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.

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Guest favorite

Cottage in Kissimmee

4.98 out of 5 average rating, 137 reviews

Runaway Beach Resort Pet Friendly: Magic Kingdom

Welcome to our 2/2 PET FRIENDLY villa just 8 minutes to Disney! Nearby you will find Lake Buena Vista Outlets, Universal Studios, Disney Springs, Old Town, restaurants and more! Stay includes: Disney Costumes Wi-Fi Washer/Dryer Free Parking Access to shuttle to Disney 4 pools including kids area/Calypso Cay Pools withTiki Bar 24 HR Gym, Volleyball/Basketball Court Mini Putt Putt Kids items available upon request. Strollers, etc. Small Pet Fee added for fur friends with complimentary pet food.

Dec 12 – 19

G$28,478 GYD per night

Superhost

Apartment in Kissimmee

4.78 out of 5 average rating, 99 reviews

Awesome charming decor near Disney up to 9 guests!

PLEASE FIND SOME TIME TO READ CAREFULLY OUR LISTING, EVERYTHING IS DETAILED SO YOU WILL KNOW EXACTLY WHAT WE’VE PREPARED FOR YOU AND YOUR GUESTS! WIll BE AMAZING HOSTING YOU ! 1700' in this beautiful and professionally decorated property! We really worked hard to provide the best in comfort, space and relaxing atmosphere to our guests. Every square inch was thought to offer the best of being close to the Florida's theme parks and at the same time having everything you would want at home.

Sep 14 – 21

G$14,135 GYD per night

Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 117 reviews

Perfect for Disney escape/first floor

Our condo is located on the first Floor at resort-style community (with No Resort FEES and FREE parking) with a nice clubhouse featuring a game room, fitness center and outside, a tranquil free-form heated pool with plenty of deck chairs for all the vacationers. This resort also features a second pool, golf cage, tennis, basketball and volleyball courts, a playground, carwash area, picnic pavilions and grills, and scenic walking trails around landscaped wooded areas, fountains and ponds.

Sep 18 – 25

G$23,046 GYD per night

Guest favorite

Cottage in Kissimmee

4.94 out of 5 average rating, 370 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.

Jun 17 – 24

G$20,633 GYD per night

Guest favorite

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.

Sep 23 – 30

G$24,310 GYD 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.

Aug 28 – Sep 4

G$19,642 GYD per night

Guest favorite

Home in Kissimmee

4.97 out of 5 average rating, 110 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!

Feb 2 – 9

G$23,040 GYD per night

Guest favorite

Townhouse in Kissimmee

4.92 out of 5 average rating, 225 reviews

Beautiful Farm House Decor near Disney, Sleeps 6

Welcome to our beautifully decorated 2-store Townhouse only 6 miles away from the Disney Parks and many other attractions. You will have the entirely house for yourself and your family while enjoying your vacation in Florida. We have sought to equip our home to a high standard and to anticipate your needs for a luxurious stay. We truly believe that our home is special based on 4 main reasons: Location, Security, Decoration and Comfort.

Sep 18 – 23

G$24,196 GYD per night

Guest favorite

Cottage in Kissimmee

4.96 out of 5 average rating, 420 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.

Mar 20 – 27

G$24,018 GYD per night

Guest favorite

Apartment in Kissimmee

4.83 out of 5 average rating, 115 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.

May 14 – 21

G$23,459 GYD per night

Guest favorite

Tiny home in Kissimmee

4.93 out of 5 average rating, 104 reviews

Tiny House Vacation Home Near Disney & Universal

Located in the family friendly Mill Creek RV Resort. This tiny home is the perfect place to stay while visiting the Orlando area. Located close to the LOOP with shopping, entertainment, and restaurants and within 15 miles of both Walt Disney World and Universal Studios. Less then 10 miles from MCO airport.

May 23 – 30

G$18,339 GYD per night

Guest favorite

Tiny home in Kissimmee

4.95 out of 5 average rating, 144 reviews

Disney Tiny House Getaway!

Discover your dream Orlando escape in our 1-bedroom + loft tiny house! Ideal for Disney, Universal, and Sea World adventures, it's only 15 miles from major attractions. Enjoy a full kitchen, cozy porch, and resort amenities like a pool, fitness center, and playground. Book now!

Oct 2 – 9

G$19,250 GYD per night