Vacation rentals with a pool in Kissimmee

4.98 out of 5 average rating, 288 reviews

A resort-style water complex is surrounded by lush landscaping and palm trees. The winding pool features clear, inviting water with lounge areas and shaded cabanas. Bright blue skies filled with clouds create a serene backdrop for this recreational oasis.

Townhouse in Kissimmee

Disney 5BR • Private Pool Free Heat • Pet Friendly

Welcome to this gem near all major attractions: Disney (5 miles), SeaWorld (7 miles), Universal (12 miles), Convention Center (9 miles), and Airport (20 miles). Nearby are outlets, restaurants, and supermarkets. This luxurious home features 5 bedrooms, 4 bathrooms, a private heated pool/spa, fully equipped kitchen, laundry, and free stroller, playpen, and highchair. Resort amenities include a water complex, lazy river, bar, fitness center, mini golf, kayaking, and more! Pets friendly & welcome!

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4.9 out of 5 average rating, 129 reviews

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

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4.99 out of 5 average rating, 164 reviews

10 Minutes to Disney | Heated Pool, Arcade, Kings

🏡 Tucked inside a gated community near Kissimmee’s top attractions, this bright, themed home is made for memorable family getaways. Enjoy friendly competition in the game room, unwind in the heated private pool (available upon request), or relax on the covered patio beneath the Florida sun. Just 11 minutes to Fun Spot America, 11 minutes to Old Town, and 12 minutes to Disney World, it’s the perfect home base for your Florida adventure. Book now and start creating unforgettable memories!

FamilyLocationParking

4.86 out of 5 average rating, 148 reviews

Villa in Kissimmee

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

LocationFamilyAccuracy

4.97 out of 5 average rating, 193 reviews

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

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The image displays the Summerville Resort sign, highlighting its proximity to Disney. A comfortable bedroom is shown, featuring two spacious beds and colorful wall art. An inviting patio area with outdoor seating is visible, alongside a community pool surrounded by lounge chairs and palm trees.

4.87 out of 5 average rating, 129 reviews

Comfy Family Villa|5min->Disney!

Summerville Resort is a new and prestigious collection of town-home villas just 5 miles from the entrance to Walt Disney World! Be among the first to stay in this contemporary vacation rental with pristine finishes & amenities. No need to wait in line to shower here; each of the 4 bedrooms has its own attached bath. After a day exploring the parks, come home to indulgence at the Resort, which features a community hot tub, heated pool, fitness center, playground, and a sleek Clubhouse.

FamilyValueHot tub

4.95 out of 5 average rating, 139 reviews

Villa in Kissimmee

Storey Lake 10BR Villa Near Disney, Pool Waterpark

✨ Step into your own Disney adventure! Once an NBA star’s vacation home, this villa sleeps 23 and blends luxury with fun: • 🛏 Themed Bedrooms (Frozen, Cars, Harry Potter, Star Wars & more) • 🎬 Galactic Theater w/ 86” Screen, Surround Sound, Arcade, Xbox & Nintendo • 💦 Heated Pool & Spa w/ Lounge Seating + Peaceful Forest Views • 🎢 Resort Water Parks w/ Lazy River, Pirate Ship, Water Slides & Mini Golf • 📍 Prime Location: Only 7 Miles to Disney & 19 Miles to MCO attractions

LocationValueNearby

4.99 out of 5 average rating, 161 reviews

The exterior of a single-story home is presented, featuring a paved driveway leading to a two-car garage. Lush green grass surrounds the house, and palm trees are positioned near the entrance. A colorful sunset sky provides a picturesque backdrop.

Villa in Kissimmee

Pet-Friendly Disney Theme 4BR•Heated Pool•Game Rm

Escape the crowds in an upscale, gated oasis featuring your own private screened pool with complimentary pool heat, a fully loaded game room, and 3 custom-themed bedrooms kids will love (Star Wars, Mickey Mouse, and a magical Princess room). Complete with a spacious adult primary suite featuring a spa-like private bath and workstation, this pet-friendly home offers premium comfort for parents and pure magic for kids just minutes from Disney World and Universal Studios!

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4.91 out of 5 average rating, 157 reviews

The image showcases various themed sleeping areas within the vacation home. A Superhero Room displays colorful walls with superhero motifs, while the Princess Room features castle imagery. A cozy nook with a bunk bed is visible, alongside arcade machines that add to the playful environment.

Townhouse in Kissimmee

Magical Hideaway - 15 min to Disney - Storey Lake

Welcome to The Magical Hideaway! Bring your family an immersive experience into our Disney-themed vacation home in Storey Lake community. Our home includes a specially themed Princess and Superhero rooms. Dive into fun at the resort pool with a lazy river and water slides. Enjoy your own plunge pool and our photo-op green wall. Entertainment includes 4 Roku TVs, Disney board games, and puzzles. We've also got you covered with a stroller, crib, and highchair provided.

FamilyValueAir conditioning

4.96 out of 5 average rating, 122 reviews

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

ValueFamilyRiver

4.86 out of 5 average rating, 102 reviews

Modern 12 BR 11.5 BA, Sleeps 32, 15 mins to Disney

Welcome to this modern 12-bedroom, 11.5-bath home—perfect for your next family getaway! Comfortably sleeping up to 32 guests, this centrally located retreat is just 15 minutes from the Disney parks. Enjoy fantastic amenities including a private pool and spa, a home theater for movie nights, and a fun-filled game room. With plenty of space and entertainment for all ages, it’s the ideal spot for family reunions, group vacations, and special get togethers.

FamilyLocationCheck-in

4.97 out of 5 average rating, 269 reviews

Near Disney • 4BR • Perfect for Families

Guests love this home! It’s usually fully booked! Location is incredible! Heart our property and save it to your wishlist! IMPORTANT: parking available only for one car. 9 min - Hollywood Studios (6 mi) 10 min - Animal Kingdom (8 mi) 12 min - Disney Springs (5 mi) 15 min - Magic Kingdom (10 mi) Just 3’ from Walmart, Publix, and a big strip mall full of restaurants, grocery stores, and shopping! Experienced host, 10 years on Airbnb!

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Popular amenities for Kissimmee rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.79 out of 5 average rating, 136 reviews

The Real Florida Whispering Oaks

ValueFamilyCheckout

4.95 out of 5 average rating, 100 reviews

MoanaTheme| YES Pets| Heated POOL & SPA| Disney

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A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.

4.94 out of 5 average rating, 169 reviews

Luxury Encore Pool Spa Pets Game Rm Theater Gym

FamilyLocationLaundry

5.0 out of 5 average rating, 128 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

ValueFamilyWalkability

An expansive backyard is featured, showcasing a striped hammock stretched between two posts. Lounge chairs are arranged nearby, with a swing set positioned to one side. The heated pool is enclosed within a screened area, providing a view of the clear, blue sky.

4.92 out of 5 average rating, 121 reviews

Kissimmee, Heated Pool, Game Room. Luxury

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Superhost

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

Home in Buenaventura Lakes

Villa Resort Club

FamilyLocationTV

4.87 out of 5 average rating, 189 reviews

4.93 out of 5 average rating, 166 reviews

Private Pool + Spa Game Room •4m Disney •Pinball

ValueFamilyBeach

The front exterior of the home is presented, featuring a well-maintained lawn and a driveway leading to a two-car garage. The architecture includes a central arched entrance and large windows, complementing the inviting landscape lit by sunset colors.

4.83 out of 5 average rating, 104 reviews

5390 Vacation Sunset House Private Pool Grill

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Condo rentals with a pool

A master bedroom features a spacious bed with a white quilted coverlet, accented by a blue tufted headboard. Two bedside tables with lamps provide soft lighting. A ceiling fan hangs above, while light-colored walls and flooring enhance the room's bright atmosphere.

4.86 out of 5 average rating, 126 reviews

Disney Retreat

FamilyLocationTV

A private balcony offers a relaxing seating area with wicker chairs and a glass table, overlooking scenic water views. A vibrant floral cushion adds a touch of color, while expansive blue skies and fluffy clouds create a serene backdrop.

4.89 out of 5 average rating, 100 reviews

Luxury Lake View Condo near Disney/Orlando.Dream Condo. Free Water Park.2 bedrooms, 2 bathrooms, 3131

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A balcony is depicted with four cushioned chairs arranged around a small table. The railing provides a view of a serene landscape with water and greenery in the background. Light fabric drapes softly from the sliding door frame.

4.9 out of 5 average rating, 168 reviews

Modern Condo with Lake View Near Disney 3151

LocationFamilyView

4.95 out of 5 average rating, 196 reviews

A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.

Condo in Orlando

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

ValueFamilyAmenities

4.93 out of 5 average rating, 149 reviews

The image captures a vibrant pool area surrounded by lush palm trees and comfortable lounge chairs. An inviting infinity pool is centrally located, accompanied by cabanas and umbrellas. Multiple water slides are visible in one corner, enhancing the family-friendly atmosphere of the space.

Condo in Celebration

Pet friendly Orlando area near ESPN Center

ValueFamilyIndoor spaces

Aerial view of a resort-style pool area features winding lazy river and miniature golf course set amidst lush greenery and palm trees. Bright blue water complements the surrounding landscaping, with lounge chairs and umbrellas positioned for relaxation. A community building is visible in the background.

4.97 out of 5 average rating, 124 reviews

Top Floor, 3bd, FREE Clubhouse, Kids Room, Disney

LocationFamilyCheckout

Superhost

A bright living space is showcased, featuring a circular dining table set with four plates. A comfortable teal seating area is arranged against the wall, complemented by a nature-inspired wall art piece and greenery. Large glass doors provide a view of the outdoors and invite natural light.

4.86 out of 5 average rating, 150 reviews

Stylish Condo 20 mins to Disney/King Bed

ValueFamilyNearby

4.95 out of 5 average rating, 140 reviews

Condo in Orlando

Modern Lake view Condo 1 mile from Disney

LocationFamilyView

Other vacation rentals with a pool

5.0 out of 5 average rating, 48 reviews

Townhouse in Kissimmee

Disney Theme Rooms | Private Pool | Storey Lake

FamilyLocationDecor

4.83 out of 5 average rating, 6 reviews

Newly Renovated 5BR Home at Storey Lake Resort

LocationFamilySleep quality

4.95 out of 5 average rating, 65 reviews

Apartment in Orlando

Epic stay at Vista Cay!

LocationValueCheck-in

5.0 out of 5 average rating, 8 reviews

Luxe Family Escape | Pool Oasis Near Disney

FamilyLocationHospitality

5.0 out of 5 average rating, 25 reviews

4BR Disney & Universal Themed Villa Reunion Resort

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A private heated pool is surrounded by a screened patio, with two lounge chairs positioned nearby. A small dining area with a table and chairs is visible, enhancing the relaxing outdoor space. The backdrop features the home’s elegant design and a cozy seating area beyond.

4.91 out of 5 average rating, 76 reviews

Disney/Universal Villa w/ Pool

LocationFamilyBathroom

Superhost

Villa in Orlando

Amazing 11 bedrooms - Paradiso Grande 5 Location

LocationNearbyCheck-in

5.0 out of 5 average rating, 4 reviews