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

Home in Kissimmee

4.86 out of 5 average rating, 224 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.

Superhost

Villa in Kissimmee

4.89 out of 5 average rating, 102 reviews

Beautiful Home with Pool near Golf & Disney

This luxury 4 bedroom home with a private pool and waterview is located in the gated golf community of Remington, within 20 mins of all Disney Parks, Universal Studios and the Orlando Airport Perfect for 1 or 2 families with 2 master bedrooms with ensuites bathrooms and 2 additional bedrooms with 2 twin beds each and a shared bathroom. Each bedroom has a flat TV as well as a 55 " flat screen in the living area. Fully equipped kitchen, plus washer and dryer We welcome you to enjoy our villa!

Guest favorite

Guest suite in Kissimmee

4.83 out of 5 average rating, 551 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 favorite

Villa in Osceola County

4.99 out of 5 average rating, 101 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Guest favorite

Guesthouse in Kissimmee

4.9 out of 5 average rating, 115 reviews

Cozy 1BR apt-Pool/Tennis/Gym/Near attractions

Welcome to The Lopes Cozy Apt! We are delighted to have you. This gorgeous and safe garage/apt, has been renovated renovated and furnished in a peaceful neighborhood with great community amenities. Pack your bags and get ready to escape to NE Kissimmee, just 6 miles from MCO Airport, 12 miles from Sea World, 18 miles from Universal. Disney World is #1 in the US tourism, only 15 miles from the apt. adittionally Coco a beach Florida only 58 miles to get your sun kissed look.

Guest favorite

Tiny home in Kissimmee

4.94 out of 5 average rating, 160 reviews

Disney Tiny House Getaway!

Unleash your Orlando Holliday adventure in our captivating 1-bedroom + loft tiny house! Perfectly situated for thrilling escapades at Disney, Universal, and Sea World, it's just 15 miles from the heart of the action. Whip up culinary delights in the full kitchen, relax on the charming porch, and dive into resort-style amenities including a sparkling pool, brand new fitness center, exciting playground, pickleball court, and so much more. Your unforgettable getaway starts here!

Superhost

Tiny home in Kissimmee

4.93 out of 5 average rating, 299 reviews

Awesome 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, 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.

Guest favorite

Guest suite in Kissimmee

4.86 out of 5 average rating, 605 reviews

Private Studio in POOL home

Hello travelers! 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 to travelers.

Guest favorite

Home in Kissimmee

4.96 out of 5 average rating, 136 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!

Guest favorite

Cottage in Kissimmee

4.95 out of 5 average rating, 451 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.

Superhost

Home in Kissimmee

4.82 out of 5 average rating, 110 reviews

Beautiful Vacation Home With Private Pool.

Find your perfect vacation home with us!. With a private patio and pool, this 3 bedroom home is fully equipped. Based on GPS apps, Disney and Universal Studios are just 25 minutes away. Located in a quiet and peaceful neighborhood, the house is a perfect place to relax and it is close to local shopping, Walmart, dining and attractions. Sleeps 6+ guest in 3 bedrooms, the Master bedroom also has a private master bathroom.

Guest favorite

Home in Kissimmee

4.91 out of 5 average rating, 102 reviews

Entire Private Vacation Pool Home Near Disney

Welcome to our beautifully renovated home Central to everything Orlando and Kissimmee has to offer. Make memories with your family and friends in this private pool home featuring 3 bedrooms and 2 baths. Convenient check in and check out with our Keyless entry lock. Property is located in the gorgeous safe gated community of Cumbrian Lakes.