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 favourite

Cottage in Kissimmee

4.98 out of 5 average rating, 140 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.

Aug. 3 – 10

$216 CAD per night

Guest favourite

Condo in Kissimmee

4.97 out of 5 average rating, 160 reviews

New Lovely 3-bedroom Condo 5 minutes from Disney’s

This is a totally remodel Beautiful Condo! Nice small community with heated pool, fitness center, barbecue area, tennis courts in a quiet private park like setting! Enjoy breakfast on a comfortable screened balcony overlooking a serene conservation area. This 3/2 First floor condo is in a perfect location, just 5 miles from Disney World with lots of shopping & restaurants close by...for golfers, the property is surrounded by lots of beautiful courses, don't delay schedule your Vacations today!

Sep. 23 – 30

$186 CAD per night

Guest favourite

Condo in Kissimmee

4.91 out of 5 average rating, 110 reviews

Modern Storey Lake Resort Disney Orlando 3171-206

Minutes from Disney, stylish & modern 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. Enjoy our pond view from the balcony. Master suite has a King bed & 55" TV. Second bedroom has a Queen bed & a Twin bunk bed. The open floor plan blends Kitchen, Dining and Living room. Close to outlet malls & retail stores. Great amenities: Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop.

Sep. 19 – 26

$217 CAD per night

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.

Mar. 8 – 15

$204 CAD per night

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.

May 1 – 8

$166 CAD per night

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.

Oct. 12 – 19

$161 CAD per night

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.

Aug. 13 – 20

$153 CAD per night

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.

Sep. 5 – 12

$187 CAD per night

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.

Nov. 18 – 25

$115 CAD per night

Superhost

Townhouse in Kissimmee

4.79 out of 5 average rating, 222 reviews

Perfect home near Disney, Affordable & Comfortable

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.

Nov. 11 – 16

$189 CAD per night

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.

Sep. 10 – 17

$174 CAD per night

Guest favourite

Condo in Kissimmee

4.91 out of 5 average rating, 372 reviews

Newly Renovated 3/2 close to Disney parks

Recently renovated 2019 stylish villa just minutes away from major attractions such as Disney, Universal, SeaWorld and world-famous Orlando outlets. All these attractions are within 16-26 minute’s drive. Spacious home on the second floor with large windows and living area. It also features a private balcony outside of your master bedroom. Fully furnished with all the amenities for your enjoyment.

Dec. 1 – 8

$185 CAD per night