
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.

Virtual Reality | Simulators | Pool | Disney 20min
Happy 2026 from Kissimmee! Westside Villa has just a few openings - snag it while you can! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charge on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs; dedicated work space -2 pack-n-plays, highchair, strollers, wagon -Resort access: lazy river, splash pad, tiki bar, fitness center Arriving early in the day or leaving late? Ask about our half day add-on, if our cal

Near Disney Gated LakeView Pvt Heated Pool
LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

Enchanted Villa with Lake View 6-Bedroom in Resort
In the exclusive Lake Berkley Resort, this magical manor is a spacious 6 bedroom, 3.5 bathroom home with private pool & spectacular lake views. A 10 minute drive to Disney World, 15 minutes to Sea World and 20 minutes to Universal’s Wizarding World of Harry Potter. Ensure an immersive experience at this thematic home, perfect for families & groups of friends looking to cook in the well stocked kitchen, enjoy meals together in Great Hall or patio by the pool and watch movies & more in the Common

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!
Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

Private Pool & Free Heat - Close to Disney!
3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms

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

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

Near Disney | Heated Pool, King Bed, Arcade
✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

Luxury Villa! /Game Room/ Pool Heater
Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

Modern 4bdr Storey Lake w/themed rooms near disney
Have fun with the whole family at this stylish place: themed bedrooms and a peaceful feeling. With Disney just 5 miles away and Universal Studios 15-20 minutes away, the resort offers endless fun. Storey Lake Resort also has many nearby shopping malls and dining options. From its resort-style pool, splash pad, and watersides to its clubhouse, poolside bars, fitness center, and lake-based activities, Storey Lake is the happy ending to your vacation rental search.

Amazing House near Disney!
This home is only 30 minutes away from the world renowned Disney World theme parks and 15 minutes from Sea World and Orlando Premium Outlets. Major SuperMarkets such as Walmart, Target or Publix are just a few minutes away. Enjoy our amazing Club House with all it has to offer such as resort style pool, fitness center, jacuzzi and lazy river only a block away. Adults can enjoy the outdoor Tiki bar while ordering your favorite food poolside!
Popular amenities for Kissimmee rentals with a pool
House rentals with a pool

Game Room/HeatedPool/Piano Upscale Waterfront Home

Villa Resort Club

Disney Retreat | Huge Pool with Spa | 2 King beds

Modern Luxury 5BR Pool Movie+Game Rm @Encore 7770

Private Pool, Spa and Games Room - 16009

Wheelchair Accessible Home | ADA Bath + Pool Lift

2362 SW 6BD - Amazing Sunny Pool - Near Disney

Boho Luxe Retreat • Near Disney Parks
Condo rentals with a pool

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Stylish Condo 20 mins to Disney/King Bed

Magical Stay Near Disney & ESPN

Resort Style Sunshine Oasis near Theme Parks

202_Magical and Cozy 2BR minutes from Disney

Stunning view, near Disney.

Chic Disney Resort Condo • Pool Access Near Parks

Luxurious Spot 10 Mins Away to Most Attractions!!!
Other vacation rentals with a pool

Magic Stay near Disney

Epic stay at Vista Cay!

Upstay-Luxury 3BR Home w Private Pool & Games Room

Disney Getaway, Hot Tub, 10 min to Parks, 6 people

WaterView 4 miles to Disney 3Br 2Ba Pool Home

Modern Luxury Kissimmee Retreat

Luxury 4 Bedroom Home - Resort Access! Disney!

4BR/3BA Townhouse w/ Private Pool in Storey Lake
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$30,706 GYD | G$31,124 GYD | G$32,586 GYD | G$31,959 GYD | G$27,990 GYD | G$29,870 GYD | G$31,332 GYD | G$27,573 GYD | G$25,484 GYD | G$26,946 GYD | G$30,288 GYD | G$35,719 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$4,178 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
- Tampa Vacation rentals
- Four Corners Vacation rentals
- Key West Vacation rentals
- Tampa Bay Vacation rentals
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- Vacation home rentals Kissimmee
- Cabin rentals Kissimmee
- Rentals with a kayak Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a home theater Kissimmee
- Guesthouse rentals Kissimmee
- Mansion rentals Kissimmee
- Rentals with breakfast Kissimmee
- Hotel rooms Kissimmee
- House rentals Kissimmee
- Rentals with lake access Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Beach house rentals Kissimmee
- Rentals with an accessible height bed Kissimmee
- Lakehouse rentals Kissimmee
- Tiny house rentals Kissimmee
- Family-friendly rentals Kissimmee
- Rentals with a washer and dryer Kissimmee
- Pet-friendly rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Waterfront rentals Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with an EV charger Kissimmee
- Rentals with outdoor seating Kissimmee
- Serviced apartment rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Apartment rentals Kissimmee
- Condo rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Resort rentals Kissimmee
- Private suite rentals Kissimmee
- Villa rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with beach access 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
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Give Kids the World Village
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Shingle Creek Golf Club
- Universal's Islands of Adventure






