
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.

PentHouse Suite with 2X View
Located at the gates of Walt Disney World, this Awesome PentHouse Suite offers easy access to area theme parks, and entertainment venues in the surrounding area, including Walt Disney World, Universal Studios, Sea-world, Legoland + Amazing Restaurants, Shopping and many more. Best of all wonderful views with 2 Large Balcony's, 1 for Sunrise @ East Side and 1 for Sunset @ West side overlooking Disney World with amazing fireworks every night, Enjoy! **Security camera for safety @ Entry door only!

Disney Luxury Townhouse 2B Hot Tub/ No Resort Fees
Modern two master bedrooms and 2.5 Bath.Townhouse with Tile and Vinyl plank floors ( not carpet) at La Encantada Resort! Exclusive and gated at Disney area and all the attractions. Beautifully furnished. comfortable living room with a sofa bed, open dinning area and private oversized screened patio/lanai with Hot Tub. Full access to all the amenities: 2 heated pools, arcade room, fishing pond, and more! 10 min drive to Orlando attractions and 15 minute drive to famous Orlando shopping Outlets

Neverland Found-Minutes from Disney Free Waterpark
Welcome to Neverland Found! This unique property inspires us to never grow up with themed rooms of Peter Pan, The Lost Boys, and Tinkerbell. Our home has 2 Master Suites, a fully equipped kitchen, 5 bedrooms, 5 baths, pool and spa, Pirates of the Caribbean game room, and loft area. Our home is located in the resort community of Storey Lake with access to multiple clubhouses and pools and all of it's amenities. Located within minutes of the theme parks & attractions that Orlando has to offer.

Orlando Disney Premium Home in Resort & Lake View!
Renewed house in Resort with fantastic lake view and an Amazing Clubhouse. (NO resort fees) | 1 min | Old Town Kissimmee | 3 min | Publix® | 3 min | McDonald's®, Wendy's®, Miller's Ale House® and much more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | Premium Outlet® I-4 | 9 min | DISNEY® AREA (All Parks) | 10 min | ESPN Sports | 10 min | Convention Center | 14 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 60 min | Bush Garden's® | 95 min | Sarasota & Clearwater

15 minutes from Disney Luxury Retreat at Reunion
Relax after a magical day at Disney or Universal. Welcome to Reunion Luxury Retreat, experience the perfect blend of luxury comfort, and privacy in this elegant villa, located within the exclusive gate community of Reunion Village, just minutes from Orlando's world-famous theme parks. Our Home offers everything you need for an unforgettable stay. 4 spacious bedrooms, 5 different pools in our resort. Gate community with 24-7 security. Fast wifi , smart TV, fully equipped kitchen.

Cozy 2Bed Boho Hideaway 10 Min to Parks Allows Pet
Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 8 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

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!

No Airbnb Fee | Newly Renovated 4BR w/ Pool!
**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

Home 6 BDR at Solara Resort/Private Pool LED
The Space * Accommodates: 16 * Bedrooms: 6 * Bathrooms: 4.5 * Property type: Luxury Villa * Location: Solara Resort * ONLY 0.2 miles away from The Clubhouse! * 12 miles from Magic Kingdom * 8 miles from Animal Kingdom * 16 miles from SeaWorld * 21 miles from Universal Studios * Property and resort close to the US 27 highway where some restaurants, market, gas station, pharmacies are located.

Sunny Lake Escape | Pool, Game Resort | Nr Disney
• Stunning lake-view home in Solterra Resort near Disney • South-facing private screened pool with large pool deck • Sleeps 14 | 6 bedrooms | 5 bathrooms • Large upstairs movie room with 100-inch projector • NBA-themed game room with pool table & arcade games • Home office with desk, sofa & TV • Two bedrooms downstairs – great for families • 🎁 Complimentary welcome pack of goodies on arrival

202_Magical and Cozy 2BR minutes from Disney
The ultimate choice for your Orlando getaway! Our cozy apartment is thoughtfully designed to make you feel right at home, with all the comforts and amenities you need. Plus, enjoy complimentary access to the waterpark – the perfect way to relax and have fun after a day of exploring the parks or shopping in Orlando!

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.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Group Getaway • 14 Beds • Sleeps Up to 20

6BR 3.5BA Family Vacation Home

Villa Resort Club

7BR Mega Mansion in Solara Resort

Fairy Tale House at Solara Resort

Experience Luxury in Your 11 En-Suites Mansion

ECR313 Resort Style Mansion + Pool/Spa/Theater/Gym

Adult Luxury - Magic for Families!
Apartment rentals with a pool

P-Gated Resort-5 miles to Disney-2 FREE Water Park

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Disney Dream Condo & Pool

3 Bedroom w/large patio on Resort Golf Course

VISTA CAY RESORT, 2 BEDROOM STANDARD APARTMENT

3171-107 Resort Lake View Disney Universal Orlando

Westgate Vacation Villas - 1 Bedroom

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

ClosetoDisney/southpool/4bdrm

Charlie's Funhouse and Games near Animal Kingdom

NEW House Magic Orlando close to Disney

Windsor Hills Home w/Arcade Game Room|Near Disney

Solara Villa with Themed Rooms and Private Pool

Disney 10 Min • Universal 20 Min • Pool Home

Boho Luxe Retreat • Near Disney Parks

Lake Louisa Lodge near Disney
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






