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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
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Venetian Beauty

Vacation Home

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Osceola
Venetian Beauty Location
With a stay at this vacation home in Kissimmee (Venetian Bay Villages), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.4 mi (15.1 km) from Disney Springs™ and 10.4 mi (16.8 km) from Walt Disney World® Resort.

Venetian Beauty Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

Venetian Beauty Rooms
Make yourself comfortable in your vacation home, which features a refrigerator. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower and a hair dryer. Conveniences include a phone and a dryer.

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Fantastic Townhome 5min-disneyworld 134

Vacation Home

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Osceola
Fantastic Townhome 5min-disneyworld 134 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 Old Town. This vacation home is 5 mi (8 km) from ESPN Wide World of Sports Complex and 5.6 mi (9.1 km) from Disney's Hollywood Studios®.

Fantastic Townhome 5min-disneyworld 134 Facility and Service
Enjoy the recreation opportunities such as a fitness center or make use of other amenities including complimentary wireless internet access.

Fantastic Townhome 5min-disneyworld 134 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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C1658mvd-the Retreat at Championsgate

Vacation Home

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Osceola
C1658mvd-the Retreat at Championsgate Location
When you stay at this vacation home in Four Corners, you'll be next to a golf course, within a 15-minute drive of ChampionsGate Golf Club and Mystic Dunes Golf Club. This golf vacation home is 11.4 mi (18.4 km) from Old Town and 12.2 mi (19.6 km) from ESPN Wide World of Sports Complex.

C1658mvd-the Retreat at Championsgate Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

C1658mvd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Midnight Sunset at Margaritaville Resort

Private Vacation Home

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Osceola
Midnight Sunset at Margaritaville Resort Location
With a stay at this vacation home in Kissimmee, you'll be a 5-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 6.4 mi (10.2 km) from Disney's Animal Kingdom® Theme Park and 6.8 mi (10.9 km) from Old Town.

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

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Windsor Hills Resort Vacation Home Ts7718

Vacation Home

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Osceola
Windsor Hills Resort Vacation Home Ts7718 Location
Located in Kissimmee (Windsor Hills), this cottage is within a 10-minute drive of Walt Disney World® Resort and Old Town. This cottage is 5.7 mi (9.1 km) from ESPN Wide World of Sports Complex and 6.1 mi (9.9 km) from Disney's Hollywood Studios®.

Windsor Hills Resort Vacation Home Ts7718 Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. There's a private patio. Conveniences include a dryer and an iron/ironing board.

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8944cuban

Vacation Home

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Osceola
8944cuban Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 8 mi (12.9 km) from Disney's Animal Kingdom® Theme Park and 8.9 mi (14.4 km) from ESPN Wide World of Sports Complex.

8944cuban Facility and Service
Be sure to enjoy recreational amenities including an outdoor pool and a fitness center.

8944cuban Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a microwave. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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4 Bed townhome with Private Pool Near Disney! townhouse

Vacation Home

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Osceola
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Four Bedrooms TownHome Close to Disney 5162A

Vacation Home

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Osceola
Four Bedrooms TownHome Close to Disney 5162A Location
When you stay at this vacation home in Kissimmee, you'll be on a lake, a 5-minute drive from Old Town and 7 minutes from Orlando Vineland Premium Outlets. This family-friendly vacation home is 5.3 mi (8.5 km) from Disney Springs™ and 6 mi (9.6 km) from Walt Disney World® Resort.

Four Bedrooms TownHome Close to Disney 5162A Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Four Bedrooms TownHome Close to Disney 5162A 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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3.6/5
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Magical Village Gem

Vacation Home

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Osceola
Magical Village Gem 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 5 mi (8 km) from ESPN Wide World of Sports Complex and 5.8 mi (9.3 km) from Disney's Hollywood Studios®.

Magical Village Gem Rooms
Make yourself comfortable in your vacation home. Complimentary wireless internet access is available to keep you connected. The bathroom has a bathtub or shower.

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Sport & Beauty

Ip60387 - Paradise Palms - 5 Bed 4 Baths Townhome

Vacation Home

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Osceola
Ip60387 - Paradise Palms - 5 Bed 4 Baths Townhome Location
With a stay at this vacation home in Kissimmee, you'll be within a 15-minute drive of Walt Disney World® Resort and Old Town. This family-friendly vacation home is 8.1 mi (13.1 km) from Disney's Animal Kingdom® Theme Park and 9 mi (14.5 km) from ESPN Wide World of Sports Complex.

Ip60387 - Paradise Palms - 5 Bed 4 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ip60387 - Paradise Palms - 5 Bed 4 Baths Townhome 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. A flat-screen television with cable programming is available for your entertainment, and a video-game console is also provided. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home. Quench your thirst with your favorite drink at the poolside bar.

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Exterior & Views

Emerald Island Happy Place

Vacation Home

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Osceola
Emerald Island Happy Place Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7.4 mi (12 km) from ESPN Wide World of Sports Complex and 7.9 mi (12.7 km) from Disney's Hollywood Studios®.

Emerald Island Happy Place Facility and Service
Take advantage of recreation opportunities such as an outdoor pool, or other amenities including complimentary wireless internet access and an arcade/game room.

Emerald Island Happy Place Rooms
Make yourself comfortable in this individually decorated vacation home, featuring a kitchen with a refrigerator and an oven. There's a private furnished lanai. A 65-inch flat-screen television is provided, with digital programming available. Conveniences include a separate sitting area and a microwave.

Important Information
The property will be renovating from October 12 2026 to April 12 2027 (completion date subject to change). The following areas are affected:
  • Exterior
During renovations, the vacation home will make every effort to minimize noise and disturbance.

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Bathroom

Chun's Bella Vida Resort Vacation Home

Vacation Home

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Osceola
Chun's Bella Vida Resort Vacation Home Location
With a stay at this cottage in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This cottage is 8.9 mi (14.3 km) from Disney Springs™ and 8.9 mi (14.3 km) from ESPN Wide World of Sports Complex.

Chun's Bella Vida Resort Vacation Home Facility and Service
Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room.

Chun's Bella Vida Resort Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen.

See details
1.0/5
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Bedroom

4563nl - Storey Lake Resort

Vacation Home

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Osceola
4563nl - Storey Lake Resort Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This golf vacation home is 6.5 mi (10.5 km) from Disney Springs™ and 7.5 mi (12.1 km) from Walt Disney World® Resort.

4563nl - Storey Lake Resort Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

4563nl - Storey Lake Resort Rooms
Make yourself comfortable in your vacation home.

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Bedroom

Calabria by PRP

Vacation Home

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Osceola
Calabria by PRP Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This vacation home is 6.9 mi (11.1 km) from Walt Disney World® Resort and 8.5 mi (13.8 km) from Disney's Animal Kingdom® Theme Park.

Calabria by PRP Rooms
Make yourself comfortable in this vacation home, which features a private pool. There's a private patio. A kitchen is outfitted with a refrigerator. Complimentary wireless internet access is available to keep you connected.

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Enchanted Clock Tower

Private Vacation Home

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Osceola
Enchanted Clock Tower Location
When you stay at this vacation home in Kissimmee, you'll be in a shopping district, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 5.6 mi (9 km) from Disney Springs™ and 6.6 mi (10.7 km) from Walt Disney World® Resort.

Enchanted Clock Tower Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Enchanted Clock Tower Rooms
Make yourself comfortable in your air-conditioned vacation home, featuring a refrigerator and a microwave. 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 coffee/tea maker and a washer/dryer.

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Exterior & Views

7662reclife

Vacation Home

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Osceola
7662reclife 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®.

7662reclife Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave.

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Sport & Beauty

Grhbch3043 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse

Vacation Home

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Osceola
Grhbch3043 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Flamingo Crossings Town Center and Mystic Dunes Golf Club. This family-friendly vacation home is 6.3 mi (10.2 km) from Walt Disney World® Resort and 8 mi (12.8 km) from Disney's Animal Kingdom® Theme Park.

Grhbch3043 - Paradise Palms Resort - 4 Bed 3 Baths Townhouse Facility and Service
Practice your swing on the golf course or dip into one of the 2 hot tubs. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhbch3043 - Paradise Palms 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
Satisfy your appetite at the vacation home's coffee shop/cafe, or stop in at the grocery/convenience store. Relax with your favorite drink at the bar/lounge or the poolside bar.

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C1555fd-the Retreat at Championsgate

Vacation Home

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Osceola
C1555fd-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 Reunion Resort Golf Course. This golf vacation home is 11.3 mi (18.1 km) from Old Town and 12 mi (19.4 km) from ESPN Wide World of Sports Complex.

C1555fd-the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

C1555fd-the Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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No Rear Neighbor 6BR Private Pool/spa Near Disney

Vacation Home

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Osceola
No Rear Neighbor 6BR Private Pool/spa Near Disney Location
Located in Kissimmee (Windsor Hills), this vacation home is within a 10-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 6.2 mi (9.9 km) from ESPN Wide World of Sports Complex and 6.2 mi (10 km) from Disney's Hollywood Studios®.

No Rear Neighbor 6BR Private Pool/spa Near Disney Facility and Service
Don't miss out on recreational opportunities including an outdoor tennis court and a fitness center. This vacation home also features complimentary wireless internet access, an arcade/game room, and barbecue grills.

No Rear Neighbor 6BR Private Pool/spa Near Disney Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private patio. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washing machine.

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2.0/5
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Exterior & Views

9073hs-the Retreat at Championsgate

Vacation Home

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Osceola
9073hs-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 Reunion Resort Golf Course. This golf vacation home is 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

9073hs-the Retreat at Championsgate Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center. This vacation home also features an arcade/game room and barbecue grills.

9073hs-the Retreat at Championsgate Rooms
Make yourself comfortable in this air-conditioned vacation home, 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.

See details
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Vacation Homes in Osceola

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