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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
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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
STAR WARS GAME ROOM * Private Pool * FREE Waterpark
9
6.0
22
Kissimmee Florida Private vacation home
From $853 per night
(USD)
Indulge in Luxury: Stylish 5bd Townhouse near Disney, Private Pool, BBQ, Resort
5
4.0
12
Kissimmee Florida Private vacation home
From $263 per night
(USD)
Gorgeous 6BR\/5BA Free Water Park-15Mins to Disney
6
5.0
14
Kissimmee Florida Private vacation home
From $269 per night
(USD)
Cozy Lake Cottage - 4 miles to Disney
2
1.0
5
Kissimmee Florida Cottage
From $133 per night
(USD)
Cozy Tropical Cottage - 4 mi to Disney
2
1.0
7
Kissimmee Florida Cottage
From $133 per night
(USD)
Liberty Bluff Excitement | Games Room | Reunion Membership
5
6.0
10
Kissimmee Florida Private vacation home
From $256 per night
(USD)
Lovely Condo with Resort pool, Hot tub, Gym
3
2.0
8
Davenport Florida Apartment
From $100 per night
(USD)
Luxury 5 bd w Custom game\/Theater Room - Close to Disney!
5
5.0
10
Reunion Florida Private vacation home
From $215 per night
(USD)
Fully-Stocked Cozy Tropical Cottage-4 mi to Disney\n
2
1.0
7
Kissimmee Florida Cottage
From $135 per night
(USD)
Mickey's Getaway- MODERN 4BR3BA 2MasterSuite Gated
4
3.0
8
Kissimmee Florida Private vacation home
From $140 per night
(USD)
Amazing renovated Town House very well located!!!\n
3
2.0
10
Kissimmee Florida Private vacation home
From $150 per night
(USD)
Storey Lake 5 Bedroom Vacation Home 4894
5
4.0
14
Kissimmee Kissimmee Private vacation home
From $199 per night
(USD)
7BR| Near Disney| Veranda Palms| Pool & BBQ
7
6.0
21
Kissimmee Florida Private vacation home
From $140 per night
(USD)
6BR| Champions Gate Resort| Near Disney|BBQ Grill
6
6.0
12
Davenport Florida Private vacation home
From $139 per night
(USD)
Spacious home with private pool & hot tub, game room, tennis
7
7.0
15
Kissimmee Florida Private vacation home
From $290 per night
(USD)
Stylish, Modern 2 Bed\/2 Bath Apartment in Kissimmee, Florida! Sleeps up to 6!
2
2.0
6
Kissimmee Florida Apartment
From $133 per night
(USD)
The Kates Experience
3
3.0
8
Kissimmee Florida Private vacation home
From $123 per night
(USD)
2 Bedroom Condo minutes from Disney 325
2
2.0
6
Kissimmee Florida Condo
From $168 per night
(USD)
*NEW*5mins2disney\/FREEwtrprk\/sleeps12\/3Bdm\/arcade
1
1.0
12
Kissimmee Florida Private vacation home
From $137 per night
(USD)
Oasis Villa- Perfect getaway
8
7.0
16
Kissimmee Florida Private vacation home
From $350 per night
(USD)
2936ST-Amazing home in the BEST resort near Disney
9
5.0
23
Kissimmee Kissimmee Private vacation home
Click For Pricing
New pool home on a popular resort with clubhouse, water park and lazy river
4
3.0
8
Davenport Florida Private vacation home
From $165 per night
(USD)
Our Newest Listing in Orlando Kissimmee, part of MCMH Vacation Rental Group
6
4.0
14
Kissimmee Florida Private vacation home
From $298 per night
(USD)
Resort Townhouse Near Disney w Pool and BBQ
4
3.0
8
Davenport Florida Private vacation home
Click For Pricing
Beautiful Town Home with Splash Pool-8973SLTCCD
4
3.0
8
Reunion Florida Private vacation home
From $205 per night
(USD)
Vrbo Property
3
3.0
6
Kissimmee Florida Private vacation home
Click For Pricing
Stylish Condo near Disney w\/ Hotel Amenities - 7770 - 28 - 116
3
3.0
8
Four Corners Four Corners Villa
From $194 per night
(USD)
Beautiful Condo near Disney w\/ Hotel Amenities - 7740 - 20 - 123
3
3.0
8
Four Corners Four Corners Condo
From $200 per night
(USD)
Relaxing Condo with Resort Amenities near Disney - B49 #115
3
3.0
8
Four Corners Four Corners Condo
From $180 per night
(USD)
Pristine Home Sweet Home at Kissimmee, FL
4
3.0
11
Kissimmee Florida Private vacation home
Click For Pricing
A Dreamy Florida Vacation! 5 BDR Sleeps 10, Just 15 Min to All Theme Parks!
5
5.0
12
Kissimmee Florida Private vacation home
From $187 per night
(USD)
House of Fun at Windsor Westside w\/ Pool!
5
5.0
12
Kissimmee Florida Private vacation home
From $178 per night
(USD)
Splendid 6Bd w\/ Pool at Solara Resort 2154
6
5.0
15
Kissimmee Florida Private vacation home
From $186 per night
(USD)
Beautiful 2bedrooms Condo close to Disney Resort!
2
2.0
4
Davenport Florida Apartment
From $84 per night
(USD)
Cozy 3bedrooms Condo next to Disney!
3
2.0
6
Davenport Davenport Apartment
From $94 per night
(USD)
Luxury Condo With Water Park & Reunion Resort Access near Disney at Spectrum Resort Orlando By Rentyl - B20 #223
5
5.0
12
Four Corners Four Corners Condo
From $286 per night
(USD)
4 Bedroom Gated Orlando Vacation Rental Pool Home with Lake View & Games Room!
4
3.0
8
Kissimmee Florida Private vacation home
From $204 per night
(USD)
New! Resort Home with Private Pool & Arcade, Near the Parks
5
4.0
14
Kissimmee Florida Private vacation home
From $421 per night
(USD)
Magical Residence Resort, 5 min Disney
4
5.0
10
Kissimmee Florida Private vacation home
From $232 per night
(USD)
Relax and Play near Orlando Attractions! Outdoor Pool, Pet-friendly Hotel!
1
1.0
2
Kissimmee Florida Private vacation home
Click For Pricing
Your Home Away from Home! 2 Relaxing Units, Outdoor Pool, Free Parking!
2
2.0
8
Kissimmee Florida Private vacation home
Click For Pricing
Your Home for Disney Adventures! Swimming Pool, Pets Allowed, Free Parking!
1
1.0
4
Kissimmee Florida Private vacation home
Click For Pricing
Spacious 5Bed Pool Home with Game Room-1577SW
5
5.0
10
Reunion Florida Private vacation home
From $320 per night
(USD)
Spacious family villa Near Disney 6BR 5BT PVT pool
6
5.0
16
Davenport Florida Private vacation home
From $270 per night
(USD)
House of Mouse Disney Oasis
5
5.0
10
Davenport Florida Private vacation home
From $229 per night
(USD)
Storey Lake Resort 6br Family Villa Pool by Disney
6
5.0
16
Kissimmee Florida Private vacation home
From $341 per night
(USD)
Headline
7
6.0
16
Kissimmee Florida Villa
From $499 per night
(USD)
Family Retreat: Poolside Haven in Kissimmee
4
2.0
8
Kissimmee Florida Private vacation home
From $249 per night
(USD)
Getaway Delight-8 Bedrooms, Pool & Great Location
8
5.0
16
Four Corners Florida Private vacation home
From $262 per night
(USD)
4 Bedrooms\/ 3 Bathrooms\/ Paradise Palms (2955 BP)
4
3.0
10
Kissimmee Florida Private vacation home
From $121 per night
(USD)
Gorgeous 4 Suites DREAM Villa 5 min to Disney
4
5.0
9
Kissimmee Kissimmee Private vacation home
From $207 per night
(USD)
Cozy 6 Bed Pool Home with Spa and Game Room-1117KS
6
6.0
14
Davenport Florida Villa
From $320 per night
(USD)
Spacious 4 Bed Town Home with Splash Pool-4829LL
4
3.0
9
Kissimmee Florida Private vacation home
From $200 per night
(USD)
Spacious 12 Bed Pool Home with Game Room-4473MD
12
10.0
26
Kissimmee Florida Villa
From $851 per night
(USD)
15min from Theme Parks: Cozy Resort Home
4
3.0
8
Kissimmee Kissimmee Private vacation home
From $205 per night
(USD)
Beautiful Spacious 5Bed Pool Home-2669PL
5
5.0
10
Kissimmee Florida Villa
From $320 per night
(USD)
4 Bedroom\/ 3 Bathroom\/ Paradise Palms (8963SP)
4
3.0
12
Kissimmee Florida Private vacation home
From $273 per night
(USD)
GS1117 Champions Gate Condo 3Bedrooms 2Bathrooms Free Waterpark
3
2.0
10
Kissimmee Florida Apartment
From $123 per night
(USD)
Spacious 5 Bed Town Home with Splash Pool-4391SL
5
4.0
10
Kissimmee Florida Private vacation home
Click For Pricing
Beautiful 4 Bed Town Home with Splash Pool-4891CTD
4
3.0
9
Kissimmee Florida Private vacation home
From $200 per night
(USD)
Beautiful 7 Bed Pool Home with Game Room-9092SHD
7
6.0
16
Davenport Florida Villa
From $480 per night
(USD)
Fabulous 6 Bed Pool Home with Themed Rooms-4358PS
6
5.0
12
Kissimmee Florida Villa
From $5250 per night
(USD)
Reunion Encore Resort Villa W\/ Pool Spa Gameroom
6
6.0
12
kissimmee Florida Villa
From $227 per night
(USD)
3 BDR Condo in Emerald Island – 5 Min from Disney w\/ Tons of Onsite Amenities!
3
3.0
6
Kissimmee Florida Private vacation home
From $129 per night
(USD)
Hunky Dory II | Margaritaville Resort!
3
4.0
10
Kissimmee Florida Cottage
From $163 per night
(USD)
Lakeside 5BR Family Friendly Pool Home Near Disney
5
5.0
10
Osceola County Florida Private vacation home
Click For Pricing
Toon & Toys Themed 6BR Resort Pool Home Near Disney World
6
6.0
16
Four Corners Florida Private vacation home
From $185 per night
(USD)
5 Bedrooms\/ 4.5 Bathrooms\/ Windsor Westside (8907 SA)
5
5.0
12
Kissimmee Florida Private vacation home
From $236 per night
(USD)
9 Bedroom\/ 5 Bathroom\/ Storey Lake (4564TB)
9
5.0
24
Kissimmee Florida Private vacation home
From $608 per night
(USD)
Club Cortile Condo | Condo in Kissimmee
3
2.0
6
Kissimmee Florida Condo
From $241 per night
(USD)
Candy Palm Retreat | Townhouse in Kissimmee with resort amenities
4
3.0
8
Kissimmee Florida Private vacation home
From $209 per night
(USD)
May Special! - 6 Bed Home w\/ Pool\/Spa by Disney!
6
5.0
12
Kissimmee Florida Private vacation home
From $266 per night
(USD)
Welcoming 5 BR\/4BA Home – Everything you need! 8 minutes from Disney World!
5
4.0
10
Kissimmee Florida Private vacation home
From $239 per night
(USD)
Allen, Lisa & Holland's Champions Gate Home
4
3.0
8
Davenport Davenport Villa
Click For Pricing
Spectacular Champions Gate Vacation Home
5
4.0
10
Davenport Davenport Private vacation home
From $151 per night
(USD)
Spacious 6 bedroom home with private pool Gated community Lake Berkley Resort
6
3.0
12
Kissimmee Florida Villa
From $223 per night
(USD)
Beautiful 4 Bed | 3 Bath Lucaya Village Townhome | Minutes from Disney!
4
3.0
11
Kissimmee Florida Private vacation home
From $125 per night
(USD)
Colorful stay minutes from Disney with resort amenities and children's items
4
3.0
8
Kissimmee Florida Private vacation home
From $121 per night
(USD)
Disney-Themed Luxury Apartment: Simply Amazing! Family Size!!!3BR 2BR
3
2.0
6
Davenport Florida Condo
From $150 per night
(USD)
New Luxury 12 BR 11.5 BA Pool Villa\/ 15Min to Disney\/ Sleep 30
12
11.0
30
Kissimmee Florida Villa
From $673 per night
(USD)
UNIQUE MASTERPIECE|15 Suites|Sleeps 30
15
15.0
30
Kissimmee Florida Private vacation home
From $1069 per night
(USD)
Spacious Pool Home Close To Disney
6
7.0
12
Kissimmee Florida Private vacation home
From $282 per night
(USD)
Disney-themed townhome in Carriage Point with fantastic resort amenities
3
3.0
8
Kissimmee Florida Private vacation home
From $172 per night
(USD)
Snowbird-friendly townhouse near Disney with pool, tennis, gym, enclosed patio
3
3.0
8
Kissimmee Florida Private vacation home
From $181 per night
(USD)
Resort Home With Pool-Sleeps 14 Free Wifi \/Parking
5
5.0
14
Four Corners Florida Private vacation home
From $226 per night
(USD)
6 Beds\/ 5 Baths Reunion Resort
6
3.0
16
Kissimmee Florida Private vacation home
From $264 per night
(USD)
Escape to luxury and comfort in our stunning 14-bedroom oasis nestled within the exclusive Veranda Palms Resort.
14
15.0
30
Kissimmee Florida Private vacation home
From $1055 per night
(USD)
Special Offer! Back to Ravine\/Near Disney\/Private Pool 2477RT
4
3.0
11
Kissimmee Florida Private vacation home
From $160 per night
(USD)
5 Bedroom\/ 4 Bathroom\/ Paradise Palms (8964CA)
5
4.0
10
Kissimmee Florida Private vacation home
From $330 per night
(USD)
Near Disney\/Back to Ravine\/Private Pool 23112
4
3.0
11
Kissimmee Florida Private vacation home
From $163 per night
(USD)
Located at Champions Gate area townhome close to major Themes & Acuatic Parks.
5
4.0
16
Four Corners Florida Private vacation home
From $322 per night
(USD)
Toy Story Condohotel Room 9min to Disney\/1st floor
1
1.0
4
Kissimmee Florida Apartment
From $70 per night
(USD)
3012- Great Family Home near Disney (private pool)
4
3.0
8
Kissimmee Florida Private vacation home
From $151 per night
(USD)
St Cloud Vacation Rental - Walk to Lakefront Park!
2
1.0
6
St Cloud Florida Private vacation home
Click For Pricing
Paradise Palms Resort 5 Bedroom Private Pool+Spa Home
5
5.0
11
Kissimmee Florida Private vacation home
From $315 per night
(USD)
411 Wanderlust heaven 5bed\/Pool
6
7.0
14
kissimmee Florida Private vacation home
From $408 per night
(USD)
Mickeys Happy Place (Disney, Pool)
5
1.0
6
Kissimmee Florida Condo
From $85 per night
(USD)
BRAND NEW! 4BR House Waterpark Disney Orlando 2693
4
3.0
8
Kissimmee Florida Private vacation home
From $136 per night
(USD)
FREE Pool Heat / 10 mins 2 Disney / Lake View
7
5.0
14
Kissimmee Florida Villa
From $170 per night
(USD)
Charming 4 bedroom TH
4
3.0
11
Kissimmee Florida Private vacation home
From $133 per night
(USD)
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