Accommodation with a pool in Osceola County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Osceola County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in Kissimmee

4.83 out of 5 average rating, 509 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.

21 – 28 Jan

$875 AUD total

Guest favourite

Home in Kissimmee

4.84 out of 5 average rating, 205 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, 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.

28 June – 5 July

$1,931 AUD total

Guest favourite

Condo in Kissimmee

4.9 out of 5 average rating, 179 reviews

Perfect Condo | Pool & Tiki Bar | 15 min. Disney

Perfect Space! Perfect Vibe! Perfect location! Perfect Price! Very close to DISNEY and H2O WATER PARK. Conveniently located in the gated Windsor Palms resorts with lots of restaurants and activities nearby. Tastefully furnished, top floor, two-bedrooms / two-bathrooms condominium (Quiet 3rd-floor unit). Included high-speed internet allows you to work while you are away. If you have a bigger party, check my other condo in the building by looking at Airbnb.com rooms/52778689

12 – 19 May

$1,372 AUD total

Guest favourite

Condo in Kissimmee

4.96 out of 5 average rating, 136 reviews

55B-DISNEY-STAR ISLAND, 1 BR DELUX-TENNIS/POOL/SPA

Parking & resort fees included. An Orlando Adventure with All the Extras. Star Island, a 5 star resort located Just 10 minutes from Walt Disney World®, offers so many fun on-site amenities and activities, it actually rivals the magic of Orlando itself. Enjoy the resort at a fraction of the cost of the parks. 2 pools, SPA's, Fitness center, Golf-Driving range, Tennis Courts, Basketball Courts, Pickle Ball courts, Volleyball courts, Water sports, Pool Bar, Ping Pong, Game Room.

1 – 8 May

$1,300 AUD total

Guest favourite

Condo in Kissimmee

4.94 out of 5 average rating, 109 reviews

Cheery 2BR Condo w/zero entry pool near Disney

Ideal location 15 minutes from Disney yet removed from the melee! **New Dishwasher** Second floor condo with fully equipped kitchen in gated community. Free WIFI and parking. Everything you need to have a magical Orlando holiday! King master bedroom, 2 twin beds in second bedroom, a queen sofa bed in living room. Private screened balcony facing lake to enjoy a tranquil moment. Community zero-entry pool, fitness center, game room, sports courts. Smoke and pet free.

14 – 21 Oct

$1,245 AUD total

Guest favourite

Cottage in Kissimmee

4.94 out of 5 average rating, 371 reviews

Entire Cottage close to Disney, Universal, Airport

A full cottage for 4! The perfect place stay. 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 out 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.

4 – 11 Dec

$1,127 AUD total

Guest favourite

Home in Kissimmee

4.9 out of 5 average rating, 294 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.

24 – 31 Aug

$1,472 AUD total

Guest favourite

Tiny home in Kissimmee

4.94 out of 5 average rating, 328 reviews

Blue Bungalow Tiny House 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 a private bedroom, full kitchen, large island, living room, bathroom, 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.

1 – 8 Apr

$1,305 AUD total

Guest favourite

Guest suite in Kissimmee

4.86 out of 5 average rating, 567 reviews

Private Studio in POOL home

Hello! We offer a portion of our home with a King sized bed, a large private bathroom with a Jacuzzi tub, and a Harry Potter play area accessed by rock climbing wall. The mini kitchen has a microwave, bread toaster, coffee maker, and refrigerator. There's an internet TV in the apartment with access to Prime. The pool and garden areas are shared with my family and another set of travelers. We are happy to offer our studio with a 5-star cleanliness rating.

5 – 12 Dec

$898 AUD total

Guest favourite

Cottage in Kissimmee

4.96 out of 5 average rating, 421 reviews

Bright & Cozy Cottage Near Disney

My place located within 10 miles of: Disney World, Celebration, Universal, Water Parks, Old Town & Fun Spot USA's More than 70 Restaurants and Dining, Gifts Shop. My place is good for couples, solo adventurers, business travelers, and families (with kids). You’ll love my place because of In Our Cozy and Comfortable Sand Castle Cottage You'll discover that perfect Mix of High-Energy Fun and Laid Back Florida Lifestyle Right Here.

28 July – 4 Aug

$1,341 AUD total

Guest favourite

Apartment in Kissimmee

4.83 out of 5 average rating, 116 reviews

Spacious Apartment near Disney

Welcome to our charming apartment in the heart of The Loop, Kissimmee! Perfectly situated to offer you the ultimate convenience and a comfortable stay, this delightful accommodation is an ideal choice for couples, solo adventurers, extended stay, and business travelers. Whether you're in town for a magical Disney vacation, a business trip, or a romantic getaway, our apartment provides the perfect home base for your adventures.

20 – 27 July

$1,745 AUD total

Guest favourite

Cottage in Kissimmee

4.93 out of 5 average rating, 193 reviews

Tiny house, BIG FUN!!! Close to parks and shopping

Tiny House, BIG fun!!! Experience tiny house living in this super cute, newly re-decorated cottage. This tiny house has everything you need to enjoy your vacation - even a full kitchen!! Relax on your own private porch or take a dip in the heated saltwater pool after a day at the parks. This tiny house is conveniently located close to parks, airport and shopping!!!

28 Sept – 5 Oct

$1,071 AUD total