Vacation rentals in Kissimmee

A themed bedroom designed with space motifs features a twin over twin bunk bed with a ladder for access. The walls are decorated with an illustrated planet scene, while a playful area rug adds color to the carpeted floor.

4.96 out of 5 average rating, 112 reviews

Virtual Reality | Simulators | Pool | Disney 20min

Happy 2026 from Kissimmee! Westside Villa has just a few openings - snag it while you can! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charge on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs; dedicated work space -2 pack-n-plays, highchair, strollers, wagon -Resort access: lazy river, splash pad, tiki bar, fitness center Arriving early in the day or leaving late? Ask about our half day add-on, if our cal

A private pool is framed by a screened enclosure, featuring a gentle waterfall and bordered by comfortable lounge chairs. The serene lake view is visible beyond the pool, complemented by lush greenery lining the shore.

4.86 out of 5 average rating, 198 reviews

Near Disney Gated LakeView Pvt Heated Pool

LIMITED PROMOTION! FREE CLEANING FOR BOOKING 2 WKS OR MORE! LOWEST CLEANING FEE! Military dscnts. New Pool Heatr, Dolby ATMOS, 65" LED TV w/ Airplay. Remote office setup. Sunset Lakes a secure gated comnty ~12 min from Disney & other parks. Villa offers Lake View pvt pool, gorgeous sunset, Playroom, Fishing dock. Fully furnished, sparkling clean w/ 5 bds - 1 King, 2 Qns, 2 Twin beds w/ 3 baths, kitchen & lndry. Come & enjoy your next trip to Disney & leave everything to a fantastic experience!

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.

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**

A screened-in pool area features a clear blue pool with floatation devices, surrounded by a sunlit deck. A Tiki bar with seating stands to one side, while lounge chairs are arranged along the edge. Lush greenery is visible beyond the enclosure.

4.95 out of 5 average rating, 118 reviews

Disney Retreat | Huge Pool with Spa | 2 King beds

Don’t leave that Disney Magic at the parks - experience it by coming home to your spacious 5 BR with 2 King suites, 3.5 baths, and newly renovated design. The high ceilings and open floor plan make it perfect for family time, while the private backyard oasis, complete with a pool and spa (heating optional) and Tiki Bar, offers a great space for relaxation. The themed bedrooms, including Star Wars, Frozen, and Mickey & Minnie, add a fun and whimsical touch that’s perfect for guests of all ages.

4.99 out of 5 average rating, 189 reviews

A themed kitchenette features a bamboo bar with high seating and colorful pendant lighting. The walls are adorned with tribal art and shelves hold various artifacts. Kitchen appliances, including a refrigerator and counter space, reflect a blend of modern convenience and cultural decor.

Cottage in Kissimmee

Tahiti Gil’s Mananui: Disney Poly & Tiki Inspired!

Aloha Adventurers! Welcome to Faré Mananui. Your passport to a far away tropical hideaway awaits, so get ready to grab your favorite Aloha shirt! Mananui was made for the Disney/Tiki ADULT in mind! Imagined by artist @TahitiGil & designed by @TyphoonTommy (Former Disney/Universal creative team & designer of the Suffering Bastard Tiki Bar in Sanford, Fl. Experience your next Adventureland/ Enchanted Tiki Room “story dwelling” adventure from the moment you step thru the door! - Kungaloosh!!

The image captures a view from the pool, showcasing the villa's large glass windows and covered outdoor seating area. Loungers are positioned around the pool, offering ample space for relaxation. The sparkling water reflects the modern architecture above, framed by a screened enclosure.

4.94 out of 5 average rating, 111 reviews

Private Pool & Free Heat - Close to Disney!

3 bed, 3 bath luxury villa in exclusive gated community 10 mins from Disney. Private pool & hot tub with free heat not overlooked by other homes. Main rooms open onto pool. Kitchen with granite counter tops. Outside bar, loungers, table & chairs. Master bedroom with double sink ensuite and twin with ensuite shower room. Queen is separate to main house providing additional privacy when travelling with friends/family. 32 inch tv's and comfortable beds with pillow top mattresses in all bedrooms

4.87 out of 5 average rating, 105 reviews

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.

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.

4.93 out of 5 average rating, 102 reviews

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 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.

A private pool area is surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.

4.91 out of 5 average rating, 253 reviews

House by the Mouse: Something for Everyone!

Welcome to our completely remodeled solar four bedroom, three bath villa, less then four miles to Disney World, and only a short drive to Universal, Sea World, Lego Land, and other local attractions. Designed themed bedrooms include Harry Potter, Mickey and Minnie Mouse, Star Wars, and a romantic master bedroom that allows you to relax in comfort. The pool, spa, and the entire villa is just for you, no need to share with anyone else, so kick back and enjoy!

A grand living area showcases a striking stone wall adorned with an extensive collection of framed artwork. Soft seating is arranged around a fireplace, providing a cozy yet elegant atmosphere. A staircase leads to the upper level, while rich drapery frames the large windows, allowing natural light to flow in.

4.95 out of 5 average rating, 195 reviews

Waterfront Wizarding Near Universal's Harry Potter

This spellbound stay, situated in the prestigious Lake Berkley Resort, boasts lake views & private pool. With 6 bedrooms, 3 bathrooms, well equipped kitchen & comfy living spaces, this thematic home is ideal for families & friends seeking an immersive vacation. A 10min drive to Disney, 15min to Sea World & 20min to Universal's Wizarding World of Harry Potter, this magical manor provides a convenient home base for exploring Orlando's famous attractions.

4.98 out of 5 average rating, 125 reviews

The cottage features a charming exterior with bright yellow siding and a classic gabled roof. Lush palm trees and manicured hedges frame the entrance, which includes a welcoming porch with yellow chairs. Large windows allow natural light to enhance the inviting facade.

Cottage in Kissimmee

1BD Cottage "Limoncello" in Margaritaville

Welcome to your own island-inspired oasis. Our charming cottage is the perfect home base for your next dream Orlando vacation. The unit comes with all the comforts from home but worlds away. Conveniently located minutes from the Disney parks, a state-of-the art water park and newly opened 196,000 square foot shopping and dining district with multiple dining food and beverage options & brand-new movie theater. All Pets Must Be Preapproved :)

4.89 out of 5 average rating, 118 reviews

Mi Casita Near Disney/Universal

Welcome to your own private oasis in Kissimmee! Our charming 3-bedroom home boasts a beautiful private pool. Unwind in the serene surroundings while still being just moments away from the excitement of world-class theme parks and entertainment. Enjoy a fully-equipped kitchen, comfortable living areas, and spacious bedrooms for a memorable stay that combines the comforts of home with a sun-soaked Florida experience. Book your escape today!

Popular amenities for Kissimmee vacation rentals

Self check-in

Beachfront

Gym

BBQ grill

Laptop-friendly workspace

Stay near Kissimmee's top sights

Kissimmee Lakefront Park

329 locals recommend

FantasyWorld Resort

7 locals recommend

Silver Spurs Arena

21 locals recommend

Walmart Supercenter

978 locals recommend

Lake Buena Vista Factory Stores

331 locals recommend

Kissimmee Gateway Airport

15 locals recommend

Private vacation rentals in Kissimmee

4.98 out of 5 average rating, 53 reviews

A private balcony features two black chairs positioned for relaxation. Below, a green landscape borders a calm waterway, with trees lining the banks. Industrial buildings can be seen in the distance under a clear blue sky.

Apartment in Kissimmee

Modern King Apt w Water view, Pool Gym Near Parks

5 out of 5 average rating, 6 reviews

Charming vacation villa on resort w/private pool

4.85 out of 5 average rating, 13 reviews

Amazing Retreat at Lake Berkley

4.63 out of 5 average rating, 16 reviews

Luxurious 5BR Villa Your Disney Getaway

5 out of 5 average rating, 31 reviews

An open-concept living area showcases a spacious sectional sofa adorned with various cushions. A modern dining area is visible, featuring a round table and four chairs. Elegant decor elements include framed wall art and a sleek light fixture, all set against a neutral color palette.

Townhouse in Clermont

Upstay-Luxury 3BR Home w Private Pool & Games Room

5 out of 5 average rating, 3 reviews

A Stay that Fells Like Magic

A game room is designed for entertainment, featuring a pool table and air hockey table. Colorful artwork adorns the walls, including a vibrant mural. Modern ceiling lights enhance the atmosphere, while seating is available for relaxation between games.

4.96 out of 5 average rating, 49 reviews

Lake House-Gameroom, Theater, and Disney

A private pool is surrounded by a screened enclosure, offering views of lush green grass and nearby landscaping. The clear blue water reflects the sky above, and a spillover spa is visible at one end. Sun loungers are positioned beside the pool deck.

4.89 out of 5 average rating, 28 reviews

Windsor Palms Villa with Very Private Pool

Kissimmee beach vacation rentals

A tranquil pool area is surrounded by lush greenery and palm trees. The water appears clear and inviting, with a rock formation creating a natural aesthetic. Lounge chairs are positioned around the pool, providing ample space for relaxation.

Apartment in Kissimmee

STar Island 1 Bedroom

4.97 out of 5 average rating, 117 reviews

The room features a spacious bed with a dark headboard and a blue accent pillow. A small table with two chairs is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through a window dressed with sheer curtains.

Home in St. Cloud

Comfy Studio w/ private Entrance

4.79 out of 5 average rating, 24 reviews

A two-story building features a yellow exterior with white railings and a distinctive cupola. Palm trees and lounge chairs are situated near the swimming pool, creating a tropical ambiance. A large blue umbrella provides shade in the outdoor area, contributing to a relaxed setting.

Condo in Davenport

Perfect Disney\Golf Vacation

4.96 out of 5 average rating, 196 reviews

The expansive lake is showcased during sunset, reflecting vibrant colors in the sky. Surrounding greenery adds a natural touch, while a dock extends into the water, offering a serene view of the landscape. Soft light illuminates the pathway along the lake's edge.

Hotel room in Orlando

PentHouse Suite with 2X View

A spacious balcony is visible, featuring a dining set and two rocking chairs. A table with two glasses and a pineapple is centered, highlighting a serene lake view. The setting sun casts warm hues across the sky, creating a tranquil atmosphere.

Apartment in Orlando

4.72 out of 5 average rating, 232 reviews

Luxury Waterfront | 1 Mile to Disney | Sleeps 7

4.78 out of 5 average rating, 114 reviews

Condo in Orlando

Your Family's Disney HQ~Sleeps 8~No Extra Fees!

A modern kitchen is complemented by stainless steel appliances and a round dining table surrounded by white chairs. A decorative wall featuring greenery adds a touch of nature, while the open space leads to a cozy living area with a comfortable sofa.

Villa in Clermont

Charming Villa near Disney, pool, 3 beds, sleeps 4

4.89 out of 5 average rating, 9 reviews

An expansive outdoor pool area features palm trees, sandy beach volleyball courts, and thatched umbrellas. Lounge chairs in blue and white are arranged around the pool, creating a vibrant atmosphere. The lush greenery of the surrounding landscape adds natural beauty to the setting.

Home in Davenport

Beach Resort with pool tiki bar near Disney World

Family friendly vacation rentals in Kissimmee

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.

4.99 out of 5 average rating, 148 reviews

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

4.94 out of 5 average rating, 129 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

4.76 out of 5 average rating, 133 reviews

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

4.86 out of 5 average rating, 433 reviews

OMG! Disney Area, Movie Theater, Game Room & Pool!

4.91 out of 5 average rating, 151 reviews

Home in Davenport

Magical Pool Villa-close to Disney Game/movie Room

4.87 out of 5 average rating, 374 reviews

Townhouse in Kissimmee

Be Our Guest !

A vibrant hallway showcases colorful murals featuring beloved characters, including Mickey Mouse and his friends, amidst playful scenes of amusement and adventure. The walls are painted with a blend of whimsical colors that add charm to the spacious area, complemented by a clean marble floor.

4.97 out of 5 average rating, 129 reviews

DisneyTheme Storey Lake Resort Pool/Spa/BBQ6Br/5b