
Vacation 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.

Private Rooftop Suite! No resort fees!
Enjoy a stylish experience at this centrally-located rooftop terrace. Located at the Enclave Suites, this unit features a rooftop terrace with views overlooking Sandy Lake. Recently remodeled, it boasts practical functionality with beautiful design. This unit is everything you need to enjoy a vacation in Orlando. It is centrally located off of International Drive and minutes from Universal Studios, Volcano Bay, SeaWorld, Disney World and much more. Enjoy a luxurious stay without the hefty price.

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!

3 bedroom Villa in Kissimmee
The villa is in a residential area within a 5-min drive to local amenities including, a pharmacy, 3 supermarkets and 2 gas stations. The property is between 15 - 40 mins drive from Disney, Epic Universe, SeaWorld, Gatorland & Universal Studios. Orlando International Airport is only about 17 mins drive away. Osceola Heritage Park, the home of the world’s largest collector car auction is only 4 mins drive from the villa. The Florida Turnpike that runs through Miami is 6 mins from the property.

Resort Style Sunshine Oasis near Theme Parks
Discover Orlando's charm at our resort-style oasis in a gated community with lots of amenities! Nestled near Disney, this modern haven features 2 stunning pools for ultimate relaxation. Delight in nearby restaurants, perfect for foodies. Families will love the kid-friendly atmosphere, and fitness enthusiasts can stay active in the on-site gym. Our clean, contemporary design ensures a comfortable stay, making it an ideal choice for your Orlando getaway. Conveniently located on the first floor.

Adorable 2 bdr lakefront w/jacuzzi 5 min *Disney*
This townhouse provides an open main living space that allows you to connect the dining and a fully equipped kitchen. The house can accommodate up to 6 guests, divided into one luxe king en-suite, and a design theme two full en-suite. After a long day at the parks with a beautiful lakefront view, relax in your private spa. Clubhouse with a gym, amazing heated pool, pool bar, a restaurant, and only 5 min from Disney and golfing area Free Parking Close to lakes, camping, beach, vineyards, farms

Disney Home! Heated Pool/Spa•Arcade•Gated Comm•4BR
This gorgeous private heated pool/Spa home in a gated community is perfect for families, and groups. Located close to major theme parks. Only a short drive from Disney, Universal and the all new Epic Universe! Relax in your own private heated pool & hot tub or enjoy the heated clubhouse pool complete with a water slide, kids splash pad and personal workout center, all within walking distance. Make memories in your private arcade room with a ping pong table, air hockey table and arcade games.

13 Minutes To Disney, King Size, No Fees, Pool
- No Airbnb Service Fees -Weekly & Monthly discounts! - 3 bedroom, 3 bath townhome located in the heart of Disney. Gated Community. Pool. Gym. - Disney property (13 minutes), Disney Springs (20 min), Universal Studios (25 minutes), Sea World (24 minutes), Convention Center (17 minutes) - 5 minutes shopping, attractions and dining - Professionally maintained to give you and your family the best guest service experience - Movie Room - 75" flat screen TV - Fully stocked with all essentials

Stunning Orlando Condo 3 BR/2 bath, pets OK
This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Cozy Orlando Area Cottage - 4 Miles to Disney
With Disney, popular attractions, restaurants, shops, and famous southern sunshine just minutes from your doorstep, we welcome guests to our cozy cottage for your vacation getaway. Our 1 bedroom, 1 bath cottage boasts modern amenities and entertainment options to help you relax during your stay. The cottage is located in a quiet, gated, resort community. Community amenities include an outdoor pool, hot tub, mini golf, game room, fitness center, planned activities, and tennis court.

Chic Vibes Comfy King Bed Next to Parks/Food/shops
Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

It's too much like a elegant mini-hotel (5)
It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless friendly and courteous guests from Brazil. We will always welcome you!

Gorgeous 3 bed, 2 bath villa w/ pool and jacuzzi
Gorgeous 3 bedroom, 2-bathroom villa set on a 1/4 acre of land, with our own screened, private, heated swimming pool & Jacuzzi, and high speed internet. Situated in a quiet residential community on the sought after Sunridge Woods in Davenport, only 9 miles from Disney. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

3BR / 2BR Heated Pool Home 7 Min to Disney |

South Facing Pool Home! 5 Miles from Disney

10 Min to Disney • Cozy Townhome + Jacuzzi + BBQ

Harmony Place - W/ Pool - Near Walt Disney

Mickey and Donald

Disney New Neighbor

*Pool-Jacuzzi & Palm Trees/ 8 Universal/ 15 Disney

Kissimmee/20 min to Disney/Private Heated Pool
Condo rentals with a pool

New Lovely 3-bedroom Condo 5 minutes from Disney’s

Near Disney/Universal Lovely 2bedroom/2bath Condo

202_Magical and Cozy 2BR minutes from Disney

Modern Lake view Condo 1 mile from Disney

Luxurious Spot 10 Mins Away to Most Attractions!!!

Newly Updated 2BR/2BA Luxury Unit at Storey Lake

*NEW* Adventureland Stay / Sleeps 6 / Near Disney

SL106 - Modern Condo - Resort Access included
Other vacation rentals with a pool

Relax in Cozy Apt 1/1 near to Disney

Waterfront 2BR home close to Disney

Disney Area! Modern Luxe King Villa! Resort Pool!

Family Vacay with Pool near WDW!

Serene 4BR Pool Home Near Disney

Amazing 3 bedroom getaway

Enchanting Escape|Private Hot Tub|Near Disney

Disney’s Epic Poolside Paradise!
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$30,518 GYD | G$30,934 GYD | G$32,387 GYD | G$31,764 GYD | G$27,820 GYD | G$29,688 GYD | G$31,141 GYD | G$27,404 GYD | G$25,328 GYD | G$26,989 GYD | G$28,858 GYD | G$34,048 GYD |
| 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 vacation rentals with a pool in Kissimmee

Total vacation rentals
Explore 6,620 vacation rentals in Kissimmee

Nightly prices starting at
Kissimmee vacation rentals start at G$4,152 GYD per night before taxes and fees

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

Family-friendly vacation rentals
5,800 properties offer extra space & kid-friendly amenities

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

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

Wi-Fi availability
6,590 of Kissimmee vacation rentals include wi-fi 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
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Key West Vacation rentals
- Tampa Bay Vacation rentals
- Rentals with an accessible height toilet Kissimmee
- Rentals with beach access Kissimmee
- Cabin rentals Kissimmee
- Rentals with a home theater Kissimmee
- Rentals with a kayak Kissimmee
- Pet-friendly rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Rentals with a fireplace Kissimmee
- Private suite rentals Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with a sauna Kissimmee
- Beachfront rentals Kissimmee
- Apartment rentals Kissimmee
- Rentals with breakfast Kissimmee
- Hotel rooms Kissimmee
- Rentals with an accessible height bed Kissimmee
- Serviced apartment rentals Kissimmee
- Guesthouse rentals Kissimmee
- Mansion rentals Kissimmee
- Tiny house rentals Kissimmee
- Beach house rentals Kissimmee
- Condo rentals Kissimmee
- Rentals with lake access Kissimmee
- Vacation home rentals Kissimmee
- Resort rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with an EV charger Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- House rentals Kissimmee
- Villa rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with outdoor seating Kissimmee
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with pools Osceola County
- Rentals with pools Florida
- Rentals with pools United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Give Kids the World Village
- Walt Disney World Resort Golf
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Discovery Cove
- Magic Kingdom Park
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Epcot
- Old Town
- Kia Center
- Reunion Resort Golf Courses - Palmer & Watson
- Universal's Volcano Bay
- Aquatica
- Bluegreen Vacations Fountains, Ascend Resort Collection
- Disney's Hollywood Studios
- Island H2O Live!
- ICON Park
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club






