24+ Vacation Rentals Near Kissimmee |
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Ski Hotels - Vacation Rentals in Kissimmee

Home Sunset Lake5 dormitorios, 3½ baños, piscina y spa cerca de Disney From US $257
         

New
Ski Chalet
Home Sunset Lake5 dormitorios, 3½ baños, piscina y spa cerca de Disney
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  • Parking
  • Pool

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5BR Amazing Cozy House with Private Pool and Jacuzzi From US $135
         

New
Ski Chalet
5BR Amazing Cozy House with Private Pool and Jacuzzi
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Glamorous Townhouse 4Bed/3Bath/Pool/5Min Disney From US $241
         

New
Ski Chalet
Glamorous Townhouse 4Bed/3Bath/Pool/5Min Disney
  • Air Conditioner
  • Pet Friendly
  • Pool

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Charming 3-bedroom chalet with WiFi and AC in Kissimmee From US $194
         

New
Ski Chalet
Charming 3-bedroom chalet with WiFi and AC in Kissimmee
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

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Modern Townhouse 4Bed/3Bath/Pool/5Min Disney From US $318
         

10.0 (4 Reviews)
Ski Chalet
Modern Townhouse 4Bed/3Bath/Pool/5Min Disney
  • Air Conditioner
  • Pet Friendly
  • Pool

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Sweet Townhouse 4Beds/3Baths/Pool/18Min Disney From US $360
         

10.0 (2 Reviews)
Ski Chalet
Sweet Townhouse 4Beds/3Baths/Pool/18Min Disney
  • Air Conditioner
  • Pet Friendly
  • Pool

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Brand New Townhouse 4Bed/3Bath/Pool/5Min Disney From US $311
         

10.0 (1 Review)
Ski Chalet
Brand New Townhouse 4Bed/3Bath/Pool/5Min Disney
  • Air Conditioner
  • Pet Friendly
  • Pool

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Enjoyable Townhouse 4Bed/3Bath/Pool/5Min From Disney From US $337
         

9.6 (5 Reviews)
Ski Chalet
Enjoyable Townhouse 4Bed/3Bath/Pool/5Min From Disney
  • Air Conditioner
  • Pet Friendly
  • Pool

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Luxury Places to Stay in Kissimmee

Over 10000+ Luxury Places to Stay in or Near Kissimmee
10.0 (1 Review)
House
6 Bed villa close to disney
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  • Pool
  • TV

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8.0 (2 Reviews)
Villa
BRAND NEW Storey Lake- 5 bedrooms, 5 bathrooms, private pool - Harry Potter & Minions theme
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8.8 (3 Reviews)
House
BRAND NEW Solara Resort - 5 bedrooms, Private Pool - FROZEN & HARRY POTTER Themed Rooms
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8.8 (11 Reviews)
House
Storey Lake BRAND NEW - 6 Bedrooms, Private Pool, Themed Bedrooms
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New
House
Solara Resort - 5 bedrooms, Private Pool - FROZEN & HARRY POTTER - DISNEY AREA
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  • Pool
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New
House
FROZEN & HARRY POTTER Themed Rooms * Solara Resort - 5 bedrooms, Private Pool
  • Air Conditioner
  • Pool
  • TV

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8.2 (11 Reviews)
House
Brand New Pool Home - 10 Minutes From Disney, Universal, Sea World And Outlets
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  • Pool

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10.0 (58 Reviews)
Villa
⭐️ The Mediterranean Villa Orlando 😀 DISNEY ⭐️ Private Pool & Games Room
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Kissimmee

Over 10000+ Top-Rated Vacation Rentals with a Pool in or Near Kissimmee
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear From US $455
         

10.0 (374 Reviews)
House
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
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  • Parking
  • Pet Friendly

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4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192 From US $179
         

10.0 (325 Reviews)
Villa
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
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  • Parking
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Water View - Pool & Spa - 3.5 miles to Disney - BBQ From US $249
         

10.0 (320 Reviews)
House
Water View - Pool & Spa - 3.5 miles to Disney - BBQ
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Windsor Poolside Escape with Stunning Pool View-Perfect for Families! From US $212
         

10.0 (314 Reviews)
Condo
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
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Amazing villa close to Disney with 5* Reviews From US $316
         

10.0 (280 Reviews)
Villa
Amazing villa close to Disney with 5* Reviews
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  • Parking
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Conservation View - Hot Tub - Free Pool Heat - Very Private From US $245
         

10.0 (263 Reviews)
Villa
Conservation View - Hot Tub - Free Pool Heat - Very Private
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  • Parking
  • Pool

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Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat! From US $229
         

10.0 (263 Reviews)
House
Quiet, Clean, Disney-3.5 miles, Well kept home! Free Pool/spa Heat!
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BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED From US $154
         

10.0 (262 Reviews)
House
BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED
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Pet-Friendly Vacation Rentals in Kissimmee

Over 7024+ Pet-Friendly Vacation Rentals in or Near Kissimmee
Elegant, Spacious Townhome within 4 Miles to Walt Disney World From US $216
         

10.0 (191 Reviews)
House
Elegant, Spacious Townhome within 4 Miles to Walt Disney World
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  • Parking
  • Pet Friendly

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Tuscana Resort Orlando by Aston From US $99
         

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7.7 (804 Reviews)
Apartment
Tuscana Resort Orlando by Aston
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stunning 5-Bedroom Home with Pool From US $620
         

10.0 (1 Review)
House
Stunning 5-Bedroom Home with Pool
  • Air Conditioner
  • Pet Friendly
  • TV

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5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area From US $284
         

10.0 (185 Reviews)
House
5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area
  • Air Conditioner
  • Parking
  • Pet Friendly

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Sunset View Villa, pool and spa -lake view - game room, resort, Nr Disney/Golf From US $529
         

9.8 (130 Reviews)
Villa
Sunset View Villa, pool and spa -lake view - game room, resort, Nr Disney/Golf
  • Air Conditioner
  • Parking
  • Pet Friendly

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Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2 From US $155
         

9.6 (199 Reviews)
Condo
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
  • Air Conditioner
  • Parking
  • Pet Friendly

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Hot Tub. Little Mermaid and Harry Potter Theme. Closest To Disney Private Pool From US $283
         

9.6 (132 Reviews)
Villa
Hot Tub. Little Mermaid and Harry Potter Theme. Closest To Disney Private Pool
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  • Parking
  • Pet Friendly

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Magnificent Award Winning Newly Renovated Condo Near Disney 2+2 Great Amenities From US $149
         

9.4 (161 Reviews)
Condo
Magnificent Award Winning Newly Renovated Condo Near Disney 2+2 Great Amenities
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  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Kissimmee

Over 28034+ Large Vacation Homes & Villas in or Near Kissimmee
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills From US $469
         

10.0 (201 Reviews)
Villa
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
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Discover Unparalleled Elegance Our Newest Candlelight Pool Home From US $285
         

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New
House
Discover Unparalleled Elegance Our Newest Candlelight Pool Home
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Best Location in Solara Resort! From US $693
         

10.0 (4 Reviews)
House
Best Location in Solara Resort!
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BEST HOUSE! Harry Potter, CARS, Princesses, StarWars, Avengers. Disney 8-10 min! From US $805
         

10.0 (166 Reviews)
Villa
BEST HOUSE! Harry Potter, CARS, Princesses, StarWars, Avengers. Disney 8-10 min!
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Private Pool/Spa, Outdoor TV, Woodland Views, Windsor Palms, Minutes to Disney From US $346
         

10.0 (124 Reviews)
Villa
Private Pool/Spa, Outdoor TV, Woodland Views, Windsor Palms, Minutes to Disney
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Luxury 5 Stars Home w/Princess & Mickey Themed Rooms, Game Room Private Pool/Spa From US $354
         

10.0 (107 Reviews)
House
Luxury 5 Stars Home w/Princess & Mickey Themed Rooms, Game Room Private Pool/Spa
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Luxurious Executive Villa 20 mins from Disney, Private Pool/Spa, Games Room From US $274
         

10.0 (73 Reviews)
Villa
Luxurious Executive Villa 20 mins from Disney, Private Pool/Spa, Games Room
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✦ 5min2Disney ✦ 7BR/4.5BA ✦ South Pool/Spa ✦ A/C Star Wars Gameroom ✦ Modern From US $395
         

10.0 (46 Reviews)
Villa
✦ 5min2Disney ✦ 7BR/4.5BA ✦ South Pool/Spa ✦ A/C Star Wars Gameroom ✦ Modern
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  • Parking
  • Pool

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Wheelchair Accessible Vacation Homes in Kissimmee

Over 4104+ Wheelchair Accessible Vacation Homes in or Near Kissimmee
⭐ SALE MAY 26-30 $75! PREMIER HOST, MINUTES TO DISNEY! GREAT PRICE/LOCATION!⭐ From US $128
         

10.0 (233 Reviews)
Condo
⭐ SALE MAY 26-30 $75! PREMIER HOST, MINUTES TO DISNEY! GREAT PRICE/LOCATION!⭐
  • Air Conditioner
  • Parking
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Fabulous Apartment at Storey Lake only 10 minutes from Disney SL4731-103 From US $122
         

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8.9 (13 Reviews)
House
Fabulous Apartment at Storey Lake only 10 minutes from Disney SL4731-103
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New! Epic Cabana Court Luxe Retreat From US $704
         

New
Condo
New! Epic Cabana Court Luxe Retreat
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Style, Luxury & Stunning Views, Star Wars From US $236
         

10.0 (99 Reviews)
Condo
Style, Luxury & Stunning Views, Star Wars
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5 STAR TOP FLOOR CONDO WITH AMAZING GOLF VIEWS! From US $194
         

10.0 (88 Reviews)
Condo
5 STAR TOP FLOOR CONDO WITH AMAZING GOLF VIEWS!
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Fantastic Pool & Free Water Park only Minutes to Walt Disney Worlds Front Gate! From US $205
         

9.8 (218 Reviews)
Condo
Fantastic Pool & Free Water Park only Minutes to Walt Disney Worlds Front Gate!
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Attractive 3 bed townhome | 3 Bed, 2.5 Bath From US $171
         

9.6 (24 Reviews)
Condo
Attractive 3 bed townhome | 3 Bed, 2.5 Bath
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Palm Tree Paradise! Bright Tropical Fun with “Frozen” Bedroom - 3 mi from WDW From US $172
         

9.8 (25 Reviews)
Condo
Palm Tree Paradise! Bright Tropical Fun with “Frozen” Bedroom - 3 mi from WDW
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Kissimmee Vacation Rentals and Airbnb Places to Stay Under $200

Over 11272+ Kissimmee Vacation Rentals and Airbnb Places to Stay Under $200
4BR Private Pool Home Near Disney – Family Friendly Sleeps 8 Screened Pool From US $178
         

10.0 (49 Reviews)
House
4BR Private Pool Home Near Disney – Family Friendly Sleeps 8 Screened Pool
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Cozzy Townhouse! 925PTC-SVH From US $100
         

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New
House
Cozzy Townhouse! 925PTC-SVH
  • Air Conditioner
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  • Balcony/Terrace

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Elegant Villa W/private Pool/spa & Game Room! From US $190
         

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10.0 (1 Review)
House
Elegant Villa W/private Pool/spa & Game Room!
  • Air Conditioner
  • Pool
  • TV

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Outstanding, owner operated Townhome, even a TV in the pool area! From US $179
         

9.8 (168 Reviews)
House
Outstanding, owner operated Townhome, even a TV in the pool area!
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WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE From US $169
         

9.8 (120 Reviews)
House
WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE
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Family Memories/Private South Facing Pool/Lake View/AC/BBQ Grill/Wifi/Game Room. From US $194
         

9.8 (98 Reviews)
House
Family Memories/Private South Facing Pool/Lake View/AC/BBQ Grill/Wifi/Game Room.
  • Air Conditioner
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  • Pool

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Premier Host-Beautiful 4BR/2BA Pool Home on Conservation Lot - Disney 15 Minutes From US $186
         

9.6 (287 Reviews)
House
Premier Host-Beautiful 4BR/2BA Pool Home on Conservation Lot - Disney 15 Minutes
  • Air Conditioner
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3 MILES FROM DISNEY! Private SOUTH facing Pool. Awesome family villa From US $191
         

9.6 (239 Reviews)
Villa
3 MILES FROM DISNEY! Private SOUTH facing Pool. Awesome family villa
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Instantly Bookable Vacation Homes in Kissimmee

Over 30809+ Instantly Bookable Vacation Homes in or Near Kissimmee
Lots of Privacy On A Lake 20 Minutes From Disney With A Private Pool and Spa! From US $238
         

10.0 (202 Reviews)
House
Lots of Privacy On A Lake 20 Minutes From Disney With A Private Pool and Spa!
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Near Disney| Private Pool & BBQ|Cozy Townhouse 4Bd From US $605
         

10.0 (1 Review)
House
Near Disney| Private Pool & BBQ|Cozy Townhouse 4Bd
  • Air Conditioner
  • Pet Friendly
  • TV

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CYBER WEEK WAS 180 NOW 175 Near Disney World: 4BR/2BA Pool Home + Free Internet From US $234
         

9.8 (156 Reviews)
House
CYBER WEEK WAS 180 NOW 175 Near Disney World: 4BR/2BA Pool Home + Free Internet
  • Air Conditioner
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Stunning Lakeview Pool/Spa-Games Room,Free Wi-Fi, 2 mls to Disney From US $327
         

9.8 (104 Reviews)
House
Stunning Lakeview Pool/Spa-Games Room,Free Wi-Fi, 2 mls to Disney
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4 Bedrooms 3.5 Bathrooms - Inc 2 King Bed Master Suites-Next to Disney World From US $210
         

9.8 (103 Reviews)
House
4 Bedrooms 3.5 Bathrooms - Inc 2 King Bed Master Suites-Next to Disney World
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Disney Themed Villa Lakeside Private Heated Pool 4 Bed only 3 miles to Disney From US $269
         

9.8 (87 Reviews)
House
Disney Themed Villa Lakeside Private Heated Pool 4 Bed only 3 miles to Disney
  • Air Conditioner
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5 BR/4 BA/2-Floors/Keyless Entry/Contactless Check-In/1-Day Between Rentals/WiFi From US $279
         

9.6 (240 Reviews)
House
5 BR/4 BA/2-Floors/Keyless Entry/Contactless Check-In/1-Day Between Rentals/WiFi
  • Air Conditioner
  • Parking
  • Pool

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Luxury 4 Bedroom Villa on the gated Bellavida Resort close to the Theme parks From US $249
         

9.6 (189 Reviews)
Villa
Luxury 4 Bedroom Villa on the gated Bellavida Resort close to the Theme parks
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About Kissimmee Vacation Rentals

With more than 24 Kissimmee vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Skihotels and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Kissimmee.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Skihotels Kissimmee, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Kissimmee. Places to stay near Kissimmee are 2173.5 ft² on average, with prices averaging US $285 a night.

Skihotels makes it easy and safe to find and compare vacation rentals in Kissimmee with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Kissimmee

Type Count
Ski Chalet Rentals 24

Use these Quick Filters to Find a Vacation Rental in Kissimmee

★ Pro Tip: Skihotels makes it easy to compare the best listings on Skihotels homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Skihotels homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Kissimmee.

Weather in Kissimmee

View the weather forecast for Kissimmee before booking your Kissimmee Vacation Rentals to confirm your best time to go.

December - February
High 79°F       Low 53°F
March - May
High 91°F       Low 57°F
June - August
High 92°F       Low 71°F
September - November
High 90°F       Low 60°F

Top Attractions Around Kissimmee, FL

Skihotels offers a large selection of top attractions around Kissimmee. Research things to do on your vacation before you visit Kissimmee.


Old Town Osceola Heritage Park Silver Spurs Arena Kissimmee Lakefront Park Mystic Dunes Golf Club Medieval Times Fun Spot America Reunion Resort Golf Course Lake Tohopekaliga Give Kids the World Village 192 Flea Market Osceola Performing Arts Center Kissimmee Civic Center Boggy Creek Airboat Rides Capone's Dinner Show Osceola Regional Medical Center Austin-Tindall Regional Park Skate Reflections Falcon's Fire Golf Club Kissimmee Go-Karts

Other Places to Stay Near Kissimmee, FL


Disney's Maingate West 16,187 Properties Four Corners 15,223 Properties West Kissimmee 13,744 Properties Historic Downtown Kissimmee 6,951 Properties Reunion 1,752 Properties Windsor Hills 1,258 Properties Disney's Maingate East 1,027 Properties Windsor Palms 655 Properties Bellavida 240 Properties Lake Berkley 139 Properties Buena Ventura Lakes 100 Properties Veranda Palms 88 Properties

Complexes around Kissimmee, FL


Kissimmee 310 Properties Disney 39 Properties Orlandos Sunshine Orlando 97 Properties Corners 49 Properties Paradise Townhome 26 Properties Emerald Island Resort 46 Properties Garden 34 Properties Umco Clermont 29 Properties Kissimmee 33 Properties Solara Resort 11 Properties Bella Vida Resort 10 Properties Paradox Circle 14 Properties Indian Creek 5 Properties Lucaya Village Resort 10 Properties Seasons 10 Properties
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Kissimmee Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Kissimmee?

There are a lot of options in Kissimmee. If you plan on staying in the Kissimmee area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Kissimmee:

How many vacation rentals are available in Kissimmee?

Currently, the total number of properties listed in 2026 is over 24 in the Kissimmee area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Kissimmee.