
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.

Jacuzzi 3BR Villa near Disney, resort amenities
Welcome to your private villa! With 3 bedrooms and 2.5 baths, this well equipped townhome is just 15 minutes from the Disney attractions. A screened private patio adds to the fun in this gated community. Take a walk around the greenway or enjoy the club house amenities: outdoor pool, volleyball court, basketball half court, fitness room, and movie room. This villa is private and convenient. It includes all the amenities you expect, including linens. You will want to return on your next vacation!

Blue Door Escape - Private Pool - Close to Disney
This cozy and beautifully maintained pool home is located in the sunny Veranda Palms neighborhood less than 5 miles from Disney, Sea World, and Universal! Breathe easy in the spacious bedrooms and open living space or unwind outside on the patio enjoying the clean pool and spa. TVs in every bedroom! The game room includes a pool table and foosball table. Family friendly! Resort Style amenities (including heated pool, kids splash pad, gym, etc.) available at the Clubhouse, a 3-minute walk away.

Themed rooms - gated community
Beautiful modern home with 3 full suites and 3 bathrooms — a rare find in the area! Located in the gated community THE HUB, featuring new construction, an American-style kitchen integrated with the TV room, and pet-friendly accommodations (rules apply). The community also offers a swimming pool and a small gym for guests. Guests enjoy: 🕒 24h self check-in 🔐 Unique access code valid only during the stay 🛏️ Linens and towels provided 🐾 Pet-friendly (check rules) 🏊 Community pool & small gym

Luxury Townhouse Near Disney | 3BR
Enjoy a brand new, beautifully designed townhouse located in the exclusive Magic Village community, just minutes away from Disney Parks. What you’ll love: • Private patio with outdoor furniture • Free Wi-Fi • Fresh towels & linens • Fully equipped kitchen • BBQ grill (no additional fee) • Free parking (no extra cost) The pool, tennis court and fitness center should pay $100 extra fee per group per day. ✨ Book now and enjoy a memorable stay near the magic!

Waterfront Wizarding Near Universal's Harry Potter
This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

Wonderfull home near Disney & FREE Waterpark 2421
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!

Lush Green Retreat 10 Min to Parks Pets Allowed
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 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Getaway w/ Private Pool & SPA + BBQ | 10min Disney
Welcome to your dream vacation home! Perfectly located in Emerald Island Resort, this charming single-story 4-bedroom, 3-bath villa offers comfort, space, and privacy for families. Enjoy a private pool with spa and BBQ grill under the Florida sun, plus an open-concept layout ideal for relaxation. Just minutes from Walt Disney World, restaurants, and shops. Plus full resort amenities with heated pool, spa, gym, and clubhouse!

4420 Le Reve 4BDRM townhouse close to Disney
Our townhouse can accommodate up to 10 people, with 4 bedrooms and 3.5 bathrooms and has a small jacuzzi for you to relax after a long day at the parks or outlets. Our property is only 10 miles to Disney’s theme parks and 15 miles to Universal Studio and major Outlets. It has many restaurants and supermarkets (Walmart, Target, Sam’s Club) nearby. Walmart Superstore is just 0.2 miles or 5 minutes walk.

NEW Bella Vida Resort 4/3 home minutes theme parks
Spacious 4/3 townhome located in Bella Vida Resort. Bella Vida Resort is an elegant Mediterranean-style community. Our lovely townhome is conveniently located next to US192, and near the Happiest Place on Earth Disney Theme Parks (~ 16 minutes) and Orlando’s world-famous outlets (~ 27 minutes). We will enjoy easy access to everything from this centrally located place.

Private Pool Home Near Disney | 4BR Sleeps 10
Modern designer home with private pool, perfect for families and groups near Disney. Sleeps 10 in 4 stylish bedrooms and features a chef-style quartz kitchen, elegant dining for 8, spacious living area, and a fun kids’ room. Located in a quiet upscale community just 20–25 minutes from Disney, with easy access to Universal and Orlando’s top attractions.

2186 Amazing Townhouse W/Pool Solara Resort
Welcome to your home away from home at Solara Resort! This stunning 3-bedroom, 3.5-bathroom townhouse is the ideal retreat for families and groups of up to 12 guests. With spacious bedrooms, a private pool, and all the amenities you could need, it offers the perfect combination of comfort and fun.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Luxurious five-bedroom villa with modern comforts

Pool+Game Room 10 min to Disney sleeps 10

Cozy House with Private Pool. Kissimmee/Orlando

Epic Luxe Home W/Free Water Park/ 10 Miles Disney!

Luxury Villa with Private Pool Near Disney World

Enchanting Storey Lake-FREE WaterPark-close to ALL

Brand-New Renovated 5BR Home at Storey Lake

Disney 6 bedroom Luxury Villa Arcade Pool Heat bbq
Apartment rentals with a pool

Great for Two Families • Sleeps 8 • Prime Location

Beautiful Lake View Condo. Close to Disney.

3191-103 Resort Lake View Disney Universal Orlando

Chic Disney Resort Condo • Pool Access Near Parks

1-310 Legacy Dunes - Heated Pool, Close to Disney

A 3BR Resort Style Divine Getaway Near Theme Parks

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

Comfortable Family Condo Disney Orlando Universal
Other holiday rentals with a pool

New and Unique Disney Airbnb!

Sunkissed Oasis 5 BR Home, Pool, Spa & Game Room

6BR Disney Villa | Pool, Spa & Theater | Sleeps 14

Amazing 3 bedroom getaway

New Themed home w/pool in Margaritaville Poco Loco

Magical Townhouse near Disney with private hot tub

Modern Luxury Kissimmee Retreat

Magical Stays Near Disney
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $197 SGD | $206 SGD | $221 SGD | $196 SGD | $172 SGD | $183 SGD | $192 SGD | $169 SGD | $156 SGD | $165 SGD | $186 SGD | $219 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 6,460 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 243,320 verified reviews to help you choose

Family-friendly holiday rentals
5,500 properties offer extra space & child-friendly amenities

Pet-friendly holiday 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 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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- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Camping World Stadium
- Magic Kingdom Park
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ICON Park
- Aquatica
- ChampionsGate Golf Club
- Tinker Field







