
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.

3171-206 Resort Lake View Disney Universal Orlando
Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Luxury 5BR free heat private pool Disney Universal
Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

Heated Pool 15 Minutes to Disney PS5 l Switch
Spacious 4BR Home with a Private Heated Pool – 15 Minutes from Disney! Enjoy a large south-facing pool, Propane grill, Smart TVs with Disney+ in every room. Nintendo Switch in Living Room and an 85" screen with a PS5 in a temperature-controlled garage / game room. Fast WiFi, shuffleboard, pool table and plenty of board games. 🌴 Outdoor Fun Patio Seating for 14 + two lounge chairs. Propane Grill: $50 for length of stay Pool heat: $200 per stay (24-hour notice)

Spectacular Lake View - Game Room- Close to Disney
Our home has all the features to comfortably provide your family with the amenities while on vacation! A kitchen ready for your cooking needs, a pool and spa(heating fee required), a Game/Media Room, and TVs throughout the house. The resort offers many amenities, including tennis courts, a sand volleyball court, walking trails, bike rentals, a huge pool, a poolside Tiki bar, a fitness center, a mini-golf, and so much more! Just a short walk away.

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!

Retreat w/ Pvt Pool + Club Access | Disney 15min
Experience luxury in this spacious 5-bedroom, 5.5-bathroom home located just 15 minutes from Disney. Relax in elegant living areas with Smart TVs and an Xbox One, or step outside to your private pool with stylish patio furniture and BBQ grill. The open-concept kitchen and dining area are perfect for gathering, while the Windsor at Westside resort offers a lazy river, pools, fitness center, playgrounds, and sports courts, all just steps away.

Luxe Saltwater Pool Home | Golf | 1 Exit to Disney
Plentiful Views | Reunion Resort Luxury Home | Private Saltwater Pool + Golf Views | 1 Exit from Disney A private golf-course retreat inside Reunion Resort — just one exit from Walt Disney World®. Designed for families and groups who want space, privacy, and elevated comfort, this 5-bedroom home blends resort-level amenities with the ease of a fully private residence. Minutes from Disney. Worlds away from ordinary.

Amazing Villa near DisneyWorld FREE heated-pool
Have fun with the whole family at this stylish place. Our home has everything you will need for you and your guest to have a great experience. This home is a short drive from Walt Disney World and Orlando Attractions!! Don’t wait book with us now and give you and your family the vacation you all deserve. We can’t wait to welcome you . BBQ ( free to use ) Heated pool (free) Dogs friendly! Extra fee $120 per stay

Upstay Spacious 5BR Villa Private Pool and Hot Tub
This 5-bedroom, 6-bathroom home is the ultimate family retreat! With over 3,200 sq ft of space, a private pool and hot tub, and fun extras like a foosball table and Roku TVs, it’s built for comfort and entertainment. Located in a secure gated community just minutes from Orlando’s top attractions, it’s perfect for family holidays, group getaways, or a sun-soaked work-from-home escape. Book your stay now!

3BR-Private Jacuzzi-Resort Amenities-7 mls Disney
Private and Clean 3 bedroom 2.5 bathroom Townhouse in a most prestigious resort near the Disney area - Terra Verde Resort. Private HOT Jacuzzi (professionally cleaned once a week every week), BBQ, WIFI, TVs in all Rooms, and more. Pets are considered (fees/restrictions apply)

4BR Retreat | Pool | Close to Disney
Home at Bella Vida. If you want a heated pool, you must notify us in advance and we charge $30 per day for pool heating and one time fee of $50 for the bbq. Starter amenities are provided for your arrival, intended for short stays or your first night convenience.

Fairview at Reunion - Games Room
This beautiful 6 bedroom, 6 bathroom villa offers families the enjoyment of a private pool area with plenty of privacy. Located in the prestigious resort of Reunion where our guests receive access to the 7 resort pools.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Restful 4BR / 3BA with BBQ, Heated Pool & SPA.

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

Themed Disney Villa 6BD Resort WaterSlide Pool Spa

30% off over 2 months stay 5br pool home

Peaceful 5 BR Home w/Private Pool/Spa & Game Room!

Disney 6 bedroom Luxury Villa Arcade Pool Heat bbq

Disney Mega Villa • Escape Rm • Cinema • Pool

Newly Updated Windsor Hills 5 bed/5 bath Pool Home
Apartment rentals with a pool

Perfect for Two Families • Sleeps 8 • Top Location

Stylish Condo 20 mins to Disney/King Bed

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Chic Disney Resort Condo • Pool Access Near Parks

Luxurious Spot 10 Mins Away to Most Attractions!!!

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

*Sunset Perch: Views, Reunion Resort, XBox, 2Pools
Other holiday rentals with a pool

Inviting vacation spot at Reunion Resort close to

Epic stay at Vista Cay!

4 BR/2Master Private Pool & Spa

Luxury Home w/ Pool & 6 Beds near Disney

New! Epic Dream House with Pool

Emerald Island Lake View

NEW*Avatar/Inside Out• Pool & StoreyLake Resort

Townhouse in Champions Gate with private pool
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $188 SGD | $190 SGD | $199 SGD | $195 SGD | $171 SGD | $183 SGD | $192 SGD | $169 SGD | $156 SGD | $165 SGD | $185 SGD | $218 SGD |
| 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 holiday rentals with a pool in Kissimmee

Total holiday rentals
Explore 6,620 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $26 SGD per night before taxes and fees

Verified guest reviews
Over 238,760 verified reviews to help you choose

Family-friendly holiday rentals
5,800 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 1,070 rentals that welcome pets

Rentals with dedicated workspaces
3,700 properties have a dedicated workspace

Wifi availability
6,590 of Kissimmee holiday 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
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Give Kids the World Village
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club






