Holiday rentals with outdoor seating in Kissimmee

4.96 out of 5 average rating, 161 reviews

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

Villa in Kissimmee

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

LocationOutdoor spacesLayout

4.99 out of 5 average rating, 146 reviews

10 Min to Disney | Heated Pool, Games, King Bed

🏡 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!

LocationValueAmenities

4.98 out of 5 average rating, 171 reviews

An open living and dining area features a modern aesthetic with a light wood accent wall. A spacious dining table accommodates six, complemented by stylish seating. The kitchen is equipped with stainless steel appliances, and a large flat-screen TV is mounted on the wall.

Townhouse in Kissimmee

13 Minutes To Disney, Pool, King Size, No Fees

- No Airbnb Service Fees -Weekly & Monthly discounts! - 3 bedroom, 3 bath townhome located in the heart of Disney. Gated Community. Pool. Gym. - Disney property (13 minutes), Disney Springs (20 min), Universal Studios (25 minutes), Sea World (24 minutes), Convention Center (17 minutes) - 5 minutes shopping, attractions and dining - Professionally maintained to give you and your family the best guest service experience - Movie Room - 75" flat screen TV - Fully stocked with all essentials

LocationOutdoor spacesPool

4.93 out of 5 average rating, 113 reviews

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

Villa in Kissimmee

Luxury Villa! /Game Room/ Pool Heater

Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and overflow Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

ValueOutdoor spacesParks

4.87 out of 5 average rating, 127 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.

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5 out of 5 average rating, 6 reviews

Orlando Dream Escape | Private Pool | Disney

Disfruta de esta hermosa casa renovada con piscina privada en Kissimmee. Ideal para familias y grupos de hasta 8 huéspedes. Cuenta con 3 habitaciones, 2 baños, sofá cama, cocina totalmente equipada, Wi-Fi, lavadora, secadora y estacionamiento gratuito. Ubicada cerca de Disney, Universal, SeaWorld, restaurantes y tiendas. Relájate, disfruta del sol y crea recuerdos inolvidables con familia y amigos. ¡A solo minutos de las principales atracciones de Orlando ✅ Piscina privada

LocationKitchenAccuracy

5 out of 5 average rating, 16 reviews

4BR Disney & Universal Themed Villa Reunion Resort

Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.

LocationFamilyHospitality

4.95 out of 5 average rating, 107 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!

Outdoor spacesValueFamily

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

5 out of 5 average rating, 78 reviews

Luxury Home w/ Pool & 6 Beds near Disney

Welcome to your modern escape in Kissimmee! Just 15 minutes from Orlando International Airport, this beautifully renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and luxury. Every detail has been thoughtfully upgraded—from the brand-new kitchen and spa-like bathrooms to the pristine private pool area—ensuring a relaxing stay. With sleeping arrangements for up to 9 guests across six beds, there’s plenty of space to unwind.

Outdoor spacesValueBack garden

A tranquil outdoor space features a private pool under a protective screen enclosure, framed by reclining lounge chairs. The setting offers a view of the lake, contrasting with the colorful sunset sky, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 120 reviews

Lakefront Villa w/pool 4mi to Walt Disney World

"Private South-Facing Pool (Sun All Day!)" and "Peaceful Lakefront Views with Local Wildlife "are just some of our guest's comments. Please see house rules. Located in beautiful Sunset Lakes – it's hard to find a vacation home closer to Walt Disney World with all that's offered at Mickey’s Lakefront Villa. Be amazed at how quiet and secluded you will feel yet just minutes away from all of the entertainment that you came here to enjoy.

Outdoor spacesLocationCondition

5 out of 5 average rating, 118 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

Stylish Design, Luxurious Comfort & Endless Entertainment, with a sprawling 2200 ft2 southwest facing pool deck & outdoor kitchen, no rear neighbors on a beautiful forest in the stunning 3.5 square mile Reunion Resort. You will have your own private pool with overflow spa, movie room, billiards - game room, 4 theme rooms: OUTER SPACE, MARVEL SUPERHEROES with a TUBE SLIDE, FROZEN II, HARRY POTTER CUPBOARD, PS5, within minutes to Disney.

Outdoor spacesValueIndoor spaces

5 out of 5 average rating, 5 reviews

7851 Luxury 5BR Home w/ Private Pool Near Disney

Create unforgettable memories in this modern 5-bedroom, 5-bathroom home in Reunion Village, near Disney. Enjoy a private screened-in pool, game room, second-floor loft, open-concept living and dining area, modern kitchen, multiple king-sized bedrooms, themed bedrooms, high-speed Wi-Fi, TVs, washer/dryer, free parking, self check-in, and access to eligible Encore Club amenities. Ideal for families and groups.

LocationNearbyCleanliness

Popular amenities for outdoor seating rentals in Kissimmee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.95 out of 5 average rating, 22 reviews

A private pool is framed by a tiled deck featuring six blue lounge chairs. The space overlooks a lush golf course, with manicured grass visible in the background. Palm trees are situated along the perimeter, enhancing the outdoor ambiance.

Home in Reunion

Reunion Resort Villa: Private Pool, Full Amentiy A

ValueLocationFamily

5 out of 5 average rating, 8 reviews

Elegant 5B & 3B Private Pool Villa near Disney

LocationAccuracyKitchen

A spacious living area features a modern sectional sofa and two blue lounge chairs. A large flat-screen television displays a fireplace design, creating a cozy focal point. Natural light fills the room through window coverings, and a potted plant adds a touch of greenery.

4.91 out of 5 average rating, 266 reviews

Cozy House with Private Pool. Kissimmee/Orlando

Outdoor spacesLocationCondition

5 out of 5 average rating, 65 reviews

An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.

Home in Four Corners

Gorgeous 5BR at Encore Resort next to Disney - 305

LocationOutdoor spacesComfort

4.89 out of 5 average rating, 9 reviews

Home in Clermont

Private Pool Home Near Disney | 4BR Sleeps 10

ValueLocationLaundry

5 out of 5 average rating, 15 reviews

BRAND NEW 06 Bedrooms at Solara Resort/Game Room

LocationHospitalityTV

A bright living area is presented, featuring a round dining table with elegantly styled chairs. Natural light filters through an arched window, illuminating the neutral walls. A cozy seating area includes a navy sofa, while a view of the private pool is visible through glass sliding doors.

4.92 out of 5 average rating, 125 reviews

8615 Vacation Oasis House Private Pool Grill

LocationValueParks

4.98 out of 5 average rating, 90 reviews

The exterior of a large, two-story home is displayed, featuring a light-colored facade and a covered front porch. Lush landscaping surrounds the driveway, which is paved with stone. A garage door is positioned on the right side, complemented by decorative lanterns and palm trees.

Home in Osceola County

Large Private Home on Golf course by Disney

Outdoor spacesLocationCheckout

Apartment rentals with outdoor seating

4.87 out of 5 average rating, 31 reviews

A modern villa with warm yellow siding is complemented by a well-maintained lawn. A bright green sports car is parked in the driveway. The sun casts a gentle glow, creating a serene atmosphere, while multiple large windows reflect the surrounding landscape.

Flat in Osceola County

Serenity Reunion Living and Near Disney

LocationValueCondition

Superhost

The inviting living area features a pair of modern teal sofas arranged around a glass-topped coffee table. A large TV is mounted on the wall opposite, with sunlight filtering in through sliding glass doors that lead to a balcony overlooking a scenic view.

4.82 out of 5 average rating, 169 reviews

*LaKe ViEwS* NEW!Condo 3/2 10 min to DiSnEy*

LocationValueQuiet

4.9 out of 5 average rating, 31 reviews

3141-208 - 3BD -Sunset View – Minutes from Disney

ValueLocationFamily

Superhost

4.86 out of 5 average rating, 116 reviews

Cozy Apartment Close to Disney

ValueOutdoor spacesHospitality

4.97 out of 5 average rating, 65 reviews

Modern Condo: 10 Min to Disney + Fireworks Views!

LocationValueFamily

5 out of 5 average rating, 5 reviews

3BR Resort NR Disney/Pets/Pool/ Gym & Sports Court

LocationFamilyCleanliness

Superhost

Flat in Davenport

4.84 out of 5 average rating, 31 reviews

Peaceful Retreat minutes from Disney 3BD/2BA

ValueLocationAccuracy

4.96 out of 5 average rating, 26 reviews

Haunted Mansion-inspired Ghoulish Sanctuary

LocationValueFamily

Apartment rentals with outdoor seating

A spacious living area features two light blue sofas with orange accent pillows, positioned around a wooden coffee table. A decorative wall clock and art pieces add character, while a glimpse of the kitchen is visible in the background, showcasing modern appliances and an inviting atmosphere.

4.9 out of 5 average rating, 348 reviews

Beautiful Beach Style Condo minutes from Disney

Outdoor spacesLocationBathroom

4.97 out of 5 average rating, 262 reviews

Ideal for Two Families • Sleeps 8 • Top Location

LocationValueSleep quality

A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.

4.97 out of 5 average rating, 215 reviews

303_To Infinity & the Ocean Breeze Apartment

LocationValueAmenities

4.97 out of 5 average rating, 439 reviews

A private balcony offers serene views of Lake Bryan and a swimming pool area. A small round table with two chairs invites relaxation, while warm colors from the sunset enhance the tranquil setting. Lush trees frame the scene, creating a peaceful atmosphere.

Apartment in Orlando

Waterfront Condo minutes to Disney & Universal

Outdoor spacesValueNearby

4.91 out of 5 average rating, 176 reviews

Chic Disney Resort Condo • Pool Access Near Parks

LocationValueLaundry

5 out of 5 average rating, 111 reviews

Cozy Condo at Secret Lake near Disney

LocationBathroomFamily

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, 155 reviews

Modern Condo with Lake View Near Disney 3151

LocationValueNearby

An aerial view captures the expansive resort-style pool area, featuring tropical landscaping and winding water features. Sun loungers and cabanas line the poolside, while a lazy river and splash park invite guests to relax and enjoy. The serene water is bordered by a scenic lake.