Kissimmee Holiday Rentals
287 Kissimmee Holiday Rentals were found matching your criteria. These vacation rentals are presented by their owners or managers. Please click on the photos or links below, then contact them directly with your inquiries. Use the search criteria box on the left of the page to refine your search within Kissimmee, Central Florida-Orlando-Disney, Florida, United States.
Central Florida-Orlando-Disney Top Cities
Villa:
3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: Why stay in a hotel room when you can rent this 3 bedroom 2 baths condominium located in Sweetwater Club. This cozy condo has all the amenities one... Learn More
Location: Kissimmee, Florida, United States
Description: Why stay in a hotel room when you can rent this 3 bedroom 2 baths condominium located in Sweetwater Club. This cozy condo has all the amenities one... Learn More
Rates
$85 - $105 night
$595 - $735 week
$85 - $105 night
$595 - $735 week
Featured
Villa:
6 Bedroom, 4 Bathroom, Sleeps 14
Location: Kissimmee, Florida, United States
Description: This tastefully decorated 2-storey villahas 6 bedrooms, 4 bathrooms and is located on cue de sac. It is spacious enough for large families or for ... Learn More
Location: Kissimmee, Florida, United States
Description: This tastefully decorated 2-storey villahas 6 bedrooms, 4 bathrooms and is located on cue de sac. It is spacious enough for large families or for ... Learn More
Rates
$213 - $444 night
$1491 - $3108 week
$213 - $444 night
$1491 - $3108 week
Featured
Villa:
3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kissimmee, Florida, United States
Description: Windsor Hills Resort is a secure guard gated community located 1.5 miles to Disney World within the heart of Orlando’s premier tourist attractions!... Learn More
Location: Kissimmee, Florida, United States
Description: Windsor Hills Resort is a secure guard gated community located 1.5 miles to Disney World within the heart of Orlando’s premier tourist attractions!... Learn More
Rates
$105 - $130 night
$735 - $910 week
$105 - $130 night
$735 - $910 week
Featured
Home:
3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kissimmee, Florida, United States
Description: Enjoy this classic 3 bedroom 2 bath beautiful home in the established community of Lindfields just 10 minutes from Disney. A great location for all... Learn More
Location: Kissimmee, Florida, United States
Description: Enjoy this classic 3 bedroom 2 bath beautiful home in the established community of Lindfields just 10 minutes from Disney. A great location for all... Learn More
Rates
$85 - $120 night
$595 - $840 week
$85 - $120 night
$595 - $840 week
Featured
Home:
6 Bedroom, 4 Bathroom, Sleeps 12
Location: Kissimmee, Florida, United States
Description: Spacious 2 storey home in the gated community of Villa Sol offering 6 bedrooms (including 2 masters), 4 bathrooms, 2 living areas, dining room, ful... Learn More
Location: Kissimmee, Florida, United States
Description: Spacious 2 storey home in the gated community of Villa Sol offering 6 bedrooms (including 2 masters), 4 bathrooms, 2 living areas, dining room, ful... Learn More
Rates
$169 - $199 night
$1183 - $1393 week
$169 - $199 night
$1183 - $1393 week
Featured
Condo:
3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: This luxurious 3 bedroom and 2 full bath condo is tastefully furnished and tiled throughout with all the comforts of home. There are 4 TV's, a DVD ... Learn More
Location: Kissimmee, Florida, United States
Description: This luxurious 3 bedroom and 2 full bath condo is tastefully furnished and tiled throughout with all the comforts of home. There are 4 TV's, a DVD ... Learn More
Rates
$100 - $174 night
$700 - $1218 week
$100 - $174 night
$700 - $1218 week
Featured
Home:
5 Bedroom, 4.5 Bathroom, Sleeps 10
Location: Kissimmee, Florida, United States
Description: 4200 sq ft of luxury! Pamper yourself when you stay in this beautifully furnished two storey 5 bedroom, 4.5 bathroom home located in the gated com... Learn More
Location: Kissimmee, Florida, United States
Description: 4200 sq ft of luxury! Pamper yourself when you stay in this beautifully furnished two storey 5 bedroom, 4.5 bathroom home located in the gated com... Learn More
Rates
$155 - $185 night
$1085 - $1295 week
$155 - $185 night
$1085 - $1295 week
Featured
Home:
4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: DescriptionHome 2916 is a luxurious recently renovated single story 4 bedroom, 3 bathroom home with Wi-Fi, situated in a quiet cul-de-sac with its ... Learn More
Location: Kissimmee, Florida, United States
Description: DescriptionHome 2916 is a luxurious recently renovated single story 4 bedroom, 3 bathroom home with Wi-Fi, situated in a quiet cul-de-sac with its ... Learn More
Rates
$151 - $193 night
$1022 - $1316 week
$151 - $193 night
$1022 - $1316 week
Featured
Condo:
3 Bedroom, 2 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: Windsor Palms is a family resort, only 3 miles from Disney World! With a luxury 7,500 square foot clubhouse with amenities that consisting of a la... Learn More
Location: Kissimmee, Florida, United States
Description: Windsor Palms is a family resort, only 3 miles from Disney World! With a luxury 7,500 square foot clubhouse with amenities that consisting of a la... Learn More
Rates
$85 - $150 night
$595 - $1050 week
$85 - $150 night
$595 - $1050 week
Featured
Villa:
3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kissimmee, Florida, United States
Description: This 3 bedroom, 2 bathroom villa sleeps up to 6 people comfortably. The inviting, heated pool lures at you from the many windows overlooking it. Gr... Learn More
Location: Kissimmee, Florida, United States
Description: This 3 bedroom, 2 bathroom villa sleeps up to 6 people comfortably. The inviting, heated pool lures at you from the many windows overlooking it. Gr... Learn More
Rates
$73 - $99 night
$542 - $903 week
$73 - $99 night
$542 - $903 week
Featured
Condo:
3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kissimmee, Florida, United States
Description: Windsor Palms is a family resort, only 3 miles from Disney World! With a luxury 7,500 square foot clubhouse with amenities that consisting of a la... Learn More
Location: Kissimmee, Florida, United States
Description: Windsor Palms is a family resort, only 3 miles from Disney World! With a luxury 7,500 square foot clubhouse with amenities that consisting of a la... Learn More
Rates
$85 - $150 night
$595 - $1050 week
$85 - $150 night
$595 - $1050 week
Featured
Home:
4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: Enjoy your next Disney vacation when you stay at The Captiva - a spacious 4 bedroom, 3 bathroom home with private pool and spa. Bed configuration:... Learn More
Location: Kissimmee, Florida, United States
Description: Enjoy your next Disney vacation when you stay at The Captiva - a spacious 4 bedroom, 3 bathroom home with private pool and spa. Bed configuration:... Learn More
Rates
$129 - $149 night
$903 - $1043 week
$129 - $149 night
$903 - $1043 week
Home:
7 Bedroom, 4.5 Bathroom, Sleeps 16
Location: Kissimmee, Florida, United States
Description: This is an exquisite home which will leave you, your family and guests with warm memories in a home styled, furnished and decorated with no expense... Learn More
Location: Kissimmee, Florida, United States
Description: This is an exquisite home which will leave you, your family and guests with warm memories in a home styled, furnished and decorated with no expense... Learn More
Rates
$190 - $425 night
$190 - $425 night
Home:
3 Bedroom, 2 Bathroom, Sleeps 6
Location: Kissimmee, Florida, United States
Description: Single storey waterfront property with 3 bedrooms, 2 bathrooms and private pool. This home is in a great location just a short drive to Disney Wor... Learn More
Location: Kissimmee, Florida, United States
Description: Single storey waterfront property with 3 bedrooms, 2 bathrooms and private pool. This home is in a great location just a short drive to Disney Wor... Learn More
Rates
$115 - $135 night
$805 - $945 week
$115 - $135 night
$805 - $945 week
Home:
4 Bedroom, 2 Bathroom, Sleeps 10
Location: Kissimmee, Florida, United States
Description: Enjoy this spacious 4 bedroom 2 bath Orlando Florida-style vacation home situated in the tranquil estate of Windwood Cay. An attractive and quite l... Learn More
Location: Kissimmee, Florida, United States
Description: Enjoy this spacious 4 bedroom 2 bath Orlando Florida-style vacation home situated in the tranquil estate of Windwood Cay. An attractive and quite l... Learn More
Rates
$125 - $140 night
$875 - $980 week
$125 - $140 night
$875 - $980 week
Home:
6 Bedroom, 4 Bathroom, Sleeps 13
Location: Kissimmee, Florida, United States
Description: Our Luxurious Villa features: • 6 bedroom 4 bath 2,812 sq feet • 2 King Master bedrooms, 1 Queen bedroom, 1 Double bedroom and 2 Twin bedrooms • Sl... Learn More
Location: Kissimmee, Florida, United States
Description: Our Luxurious Villa features: • 6 bedroom 4 bath 2,812 sq feet • 2 King Master bedrooms, 1 Queen bedroom, 1 Double bedroom and 2 Twin bedrooms • Sl... Learn More
Rates
$200 - $275 night
$200 - $275 night
Home:
6 Bedroom, 3.5 Bathroom, Sleeps 14
Location: Kissimmee, Florida, United States
Description: Windsor Hills is a brand new secure guarded/gated resort community located 1.5 miles to Disney World within the heart of Orlando's premier tourist ... Learn More
Location: Kissimmee, Florida, United States
Description: Windsor Hills is a brand new secure guarded/gated resort community located 1.5 miles to Disney World within the heart of Orlando's premier tourist ... Learn More
Rates
$200 - $349 night
$1400 - $2000 week
$200 - $349 night
$1400 - $2000 week
Home:
4 Bedroom, 3 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: Within the small gated community of Sunset Lakes, we have a 4 bed and 3 bath air conditioned villa with a private pool situated on the lake front. ... Learn More
Location: Kissimmee, Florida, United States
Description: Within the small gated community of Sunset Lakes, we have a 4 bed and 3 bath air conditioned villa with a private pool situated on the lake front. ... Learn More
Rates
$130 - $150 night
$910 - $1050 week
$130 - $150 night
$910 - $1050 week
Home:
4 Bedroom, 3 Bathroom, Sleeps 10
Location: Kissimmee, Florida, United States
Description: Do you want Orlando comfort? Come stay at this completely remodeled 4 bed, 3 bath luxury guest home in the gated Windsor Palms resort. Two master... Learn More
Location: Kissimmee, Florida, United States
Description: Do you want Orlando comfort? Come stay at this completely remodeled 4 bed, 3 bath luxury guest home in the gated Windsor Palms resort. Two master... Learn More
Rates
$140 - $275 night
$1050 - $1950 week
$140 - $275 night
$1050 - $1950 week
Villa:
4 Bedroom, 3.5 Bathroom, Sleeps 10
Location: Kissimmee, Florida, United States
Description: Venetian Bay Village Townhouse Vacation Rental 4 Bedroom/3 Bath Our 1470 sq. ft. Townhouse has 4 bedrooms with enough room to sleep up to 10 adul... Learn More
Location: Kissimmee, Florida, United States
Description: Venetian Bay Village Townhouse Vacation Rental 4 Bedroom/3 Bath Our 1470 sq. ft. Townhouse has 4 bedrooms with enough room to sleep up to 10 adul... Learn More
Rates
$92 - $115 night
$644 - $805 week
$92 - $115 night
$644 - $805 week
Home:
3 Bedroom, 3 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: This wonderful 3 bedroom 2 1/2 bath townhouse is located in the exclusive gated community of Lake Berkley Resort. The townhouse offers a living are... Learn More
Location: Kissimmee, Florida, United States
Description: This wonderful 3 bedroom 2 1/2 bath townhouse is located in the exclusive gated community of Lake Berkley Resort. The townhouse offers a living are... Learn More
Rates
$95 - $115 night
$665 - $805 week
$95 - $115 night
$665 - $805 week
Home:
2 Bedroom, 2 Bathroom, Sleeps 6
Location: Kissimmee, Florida, United States
Description: Located in the Villages at Mango Key this 2 bedroom 2 bathroom townhouse is ideally located for all the Disney theme parks.The property is in a sma... Learn More
Location: Kissimmee, Florida, United States
Description: Located in the Villages at Mango Key this 2 bedroom 2 bathroom townhouse is ideally located for all the Disney theme parks.The property is in a sma... Learn More
Rates
$395 - $525 week
$395 - $525 week
Home:
3 Bedroom, 2 Bathroom, Sleeps 11
Location: Kissimmee, Florida, United States
Description: Do you want to go on a orlando vacation with your family pet, but can't find a kissimmee vacation home that allows pets? Rent this 3 bed 2 bath dog... Learn More
Location: Kissimmee, Florida, United States
Description: Do you want to go on a orlando vacation with your family pet, but can't find a kissimmee vacation home that allows pets? Rent this 3 bed 2 bath dog... Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
Home:
4 Bedroom, 2 Bathroom, Sleeps 8
Location: Kissimmee, Florida, United States
Description: 4 bedroom, 2 bathroom pool home in the gated community of Villa Sol. Bed arrangements: queen in master, queen, two twins, two twins. Home comfort... Learn More
Location: Kissimmee, Florida, United States
Description: 4 bedroom, 2 bathroom pool home in the gated community of Villa Sol. Bed arrangements: queen in master, queen, two twins, two twins. Home comfort... Learn More
Rates
$140 - $160 night
$980 - $1120 week
$140 - $160 night
$980 - $1120 week
Home:
5 Bedroom, 3 Bathroom, Sleeps 10
Location: Kissimmee, Florida, United States
Description: Are you searching for a dog friendly rental home in orlando,Florida? Reserve this kissimmee pet welcome disney vacation rental home! Learn More
Location: Kissimmee, Florida, United States
Description: Are you searching for a dog friendly rental home in orlando,Florida? Reserve this kissimmee pet welcome disney vacation rental home! Learn More
Rates
Contact Owner
Directly For Rates
Contact Owner
Directly For Rates
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Please confirm the exact location with the property owner or manager.
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