Vacation rentals 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 favorite

Guest suite in Kissimmee

4.83 out of 5 average rating, 513 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.

Jan 17 – 24

$58 per night

Guest favorite

Apartment in Kissimmee

5.0 out of 5 average rating, 8 reviews

Stylish Retreat w/ 2 Queen Beds-Pool-Gym-Game Room

You'll fall in love with this CLEAN, beautifully decorated apartment in the heart of Kissimmee (The Loop!), mins from Disney and Universal. Greeted with snacks in your fully-equipped kitchen, you'll make yourself at home quickly in this spacious pad that's perfect for families. With a studio-style living/bedroom and a private bedroom, enjoy fresh white linen, a shower/soaker tub, and lux essentials. Sunbathe by the pool, hit the gym/yoga studio, then watch your fur baby at the pet park.

Jun 24 – Jul 1

$94 per night

Guest favorite

Guest suite in St. Cloud

4.93 out of 5 average rating, 137 reviews

Cypress Lodge w/ Pool & Theater

This prime location is a 30 min drive to the airport, a 35-45 min drive west to major attractions including Disney, Universal, SeaWorld, and gator parks and a 45-60 mim drive east takes you to the stunning Atlantic beaches and the Space Coast. After your adventures, recharge at a serene 12-acre nature retreat that boasts of cypress wood walls and vaulted ceilings. Relax in the pool and transform the family room into your own movie theater! (Unapproved parties/events will not be allowed)

Aug 16 – 23

$148 per night

Guest favorite

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.

Apr 21 – 28

$103 per night

Guest favorite

Condo in Kissimmee

4.9 out of 5 average rating, 180 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

Jul 21 – 28

$91 per night

Guest favorite

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.

Jul 30 – Aug 6

$83 per night

Guest favorite

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.

Oct 28 – Nov 4

$85 per night

Guest favorite

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.

Jul 7 – 14

$65 per night

Superhost

Apartment in Kissimmee

4.82 out of 5 average rating, 229 reviews

☆ SPECTACULAR CONDO ☆ only 4 Miles to Disney!

Dazzling Condominium and Amazing location: Cozy modern decoration, newly renovated, cleanliness is our priority, fully equipped kitchen, Air Fryer, The open-concept living room , receives ample lighting through the large windows that overlook the balcony. Gated community with elevator, pool, gym, BBQ areas, parking included. 4 miles to Disney. With various dining destinations nearby. No additional resort fees : : Enhanced cleaning protocol : :

Nov 21 – 28

$102 per night

Guest favorite

Townhouse in Osceola County

4.98 out of 5 average rating, 54 reviews

Amazing townhouse near Orlando theme parks

Welcome! This is your place to gather, relax and enjoy, near everything! Orlando theme parks are only between 6 to 20 miles away, and other attractions for all ages and preferences are also nearby. This spacious 4 beds and 2.5 baths home is fully equipped. It is also family friendly, so you will have the basic items for your children's stay. We are sure that you will experience a cozy ambience and that you will enjoy your stay here!

Sep 26 – Oct 3

$105 per night

Guest favorite

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.

Sep 17 – 24

$85 per night

Guest favorite

Cottage in Kissimmee

4.93 out of 5 average rating, 196 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!!!

Aug 15 – 22

$79 per night