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Vacation Homes in Osceola

Osceola
Mon, 16 Nov 2026 - Tue, 17 Nov 2026 (1 night)
1 Adult, 0 Children
Showing 1.000+ Vacation Homes in Osceola
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Grhmvd1638 - Champions Gate Resort - 6 Bed 5 Baths House

Vacation Home

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Osceola
Grhmvd1638 - Champions Gate Resort - 6 Bed 5 Baths House 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 (19.7 km) from ESPN Wide World of Sports Complex.

Grhmvd1638 - Champions Gate Resort - 6 Bed 5 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. Additional features at this vacation home include complimentary wireless internet access, concierge services, and a television in a common area.

Grhmvd1638 - Champions Gate Resort - 6 Bed 5 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.

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Bedroom

4 Bdrm With Private Pool

Private Vacation Home

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Osceola
4 Bdrm With Private Pool Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of Mystic Dunes Golf Club and ChampionsGate Golf Club. This vacation home is 11.4 mi (18.4 km) from Old Town and 12.4 mi (19.9 km) from Walt Disney World® Resort.

4 Bdrm With Private Pool Facility and Service
Don't miss out on recreational opportunities including an outdoor pool and a fitness center.

4 Bdrm With Private Pool 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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Grhmvd1554 - Champions Gate Resort - 5 Bed 4 Baths House

Vacation Home

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Osceola
Grhmvd1554 - Champions Gate Resort - 5 Bed 4 Baths House Location
With a stay at this vacation home in Four Corners, you'll be within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This family-friendly vacation home is 11.6 mi (18.6 km) from Old Town and 12.3 mi (19.9 km) from ESPN Wide World of Sports Complex.

Grhmvd1554 - Champions Gate Resort - 5 Bed 4 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.

Grhmvd1554 - Champions Gate Resort - 5 Bed 4 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. Unwind at the end of the day with a drink at the bar/lounge or the poolside bar.

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Exterior & Views

Villa Compass- Compass Bay

Vacation Home

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Osceola
At Villa Compass- Compass Bay, exceptional service and top-notch amenities create a memorable experience for guests. Complimentary internet access is available in the home to ensure you stay connected during your visit.Complimentary parking is available for guests.At the home, utilize the convenient laundromat to maintain your preferred travel attire fresh, allowing you to pack lighter.Accommodations come equipped with all the conveniences required for a restful night's slumber.A selection of rooms at Villa Compass- Compass Bay come furnished with linen service to cater to your needs and comfort.A number of rooms feature television for guest amusement and enjoyment.In certain rooms, the home offers visitors access to a refrigerator and a coffee or tea maker.At Villa Compass- Compass Bay, select bathrooms are equipped with a hair dryer to enhance your comfort during your stay. At Villa Compass- Compass Bay, guests can take pleasure in the delightful recreational amenities provided for their entertainment.At the home fitness center, you have the option to engage in your daily exercise routine or simply alleviate your jet lag by breaking a sweat.
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Amazing 4/3 Home at Reunion!! With Private Pool, Near Disney and Universal!!

Vacation Home

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Osceola
Amazing 4/3 Home at Reunion!! With Private Pool, Near Disney and Universal!! Location
With a stay at this vacation home in Kissimmee, you'll be within a 10-minute drive of Reunion Resort Golf Course and Mystic Dunes Golf Club. This vacation home is 5.5 mi (8.9 km) from Walt Disney World® Resort and 7.7 mi (12.5 km) from ESPN Wide World of Sports Complex.

Amazing 4/3 Home at Reunion!! With Private Pool, Near Disney and Universal!! Rooms
Make yourself comfortable in this vacation home, which features a private pool. Complimentary wireless internet access is available to keep you connected.

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Exterior & Views

9077hs-the Retreat at Championsgate

Vacation Home

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Osceola
9077hs-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 11.5 mi (18.6 km) from Old Town and 12.3 mi (19.8 km) from ESPN Wide World of Sports Complex.

9077hs-the Retreat at Championsgate Facility and Service
Take advantage of recreation opportunities including an outdoor pool and a fitness center.

9077hs-the Retreat at Championsgate Rooms
Make yourself comfortable in this vacation home, which has a kitchen.

Restaurant and Cafe
Quench your thirst with your favorite drink at the bar/lounge.

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Others

All-new, Charming Home With Screened Pool With Spa, Game Room, & Foosball

Vacation Home

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Osceola
All-new, Charming Home With Screened Pool With Spa, Game Room, & Foosball Location
With a stay at this vacation home in Four Corners, you'll be near the beach, within a 10-minute drive of ChampionsGate Golf Club and Highland Reserve Golf Club. This vacation home is 12.2 mi (19.7 km) from Old Town and 13 mi (21 km) from ESPN Wide World of Sports Complex.

All-new, Charming Home With Screened Pool With Spa, Game Room, & Foosball 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.

All-new, Charming Home With Screened Pool With Spa, Game Room, & Foosball Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Room

Adorable 4BR Home Cute Mickey Tangled Rooms

Vacation Home

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Osceola
Adorable 4BR Home Cute Mickey Tangled Rooms Location
Located in Four Corners, this vacation home is within a 15-minute drive of ChampionsGate Golf Club and Reunion Resort Golf Course. This vacation home is 12.1 mi (19.4 km) from Old Town and 12.8 mi (20.7 km) from ESPN Wide World of Sports Complex.

Adorable 4BR Home Cute Mickey Tangled Rooms Facility and Service
Take in the views from a garden and make use of amenities such as barbecue grills.

Adorable 4BR Home Cute Mickey Tangled Rooms Rooms
Make yourself comfortable in your vacation home.

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Others

8157 sun Palm dr

Private Vacation Home

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Osceola
8157 sun Palm dr 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 Old Town. This golf vacation home is 8.4 mi (13.5 km) from Disney's Hollywood Studios® and 9.4 mi (15.1 km) from Disney's Animal Kingdom® Theme Park.

8157 sun Palm dr Facility and Service
Enjoy a range of recreational amenities, including an indoor pool, an outdoor tennis court, and a fitness center. Additional amenities at this vacation home include complimentary wireless internet access, an arcade/game room, and barbecue grills.

8157 sun Palm dr Rooms
Make yourself comfortable in your individually decorated vacation home. There's a private balcony or patio. The bathroom has a bathtub or shower and designer toiletries. Conveniences include a coffee/tea maker and a washer/dryer.

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Bedroom

3BR 2BA Home in Rolling Hiils by CV-2616

Vacation Home

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Osceola
3BR 2BA Home in Rolling Hiils by CV-2616 Location
With a stay at this vacation home in Kissimmee, you'll be a 4-minute drive from Mystic Dunes Golf Club and 8 minutes from Walt Disney World® Resort. This vacation home is 5.8 mi (9.4 km) from ESPN Wide World of Sports Complex and 6.3 mi (10.1 km) from Old Town.

3BR 2BA Home in Rolling Hiils by CV-2616 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected. Conveniences include a microwave and a coffee/tea maker.

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Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560

Vacation Home

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Osceola
Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 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 (13.8 km) from Walt Disney World® Resort.

Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 Facility and Service
Take in the views from a garden and make use of amenities such as barbecue grills.

Spacious 4Bd W/ Pool & Close To Disney @ Storey Lake 2560 Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a full-sized refrigerator/freezer and a stovetop. Conveniences include a desk and a microwave.

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5.0/5
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Exterior & Views

5 Bedroom 5 Bathroom Villa

Vacation Home

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Osceola
5 Bedroom 5 Bathroom Villa 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 family-friendly villa is 11.4 mi (18.3 km) from Old Town and 12.1 mi (19.5 km) from ESPN Wide World of Sports Complex.

5 Bedroom 5 Bathroom Villa Facility and Service
Take time to pamper yourself with a visit to the full-service spa. This villa also features complimentary wireless internet access and an arcade/game room.

5 Bedroom 5 Bathroom Villa Rooms
Make yourself comfortable in this villa, which has a kitchen. There's a private lanai. Complimentary wireless internet access keeps you connected, and a flat-screen television is provided for your entertainment.

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Charming Resort House w/ Private Pool & Fast Wifi

Vacation Home

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Osceola
Charming Resort House w/ Private Pool & Fast Wifi 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 6.7 mi (10.8 km) from Walt Disney World® Resort and 8.2 mi (13.2 km) from Old Town.

Charming Resort House w/ Private Pool & Fast Wifi Facility and Service
Enjoy a range of recreational amenities, including an outdoor pool, an outdoor tennis court, and a fitness center.

Charming Resort House w/ Private Pool & Fast Wifi Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Villa Rodrigues - Encantada Resort

Vacation Home

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Osceola
Villa Rodrigues - Encantada Resort 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 6.9 mi (11.2 km) from Disney's Animal Kingdom® Theme Park and 8.1 mi (13.1 km) from ESPN Wide World of Sports Complex.

Villa Rodrigues - Encantada Resort Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with an oven and a stovetop. Complimentary wireless internet access is available to keep you connected. Conveniences include a dryer and an iron/ironing board, and housekeeping is provided once per stay.

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Exterior & Views

Cane Island Resort by Amazing Vacation Homes FL. Inc

Vacation Home

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Osceola
Cane Island Resort by Amazing Vacation Homes FL. Inc Location
With a stay at Cane Island Resort by Amazing Vacation Homes FL. Inc in Kissimmee, you'll be a 4-minute drive from Old Town and 9 minutes from Orlando Vineland Premium Outlets. This vacation home is 5.5 mi (8.9 km) from ESPN Wide World of Sports Complex and 5.6 mi (9.1 km) from Walt Disney World® Resort.

Cane Island Resort by Amazing Vacation Homes FL. Inc Facility and Service
Don't miss out on the many recreational opportunities, including an outdoor pool, a hot tub, and a sauna. This vacation home also features complimentary wireless internet access and an arcade/game room.

Cane Island Resort by Amazing Vacation Homes FL. Inc Rooms
Make yourself at home in one of the 44 individually furnished guestrooms, featuring kitchens with refrigerators and stovetops. Rooms have private patios. 27-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include separate sitting areas and microwaves, as well as phones with free local calls.

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4.2/5
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Interior

Db2633 Windsor Hills Resort Vacation Home

Vacation Home

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Osceola
Db2633 Windsor Hills Resort Vacation Home Location
With a stay at this cottage in Kissimmee (Windsor Hills), you'll be a 4-minute drive from Mystic Dunes Golf Club and 7 minutes from Walt Disney World® Resort. This cottage is 5.7 mi (9.2 km) from ESPN Wide World of Sports Complex and 6 mi (9.7 km) from Old Town.

Db2633 Windsor Hills Resort Vacation Home Rooms
Make yourself comfortable in this air-conditioned cottage, which has a kitchen. Cable television is provided for your entertainment. Conveniences include a dryer and an iron/ironing board.

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Exterior & Views

Lake Breeze 6 Bedrooms

Vacation Home

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Osceola
Lake Breeze 6 Bedrooms Location
When you stay at this vacation home in Kissimmee, you'll be near the airport, within a 15-minute drive of Old Town and Orlando Vineland Premium Outlets. This family-friendly vacation home is 9 mi (14.5 km) from Disney Springs™ and 10 mi (16 km) from Walt Disney World® Resort.

Lake Breeze 6 Bedrooms Facility and Service
Enjoy recreational amenities such as an outdoor pool and a fitness center. This vacation home also features complimentary wireless internet access and an arcade/game room.

Lake Breeze 6 Bedrooms Rooms
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and an oven. There's a private lanai. A 55-inch Smart television with digital programming provides entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a separate sitting area and a microwave, as well as a phone with free local calls.

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Sport & Beauty

Paradise Palms-4 Bed Townhome W/spashpool-3015pp 4 Bedroom Townhouse by RedAwning

Vacation Home

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Osceola
Paradise Palms-4 Bed Townhome W/spashpool-3015pp 4 Bedroom Townhouse by RedAwning 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 8.3 mi (13.4 km) from Disney's Animal Kingdom® Theme Park and 9.2 mi (14.8 km) from ESPN Wide World of Sports Complex.

Paradise Palms-4 Bed Townhome W/spashpool-3015pp 4 Bedroom Townhouse by RedAwning Facility and Service
Enjoy the recreation opportunities such as an outdoor tennis court or make use of other amenities including barbecue grills.

Paradise Palms-4 Bed Townhome W/spashpool-3015pp 4 Bedroom Townhouse by RedAwning 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.Conveniences include a coffee/tea maker and a washing machine.

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2-story Snowbird-friendly Townhouse Near Disney With Patio, Streaming, W/d, AC

Vacation Home

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Osceola
2-story Snowbird-friendly Townhouse Near Disney With Patio, Streaming, W/d, AC Location
With a stay at this vacation home in Kissimmee (Crestwynd Bay), you'll be a 5-minute drive from Mystic Dunes Golf Club and 6 minutes from Walt Disney World® Resort. This vacation home is 5.3 mi (8.5 km) from ESPN Wide World of Sports Complex and 5.5 mi (8.9 km) from Old Town.

2-story Snowbird-friendly Townhouse Near Disney With Patio, Streaming, W/d, AC Rooms
Make yourself comfortable in your individually decorated vacation home. The bathroom has a bathtub or shower.

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Exterior & Views

7BR 4.5BA Home in Emerald Island Resort by CV-2708

Vacation Home

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Osceola
7BR 4.5BA Home in Emerald Island Resort by CV-2708 Location
When you stay at this vacation home in Kissimmee, you'll be on the waterfront, within a 15-minute drive of Walt Disney World® Resort and Old Town. This vacation home is 7.5 mi (12 km) from ESPN Wide World of Sports Complex and 8.1 mi (13.1 km) from Disney's Hollywood Studios®.

7BR 4.5BA Home in Emerald Island Resort by CV-2708 Rooms
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. A kitchen is outfitted with a full-sized refrigerator/freezer, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and a video-game console is provided for your entertainment. Conveniences include a microwave and a coffee/tea maker.

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Vacation Homes in Osceola

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