Vacation rentals with a pool in Kissimmee

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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

Home in Kissimmee

4.86 out of 5 average rating, 226 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 favorite

Condo in Kissimmee

4.97 out of 5 average rating, 181 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 favorite

Tiny home in Kissimmee

4.9 out of 5 average rating, 104 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 favorite

Guesthouse in Kissimmee

4.89 out of 5 average rating, 117 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, 161 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!

Guest favorite

Townhouse in Kissimmee

4.86 out of 5 average rating, 360 reviews

GORGEOUS 3BD RESORT, CLOSE TO DISNEY

Search no more ! this beautiful townhome has everything you're looking for. our number one priority are the guest because we want them to have a memorable experience that would last a lifetime. very close drive to disney, restaurants, supermarkets, souvenir shops, highways! Gorgeous newly renovated suite w/ fully equipped kitchen & all the essentials sitting in a cozy townhome w/ pool, hot tub, kids pool, clubhouse w/ gym, bbq area, free parking in front of the unit.

Guest favorite

Home in Kissimmee

4.96 out of 5 average rating, 137 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

Condo in Kissimmee

4.98 out of 5 average rating, 173 reviews

Modern Apartment with lake view Close to Disney

New, modern-style apartment with a beautiful lake view is located in the heart of the best attractions Orlando and Kissimmee has to offer. Disney World, Universal Orlando, and Sea World attractions are all located within minutes from my apartment. All guests will have access to enjoy the fantastic resort-style Hideaway Clubhouse. Nearby, you will also find restaurants and bars, and shopping malls to enjoy during the day and night.

Guest favorite

Cottage in Kissimmee

4.95 out of 5 average rating, 453 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.

Guest favorite

Cottage in Kissimmee

4.95 out of 5 average rating, 438 reviews

Entire cottage for 5, close to Disney, Universal!

Great cottage for 5, come stay! One bedroom with a adjustable com-fee queen bed, and a 19" flat screen TV. Loft 1 queen, 1 twin, don't bump your head. Located only minutes from Disney and Universal. Heated pool! Our place is completely updated, new furniture , appliances etc. we also have on property three other cottages Bitty Bungalow. Bitty Bliss, and the Bitty blossom. All are Smoke free, pet free.

Superhost

Townhouse in Kissimmee

4.82 out of 5 average rating, 148 reviews

Disney Getaway | Lake Berkley Resort | Pool | 6ppl

The resort pool has opened back up! Spacious 3/2.5 townhome located in beautiful Lake Berkley Resort! Lake Berkley is a gated Vacation Home Community and Resort, within easy reach of the US 192 corridor, where you will find all sorts of restaurants and shopping, and within 15 minutes of Disney and about 20 minutes to Sea World, Universal Studios, and all other Kissimmee, Orlando attractions!

Guest favorite

Guest suite in Orlando

4.97 out of 5 average rating, 435 reviews

Vacation & Oasis Mood with #1 location - Pool

From our family to you, we are welcoming you in our Home into our private Orlando, Florida, Oasis :-) Located a very short commute to some of the world most famous tourist attraction, Disney & Universal studio to the privacy of our fully equipped Guest area. We want to make sure that your stay to our home will be memorable and we want to see you again :-)