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Vacation Homes in Osceola

Osceola
Tue, 17 Nov 2026 - Wed, 18 Nov 2026 (1 night)
1 Adult, 0 Children
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Showing 1.000+ Vacation Homes in Osceola
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.

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1.0/5
Fully Booked
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Exterior & Views

18 Guest Resort Home - Near Disney

Vacation Home

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Osceola
18 Guest Resort Home - Near Disney 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 vacation home is 9.6 mi (15.4 km) from Disney Springs™ and 10.6 mi (17.1 km) from Walt Disney World® Resort.

18 Guest Resort Home - Near Disney Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. Additional features at this vacation home include complimentary wireless internet access and gas grills.

18 Guest Resort Home - Near Disney Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. A 32-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected.

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4.0/5
Fully Booked
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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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Sport & Beauty

Mariel Oasis 6 Bedroom Home by RedAwning

Vacation Home

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Osceola
Mariel Oasis 6 Bedroom Home by RedAwning Location
With a stay at this vacation home in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 8.5 mi (13.7 km) from Disney Springs™ and 9 mi (14.4 km) from Walt Disney World® Resort.

Mariel Oasis 6 Bedroom Home by RedAwning Rooms
Make yourself comfortable in your individually decorated vacation home. Complimentary wireless internet access is available to keep you connected.

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Stunning 4Bd W/ Pool @ Storey Lake 4239

Vacation Home

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Osceola
Stunning 4Bd W/ Pool @ Storey Lake 4239 Location
Located in Kissimmee, this vacation home is within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 7.6 mi (12.2 km) from Disney Springs™ and 8.6 mi (13.9 km) from Walt Disney World® Resort.

Stunning 4Bd W/ Pool @ Storey Lake 4239 Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

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5.0/5
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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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Room

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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Haven Station at Storey Lake by Shine Villas townhouse

Vacation Home

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Osceola
Fully Booked
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Exterior & Views

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.

See details
Fully Booked
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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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Fully Booked
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Exterior & Views

New Magic Villa Resort Townhome 3123bra

Vacation Home

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Osceola
New Magic Villa Resort Townhome 3123bra 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®.

New Magic Villa Resort Townhome 3123bra Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center.

New Magic Villa Resort Townhome 3123bra Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with a refrigerator and a microwave. A flat-screen television is provided for your entertainment.

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Fully Booked
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Bathroom

1439rf - The Retreat at Championsgate

Vacation Home

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Osceola
1439rf - The Retreat at Championsgate Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This golf vacation home is 12.8 mi (20.6 km) from Old Town and 13.4 mi (21.5 km) from Walt Disney World® Resort.

1439rf - The Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

1439rf - The Retreat at Championsgate Rooms
Make yourself comfortable in your vacation home.

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Fully Booked
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6BR Reunion Mansion Circus Room & Karaoke

Vacation Home

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Osceola
6BR Reunion Mansion Circus Room & Karaoke Location
Located in Kissimmee (Reunion), this vacation home is within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 6.8 mi (10.9 km) from Walt Disney World® Resort and 8.8 mi (14.1 km) from Old Town.

6BR Reunion Mansion Circus Room & Karaoke Facility and Service
Make use of convenient amenities such as complimentary wireless internet access, an arcade/game room, and barbecue grills.

6BR Reunion Mansion Circus Room & Karaoke Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Fully Booked
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Exterior & Views

Three Bedroom Pool House - 4684 PPB - Vusa

Private Vacation Home

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Osceola
Three Bedroom Pool House - 4684 PPB - Vusa Location
With a stay at this vacation home in Kissimmee (Indian Point), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9.2 mi (14.9 km) from Disney Springs™ and 10.1 mi (16.3 km) from ESPN Wide World of Sports Complex.

Three Bedroom Pool House - 4684 PPB - Vusa Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including barbecue grills.

Three Bedroom Pool House - 4684 PPB - Vusa Rooms
Make yourself comfortable in this vacation home, which has a kitchen. Complimentary wireless internet access is available to keep you connected.

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Fully Booked
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View from room

Unique Masterpiece15 Suitessleeps 30

Vacation Home

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Osceola
Unique Masterpiece15 Suitessleeps 30 Location
With a stay at this vacation home in Kissimmee, you'll be near the beach, within a 15-minute drive of Old Town and 192 Flea Market. This vacation home is 9.6 mi (15.5 km) from Orlando Vineland Premium Outlets and 9.8 mi (15.7 km) from Disney Springs™.

Unique Masterpiece15 Suitessleeps 30 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.

Unique Masterpiece15 Suitessleeps 30 Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

See details
Fully Booked
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Others

Grhwgd9165 - Champions Gate Resort - 4 Bed 3 Baths House

Vacation Home

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Osceola
Grhwgd9165 - Champions Gate Resort - 4 Bed 3 Baths House Location
With a stay at this vacation home in Four Corners (Champions Gate), you'll be within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This family-friendly vacation home is 12.8 mi (20.6 km) from Old Town and 13.4 mi (21.5 km) from Walt Disney World® Resort.

Grhwgd9165 - Champions Gate Resort - 4 Bed 3 Baths House Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools or 2 hot tubs. This vacation home also features complimentary wireless internet access, concierge services, and a television in a common area.

Grhwgd9165 - Champions Gate Resort - 4 Bed 3 Baths House Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private plunge pool and a private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a microwave. A flat-screen 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.

See details
Fully Booked
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Sport & Beauty

Solara 1706 IHR 1048

Private Vacation Home

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Osceola
Solara 1706 IHR 1048 Location
When you stay at this vacation home in Kissimmee, you'll be next to a golf course, within a 15-minute drive of Walt Disney World® Resort and Flamingo Crossings Town Center. This golf vacation home is 10.2 mi (16.5 km) from Disney's Animal Kingdom® Theme Park and 11.1 mi (17.9 km) from ESPN Wide World of Sports Complex.

Solara 1706 IHR 1048 Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center. Additional amenities at this vacation home include an arcade/game room and barbecue grills.

Solara 1706 IHR 1048 Rooms
Make yourself comfortable in this vacation home, which features a private pool and an outdoor private hot tub. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, a stovetop, and a microwave. Cable television is provided for your entertainment.

Restaurant and Cafe
Grab a bite from the grocery/convenience store serving guests of this vacation home.

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Bedroom

Ovm1307 - Emerald Island - 3 Bed 2.5 Baths Townhome

Vacation Home

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Osceola
Ovm1307 - Emerald Island - 3 Bed 2.5 Baths Townhome Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This golf vacation home is 6.9 mi (11 km) from Old Town and 6.9 mi (11.1 km) from ESPN Wide World of Sports Complex.

Ovm1307 - Emerald Island - 3 Bed 2.5 Baths Townhome Facility and Service
Practice your swing on the golf course or dip into one of the 2 outdoor pools. Additional amenities at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Ovm1307 - Emerald Island - 3 Bed 2.5 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 is provided for your entertainment. Conveniences include a microwave and a washer/dryer.

Restaurant and Cafe
Relax with your favorite drink at the bar/lounge or the poolside bar.

See details
Fully Booked
Let's check on other dates!
Exterior & Views

Rolando's Emerald Island Resort Townhouse

Private Vacation Home

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Osceola
Rolando's Emerald Island Resort Townhouse Location
With a stay at this villa in Kissimmee, you'll be within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club. This villa is 6.7 mi (10.8 km) from Old Town and 6.8 mi (10.9 km) from ESPN Wide World of Sports Complex.

Rolando's Emerald Island Resort Townhouse Facility and Service
Enjoy the recreation opportunities such as an outdoor pool or make use of other amenities including complimentary wireless internet access.

Rolando's Emerald Island Resort Townhouse Rooms
Make yourself comfortable in this air-conditioned villa, which has a kitchen.

See details
2.0/5
Fully Booked
Let's check on other dates!
Bathroom

Villa Linda - Bella Vida

Vacation Home

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Osceola
Villa Linda - Bella Vida Location
With a stay at this vacation home in Kissimmee (Bellavida), you'll be within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This vacation home is 9 mi (14.5 km) from Disney Springs™ and 9.5 mi (15.2 km) from Walt Disney World® Resort.

Villa Linda - Bella Vida Rooms
Make yourself comfortable in this vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Housekeeping is provided once per stay, and a rollaway/extra bed can be requested.

See details
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Vacation Homes in Osceola

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