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1,000 Rentals In Osceola Area
United States
Florida
Osceola Area
Filters
Sub Areas
Shingle Creek Regional Park
(437)
Kissimmee
(389)
Fishers Island
(302)
Indian Point
(211)
Kissimmee View
(151)
GreenPoint Kissimmee
(149)
Victory Village
(117)
Lake Tohopekaliga
(62)
Celebration
(50)
Vine Street Square
(10)
Staymore Extended Studios
(5)
Quail Hollow
(5)
Oak Run
(5)
Oak Hollow
(5)
East Lake Tohopekaliga
(5)
Remington
(4)
Whisper Woods
(3)
Westwood Forest
(3)
Shenandoah
(3)
Mill Run
(3)
Guests
Guests
1
2
3
4
5
6
7
8+
Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
Beautiful Furnished Townhome w\/ Private Pool!
4
5.0
10
Kissimmee Florida Private vacation home
From $131 per night
(USD)
Modern rental in Emerald Island Resort near Disney World (3 mi to Disney)
4
4.0
12
Kissimmee Florida Villa
From $254 per night
(USD)
Amazing 5BR Townhouse Near Disney - Private Pool!
5
4.0
16
Kissimmee Florida Private vacation home
From $85 per night
(USD)
Luxurious Townhome in Paradise Palms Resort Near Disney
4
3.0
10
Kissimmee Florida Private vacation home
From $179 per night
(USD)
Two Bedroom Beautiful Condo, Cypress Palms Resort (2304086)
2
2.0
8
Kissimmee Florida Hotel resort
Click For Pricing
Kissimmee entire home near Disney, Walmart shopping Entertainment, Resturants
3
2.0
8
Kissimmee Florida Private vacation home
From $175 per night
(USD)
Luxury New Resort Mansion, Mins To Disney, For 32Guests! 2024 Special Rates!
14
11.0
32
Kissimmee Florida Private vacation home
From $576 per night
(USD)
Luxury 6 bedroom villa (4 masters), lake view, close to the parks, gated resort
6
6.0
13
Kissimmee Florida Villa
From $237 per night
(USD)
Breathtaking 9 Bed Disney themed Amazing Villa
9
7.0
16
Four Corners Florida Private vacation home
From $432 per night
(USD)
Golf View\/Pool\/SPA\/Game room 20045
8
5.0
16
Four Corners Florida Private vacation home
From $337 per night
(USD)
Spacious Resort Home w\/ Pool - 11 Mi to Disney!
5
5.0
14
Kissimmee Florida Private vacation home
From $220 per night
(USD)
Perfect Townhome in Resort with Pool, Jacuzzi & BBQ
3
2.0
8
Kissimmee Florida Private vacation home
From $110 per night
(USD)
Headline
6
5.0
12
Kissimmee Florida Villa
Click For Pricing
Livin the Dream❤️Closest FREE Resort to Disney! AC game rm!
6
4.0
16
Kissimmee Florida Private vacation home
From $240 per night
(USD)
Less than 10 Mins to Disney!! - Vacation Villa at Fantasy World II (2 bedrooms!)
2
2.0
4
Kissimmee Florida Hotel resort
Click For Pricing
Storey Lake 9 BR Villa With Games Room and Theater
9
5.0
22
Kissimmee Florida Private vacation home
From $269 per night
(USD)
Thanksgiving in the land of Disney
3
2.0
8
Kissimmee Florida Hotel resort
Click For Pricing
WINDSOR HILLS RESORT SUPERB DISNEY 5 BED 5 BATH POOL HOME, THEMED BEDROOMS
5
5.0
12
Kissimmee Florida Villa
From $279 per night
(USD)
4926 - Modern Home w\/ Splash Pool
4
3.0
12
Kissimmee Florida Private vacation home
From $187 per night
(USD)
4738 Luxurious Home - Private Pool - Water Park
6
5.0
15
Kissimmee Florida Private vacation home
From $297 per night
(USD)
\"The Happy Place!' Upgraded Fun Windsor Home
5
5.0
11
Kissimmee Florida Private vacation home
From $268 per night
(USD)
Ultimate Orlando Getaway! 2 Elegant Units, Pool, Kids Playroom, Free Parking
6
8.0
12
Kissimmee Florida Apartment
From $632 per night
(USD)
Luxury New Champions Gate Resort Home
6
5.0
13
Davenport Florida Villa
From $254 per night
(USD)
4 Bedrooms \/ 3 Bathrooms \/ Storey Lake (3135 PP)
4
3.0
10
Kissimmee Florida Private vacation home
From $297 per night
(USD)
Full Amenities, Family-Friendly! WS 19026
5
4.0
14
Four Corners Florida Private vacation home
From $207 per night
(USD)
Lovely Condo w\/Resort Amenities - 7770-23-109
3
3.0
8
Kissimmee Florida Private vacation home
From $178 per night
(USD)
3bed Villa at Seven Dwarfs Kissimmee near Disney!
3
2.0
10
Kissimmee Florida Condo
From $125 per night
(USD)
6 bed , 5 .5 baths - 4 on-suites !! with Ping Pong Table -WIFI
6
5.0
14
Kissimmee Florida Private vacation home
From $285 per night
(USD)
(EE2731) SANITIZED Home 5\/5, Private Pool & Free Waterpark
5
5.0
15
Kissimmee Florida Private vacation home
From $241 per night
(USD)
High End Disney Condo, Better Known As The Animal Kingdom...
3
2.0
6
Kissimmee Florida Condo
From $155 per night
(USD)
Perfect For Family & Friends Getaway! Spacious 3BR Villa | Pool + Balcony
3
3.0
6
Kissimmee Florida Private vacation home
From $322 per night
(USD)
Modern 4BR Villa w\/ Kitchen and Living Rooom | Short Drive to Disney's Parks
4
4.0
8
Kissimmee Florida Private vacation home
From $339 per night
(USD)
Virtual Tour Inside! 2 Family 4BR Villa | Spacious Living Room
8
8.0
16
Kissimmee Florida Private vacation home
From $676 per night
(USD)
Luxe Terra Verde Villa w\/ Theater: 6 Mi to Disney!
6
6.0
10
Kissimmee Florida Private vacation home
From $220 per night
(USD)
Brand New Award Winning Newly Renovated Condo Near Disney and Universal Studios
2
2.0
6
Kissimmee Florida Condo
From $128 per night
(USD)
Magnificent Award Winning Newly Renovated Condo Near Disney 2+2 Great Amenities
2
2.0
6
Davenport Florida Condo
From $50 per night
(USD)
Great value 5BR\/3BA townhome with hot tub\/ lake View, Close to Disney, Seaworld
5
3.0
10
Kissimmee Florida Private vacation home
From $142 per night
(USD)
😎Popular Luxury Resort Home, Private Pool, 10 Minutes From Disney!☀️
6
5.0
14
Kissimmee Florida Private vacation home
From $250 per night
(USD)
Luxurious Award Winning Newly Renovated 2+2 Condo Near Disney and Universal
2
2.0
6
Davenport Florida Condo
From $126 per night
(USD)
Luxury Vacation home! 7 bedrooms, 4.5 baths with WiFi, Pool, Spa, Gameroom
7
5.0
16
Kissimmee Florida Private vacation home
From $173 per night
(USD)
Emerald Island - 3BR, 2BA townhome in gated resort
3
2.0
6
Kissimmee Florida Private vacation home
From $93 per night
(USD)
Perfect vacation getaway 8br\/6ba home, private pool! close to disney
8
6.0
18
Kissimmee Florida Private vacation home
From $347 per night
(USD)
Dazzling Newly Renovated Condo 1.5 miles to Disney
1
1.0
6
Kissimmee Florida Condo
From $104 per night
(USD)
Deluxe Mansion with Infinity Pool at Reunion
10
11.0
26
Kissimmee Florida Private vacation home
From $1346 per night
(USD)
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View
3
2.0
6
Kissimmee Florida Villa
From $129 per night
(USD)
Modern Home with Themed Games Room at Encore
5
5.0
10
Kissimmee Florida Private vacation home
From $493 per night
(USD)
HM302 SANITIZED Condo 2BDRM 2BATH Free Waterpark
2
2.0
6
Kissimmee Florida Apartment
From $119 per night
(USD)
MO5013 Story lake Condo 4 beds 3 bath Private Pool & Free Waterpark
4
3.0
10
Kissimmee Florida Private vacation home
From $200 per night
(USD)
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
4
3.0
10
kissimmee Florida Villa
From $150 per night
(USD)
Exclusive Estate with Gaming Loft at Reunion
7
6.0
16
Kissimmee Florida Private vacation home
From $571 per night
(USD)
9Br\/6Ba luxurious Pool House with lake view, Close To Disney
9
6.0
18
Kissimmee Florida Private vacation home
From $338 per night
(USD)
Luxury Villa w\/ SALTWATER Pool & Hot Tub very close to Disney & Universal
3
2.0
8
Kissimmee Florida Villa
From $232 per night
(USD)
Incredible Fantasy World! Newly Renovated Near Disney with Amazing Amenities
2
2.0
8
Kissimmee Florida Private vacation home
From $79 per night
(USD)
New Listing! Crystal Cove Resort, 6mi to Disney & 11mi to Universal - BT51693
4
3.0
8
Kisimmee Florida Private vacation home
From $263 per night
(USD)
Reunion Disney Villa, Luxury Guarded\/gated community only 15 minutes from WDW
4
6.0
8
Reunion Florida Private vacation home
From $500 per night
(USD)
9Br\/6Ba lake view Pool House from $280\/nt, Close To Disney
9
6.0
18
Kissimmee Florida Private vacation home
From $372 per night
(USD)
Ryans LUXURY 8BR HOME- 10min DISNEY\/MINS THEME PARKS\/RESORT\/POOL\/GAMES\/BBQ GRILL
8
5.0
20
Kissimmee Florida Private vacation home
From $229 per night
(USD)
New Listing! Veranda Palms Resort, 6mi to Disney & 10mi to Universal - BT56262
6
5.0
14
Kissimmee Florida Private vacation home
From $367 per night
(USD)
Cost-Effectiven 8BR\/5BA pool home! Near Disney,SeaWorld and Convention Ctr
8
5.0
18
Kissimmee Florida Private vacation home
From $260 per night
(USD)
Cozy 4 BR\/3 BA, private newly resurfaced pool, 3 miles to Disney, Wifi, internet
4
3.0
8
Kissimmee Florida Private vacation home
From $121 per night
(USD)
8br\/6ba pool villa, Close to Disney,Resort-style heated Pool and Lazy River
8
6.0
18
Kissimmee Florida Private vacation home
From $337 per night
(USD)
4 Bedroom 3 Bathroom Pool Home With Games Room Only Minutes From Disney
4
3.0
8
Kissimmee Florida Villa
From $169 per night
(USD)
Hidden Gem Resort Community; 3BR\/2BA w\/ Water Park. Only 9 MILES FROM DISNEY!
3
2.0
6
Kissimmee Florida Condo
From $137 per night
(USD)
Beautiful 3 BR Townhome in Gated Community Close to All Attractions !!!
3
2.0
8
KISSIMMEE Florida Private vacation home
From $120 per night
(USD)
Renovated Waterfront 4Bd\/2Bth Home w\/Pool&Spa 15-20Min to Disney\/Shops\/Universal
4
2.0
8
Kissimmee Florida Private vacation home
From $148 per night
(USD)
Affordable & Spacious 5BR 3BA Home w\/ private pool, fenced backyard for privacy
5
3.0
10
Kissimmee Florida Private vacation home
From $158 per night
(USD)
Two Bedroom Luxury Condo, Kissimmee Florida (1788933)
2
2.0
6
Kissimmee Florida Condo
Click For Pricing
4Bed Private Pool 10 Guests Champions gate - 8981
4
3.0
10
Davenport Florida Private vacation home
From $165 per night
(USD)
Family Memories. AC.Cable TV. Free WiFi. Private fenced Pool. Game Room
4
3.0
10
KISSIMMEE Florida Private vacation home
From $154 per night
(USD)
Fantastic Villa w\/ Private Pool - Amenities, Large Pool, Fitness Center, Parks
7
5.0
16
Kissimmee Florida Villa
From $216 per night
(USD)
New Listing! Veranda Palms Resort, 6mi to Disney & 10mi to Universal - BT64618
5
5.0
12
Kissimmee Florida Private vacation home
From $321 per night
(USD)
Fabulous 4 bed villa with south facing private pool and spa overlooking water
4
3.0
8
Kissimmee Florida Private vacation home
From $209 per night
(USD)
Modern Radiance with Game Room at Encore Resort
6
7.0
12
Kissimmee Florida Private vacation home
From $408 per night
(USD)
New Listing! Bella Vida Resort, 7mi to Disney & 11mi to Universal - BT45585
6
6.0
12
Kissimmee Florida Private vacation home
Click For Pricing
Resort like: Pool, BBQ & Club Access with Lazy River
5
5.0
12
Kissimmee Florida Private vacation home
From $236 per night
(USD)
WOW -Great 4 bedroom pool home - lake view -10 mins from Disney
4
2.0
8
Liberty Village, Florida Private vacation home
From $135 per night
(USD)
Water View - Pool & Spa - 3.5 miles to Disney - WiFi - BBQ
4
3.0
8
Kissimmee Florida Private vacation home
From $200 per night
(USD)
Superb Townhouse Newly Renovated 1.5 miles to Disney
2
2.0
6
Kissimmee Florida Private vacation home
From $50 per night
(USD)
Secluded Luxury Pool Home, Close to Disney w\/ Oversized pool Special offers now
5
2.0
12
Kissimmee Florida Villa
From $179 per night
(USD)
Cozy Beautiful Clean Home By Disney 2320
3
3.0
7
Kissimmee Florida Private vacation home
From $99 per night
(USD)
Luxurious Vacation Townhome with Private Pool at Westside (WW8948)
4
4.0
10
Kissimmee Florida Private vacation home
From $180 per night
(USD)
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
2
2.0
6
Kissimmee Florida Condo
From $70 per night
(USD)
Fantastic Award Winning Newly Renovated Condo (4 miles to Disney) 2+2
2
2.0
6
Kissimmee Florida Condo
From $117 per night
(USD)
Amazing Home with Themed Rooms, Private Pool\/Spa
5
5.0
12
Davenport Florida Private vacation home
Click For Pricing
5★ Magical 7BR Disney Manor: Ultimate Luxury & Comfort, Just 3 miles to Disney!
7
6.0
18
Kissimmee Florida Private vacation home
From $351 per night
(USD)
Minutes to Disney in a villa that feels like you never left the park at Reunion
6
6.0
14
Four Corners Florida Private vacation home
From $475 per night
(USD)
DH2921 Storey Lake Condo 4 Beds 3 baths Private Pool and Free Waterpark
4
3.0
10
Kissimmee Florida Private vacation home
From $162 per night
(USD)
Disney Delight, New Upgrades,6Br,4BaWindsor Hills,5min@Disney,Pool\/Spa,Billiards
6
4.0
13
Kissimmee Florida Villa
From $192 per night
(USD)
Dog-Friendly Home w\/ Private Pool, High-Speed WiFi, and Central AC
5
3.0
8
Kissimmee Florida Private vacation home
From $181 per night
(USD)
***Book 4 nights and get the 5th night at 50% DISCOUNT!!!***July 1st - July 5th!
1
1.0
4
Kissimmee Florida Hotel resort
Click For Pricing
Bright, centrally-located getaway with a pool, clubhouse, & fast WiFi
3
3.0
6
Kissimmee Florida Private vacation home
From $149 per night
(USD)
Disney Retreat: Private Pool, Theater & Game Room!
5
5.0
10
Kissimmee Florida Private vacation home
From $248 per night
(USD)
Amazing Home with Shared Pool on Disneys Doorstep
3
3.0
6
Kissimmee Florida Private vacation home
From $132 per night
(USD)
Reunion Dream home 7 bed 7 bath - Pool\/spa\/game room by Aplus
7
6.0
14
Reunion Florida Private vacation home
Click For Pricing
9004 Amazing 5BD with pool!
5
5.0
12
Kissimmee Florida Private vacation home
From $150 per night
(USD)
At Margaritaville Resort Luxurious 8 bedroom 8.5 bath Cottage Accommodates up to
7
8.0
22
Kissimmee Florida Private vacation home
Click For Pricing
Stylish Villa with Galactic Themed Room in Encore
10
9.0
22
Kissimmee Florida Private vacation home
From $707 per night
(USD)
Kissimmee FL - Alquiler de Vacaciones
8
6.0
20
Kissimmee Florida Private vacation home
Click For Pricing
Sunset View Villa, pool and spa, lake view, game room, resort, Nr Disney\/Golf
8
6.0
16
Kissimmee Florida Villa
From $338 per night
(USD)
Radiant Luxury | Theater Room | Themed Bedrooms | Games Room
9
10.0
20
Kissimmee Florida Private vacation home
From $751 per night
(USD)
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