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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Windsor Westside Resort 6 Bedroom Private Pool Home 6 Home

Vacation Home

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Osceola
Windsor Westside Resort 6 Bedroom Private Pool Home 6 Home Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.1 mi (16.3 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Windsor Westside Resort 6 Bedroom Private Pool Home 6 Home Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access is available to keep you connected. Conveniences include a coffee/tea maker and a washing machine.

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Non-renting - 1533fd - The Retreat at Championsgate

Vacation Home

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Osceola
Non-renting - 1533fd - The Retreat at Championsgate Location
With a stay at this villa in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This golf villa is 11.2 mi (18.1 km) from Old Town and 12 mi (19.3 km) from ESPN Wide World of Sports Complex.

Non-renting - 1533fd - The Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

Non-renting - 1533fd - The Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned villa, featuring a kitchen with a refrigerator and a stovetop. A flat-screen television is provided for your entertainment. Conveniences include a microwave and an iron/ironing board.

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Bedroom

Firework View 6BR Home Pool/spa/game Near Disney!

Vacation Home

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Osceola
Firework View 6BR Home Pool/spa/game Near Disney! Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 5.4 mi (8.7 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.1 km) from Disney's Hollywood Studios®.

Firework View 6BR Home Pool/spa/game Near Disney! Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and an outdoor tennis court. This vacation home also features complimentary wireless internet access and an arcade/game room.

Firework View 6BR Home Pool/spa/game Near Disney! Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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5BR Encore Sleeps 12 w/ Pool, Spa & Game Tables

Vacation Home

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Osceola
5BR Encore Sleeps 12 w/ Pool, Spa & Game Tables Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 7.6 mi (12.2 km) from ESPN Wide World of Sports Complex and 8.1 mi (13 km) from Disney's Hollywood Studios®.

5BR Encore Sleeps 12 w/ Pool, Spa & Game Tables Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a hot tub. Additional features at this vacation home include complimentary wireless internet access and an arcade/game room.

5BR Encore Sleeps 12 w/ Pool, Spa & Game Tables Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Windsor Hills Resort 6 Bedroom Pool+Spa Home 6 Home

Vacation Home

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Osceola
Windsor Hills Resort 6 Bedroom Pool+Spa Home 6 Home Location
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex and 5.9 mi (9.6 km) from Old Town.

Windsor Hills Resort 6 Bedroom Pool+Spa Home 6 Home Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and an oven. Complimentary wireless internet access keeps you connected, and a Smart television is provided for your entertainment. Conveniences include a coffee/tea maker and a washing machine.

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Living area

Modern Home, Private Pool. Sleeps 15 Ww102

Vacation Home

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Osceola
Modern Home, Private Pool. Sleeps 15 Ww102 Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Walt Disney World® Resort and ChampionsGate Golf Club. This vacation home is 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.3 mi (18.2 km) from ESPN Wide World of Sports Complex.

Modern Home, Private Pool. Sleeps 15 Ww102 Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an outdoor tennis court, and a fitness center. Additional features at this vacation home include an arcade/game room and barbecue grills.

Modern Home, Private Pool. Sleeps 15 Ww102 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Amazing house near the parks

Vacation Home

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Osceola
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Exterior & Views

Tropical Serenity at Margaritaville

Private Vacation Home

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Osceola
Tropical Serenity at Margaritaville Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This vacation home is 6.7 mi (10.8 km) from Old Town and 7.1 mi (11.4 km) from Disney's Hollywood Studios®.

Tropical Serenity at Margaritaville Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony or patio. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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4.0/5
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Comfy Modern House w Pool Perfect Location

Vacation Home

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Osceola
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5 Bedroom Home 8 Minutes To Disney! townhouse

Vacation Home

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Osceola
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Room

The Golf Vista Townhome at Reunion

Vacation Home

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Osceola
The Golf Vista Townhome at Reunion Location
With a stay at this vacation home in Kissimmee (Reunion), you'll be a 1-minute drive from Reunion Resort Golf Course and 10 minutes from ChampionsGate Golf Club. This golf vacation home is 7.1 mi (11.4 km) from Walt Disney World® Resort and 9.3 mi (15 km) from ESPN Wide World of Sports Complex.

The Golf Vista Townhome at Reunion Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills.

The Golf Vista Townhome at Reunion Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Luxurious Townhome W/ Free Wifi, Themed Kids Room & Shared Resort-style Pool

Vacation Home

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Osceola
Luxurious Townhome W/ Free Wifi, Themed Kids Room & Shared Resort-style Pool Location
When you stay at this vacation home in Kissimmee, you'll be near the beach, within a 10-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This vacation home is 7.4 mi (11.9 km) from Disney's Animal Kingdom® Theme Park and 8.2 mi (13.3 km) from ESPN Wide World of Sports Complex.

Luxurious Townhome W/ Free Wifi, Themed Kids Room & Shared Resort-style Pool Facility and Service
Take advantage of recreation opportunities such as a fitness center, or other amenities including complimentary wireless internet access and an arcade/game room.

Luxurious Townhome W/ Free Wifi, Themed Kids Room & Shared Resort-style Pool Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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C1524fd-the Retreat at Championsgate

Vacation Home

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Osceola
C1524fd-the Retreat at Championsgate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club. This golf vacation home is 11.2 mi (18 km) from Old Town and 11.4 mi (18.4 km) from ESPN Wide World of Sports Complex.

C1524fd-the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

C1524fd-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Conveniences include a coffee/tea maker and a dryer.

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1486 Moon Valley Drive

Private Vacation Home

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Osceola
1486 Moon Valley Drive Location
With a stay at this vacation home in Four Corners, you'll be near the beach, within a 15-minute drive of Reunion Resort Golf Course and ChampionsGate Golf Club. This vacation home is 11.8 mi (18.9 km) from Old Town and 12.7 mi (20.5 km) from Walt Disney World® Resort.

1486 Moon Valley Drive Facility and Service
Take advantage of recreational opportunities offered, including an outdoor pool, an indoor pool, and a fitness center.

1486 Moon Valley Drive Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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4001SB Sonoma

Vacation Home

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Osceola
4001SB Sonoma Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and 192 Flea Market. This vacation home is 9.7 mi (15.6 km) from Orlando Vineland Premium Outlets and 9.9 mi (15.9 km) from Disney Springs™.

4001SB Sonoma Rooms
Make yourself comfortable in your air-conditioned vacation home. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

Stunning 5 Bd Home w/ Pool Close to Disney 4822

Vacation Home

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Osceola
Stunning 5 Bd Home w/ Pool Close to Disney 4822 Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, a 4-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.2 mi (8.3 km) from Disney Springs™ and 6.2 mi (10 km) from Walt Disney World® Resort.

Stunning 5 Bd Home w/ Pool Close to Disney 4822 Facility and Service
Be sure to enjoy recreational amenities, including a complimentary water park, an outdoor pool, and an indoor pool. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Stunning 5 Bd Home w/ Pool Close to Disney 4822 Rooms
Treat yourself to a stay in this individually decorated vacation home, which features a private pool and a Smart TV. There's a private balcony or patio. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Wired and wireless internet access is complimentary, while a 60-inch flat-screen television with cable programming provides entertainment.

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4.4/5
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Others

7628recife

Vacation Home

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Osceola
7628recife Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 4.9 mi (8 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.4 km) from Disney's Hollywood Studios®.

7628recife Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including concierge services.

7628recife Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave. There's a private balcony.

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Food & Drinks

Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 11.5 mi (18.5 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhdog9055 - Champions Gate Resort - 4 Bed 3 Baths Townhouse Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Enjoy a meal at the restaurant or snacks in the vacation home's coffee shop/cafe. Relax with your favorite drink at the bar/lounge or the poolside bar.

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Exterior & Views

Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277

Vacation Home

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Osceola
Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277 Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 7.1 mi (11.4 km) from Disney Springs™ and 8.2 mi (13.2 km) from Walt Disney World® Resort.

Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277 Facility and Service
Don't miss out on the many recreational opportunities, including a complimentary water park, an outdoor pool, and a lazy river. Additional amenities at this vacation home include concierge services, a television in a common area, and charcoal grills.

Gorgeous 4 Bd w/ Pool at Storey Lake Resort 4277 Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a full-sized refrigerator/freezer and an oven. A 60-inch Smart television with cable programming provides entertainment, while complimentary wired internet access keeps you connected. Conveniences include a safe and a desk, and you can also request a crib/infant bed (surcharge).

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Others

Way Too Many Bottles

Private Vacation Home

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Osceola
Way Too Many Bottles Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This vacation home is 6.2 mi (9.9 km) from Old Town and 6.5 mi (10.5 km) from Disney's Hollywood Studios®.

Way Too Many Bottles Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private balcony. Digital television is provided for your entertainment. Conveniences include a separate sitting area and a microwave.

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Vacation Homes in Osceola

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