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.

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Guest favourite

Home in Kissimmee

4.85 out of 5 average rating, 220 reviews

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.

Guest favourite

Apartment in Kissimmee

4.97 out of 5 average rating, 175 reviews

Welcome to our Son Shine condo ....

Thank you for taking the time to look at our home. As you enter, our hope is that whether you are looking to escape the hustle and bustle of busy life or be close to area attractions (Disney (10 mins) Universal Studios, Walmart, Grocery Stores & various restaurants that you will be able to relax and enjoy the surroundings. Swim at the Tropical Landscape Pool, Kiddie Activity Pool or relax in the Whirlpool Spa & Fitness Center steps away from the condo. Our hope is you can relax and enjoy.

Guest favourite

Townhouse in Kissimmee

4.85 out of 5 average rating, 118 reviews

Family fun resort, close to Disney and more!

Check out LeggLife's video review of our unit: orlando vacation home review! disney touches abound. Enjoy our bit of heaven at the Terra Verde Resort; Trip Advisor Excellence Rating last 5 years in a row! Terra Verde Resort is a gated community with many ammenities: pool, playground, tennis, mini golf, theater room, exercise equipment, game room, and fishing too. Fun for the whole family or romantic getaway. Townhouse has a private hot tub on back patio too! Just minutes away from parks!

Guest favourite

Guest suite in Kissimmee

4.83 out of 5 average rating, 547 reviews

Private 2 bedroom w/bathrm in portion of POOL home

Hello travelers, we offer a portion of our home with a private entrance off the pool area. Your area has 2 bedrooms with queen beds and internet TVs and a private bathroom. The mini kitchen has a small refrigerator, a coffee maker, microwave and a bread toaster. Please note the pool is shared with my family and another set of travelers. We are happy to continue offering our apartment with a 5-star cleanliness rating. We offer our home to travelers only-we do not accept local reservations.

Guest favourite

Tiny home in Kissimmee

4.95 out of 5 average rating, 383 reviews

Sunny Tiny House Cottage near all Attractions!!

Our Tiny House in Mill Creek RV Resort is minutes away from Disney, Universal, Sea World & most area attractions. Our cozy cottage has vaulted ceilings, one bedroom, loft bedroom (40” high), full kitchen, dining table/chairs, living room, free washer/dryer, and the perfect front porch. There is a private drive and free parking. The resort is peaceful with plenty of amenities! We have four tiny house cottages - please check us out on Facebook under Tiny Mouse Houses to find the Airbnb links.

Superhost

Apartment in Kissimmee

4.86 out of 5 average rating, 171 reviews

Beautiful Resort-Style Condo with Waterpark!

JJC Vacation Home is a gated resort-style condo that has everything you need to have the best vacation! The condo is near all main attractions, fully equipped kitchen, a lazy river, water slides, pool, splash area, mini golf, fitness center, kayak/canoe rental, bar, food, and more! Our Star Wars theme room with *glow in the dark* stars wall will make you feel like you're floating in space! Complimentary coffee/tea station. Relax while having a cup as you look at the view from the balcony.

Guest favourite

Guest house in Orlando

4.87 out of 5 average rating, 250 reviews

Couples Oasis *Heated Pool* and Lake View

Have a romantic getaway in this SODO Couples Oasis Retreat with private pool or come work alone in this peaceful oasis. Perfect for couples or the busy profesional who want privacy and quiet with lake view while relaxing by the pool. Centrally located in SODO by downtown Orlando. Close to everything. Walk to great nearby eating places. Love ice cream Kelly’s Hand Made ice cream is a 5 minute walk from the house. *Heated Pool* available for $20 fee for first day and $10 every extra day.

Guest favourite

Tiny home in Kissimmee

4.9 out of 5 average rating, 101 reviews

Tiny House near DISNEY and UNIVERSAL!!!!

This cottage is one of the largest in award winning Mill Creek Resort w/ a King size bedroom, Full Kitchen, including Full size refrigerator, stove, oven, and dishwasher. Beautiful vaulted 9 foot ceilings, a sleeper sofa and lots of cabinetry. The sofa sleeper is also of higher quality. Not your average bar in the back sofa. The back "clicks to lay flat w the seat and the base pulls out and up from underneath. Pool, exercise room, shuffle board, and playground round out the amenities

Guest favourite

Rental unit in Orlando

4.88 out of 5 average rating, 115 reviews

Magical Adventure | Sea World. Fitness Room

Tru by Hilton Orlando Convention Center Hotel is off I-4, a mile from SeaWorld Orlando, the Orange County Convention Center, and Aquatica Orlando. Walt Disney World and Universal Orlando are about 10 minutes away. Attractions await you: ✔Disney’s magical kingdom ✔Marine life shows, waterslides, aquariums at Aquatica Orlando ✔Breathtaking sceneries at Lake Eola ✔Feeding the dolphins at SeaWorld Orlando ✔Tours at Universal Orlando Resort and see Harry Potters Hogwarts Castle

Superhost

Rental unit in Kissimmee

4.81 out of 5 average rating, 477 reviews

1BR w/Kitchenette near AdventHealth Orlando

A family holiday in the place where the magic begins. Melia Orlando Celebration is an oasis of comfort right next to the kingdom of dreams to be discovered with your family. Attractions await you: ✔Disney’s magical kingdom ✔Learn about space at Kennedy Space Center ✔Breathtaking sceneries at Lake Eola ✔Spend the day relaxing in the water and snorkeling with tropical fish at Discovery Cove ✔Take a tour at Universal Orlando Resort and see Harry Potters Hogwarts Castle

Guest favourite

Home in Kissimmee

4.91 out of 5 average rating, 311 reviews

Family Home minutes from Disney!

A Beautiful 2 Bed, 2 Bath home that is perfect for families going to any of the Disney parks and other central Florida attractions. Please enjoy the on-site washer/dryer, large fenced in back yard and screened in patio with grill during your stay. This home is in a quiet neighborhood minutes from Walt Disney, Sea world, Universal Studios, and many other attractions in Central Florida. Walmart and other convenience stores are also within a few minutes drive.

Guest favourite

Home in Kissimmee

4.96 out of 5 average rating, 133 reviews

Magical home! 15 minutes from all parks!

Meticulously clean home! 2 beautiful bedrooms & 2 full bathrooms. Large kitchen, washer/dryer and queen sleeper sofa in living room. Relaxing outdoor patio with Adirondack chairs. Private parking, WIFI and smart TV! Pickleball court, gym, pool, playground & shuffle board! Located 15-20 minutes from Disney parks, Universal Studios/Islands of Adventure & MCO airport. Perfect place for a family vacation, romantic getaway or work trip!