home With Pool Minutes Away From Disney Parks - Kissimmee, FL
9.6 125 reviews
Kissimmee, FL
08/29 – 09/06
$255/nighttotal: $2040 (8 )

Charming Pond View Home With Pool Minutes Away From Disney Parks

3 5
apartment, Kissimmee
Centrally located in Kissimmee's Windward Cay neighborhood, this waterfront apartment offers a tranquil retreat just a short drive from Walt Disney World Resort, SeaWorld, and Universal Studios.
This 1190 sq ft apartment accommodates up to 6 guests and features a community swimming pool, a private outdoor home theater, and is just about an hour's drive to sandy beaches.
Private House With Pool Kissimmee/orlando - Kissimmee, FL
9.8 58 reviews
Kissimmee, FL
08/02 – 08/04
$379/nighttotal: $758 (2 )

Private House With Pool Kissimmee/orlando

3 6
apartment, Kissimmee
Located in Buena Ventura Lakes, Kissimmee, this apartment is just a 5-minute drive from Silver Spurs Arena and Osceola Heritage Park, offering convenient access to nearby water parks and theme parks.
This family-friendly apartment accommodates up to 9 guests and features a refreshing swimming pool, a garden, and a deck/patio, alongside essential amenities like free WiFi and air conditioning.
Disney Magic Condo 1st Flr 3br Disney-themed Pool - Kissimmee, FL
9.5 2 reviews
Kissimmee, FL
06/15 – 06/30
$137/nighttotal: $2055 (15 )

Disney Magic Condo 1st Flr 3br Disney-themed Pool

3 2
apartment, Kissimmee
This 3-bedroom apartment in Kissimmee offers a Disney-themed getaway, located just 7.1 miles from Disney's Wide World of Sports and within 7.4 miles of Disney Springs and Hollywood Studios.
Enjoy this spacious 1350 sq ft apartment with a private entrance and patio, featuring a well-equipped kitchen, 2 bathrooms (one with a hot tub), and a fantastic swimming pool, plus a fitness center, sauna, and garden for ultimate relaxation.
Brand New Modern State Of The Art Home! Sleeps 31 - Kissimmee, FL
10 2 reviews
Kissimmee, FL
06/17 – 06/22
$1730/nighttotal: $8650 (5 )

Brand New Modern State Of The Art Home! Sleeps 31

15 17
apartment, Kissimmee
Located in Kissimmee's Sonoma Resort, this expansive villa offers easy access to major Orlando attractions, with Disney World Resort less than a 20-minute drive away.
This 15-bedroom, 16-bathroom apartment comfortably accommodates up to 31 guests and features a private swimming pool with a spa, a Vegas-themed game room, and full access to the resort's clubhouse amenities.
©2026 poolgetaway.com