Vacation rentals with a pool in Celebration

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Celebration

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Cottage in Kissimmee

4.9 out of 5 average rating, 210 reviews

Be Our Guest Sandcastle Cottage 81

Located-Encore Tropical Palms RV Resort 5 min to Disney property and minutes away from various restaurants. Old Town and Fun Spot are right next to the property. New renovated floors just installed! (May 2023) Has private bedroom with queen bed and upstairs loft with 2 twin beds for the kids. Newer sofa and recliner and washer/dryer. Stainless Steel Appliances and granite tile counter tops in kitchen. Smart TV in living room. Resort style pool with kiddie area. Miniature Golf area. Free WiFi

Sep. 16 – 23

$160 CAD per night

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.

Sep. 22 – 29

$209 CAD per night

Guest favourite

Condo in Kissimmee

4.9 out of 5 average rating, 179 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

May 14 – 21

$167 CAD per night

Guest favourite

Condo in Kissimmee

4.99 out of 5 average rating, 153 reviews

Bright, Airy Home near Disney and Attractions

This top floor condo with tall ceilings is lofty, elegant, and fresh and it is located in one of the nicest communities in the area. Reunion is an oversized, private golfing resort that is exceptionally pristine, safe and quiet. It is situated only minutes from the Disney front gates and offers a welcoming retreat after a long day at the parks. Reunion is home to six beautiful pools that are accessible to all guests and the scenic views of three award winning golf courses.

Aug. 27 – Sep. 3

$241 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. 11 – 18

$161 CAD per night

Guest favourite

Townhouse in Kissimmee

4.97 out of 5 average rating, 175 reviews

Resort-style home close to Disney with jacuzzi

This beautifully decorated vacation home sits in the quiet and well located resort of Regal Oaks. The place offers all resort style amenities with the comfort of a home away from home to enjoy and relax. Enjoy your vacation at the outdoor private spa, have a nice homemade meal in the outdoor terrace, or let others take care of you in the resort restaurant in front of the pool, while kids enjoy the slides and resort activities. The Disney parks are 10 min away!

Mar. 5 – 12

$251 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

Guest favourite

Townhouse in Kissimmee

4.92 out of 5 average rating, 226 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

$205 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.

Feb. 28 – Mar. 7

$190 CAD per night

Guest favourite

Townhouse in Kissimmee

4.94 out of 5 average rating, 163 reviews

2 BR Harmony House and Regal Oaks Resort

Come get away to our modern, super-clean, self-contained garden oasis town house in the Regal Oaks Resort - close to grocery stores and take out food - minutes walk from Old Town Kissimmee and a short drive from Disney's ESPN - World of Sports and Town Center Celebration. Our private screened in hot tub is the perfect place to relax in the Florida sun or under our sun shade.

Aug. 25 – Sep. 1

$233 CAD per night

Guest favourite

Condo in Four Corners

4.99 out of 5 average rating, 148 reviews

Orlando Fun: Minutes to Disney and Margaritaville

A cozy, comfortable, and convenient 2-bedroom condominium with 2 full bathrooms, a fully-equipped kitchen (coffee and tea provided), a beautifully decorated living/ dining room, 2 walk-in closets (with plenty of shelves, drawers, and hangers), a washer, a dryer (with laundry detergent provided), an iron, AC (or heating in winter), cable TV, WiFi, and a screened-in balcony.

Sep. 7 – 14

$169 CAD per night

Guest favourite

Tiny homes in Kissimmee

4.89 out of 5 average rating, 234 reviews

Shells Cottage, beautiful decor, for 2 near Disney

This Shell themed one bedroom one bathroom cottage is fully equipped for your stay. From the upgraded kitchen appliances and floors, to the comfortable queen sized bed and comfortable sitting room, this cottage is perfect for honeymooners, vacationers and business travelers!

Sep. 6 – 13

$185 CAD per night