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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
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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
Beautifully furnished townhome in Solara Resort!
4
4.0
10
Kissimmee Florida Private vacation home
From $337 per night
(USD)
Amazing 5BR Townhouse near Disney!
5
4.0
16
Kissimmee Florida Private vacation home
From $596 per night
(USD)
Luxurious Townhome in Paradise Palms Resort Near Disney
4
1.0
10
Kissimmee Florida Private vacation home
From $233 per night
(USD)
14Bed Mansion For 32. JumboTron Sports Bar! LED Dark Mini Golf! Luxury Decor!
14
11.0
32
Kissimmee Florida Private vacation home
From $813 per night
(USD)
Spacious 6 bedroom home (4 masters), lake view, close to the parks, gated resort
6
5.0
13
Kissimmee Florida Villa
From $376 per night
(USD)
“Magical Memories Manor” - Awesome Movie and Game Rooms
9
6.0
20
Kissimmee Florida Private vacation home
From $509 per night
(USD)
5 Mi to Walt Disney World! Gem w/ Resort Perks
5
5.0
14
Kissimmee Florida Private vacation home
From $330 per night
(USD)
Perfect Townhome in Resort with Pool, Jacuzzi & BBQ
3
2.0
6
Kissimmee Florida Private vacation home
From $242 per night
(USD)
Livin the Dream, Closest FREE Resort to Disney! 3 Kings
6
4.0
16
Kissimmee Florida Private vacation home
From $549 per night
(USD)
Enchanted Crystal Castle
5
5.0
12
Kissimmee Florida Private vacation home
From $443 per night
(USD)
SL4926 - 4BR house with pool near Disney area
4
3.0
12
Kissimmee Florida Private vacation home
From $241 per night
(USD)
\"The Happy Place!' Upgraded Fun Windsor Home
5
4.0
11
Kissimmee Florida Private vacation home
From $322 per night
(USD)
EV_8940 - 6 Bed 6 Bath Villa with Screened-In Private Pool with Spillover Spa,
6
5.0
14
Davenport Florida Villa
From $365 per night
(USD)
4 Bedrooms / 3 Bathrooms / Storey Lake (3135 PP)
4
3.0
10
Kissimmee Florida Private vacation home
From $513 per night
(USD)
(EE2731) Storey Lake VILLA 5/5, Private Pool & Free Waterpark
5
5.0
15
Kissimmee Florida Private vacation home
From $376 per night
(USD)
High End Disney Condo, Better Known As The Animal Kingdom...
3
2.0
6
Kissimmee Florida Condo
From $218 per night
(USD)
Brand New Award Winning Newly Renovated Condo Near Disney and Universal Studios
2
2.0
6
Kissimmee Florida Condo
From $133 per night
(USD)
Magnificent Award Winning Newly Renovated Condo Near Disney 2+2 Great Amenities
2
2.0
6
Davenport Florida Condo
From $165 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 $190 per night
(USD)
😎Popular Luxury Resort Home, Private Pool, 10 Minutes From Disney!☀️
6
4.0
14
Kissimmee Florida Private vacation home
From $421 per night
(USD)
Luxurious Award Winning Newly Renovated 2+2 Condo Near Disney and Universal
2
2.0
6
Davenport Florida Condo
From $178 per night
(USD)
Emerald Island - 3BR, 2BA townhome in gated resort
3
2.0
6
Kissimmee Florida Private vacation home
From $184 per night
(USD)
Perfect vacation getaway 8br/6ba home, private pool! close to disney
8
6.0
18
Kissimmee Florida Private vacation home
From $332 per night
(USD)
Dazzling Newly Renovated Condo 1.5 miles to Disney
1
1.0
6
Kissimmee Florida Condo
From $116 per night
(USD)
Beautiful Spacious 3 Bedroom Villa with Private Pool and Wonderful Lake View
3
2.0
6
Kissimmee Florida Villa
From $227 per night
(USD)
HM302 Storey Lake Condo 2BDRM 2BATH Free Waterpark
2
2.0
6
Kissimmee Florida Apartment
From $214 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 $306 per night
(USD)
*Tinkerbells Castle 2* Private Pool & Spa Overlooking Lake & Disney Fire Works
4
3.0
10
kissimmee Florida Villa
From $422 per night
(USD)
9Br/6Ba luxurious Pool House with lake view, Close To Disney
9
6.0
18
Kissimmee Florida Private vacation home
From $399 per night
(USD)
Luxury Villa w/ SALTWATER Pool & Hot Tub very close to Disney & Universal
3
2.0
10
Kissimmee Florida Villa
From $412 per night
(USD)
Incredible Fantasy World Nr Disney, Amazing Amenities.Free Shuttle to the Parks
2
2.0
8
Kissimmee Florida Private vacation home
From $190 per night
(USD)
Reunion Disney Villa, Luxury Villa in a gated community, minutes away from WDW.
4
5.0
8
Reunion Florida Private vacation home
From $1029 per night
(USD)
9Br/6Ba lake view Pool House from 300/nt, Close To Disney
9
6.0
18
Kissimmee Florida Private vacation home
From $472 per night
(USD)
Ryan's Castle: Magical Stay with Pool & Game Room- 5mi DISNEY/RESORT/BBQ
8
4.0
20
Kissimmee Florida Private vacation home
From $444 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 $408 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)
Hidden Gem Resort Community Close to DISNEY!; 3BR/2BA w/ Water Park.
3
2.0
6
Kissimmee Florida Condo
From $202 per night
(USD)
Renovated Waterfront 4Bd/2Bth Home w/Pool&Spa 20Min to Disney/Shops/Universal
4
2.0
8
Kissimmee Florida Private vacation home
From $221 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 $270 per night
(USD)
4Bed Private Pool 10 Guests Champions gate - 8981
4
3.0
10
Davenport Florida Private vacation home
From $290 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 $244 per night
(USD)
Fantastic Villa w/ Private Pool - Amenities, Large Pool, Fitness Center, Parks
7
5.0
16
Kissimmee Florida Villa
From $432 per night
(USD)
463 -4 bedroom villa with south facing private pool & Spa
4
3.0
8
Kissimmee Florida Villa
From $261 per night
(USD)
Resort like: Pool, BBQ, Xbox & Club Access with Lazy River – 15 Min to Disney!
5
5.0
10
Kissimmee Florida Private vacation home
From $366 per night
(USD)
Water View - Pool & Spa - 3.5 miles to Disney - BBQ
4
3.0
8
Kissimmee Florida Private vacation home
From $289 per night
(USD)
Superb Townhouse Newly Renovated 1.5 miles to Disney
2
2.0
6
Kissimmee Florida Private vacation home
From $127 per night
(USD)
Less than 4 miles from Disney, 6 br / 4,5 bath + Pool/Spa + Game Room
6
4.0
12
Kissimmee Florida Private vacation home
Click For Pricing
Secluded Luxury Pool Home, Close to Disney w/ Oversized pool Special offers now
5
2.0
12
Kissimmee Florida Villa
From $239 per night
(USD)
Modern Award Winning Newly Renovated, Gorgeous 2+2 Minutes Away From Disney
2
2.0
6
Kissimmee Florida Condo
From $190 per night
(USD)
Fantastic Award Winning Newly Renovated Condo 4 miles to Disney 2+2
2
2.0
6
Kissimmee Florida Condo
From $128 per night
(USD)
5★ Magical 7BR Disney Manor: Ultimate Luxury & Comfort, Just 3 miles to Disney!
7
5.0
18
Kissimmee Florida Private vacation home
From $552 per night
(USD)
Minutes to Disney in a villa that feels like you never left the park at Reunion
6
5.0
14
Four Corners Florida Private vacation home
From $620 per night
(USD)
SLEEP 17,6BR/4BADisney Villa@WindsorHills,themed,Spa,Pool,GameRoom,5mi@Disney!
6
4.0
17
Kissimmee Florida Villa
From $406 per night
(USD)
Stylish Villa with Galactic Themed Room in Encore
10
9.0
22
Kissimmee Florida Private vacation home
From $842 per night
(USD)
Sunset View, lake view, game room, Windsor at Westside resort, Nr Disney/Golf
8
6.0
16
Kissimmee Florida Villa
From $471 per night
(USD)
Now taking bookings for 2026 /2027 Book Now to get the best offer prices
5
3.0
12
kissimmee Florida Villa
From $189 per night
(USD)
Sunny Florida 3bedroom 2 bathroom Condo near Disney
3
2.0
6
Kissimmee Florida Condo
From $164 per night
(USD)
Southeast Facing Private Pool,lakeside,3 Br-2 Bath,10 Min-disney, Modern
3
1.0
6
Kissimmee Florida Private vacation home
From $237 per night
(USD)
SOUTHFACING Private Pool, Lakeview,4 BR-2 Bath,Ultra Clean Modern,10 min Disney
4
2.0
8
Kissimmee Florida Private vacation home
From $251 per night
(USD)
Anna's Cabana Windsor Hills - 5 minute walk to the waterpark
5
5.0
12
Kissimmee Florida Private vacation home
From $359 per night
(USD)
Nature Villa - Rain Forest Out Back - Awesome Location 4 Bdrm!
4
2.0
15
Kissimmee Florida Villa
From $180 per night
(USD)
Resort style near Disney and theme parks
3
2.0
8
Davenport Florida Hotel resort
From $307 per night
(USD)
Achieve your Magical Vacation! 12 Mins to Disney!
4
3.0
10
Kissimmee Florida Villa
From $187 per night
(USD)
Only four miles from Disney! 4 beds, 3 baths, private pool and spa
4
3.0
8
Kissimmee Florida Villa
From $359 per night
(USD)
Spacious Pool Villa - Beautiful Oasis close to Disney World
8
6.0
18
Kissimmee Florida Villa
From $514 per night
(USD)
Luxury Vacation condo close to theme parks<br>Extra clean
2
2.0
6
Kissimmee Florida Condo
From $217 per night
(USD)
Emerald Pleasure Villa - Private Pool, Resort Community, Near Disney
5
3.0
10
Kissimmee Florida Villa
From $358 per night
(USD)
Magic Galaxy- 3BR, Themed- Star Wars, Harry Potter, Mickey- Near Disney!
3
2.0
6
Kissimmee Florida Condo
From $156 per night
(USD)
Cozy 5Bd Storey Lake Home Near Disney 4851
5
4.0
13
Kissimmee Florida Private vacation home
From $246 per night
(USD)
Modern 3Bd w Spa Jacuzzi at Encantada Resort 3012
3
3.0
6
Kissimmee Florida Condo
From $185 per night
(USD)
Legends Palace: Private Bowling, Theater, Arcade, Private Pool, Near Disney
13
16.0
32
Kissimmee Florida Private vacation home
From $5326 per night
(USD)
Champion Gate Brand New Home with Private pool and game room
5
5.0
10
Davenport Florida Private vacation home
From $277 per night
(USD)
Family Villa @ Champions Gate/ Pool + Theater
8
5.0
20
Davenport Florida Villa
From $337 per night
(USD)
Beautiful 6-bedroom house, themed rooms, game room, wi-fi, minutes from Disney
6
4.0
12
Kissimmee Florida Private vacation home
From $533 per night
(USD)
4 Mi to Animal Kingdom: Gem w/ Pool in Kissimmee
4
3.0
10
Kissimmee Florida Private vacation home
From $372 per night
(USD)
Tuscana Resort in Championsgate near Disney
3
2.0
8
Davenport Florida Condo
From $171 per night
(USD)
EV_2826 - 9BR / 7BA Storey Lake Villa near to Disney, Private Pool & Games Room
9
5.0
24
Kissimmee Florida Private vacation home
From $524 per night
(USD)
EV_2665 - 5 Bed 5 Bath Villa with Screened-In Private Pool with Spa, Games Room
5
5.0
12
Kissimmee Florida Private vacation home
From $287 per night
(USD)
Solara Resort 7 miles to Disney
5
5.0
12
Kissimmee Florida Private vacation home
From $386 per night
(USD)
Unique. 5 Mi to Disney. True South Pool & Spa. Themed.
4
3.0
8
KISSIMMEE Florida Private vacation home
From $339 per night
(USD)
Windsor Hills Resort 3 Bedroom 4th Floor Condo with Resort Access
3
2.0
6
Kissimmee Florida Condo
From $273 per night
(USD)
Exquisite 9 BEDS POOL HOME ! 15min to Disney World!
9
2.0
20
Four Corners Florida Hotel resort
From $497 per night
(USD)
S-Facing Pool, 3.6 mi from Disney, man-gated resort, wheelchair accessible
5
3.0
11
Kissimmee Florida Private vacation home
From $436 per night
(USD)
Disney Getaway 3BR Lucaya Gated Resort Pool Gym
3
2.0
7
Kissimmee Florida Condo
From $169 per night
(USD)
Gorgeous 6Bd Pool Home Star Wars w Game Room 712
6
5.0
18
Four Corners Florida Private vacation home
From $294 per night
(USD)
Town Home in Gated Community in Great Location
3
2.0
8
Kissimmee Florida Private vacation home
From $222 per night
(USD)
LUXURY HOME/PRIVATE POOL WITH EXTENDED DECK !! POOL HEAT INCLUDED!!
6
3.0
14
Kissimmee Florida Private vacation home
From $317 per night
(USD)
Stylish 4BR Retreat in Compass Bay - Close to Disney & Universal
4
3.0
10
Kissimmee Florida Private vacation home
From $267 per night
(USD)
Relax in Five Star Resort, minutes from Walt Disney World and other attractions.
2
2.0
7
Kissimmee Florida Hotel resort
From $283 per night
(USD)
The Royal Villa - pictures taken 5/24/2024
7
6.0
16
Kissimmee Florida Villa
From $424 per night
(USD)
8954 Marvelous & Spacious Private Pool
5
5.0
10
Kissimmee Florida Private vacation home
From $314 per night
(USD)
2023 Dec23-30 7 NTs 2BD/2BA 5min to Disney World at Florida Vacation Villas
2
2.0
6
Kissimmee Florida Hotel resort
From $212 per night
(USD)
Disney Getaway w/ Splash Pool + Kids’ Theme Rooms
4
3.0
12
Kissimmee Florida Private vacation home
From $553 per night
(USD)
4BR Marvel: Private Pool, Sleeps 10 - Champions Gate - 8953
4
3.0
10
Davenport Florida Private vacation home
From $285 per night
(USD)
Rare Extended Pool Deck & Oversized Spa | Arcade Room | Kids Bedrooms
6
6.0
16
Kissimmee Florida Private vacation home
From $727 per night
(USD)
10% Wkly Disc! 5 miles from Disney and Few Mints to Universal! FREE Water Park!
2
2.0
8
Kissimmee Florida Condo
From $252 per night
(USD)
✨Luxury Disney Retreat ✨Private Pool ✨Epic Themed Rooms
3
3.0
8
Kissimmee Florida Private vacation home
From $369 per night
(USD)
Lakeview Retreat / Clubhouse Access / Near Disney Fun
2
2.0
8
Kissimmee Florida Condo
From $204 per night
(USD)
Beautiful standalone white house minutes away to theme parks!
6
5.0
12
Kissimmee Florida Private vacation home
From $394 per night
(USD)
Luxury 5 Star Vacation Villa- Free WiFi & Long Distance
4
4.0
8
Kissimmee Florida Villa
From $290 per night
(USD)
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