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

Condo in Kissimmee

4.92 out of 5 average rating, 239 reviews

Minutes To Disney World - Sparkling Clean Condo

Super clean newly renovated condo in Kissimmee, FL 🚗 15 minute drive to Walt Disney World 🚗 25 minute trip to Universal Studios 👮‍♀️Gated community with 24/7 security on site. 👨‍🍳 Full kitchen with everything you need 🧺 Washer/dryer in unit 💻 Fast wi-fi and smart tv's with access to netflix/hulu and cable. 🏊‍♂️ Zero entry heated swimming pool 💪🏼 Full Gym, basketball, tennis courts and walking trails. 🥇Airbnb Superhost We would love to have you stay! Book this Orlando condo Today!

Guest favorite

Cottage in Kissimmee

4.9 out of 5 average rating, 115 reviews

Modern Vacation Cottage near Walt Disney World

Our cozy, modern vacation cottage is nestled in a quiet, private community just 4 miles from Walt Disney World and convenient to all the fun that Orlando has to offer. The cottage features 1 bedroom with a high-quality queen bed, a living room, a full bathroom, and a fully-stocked kitchen with a new dishwasher, refrigerator, microwave, and oven. Centrally located to all of the Orlando attractions, our cottage is a very comfortable and special place to enjoy all of the magic and sunshine of FL!

Guest favorite

Cottage in Kissimmee

4.9 out of 5 average rating, 236 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

Superhost

Condo in Kissimmee

4.86 out of 5 average rating, 174 reviews

Beautiful Resort-Style Condo with Waterpark!

JJC Vacation Home is a gated resort-style condo that has everything you need to have the best vacation! The condo is near all main attractions, fully equipped kitchen, a lazy river, water slides, pool, splash area, mini golf, fitness center, kayak/canoe rental, bar, food, and more! Our Star Wars theme room with *glow in the dark* stars wall will make you feel like you're floating in space! Complimentary coffee/tea station. Relax while having a cup as you look at the view from the balcony.

Guest favorite

Condo in Kissimmee

4.92 out of 5 average rating, 131 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.

Guest favorite

Home in Kissimmee

4.91 out of 5 average rating, 321 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.

Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 203 reviews

Perfect 2 BR condo in Disney - Pool - Tiki Bar

Beautiful and cozy apartment at the Windsor Palms resort. 15 min to DISNEY and 10 min to Margaritaville Orlando WATER PARK. Lots of restaurants and fun 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

Guest favorite

Cottage in Kissimmee

4.95 out of 5 average rating, 454 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

Townhouse in Kissimmee

4.91 out of 5 average rating, 106 reviews

*NEAR DISNEY* 6 GUESTS... LOTS of Amenities

It's all about location! Our stylish yet cozy, recently renovated vacation spot. Features 3 bedroom, 2 full bathrooms, which consists of 1 king size bed, and 4 twin beds. Luxury feel, premium everything. Comfortably accommodates up to 6 guests. Conveniently located near Disney World. About 15 minutes away from Disney Springs and Premium outlets! Major parks, restaurants, supermarkets, Target and Walmart are within a short drive.

Guest favorite

Cottage in Kissimmee

4.95 out of 5 average rating, 440 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.

Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 420 reviews

Newly Renovated 3/2 close to Disney parks

Recently renovated 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.

Guest favorite

Apartment in Kissimmee

4.81 out of 5 average rating, 237 reviews

King Bed First Floor Disney Universal Family Condo

Welcome🌞! This unit is on the first floor recently renovated and updated! Your much deserved fun vacation away from home starts here 😎! Llocated in the heart 💗 of Walt Disney World and all Kissimmee and Orlando best fun spots 🎢! Includes 1 King size bed. and 1 Full size sofa bed. Just added BIG SMART TVs with Disney+, Netflix, Amazon Video perfect for relaxing after a fun-filled day.✨