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Holiday 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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Top Guest favourite
The living area features a modern sectional sofa adorned with decorative pillows. A sleek coffee table is positioned on a patterned rug, while large sliding doors lead to a balcony, enhancing natural light. An adjacent dining area with stylish chairs is visible in the background.
Apartment in Kissimmee
4.98 out of 5 average rating, 164 reviews

3121-402 Resort Lake View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Guest favourite
A shaded lounging area features comfortable seating and a glass-top table, set with refreshments. In the background, a large pool glistens under the sun, surrounded by palm trees and various seating options, including cabanas and sun loungers.
Townhouse in Kissimmee
4.83 out of 5 average rating, 211 reviews

Orlando Disney ºoº 3BD in Resort | Kissimmee

Modern Townhouse in Resort w/ preserve area and Amazing Clubhouse. (NO resort fees!) | 1 min | Old Town Kissimmee | 3 min | Publix®, McDonald's®, Wendy's®, Miller's Ale House® and more | 6 min | Walmart® & Target® | 7 min | Celebration | 9 min | DISNEY® AREA (All Theme Parks) | 9 min | Premium Outlet® | 11 min | Disney Springs | 11 min | ESPN® Sports | 13 min | Convention Center | 15 min | UNIVERSAL® STUDIOS | 26 min | Orlando Airport | 70 min | Bush Garden's® | 95 min | Sarasota & Clearwater

Top Guest favourite
The villa features a modern exterior with a sloped roof and a two-car garage. Palm trees are landscaped around the front yard, which is bordered by well-maintained grass. A clear blue sky provides a bright backdrop to the welcoming entrance.
Home in Kissimmee
4.87 out of 5 average rating, 263 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.

Top Guest favourite
An open living space features large French doors leading to a balcony, allowing natural light to brighten the area. Stylish seating is arranged around a coffee table, while artwork resembling a Marvel theme decorates a wall in the adjacent bedroom. Views of palm trees and a nearby pool can also be seen.
Condo in Kissimmee
4.97 out of 5 average rating, 128 reviews

Golf Front Luxury Penthouse: Views, Marvel, 2Pools

This modern 3-bedroom TOP FLOOR (with an ELEVATOR right to the door) luxury condo has one of the most PICTURESQUE VIEWS in the Reunion Resort of the Arnold Palmer PGA golf course. Combining STYLISH DESIGN and LUXURIOUS COMFORT, there are 2 KING bedrooms and a playful MARVEL themed bedroom with a classic Arcade machine & PlayStation. 4 TVs with DirecTV, free high-speed wifi, your own washer & dryer, access to 6 resort pools, 2 of which are only a 3 minute walk away, only a short drive to Disney.

Guest favourite
A private pool area features a crystal clear pool with a built-in spa, surrounded by a screened enclosure. A spacious patio is equipped with lounge chairs, a dining set, and a barbecue grill, offering a relaxed outdoor environment.
Home in Kissimmee
4.95 out of 5 average rating, 136 reviews

Vacation Home 3 bedroom/2 full bath/private pool

Bring the whole family to this great place with lots of room for fun. This house is perfect for you, your family, and friends! Spacious 3 bedrooms and 2 full baths that can accommodate up to 9 people. The house is fully air conditioned and has a pool. Indoor entertainment such as board games, ping pong table and TV cable. Please note smoking or parties are NOT allowed in house premises. No pool heater available during May through October. **You also MUST be 21 or older to rent this property**

Guest favourite
A modern digital door lock is mounted on a light-colored door, featuring a keypad for secure access. A blurred plant with lush green leaves is visible in the background, adding a touch of nature to the entryway.
Guest suite in Kissimmee
4.95 out of 5 average rating, 173 reviews

It's too much like a elegant mini-hotel (5)

It's too much like a elegant mini hotel with rich artistic atmosphere! All the pictures on this page are a reflection of the real condition of the house. All the furniture has been carefully selected, and comfortable mattress and pillows will quickly accompany you into sweet dreams. The biggest feature of this house are comfort, economy and convenience. All of my houses have hosted countless guests from South America, including Brazil and Argentina. You will always be welcome here!

Superhost
The exterior of the house is viewed from the sidewalk, surrounded by neatly maintained lawns. Two large trees provide ample shade. The home features a light-colored facade and a driveway visible on the right, complemented by a two-car garage.
Home in Kissimmee
4.85 out of 5 average rating, 121 reviews

Harmony Place - W/ Pool - Near Walt Disney

Welcome to Harmony Place, your perfect getaway! Relax and unwind with the whole family at this serene retreat. This stunning home features a private pool, 3 spacious bedrooms, and 2 bathrooms, comfortably accommodating up to 9 guests. Located in the exclusive Crescent Lakes community in Kissimmee, Florida, you’ll be just 11 miles from Walt Disney World, 22 miles from Universal Studios, and 18 miles from SeaWorld Orlando. Enjoy nearby dining and shopping options for added convenience!

Top Guest favourite
The living area features a comfortable gray sofa adorned with accent pillows, complemented by a wooden coffee table. A large TV is mounted on the wall, with a stylish chair placed nearby. Natural light enters through glass doors, which lead to a balcony.
Apartment in Kissimmee
4.99 out of 5 average rating, 138 reviews

Chic Vibes Comfy King Bed Next to Parks/Food/shops

Welcome to our stylish oasis in Kissimmee, which seamlessly blends sophistication with a laid-back vibe. Your stay begins in a professionally cleaned apartment for your full enjoyment. Discover resort-style amenities – a sparkling pool, a fitness center, and hammocks, offering the luxuries of a five-star retreat. Conveniently located with in walking distance of theme parks, restaurants, and shopping. Book now. We can't wait to host you in our little slice of paradise!

Guest favourite
A private balcony offers seating with a view of the shimmering lake, highlighting the surrounding landscape. Adjacent images reveal family-friendly amenities, including a vibrant water park with slides, an elegant kitchen space, and a welcoming sleeping area featuring playful decor.
Condo in Kissimmee
4.9 out of 5 average rating, 184 reviews

NEW APARTMENT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Less than 1 mile from Walmart, Target, and restaurants, your family will have everything they need. Water Park, gym, and all amenities FREE. Free parking, 24/7 security in this gated resort and with an automatic check-in with direct access code and elevator available

Top Guest favourite
A spacious bedroom features a comfortable bed with decorative pillows and a modern ceiling fan. An open kitchen area showcases stylish cabinetry and stainless steel appliances. A living area is equipped with ample seating and large windows allowing natural light. Another bedroom is similar in style with neutral tones.
Apartment in Kissimmee
4.85 out of 5 average rating, 107 reviews

Luxury Resort Style Condo Near Disney-103

A 5-star stay 3bed/ 2.5bath resort-style condos where you’ll enjoy unprecedented access to amenities that are fun for the entire family. Lounge by multiple community pools and have fun. This relaxing family-friendly home is fully equipped with all modern conveniences and has everything you will need to make your dream Orlando vacation a reality! We have multiple units therefore all photos are not exact to this unit.

Top Guest favourite
A bright living and dining area showcases a large blue sofa adorned with decorative pillows. A wooden dining table is surrounded by four chairs. Natural light floods through sliding doors leading to an outdoor seating area, complemented by a soft area rug beneath the coffee table.
Townhouse in Kissimmee
4.98 out of 5 average rating, 128 reviews

Lakeside Boho Bliss: The BohoBay

✨ Welcome to Bohobay ✨ Your cozy little hideaway just minutes from the magic of Disney and all the excitement Orlando has to offer. Tucked right by a peaceful lake, mornings here start with coffee and glittering water views, and evenings are made for a glass of wine with sunset vibes. 🌅 It’s the perfect blend of fun-filled days out and calm, soul-soothing nights in.

Top Guest favourite
A two-story home with a light brown exterior is set within a lush green landscape. A spacious driveway leads to a white garage with a large door. The property is enclosed by a white privacy fence, creating a secluded outdoor environment.
Home in Kissimmee
4.93 out of 5 average rating, 171 reviews

South Facing Pool Home! 5 Miles from Disney

Beautiful South Facing Pool Home! 5 Miles from Disney. This beautiful 4-bedroom home with two master bedrooms is located just minutes from Disney World, Sea World, Universal Studios, and other Orlando attractions.The home includes a private fenced in South facing swimming pool. We offer free Pool heat, Gas Grill, and High Speed Wireless internet and Cable TV .

Popular amenities for Kissimmee rentals with a pool

When is the best time to visit Kissimmee?

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Avg. price$246 NZD$249 NZD$261 NZD$256 NZD$224 NZD$239 NZD$251 NZD$221 NZD$204 NZD$216 NZD$243 NZD$286 NZD
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Quick stats about holiday rentals with a pool in Kissimmee

  • Total holiday rentals

    Explore 6,620 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $33 NZD per night before taxes and fees

  • Verified guest reviews

    Over 238,760 verified reviews to help you choose

  • Family-friendly holiday rentals

    5,800 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 1,070 rentals that welcome pets

  • Rentals with dedicated workspaces

    3,700 properties have a dedicated workspace

  • Wi-Fi availability

    6,590 of Kissimmee holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kissimmee rentals

  • 4.7 Average rating

    Kissimmee stays receive an average rating of 4.7 out of 5 from guests

Destinations to explore

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  3. Florida
  4. Osceola County
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  6. Rentals with pools