
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.

Mickey's Lakefront Villa at Sunset Lakes
Updated Pics Dec 2024. We have no gas burning appliances. We abide by the AirBnB enhanced cleaning protocol. We want our guests to be happy, healthy and safe in their home away from home. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

3121-402 Resort Lake View Disney Universal Orlando
Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 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!

❤NEW Gorgeous 5br/3.5ba|POOL| Game ROOM| Disney
Nestled in the peaceful 4 Corners community close to Disney & top rated attractions, Target, Publix & restaurants. Newly updated, inviting and modern 2 level, 5 bedroom/3.5 bath with comfortable luxurious beds! Equipped with a private pool (heat for an extra fee), game room, BBQ grill & free Nespresso. Out back is a mini golf putting green, corn hole and fire pit for the family to gather around under the warm vibe of string lights. A place for the family to retreat, relax, reset and have fun!

Modern House with Private Pool Getaway Kissimmee
This property is accommodated for families looking to vacation with peace of mind, the facilities are perfectly arranged so that you and your family feel at home. It has 3 rooms equipped for adults and children, the patio area is the perfect place to spend time with your family either in the pool or enjoying a barbecue on the grill.( POOL IS NOT HEATED) -No parties allowed in the house. No smoke. Do not park blocking the sidewalk, no park on the grass, nor in front of the neighbors' house.

Epcot Themed Home: Private Sunset Near Disney
LOCATION! LOCATION! LOCATION! Hello all my globetrotters! Our fun home features a diverse international culture in each room. Experience Italy in the kitchen, America in the living room, Japan in the game room, and sleep in Paris, China or Morocco bedrooms. In the backyard, Mexico awaits with amazing private pool and a glow party at sunset each night. Depend on traffic, between 10-20 min to Disney, fast WiFi, ample natural light, tons of nearby grocery stores, restaurants, and shopping

Awesome Vacation Home w/ Private Heated Pool/Spa
Sunshine living at its best! The Abbey at West Haven is an enclave of exclusive vacation homes. This gem has been totally redesigned and upgraded for your vacationing pleasure and is the IDEAL choice for your next family vacation or getaway in Central Florida. Stores, restaurants and golf courses are all within 5 mins and Disney just 15 mins away. After a long day at the Theme Parks or a round of golf, relax at the private, pool and spa or enjoy a BBQ on the enormous covered patio.

Luxury Encore Pool Spa Pets Game Rm Theater Gym
Amazing Brand New Modern Luxurious Home at Encore Resort @ Reunion. PET-FRIENDLY & Minutes to all Theme Parks. BRAND NEW HOME. Private Pool & Spa / Game Room / Movie Theater / Gym / Massage Chair / Fireplace / PS5 / Board Games & Much Much More Embrace the extraordinary and book your stay at our home, where luxury, entertainment come together for an unforgettable vacation experience. ** Please review the rules before booking. Waterpark access is not included. **

Bungalow cottage close to Disney Universal, for 4!
A full cottage for 4! The perfect place. Located just 20 minutes from Disney and Universal. Shopping and Restaurants are less than 5 minutes from the cottages. All new furnishings, fresh linens, fresh paint! Privately owned. This cottage is our favorite!!! We also just updated the A/C. Check our unit. We also have three other cottages on property, the Bitty Bungalow, Bitty Bliss, and the Bitty Blossom. All cottages are within 70 yards of each other

Luxurious Private Retreat w/Spa & Saltwater Pool
This is a beautifully furnished vacation home near all Disney theme parks, several great golf courses and a 5 minute drive from restaurants and shops. The home sleeps 8 people and has four good sized bedrooms and two full bathrooms. We take pride in our home. We have an updated kitchen, wood/tile flooring through out the home and are constantly making improvements based on the time our family uses the house and feedback we receive from guests.

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**

*NEAR DISNEY* 6 GUESTS... LOTS of Amenities
It's all about location! Our stylish yet cozy, recently renovated vacation spot. Features 3 bedroom, 2 full bathrooms, which consists of 1 king size bed, and 4 twin beds. Luxury feel, premium everything. Comfortably accommodates up to 6 guests. Conveniently located near Disney World. About 15 minutes away from Disney Springs and Premium outlets! Major parks, restaurants, supermarkets, Target and Walmart are within a short drive.

Tropical Cottage
Cozy, Rustic and very private Cottage with its own washer and dryer, it's centrally located, just minutes from all major theme parks, attractions, restaurants, and much more. Only 4 miles to Disney. Nice Manufacture home with rustic and country touches in the beautiful Encore Sherwood Forest, a community full of tranquility with a stunning poll to enjoy and relax.
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Cozy House near Disney.

Nice pond view home with pool and outdoor theatre!

Manor on Knottingham Near Disney

Disney 6 bedroom Luxury Villa Arcade Pool Heat bbq

Haven Luxe

Heated Pool 15 Minutes to Disney PS5 l Switch

Gorgeous Florida Getaway in Central Location!

Dreamy Waterside Villa | Heated Pool & Near Disney
Condo rentals with a pool

Disney Oasis by the lake

Maria Luz Studio-Huge Terrace/Universal area.

Modern, spacious, and relaxing!

Stunning view, near Disney.

Modern Lake view Condo 1 mile from Disney

Luxurious Spot 10 Mins Away to Most Attractions!!!

BRAND NEW CONDO- 2 BR 2 Bath-Great location!

Themed Resort Condo | Pool | Spa | Mins to Disney
Home rentals with a private pool

Wr001or (1stfororlando)

Disney's Championsgate: Private Pool & Arcade Fun!

Beautiful 9 Br Pool Home In the Solterra Resort!

7547oml-Solterra Resort

115ep- West Haven

Airy, Stylish Home with Pool Heat Included in Davenport

Visit Disney World from a Sunny Home with a Pool

The Manors at Westridge Home W/ 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 | $206 CAD | $208 CAD | $218 CAD | $214 CAD | $187 CAD | $200 CAD | $222 CAD | $194 CAD | $176 CAD | $182 CAD | $194 CAD | $229 CAD |
| 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 6,590 vacation rentals in Kissimmee

Verified guest reviews
Over 234,830 verified reviews to help you choose

Family-friendly vacation rentals
5,770 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 1,010 rentals that welcome pets

Rentals with dedicated workspaces
3,650 properties have a dedicated workspace

Wifi availability
6,440 of Kissimmee vacation 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
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- SeaWorld Orlando
- Disney Springs
- Discovery Cove
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Magic Kingdom Park
- Epcot
- ESPN Wide World of Sports
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Walt Disney World Resort Golf
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure
- Kissimmee Lakefront Park
- Ventura Country Club
- Shingle Creek Golf Club

