
House holiday rentals in Kissimmee
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Top-rated house rentals in Kissimmee
Guests agree: These houses are highly rated for location, cleanliness and more.

Margaritaville Cottage 10 Minutes to DisneyWorld!
Location location location! We are conveniently located at the Margaritaville Resort. We are just minutes away from DisneyWorld, Universal, and Seaworld, Sunset walk, and H20 Water Park. * THIS DOES NOT INCLUDE ACCESS TO THE RESORT AMENITIES/POOL, however many of our guests chose to purchase a membership at H20 water park with the money they’re saving in resort fees* • Sunset Walk - A brand new experience that provides a plethora of restaurants, shopping, live entertainment, and movie theatre. (Resort shuttle is available, or a 15 min walk). •H20 - A new water park located on the resort property that includes offerings for all ages. ADDITIONAL fees apply. • Formosa Garden Winery - a five minute walk to an abundance of wine and beer with incredible views. The winery is open Thursday-Sunday. We recommend a brunch reservation! Cottage Accommodations - • 2 spacious bedrooms • 2 full bathrooms • Couch that can be converted into queen bed • Free and easy parking • Free WiFi • TV’s with cable in living room and both bedrooms (Netflix & Disney plus available) • High ceilings • Back patio with lounge chairs • Balcony on second floor with two adirondack chairs • All kitchen supplies included • Security for entrances and 24 hour watch House Rules • NO parties under any circumstance per airbnb policy. • No smoking, a $200 fine will be imposed for guests who break this rule • No unregistered guests *if you’ll be bringing a pet, please let us know before your arrival, there is a $50 service fee, max 2 pets*

*Luxe Disney Home* Priv Pool/Spa- 6BR Sleeps 15
JUST ADDED! (Check out our other reviews) New Construction!!! 3000ft2! Welcome to our luxury 6-BR private pool home near Disney World, Universal Studios, and Sea World! With 8 beds, it sleeps 15 people comfortably. Enjoy the private heated pool, hot tub, and game room with ping pong, cornhole, and arcade. Located in Veranda Palms community, you also have access to a large pool, clubhouse, gym, and splash pad. Perfect for large families or groups seeking a memorable Orlando stay. Book now!

Reunion Resort Village Luxury Retreat moderna
Welcome to Reunion Luxury Retreat, experience the perfect blend of luxury comfort, and privacy in this elegant villa, located within the exclusive gate community of Reunion Village, just minutes from Orlando's world-famous theme parks. Our Home offers everything you need for an unforgattable stay. 4 spacious bedrooms , 5 different pools in our resort. Gate community with 24-7 security . Hi speed wifi , smart TV , fully equipped kitchen . Relax after a magical day al Disney or Universal.

Resort TH 2b/2.5b With Private Hot Tub near Disney
Visit Regal Oaks Resort, with an onsite waterpark and private hot tub. We're close to everything in Orlando and a 10 min drive to Disney! Our Resort-Style Villa Includes: ❤Onsite Waterpark and Heated Pools ❤Walkable to Old Town Restaurants and Shops ✔No Hidden Fees ✔Onsite Fitness Center ❤24/7 Security ✔Onsite Concierge, Restaurant and Bars Our Home Offers: ❤Private Hot Tub ✔Comfy King and 2 Full-Size Beds ❤Fast WiFi ✔Cable TVs ✔Private Patio ✔Washer/Dryer ✔Stocked Kitchen

VerandaPalms/HeatedPool/Carpet free/NearDisney
This beautiful 4 bedroom home is 10 minutes from the Disney parks !!! Walking distance from Shingle Creek Reg. Park, just in the corner of Veranda Palms main entrance. This home has 2 suites, a private heated pool and is located near Sams Club and restaurants. Complimentary XBOX and Nespresso Coffee machine. ROKU in all bedrooms. Non smoking policy. Clubhouse with large swimming pool and gym. Well-maintained home, with new appliances. Superhost awarded 34 times in a row !!!

2BD Cottage w/Spa in Margaritaville
Welcome to your own island-inspired oasis. Our charming 2Bd spa 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. Relax with the whole family at this peaceful place to stay.

Gorgeous 8BR at Encore Resort next to Disney - 281
Modern luxury home built in 2020, located at world renowned Encore at Reunion. Almost 4,000sf of a/c area, featuring 8 bedrooms, 6 full baths, game room, private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

Windsor Orlando Private Arcades,Theater,Pool-Spa
Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

Modern Escape in Kissimmee
Relax with the whole family at this peaceful,modern and clean place to stay. 20-25 mts away from Disney, Big yard to relax and have outdoor activities, quiet community, sunset view and much more to do. ALSO 35 MTS APPROXIMATELY FROM THE SOON TO BE OPEN UNIVERSAL EPIC UNIVERSE Which will be Open on MAY 22,2025 Universal’s largest park to date . house includes Netflix,wifi and Garage beeper Any booking over 30 days, the cleaning fee is $200

8052 Heated Pool Grill House Kissimmee by Disney
Relax with the whole family at this peaceful HEATED POOL & GRILL house in Kissimmee, just minutes from Disney Parks and Margarita Ville Water Park. Master Suite has a great view to screened Pool & Lanai. 3 bedrooms, 2 bathrooms, fully equipped kitchen, 4 Smart TV's and strong Wi-Fi all around the house. Enjoy our Games Room with a Foosball table and a Pool table located in the garage!

8 mins. to Disney W/Poolside Theater & Game Room
Are you looking for a vacation home with an incredible game room, a very private south facing saltwater complimentary heated pool with children's wading pool, hot tub and poolside theatre featuring a 120" screen with 4K UHD, and a new modern kitchen, in Formosa Gardens Estates (the gated community known for its large estate lots), and is very close to Disney World? This is it . . .

Heated pool~Lazy River~Mini Golf~Near DisneyResort
Welcome to Lazy Lagoon, your ultimate vacation retreat in the heart of Kissimmee, FL! Our inviting 4-bedroom, 3-bathroom home offers the perfect blend of comfort and adventure, making it ideal for families, friends, or any group getaway. With space to accommodate up to 10 guests, you'll find everything you need for an unforgettable stay just minutes from Orlando's top attractions.
Popular amenities for Kissimmee house rentals
House rentals with a pool

NEW Modern Villa Near Disney w/ Pool & Spa!

City Escape Villa

5BR Home w/Pool near Disney Animal Kingdom

Home, Private Pool, 10 min to Disney, 3 BR/2 Baths

Boho Luxe Retreat • Near Disney Parks

VillaLumine•PrvtPool•Heater•Aesthetic•NearDisney

Haven Luxury

2366 S 6B - Dream House - Sunny Pool - Near Disney
Weekly house rentals

Dream Villa at ChampionsGate -15 minutes to Disney

Indian Ridge Home w/ Pool & Game Room near Disney

Disney Pool Home / GameRoom / Free Water Park

Stunning Home with Pool Minutes to Disney!

3BR Pool Townhome Near Disney w/Game Room

Beautiful South Facing Pool Home

2.5 Aces Home with King bed & Jacuzzi! 2

Luxury Pool Home with Disney View, Guest Top Rated
Private house rentals

A Spacious and Serene Pool Home 10-min to Disney

Windsor Hills Resort 5 Bedroom Private Pool Home

Amazing Solara 7BR/ Pool /Spa /Free Waterpark

Magical 5BR Villa | Themed Rooms | Private Pool

Special Resort home! Minutes away from Disney!

Charming & Warm W/ Pool & Games Room

NEW LIST - Private Pool/Spa; Golf Course!

10 Minutes from Disney! Huge Pool! MovieTheater!
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $275 NZD | $280 NZD | $302 NZD | $299 NZD | $261 NZD | $284 NZD | $301 NZD | $261 NZD | $234 NZD | $248 NZD | $273 NZD | $318 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Quick stats about house rentals in Kissimmee

Total holiday rentals
Explore 3,600 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $34 NZD per night before taxes and fees

Verified guest reviews
Over 99,510 verified reviews to help you choose

Family-friendly holiday rentals
3,090 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 630 rentals that welcome pets

Holiday rentals with a pool
3,260 properties feature pools

Rentals with dedicated workspaces
1,880 properties have a dedicated workspace

Wi-Fi availability
3,570 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
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- House rentals Osceola County
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- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort
- Walt Disney World Resort Golf
- Disney Springs
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- ESPN Wide World of Sports
- Give Kids the World Village
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Aquatica
- Camping World Stadium
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- Reunion Resort Golf Courses - Palmer & Watson






