48273+ Vacation Rentals Near Kissimmee |
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Bespoke Usa Travel - Vacation Rentals in Kissimmee

4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192 in Kissimmee From US $218
         

10.0 (334 Reviews)
Villa
4 Bedroom Villa 2 Miles from Disney Entrance Kissimmee off Us192
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Cozzy Townhouse! 925PTC-SVH in Kissimmee From US $100
         

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

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Gorgeous Margaritaville Cottage W/private Patio! in Kissimmee From US $301
         

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10.0 (11 Reviews)
House
Gorgeous Margaritaville Cottage W/private Patio!
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  • Parking
  • TV

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Water View - Pool & Spa - 3.5 miles to Disney - BBQ in Kissimmee From US $313
         

10.0 (325 Reviews)
House
Water View - Pool & Spa - 3.5 miles to Disney - BBQ
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BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED in kissimmee From US $126
         

10.0 (273 Reviews)
House
BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY. FULLY EQUIPED
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⭐AUG 3-14,$76+tax/fees 5STAR CONDO*PREMIER HOST*GREATPRICE&CLOSE TOATTRACTIONS⭐ in Kissimmee From US $238
         

10.0 (240 Reviews)
Condo
⭐AUG 3-14,$76+tax/fees 5STAR CONDO*PREMIER HOST*GREATPRICE&CLOSE TOATTRACTIONS⭐
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Delightful modern 4 bed, 3 bath villa with private pool/spa and lake view. in Kissimmee From US $248
         

10.0 (224 Reviews)
Villa
Delightful modern 4 bed, 3 bath villa with private pool/spa and lake view.
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Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills in Kissimmee From US $530
         

10.0 (207 Reviews)
Villa
Outstanding 6 Bed Villa, Pool & Spa, Superb Lakefront Setting, 5* Windsor Hills
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Luxury Places to Stay in Kissimmee

Over 10000+ Luxury Places to Stay in or Near Kissimmee
New
House
4 Bedroom Paradise Palms With Private Pool (2600)
  • Air Conditioner
  • 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 (11 Reviews)
House
Storey Lake BRAND NEW - 6 Bedrooms, Private Pool, Themed Bedrooms
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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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New
House
FROZEN & HARRY POTTER Themed Rooms * Solara Resort - 5 bedrooms, Private Pool
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  • Pool
  • TV

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New
House
Solara Resort - 5 bedrooms, Private Pool - FROZEN & HARRY POTTER - DISNEY AREA
  • Air Conditioner
  • Pool
  • TV

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

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New
House
6BR Pool Villa at Windsor Hill - Near Disney World
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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 in Kissimmee From US $671
         

10.0 (385 Reviews)
House
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
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  • Pet Friendly

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Windsor Poolside Escape with Stunning Pool View-Perfect for Families! in Kissimmee From US $300
         

10.0 (320 Reviews)
Condo
Windsor Poolside Escape with Stunning Pool View-Perfect for Families!
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Amazing villa close to Disney with 5* Reviews in kissimmee From US $365
         

10.0 (283 Reviews)
Villa
Amazing villa close to Disney with 5* Reviews
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South Facing Pool Hot Tub Themed Rooms Home Theater Swingset Splash Pad BBQ in Kissimmee From US $514
         

10.0 (245 Reviews)
House
South Facing Pool Hot Tub Themed Rooms Home Theater Swingset Splash Pad BBQ
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Luxury Villa Disney 2 mls 7BR 40 ft Pool, Huge Spa, Cinema, Lake Views, Slps 16. in Kissimmee From US $587
         

10.0 (242 Reviews)
House
Luxury Villa Disney 2 mls 7BR 40 ft Pool, Huge Spa, Cinema, Lake Views, Slps 16.
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Disney theme rooms,Splashpad, Movie Theater, Private Pool in Kissimmee From US $533
         

10.0 (240 Reviews)
House
Disney theme rooms,Splashpad, Movie Theater, Private Pool
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Steps from Waterpark/Pool. Next to Disney w/Frozen, Aladdin, Beauty&Beast theme in Kissimmee From US $246
         

10.0 (238 Reviews)
Condo
Steps from Waterpark/Pool. Next to Disney w/Frozen, Aladdin, Beauty&Beast theme
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5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill. in Kissimmee From US $390
         

10.0 (227 Reviews)
House
5 MINS to DISNEY! Themed! Costumes, Toys, HEATED POOL/SPA, PS4, Grill.
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Pet-Friendly Vacation Rentals in Kissimmee

Over 7283+ Pet-Friendly Vacation Rentals in or Near Kissimmee
Tuscana Resort Orlando by Aston in Kissimmee From US $99
         

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

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5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area in Kissimmee From US $447
         

10.0 (191 Reviews)
House
5 Stars House With WiFi, Game Room, Private Heated Spa & Pool In a Gated Area
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  • Pet Friendly

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Willow Bend in Kissimmee From US $623
         

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10.0 (2 Reviews)
House
Willow Bend
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Sunset View, lake view, game room, Windsor at Westside resort, Nr Disney/Golf in Kissimmee From US $456
         

9.8 (132 Reviews)
Villa
Sunset View, lake view, game room, Windsor at Westside resort, Nr Disney/Golf
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Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2 in Kissimmee From US $140
         

9.6 (212 Reviews)
Condo
Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2
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Hot Tub. Little Mermaid and Harry Potter Theme. Closest To Disney Private Pool in Kissimmee From US $471
         

9.6 (134 Reviews)
Villa
Hot Tub. Little Mermaid and Harry Potter Theme. Closest To Disney Private Pool
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Magnificent Award Winning Newly Renovated Condo Near Disney 2+2 Great Amenities in Davenport From US $140
         

9.4 (170 Reviews)
Condo
Magnificent Award Winning Newly Renovated Condo Near Disney 2+2 Great Amenities
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Gorgeous Award Winning Renovated Condo Near Disney And Universal Studios in Davenport From US $204
         

9.4 (102 Reviews)
Condo
Gorgeous Award Winning Renovated Condo Near Disney And Universal Studios
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  • Pet Friendly

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Large Vacation Homes & Villas in Kissimmee

Over 28431+ Large Vacation Homes & Villas in or Near Kissimmee
Discover Unparalleled Elegance Our Newest Candlelight Pool Home in Kissimmee From US $285
         

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New
House
Discover Unparalleled Elegance Our Newest Candlelight Pool Home
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BEST HOUSE! Harry Potter, CARS, Princesses, StarWars, Avengers. Disney 8-10 min! in Kissimmee From US $640
         

10.0 (171 Reviews)
Villa
BEST HOUSE! Harry Potter, CARS, Princesses, StarWars, Avengers. Disney 8-10 min!
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Champions Gate Oasis, 4BR Vacation Haven in Davenport From US $421
         

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10.0 (3 Reviews)
Villa
Champions Gate Oasis, 4BR Vacation Haven
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Private Pool/Spa, Outdoor TV, Woodland Views, Windsor Palms, Minutes to Disney in Kissimmee From US $427
         

10.0 (125 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 in Kissimmee From US $451
         

10.0 (112 Reviews)
House
Luxury 5 Stars Home w/Princess & Mickey Themed Rooms, Game Room Private Pool/Spa
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✦ 5min2Disney ✦ 7BR/4.5BA ✦ South Pool/Spa ✦ A/C Star Wars Gameroom ✦ Modern in Kissimmee From US $367
         

9.8 (47 Reviews)
Villa
✦ 5min2Disney ✦ 7BR/4.5BA ✦ South Pool/Spa ✦ A/C Star Wars Gameroom ✦ Modern
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Premier Host-Beautiful 4BR/2BA Pool Home on Conservation Lot - Disney 15 Minutes in Kissimmee From US $206
         

9.6 (292 Reviews)
House
Premier Host-Beautiful 4BR/2BA Pool Home on Conservation Lot - Disney 15 Minutes
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5 BR/4 BA/2-Floors/Keyless Entry/Contactless Check-In/1-Day Between Rentals/WiFi in Kissimmee From US $308
         

9.6 (242 Reviews)
House
5 BR/4 BA/2-Floors/Keyless Entry/Contactless Check-In/1-Day Between Rentals/WiFi
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Wheelchair Accessible Vacation Homes in Kissimmee

Over 4334+ Wheelchair Accessible Vacation Homes in or Near Kissimmee
Fabulous Apartment at Storey Lake only 10 minutes from Disney SL4731-103 in Kissimmee 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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Style, Luxury & Stunning Views, Star Wars in Reunion From US $256
         

10.0 (100 Reviews)
Condo
Style, Luxury & Stunning Views, Star Wars
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Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts in Kissimmee From US $507
         

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10.0 (1 Review)
Condo
Fireworks @ Night -storey Lake By Shine Villas 709 2 Bedroom Apts
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  • Pool
  • Wheelchair Accessible

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5 STAR TOP FLOOR CONDO WITH AMAZING GOLF VIEWS! in Kissimmee From US $156
         

10.0 (91 Reviews)
Condo
5 STAR TOP FLOOR CONDO WITH AMAZING GOLF VIEWS!
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3 BR Condo with Beautiful Pool & Water Park Minutes to Disney Worlds Front Gate in Kissimmee From US $250
         

9.8 (218 Reviews)
Condo
3 BR Condo with Beautiful Pool & Water Park Minutes to Disney Worlds Front Gate
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Renovated Townhome at Reunion, 6 Miles to Disney! in Kissimmee From US $229
         

9.6 (24 Reviews)
Condo
Renovated Townhome at Reunion, 6 Miles to Disney!
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Palm Tree Paradise! Bright Tropical Fun with “Frozen” Bedroom - 3 mi from WDW in Kissimmee From US $216
         

9.8 (25 Reviews)
Condo
Palm Tree Paradise! Bright Tropical Fun with “Frozen” Bedroom - 3 mi from WDW
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Brand New Award Winning Newly Renovated Condo Near Disney and Universal Studios in Kissimmee From US $151
         

9.2 (163 Reviews)
Condo
Brand New Award Winning Newly Renovated Condo Near Disney and Universal Studios
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Kissimmee Vacation Rentals and Airbnb Places to Stay Under $200

Over 9902+ Kissimmee Vacation Rentals and Airbnb Places to Stay Under $200
Multi Resorts at Fantasy World in Kissimmee From US $150
         

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7.4 (19 Reviews)
House
Multi Resorts at Fantasy World
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4BR Private Pool Home Near Disney – Family Friendly Sleeps 8 Screened Pool in Kissimmee From US $190
         

10.0 (50 Reviews)
House
4BR Private Pool Home Near Disney – Family Friendly Sleeps 8 Screened Pool
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Elegant Villa W/private Pool/spa & Game Room! in Kissimmee From US $190
         

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10.0 (1 Review)
House
Elegant Villa W/private Pool/spa & Game Room!
  • Air Conditioner
  • Pool
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Outstanding, owner operated Townhome, even a TV in the pool area! in Clermont From US $192
         

9.8 (170 Reviews)
House
Outstanding, owner operated Townhome, even a TV in the pool area!
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1-101 Legacy Dunes, Just Steps to the Beach Style Pool, Minutes to Disney! in Kissimmee From US $185
         

10.0 (48 Reviews)
Condo
1-101 Legacy Dunes, Just Steps to the Beach Style Pool, Minutes to Disney!
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Family Friendly 2BR Condo at Oakwater Resort – 1.5 Miles to Disney in Kissimmee From US $179
         

9.8 (154 Reviews)
Condo
Family Friendly 2BR Condo at Oakwater Resort – 1.5 Miles to Disney
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Luxurious Mickey Themed Condo - Kids Will Love It! Only 2 Miles to Disney! in Kissimmee From US $170
         

9.8 (134 Reviews)
Condo
Luxurious Mickey Themed Condo - Kids Will Love It! Only 2 Miles to Disney!
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RLR2Disney #2! (3 Turns To Disney) in Kissimmee From US $177
         

9.8 (89 Reviews)
House
RLR2Disney #2! (3 Turns To Disney)
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Instantly Bookable Vacation Homes in Kissimmee

Over 31087+ Instantly Bookable Vacation Homes in or Near Kissimmee
WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE in Kissimmee From US $201
         

10.0 (123 Reviews)
House
WINNER:TOP VACATION RENTAL , CERTIFICATE OF EXCELLENCE
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Lots of Privacy On A Lake 20 Minutes From Disney With A Private Pool! in Kissimmee From US $155
         

10.0 (174 Reviews)
House
Lots of Privacy On A Lake 20 Minutes From Disney With A Private Pool!
  • Air Conditioner
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  • View

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CYBER WEEK WAS 180 NOW 175 Near Disney World: 4BR/2BA Pool Home + Free Internet in Kissimmee From US $260
         

9.8 (163 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 in Kissimmee From US $351
         

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 in Kissimmee From US $235
         

9.8 (104 Reviews)
House
4 Bedrooms 3.5 Bathrooms - Inc 2 King Bed Master Suites-Next to Disney World
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Family Memories/Private South Facing Pool/Lake View/AC/BBQ Grill/Wifi/Game Room. in Kissimmee From US $227
         

9.8 (99 Reviews)
House
Family Memories/Private South Facing Pool/Lake View/AC/BBQ Grill/Wifi/Game Room.
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Disney Themed Villa Lakeside Private Heated Pool 4 Bed only 3 miles to Disney in Kissimmee From US $294
         

9.8 (87 Reviews)
House
Disney Themed Villa Lakeside Private Heated Pool 4 Bed only 3 miles to Disney
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Luxury 4 Bedroom Villa on the gated Bellavida Resort close to the Theme parks in Kissimmee From US $262
         

9.6 (195 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 48273 Kissimmee vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bespokeusatravel 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 Bespokeusatravel 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 1781.03 ft² on average, with prices averaging US $403 a night.

Bespokeusatravel 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
Vacation Homes 29785
Villas 7756
Holiday Apartments 4501
Resorts 740
Hotels 525
Cottages 450
Others 27
Ski Chalet Rentals 24
B&B 13
Cabin Rentals 10
Hostels 2

Use these Quick Filters to Find a Vacation Rental in Kissimmee

★ Pro Tip: Bespokeusatravel makes it easy to compare the best listings on Bespokeusatravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bespokeusatravel 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

Bespokeusatravel 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 18,719 Properties Four Corners 17,730 Properties West Kissimmee 15,863 Properties Historic Downtown Kissimmee 7,654 Properties Reunion 2,071 Properties Windsor Hills 1,361 Properties Disney's Maingate East 1,135 Properties Windsor Palms 737 Properties Bellavida 261 Properties Lake Berkley 163 Properties Buena Ventura Lakes 105 Properties Veranda Palms 94 Properties

Complexes around Kissimmee, FL


Kissimmee 309 Properties Disney 38 Properties Orlandos Sunshine Orlando 97 Properties Corners 49 Properties Paradise Townhome 26 Properties Emerald Island Resort 46 Properties Umco Clermont 30 Properties Garden 34 Properties Kissimmee 32 Properties Solara Resort 11 Properties Bella Vida Resort 10 Properties Paradox Circle 16 Properties Retreat At Championsgate 14 Properties Seasons 10 Properties Lucaya Village Resort 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 48273 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.