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Holiday Rentals in Kissimmee

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6812 rentals in Kissimmee.
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Disney 5 Star Vacations / The Osprey Villa, holiday rental in Kissimmee
Disney 5 Star Vacations / The Osprey Villa, holiday rental in Kissimmee
Disney 5 Star Vacations / The Osprey Villa, holiday rental in Kissimmee

Disney 5 Star Vacations / The Osprey Villa

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Superb 4 Bedroom Home, just 3 minutes from Disney , holiday rental in Kissimmee
Superb 4 Bedroom Home, just 3 minutes from Disney , holiday rental in Kissimmee
Superb 4 Bedroom Home, just 3 minutes from Disney , holiday rental in Kissimmee

Superb 4 Bedroom Home, just 3 minutes from Disney

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Family-Friendly Large Villa with a Pool, Jacuzzi, , holiday rental in Kissimmee
Family-Friendly Large Villa with a Pool, Jacuzzi, , holiday rental in Kissimmee
Family-Friendly Large Villa with a Pool, Jacuzzi, , holiday rental in Kissimmee

Family-Friendly Large Villa with a Pool, Jacuzzi,

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Magical Manor, Beautiful Emerald Island Lake View Villa, holiday rental in Kissimmee
Magical Manor, Beautiful Emerald Island Lake View Villa, holiday rental in Kissimmee
Magical Manor, Beautiful Emerald Island Lake View Villa, holiday rental in Kissimmee

Magical Manor, Beautiful Emerald Island Lake View Villa

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Debbie's Florida Retreat a Luxury Vacation Home, holiday rental in Kissimmee
Debbie's Florida Retreat a Luxury Vacation Home, holiday rental in Kissimmee
Debbie's Florida Retreat a Luxury Vacation Home, holiday rental in Kissimmee

Debbie's Florida Retreat a Luxury Vacation Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Villa Linton - Beautiful Florida Home with Themed Bedrooms, holiday rental in Kissimmee
Villa Linton - Beautiful Florida Home with Themed Bedrooms, holiday rental in Kissimmee
Villa Linton - Beautiful Florida Home with Themed Bedrooms, holiday rental in Kissimmee

Villa Linton - Beautiful Florida Home with Themed Bedrooms

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Disney Sunshine Retreat, holiday rental in Kissimmee
Disney Sunshine Retreat, holiday rental in Kissimmee
Disney Sunshine Retreat, holiday rental in Kissimmee

Disney Sunshine Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Lake View House 2mls to Disney,games room, holiday rental in Kissimmee
Stunning Lake View House 2mls to Disney,games room, holiday rental in Kissimmee
Stunning Lake View House 2mls to Disney,games room, holiday rental in Kissimmee

Stunning Lake View House 2mls to Disney,games room

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Affordable Ground Floor Condo at Cane Island Resort, holiday rental in Kissimmee
Lovely Affordable Ground Floor Condo at Cane Island Resort, holiday rental in Kissimmee
Lovely Affordable Ground Floor Condo at Cane Island Resort, holiday rental in Kissimmee

Lovely Affordable Ground Floor Condo at Cane Island Resort

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oakhill Disney Villa, holiday rental in Kissimmee
Oakhill Disney Villa, holiday rental in Kissimmee
Oakhill Disney Villa, holiday rental in Kissimmee

Oakhill Disney Villa

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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CW2- 1 mile from Disney, nice town home in Gated Community, holiday rental in Kissimmee
CW2- 1 mile from Disney, nice town home in Gated Community, holiday rental in Kissimmee
CW2- 1 mile from Disney, nice town home in Gated Community, holiday rental in Kissimmee

CW2- 1 mile from Disney, nice town home in Gated Community

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., holiday rental in Kissimmee
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., holiday rental in Kissimmee
BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace., holiday rental in Kissimmee

BRUSONS RETREAT, 5 Bed Villa, South Facing Pool & Terrace.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., holiday rental in Kissimmee
Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., holiday rental in Kissimmee
Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower., holiday rental in Kissimmee

Palm Tree Villa Florida, 5 Star Review Rating with Pool Lift & Wheel in Shower.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Donald Duck's Condo, holiday rental in Kissimmee
Donald Duck's Condo, holiday rental in Kissimmee
Donald Duck's Condo, holiday rental in Kissimmee

Donald Duck's Condo

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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✦Comfortable 4 Bedrooms Town Home - Nearby Disney World✦, holiday rental in Kissimmee
✦Comfortable 4 Bedrooms Town Home - Nearby Disney World✦, holiday rental in Kissimmee
✦Comfortable 4 Bedrooms Town Home - Nearby Disney World✦, holiday rental in Kissimmee

✦Comfortable 4 Bedrooms Town Home - Nearby Disney World✦

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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*CLEAN - Afforable Townhome - 5 Miles from Disney*, holiday rental in Kissimmee
*CLEAN - Afforable Townhome - 5 Miles from Disney*, holiday rental in Kissimmee
*CLEAN - Afforable Townhome - 5 Miles from Disney*, holiday rental in Kissimmee

*CLEAN - Afforable Townhome - 5 Miles from Disney*

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Disney Vacation Villa with Lake View, holiday rental in Kissimmee
Disney Vacation Villa with Lake View, holiday rental in Kissimmee
Disney Vacation Villa with Lake View, holiday rental in Kissimmee

Disney Vacation Villa with Lake View

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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villanirvana, holiday rental in Kissimmee
villanirvana, holiday rental in Kissimmee
villanirvana, holiday rental in Kissimmee

villanirvana

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bass Lake Beauty with a Pool, WiFi and Air Conditioning, holiday rental in Kissimmee
Bass Lake Beauty with a Pool, WiFi and Air Conditioning, holiday rental in Kissimmee
Bass Lake Beauty with a Pool, WiFi and Air Conditioning, holiday rental in Kissimmee

Bass Lake Beauty with a Pool, WiFi and Air Conditioning

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Charming Mickey's Tree House,, holiday rental in Kissimmee
The Charming Mickey's Tree House,, holiday rental in Kissimmee
The Charming Mickey's Tree House,, holiday rental in Kissimmee

The Charming Mickey's Tree House,

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Secret Key Villa - villa rental in Kissimmee, Florida, holiday rental in Kissimmee
Secret Key Villa - villa rental in Kissimmee, Florida, holiday rental in Kissimmee
Secret Key Villa - villa rental in Kissimmee, Florida, holiday rental in Kissimmee

Secret Key Villa - villa rental in Kissimmee, Florida

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney, holiday rental in Kissimmee
Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney, holiday rental in Kissimmee
Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney, holiday rental in Kissimmee

Luxury 4 Bedroom Villa with Private Pool, 2 Miles from Disney

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning 5 Bed 4 Bath Villa with own private pool. Gated Resort close to Disney., holiday rental in Kissimmee
Stunning 5 Bed 4 Bath Villa with own private pool. Gated Resort close to Disney., holiday rental in Kissimmee
Stunning 5 Bed 4 Bath Villa with own private pool. Gated Resort close to Disney., holiday rental in Kissimmee

Stunning 5 Bed 4 Bath Villa with own private pool. Gated Resort close to Disney.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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6-Bedroom/5-Bathroom Private House at Storey Lake Resort |  Pool/Spa, holiday rental in Kissimmee
6-Bedroom/5-Bathroom Private House at Storey Lake Resort |  Pool/Spa, holiday rental in Kissimmee
6-Bedroom/5-Bathroom Private House at Storey Lake Resort |  Pool/Spa, holiday rental in Kissimmee

6-Bedroom/5-Bathroom Private House at Storey Lake Resort | Pool/Spa

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 6
Match: Sleeps
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Canadian Owned - South Facing Heated Pool & Spa, holiday rental in Kissimmee
Canadian Owned - South Facing Heated Pool & Spa, holiday rental in Kissimmee
Canadian Owned - South Facing Heated Pool & Spa, holiday rental in Kissimmee

Canadian Owned - South Facing Heated Pool & Spa

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Conservation View - Hot Tub - Pool Heat Included -  Very Private, holiday rental in Kissimmee
Conservation View - Hot Tub - Pool Heat Included -  Very Private, holiday rental in Kissimmee
Conservation View - Hot Tub - Pool Heat Included -  Very Private, holiday rental in Kissimmee

Conservation View - Hot Tub - Pool Heat Included - Very Private

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Like Staying In A Castle! Incredible Home, Sleeps 8, Pool, Nesr Dis, holiday rental in Kissimmee
Like Staying In A Castle! Incredible Home, Sleeps 8, Pool, Nesr Dis, holiday rental in Kissimmee
Like Staying In A Castle! Incredible Home, Sleeps 8, Pool, Nesr Dis, holiday rental in Kissimmee

Like Staying In A Castle! Incredible Home, Sleeps 8, Pool, Nesr Dis

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!, holiday rental in Kissimmee
Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!, holiday rental in Kissimmee
Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!, holiday rental in Kissimmee

Tropical Lakefront Villa, Gated, Pet-Friendly, less than 10 mins to Disney!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Sonshines Florida Villa, Peaceful Getaway  and Pool, holiday rental in Kissimmee
Sonshines Florida Villa, Peaceful Getaway  and Pool, holiday rental in Kissimmee
Sonshines Florida Villa, Peaceful Getaway  and Pool, holiday rental in Kissimmee

Sonshines Florida Villa, Peaceful Getaway and Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Summer Home, holiday rental in Kissimmee
Beautiful Summer Home, holiday rental in Kissimmee
Beautiful Summer Home, holiday rental in Kissimmee

Beautiful Summer Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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*NOV 19-25 REDUCED!!GREAT PRICES & LOCATION!PRIEMER PARTNER!100+ 5 STAR REVIEWS!, holiday rental in Kissimmee
*NOV 19-25 REDUCED!!GREAT PRICES & LOCATION!PRIEMER PARTNER!100+ 5 STAR REVIEWS!, holiday rental in Kissimmee
*NOV 19-25 REDUCED!!GREAT PRICES & LOCATION!PRIEMER PARTNER!100+ 5 STAR REVIEWS!, holiday rental in Kissimmee

*NOV 19-25 REDUCED!!GREAT PRICES & LOCATION!PRIEMER PARTNER!100+ 5 STAR REVIEWS!

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Fantasy Pool Home, holiday rental in Kissimmee
Fantasy Pool Home, holiday rental in Kissimmee
Fantasy Pool Home, holiday rental in Kissimmee

Fantasy Pool Home

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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DORAL WOODS SECLUDED VILLA  - Pool heated included Thanksgiving 2022, holiday rental in Kissimmee
DORAL WOODS SECLUDED VILLA  - Pool heated included Thanksgiving 2022, holiday rental in Kissimmee
DORAL WOODS SECLUDED VILLA  - Pool heated included Thanksgiving 2022, holiday rental in Kissimmee

DORAL WOODS SECLUDED VILLA - Pool heated included Thanksgiving 2022

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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The Beautiful Life - Family Villa, 6 miles to Disney Pk, holiday rental in Kissimmee
The Beautiful Life - Family Villa, 6 miles to Disney Pk, holiday rental in Kissimmee
The Beautiful Life - Family Villa, 6 miles to Disney Pk, holiday rental in Kissimmee

The Beautiful Life - Family Villa, 6 miles to Disney Pk

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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5 STAR Lakefront Pool Home, Great Fishing! BBQ Grill, Hi-Speed Wifi, XBox 360!, holiday rental in Kissimmee
5 STAR Lakefront Pool Home, Great Fishing! BBQ Grill, Hi-Speed Wifi, XBox 360!, holiday rental in Kissimmee
5 STAR Lakefront Pool Home, Great Fishing! BBQ Grill, Hi-Speed Wifi, XBox 360!, holiday rental in Kissimmee

5 STAR Lakefront Pool Home, Great Fishing! BBQ Grill, Hi-Speed Wifi, XBox 360!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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EAGLE POINTE SOUTH ON THE LARGER LAKE  A NEW VACATION/HOLIDAY EXPERIENCE, holiday rental in Kissimmee
EAGLE POINTE SOUTH ON THE LARGER LAKE  A NEW VACATION/HOLIDAY EXPERIENCE, holiday rental in Kissimmee
EAGLE POINTE SOUTH ON THE LARGER LAKE  A NEW VACATION/HOLIDAY EXPERIENCE, holiday rental in Kissimmee

EAGLE POINTE SOUTH ON THE LARGER LAKE A NEW VACATION/HOLIDAY EXPERIENCE

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY... FULLY EQUIPED, holiday rental in Kissimmee
BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY... FULLY EQUIPED, holiday rental in Kissimmee
BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY... FULLY EQUIPED, holiday rental in Kissimmee

BEAUTIFUL LAKEVIEW TOWNHOME, 5 MILES TO DISNEY... FULLY EQUIPED

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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WINNER! TRIP ADVISOR CERTIFICATE OF EXCELLENCE,  WINDSOR HILLS  3B/ 3B TOWN HOME, holiday rental in Kissimmee
WINNER! TRIP ADVISOR CERTIFICATE OF EXCELLENCE,  WINDSOR HILLS  3B/ 3B TOWN HOME, holiday rental in Kissimmee
WINNER! TRIP ADVISOR CERTIFICATE OF EXCELLENCE,  WINDSOR HILLS  3B/ 3B TOWN HOME, holiday rental in Kissimmee

WINNER! TRIP ADVISOR CERTIFICATE OF EXCELLENCE, WINDSOR HILLS 3B/ 3B TOWN HOME

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Special! Near Disney World: 4BR/2BA Pool Home + Free Internet, holiday rental in Kissimmee
Special! Near Disney World: 4BR/2BA Pool Home + Free Internet, holiday rental in Kissimmee
Special! Near Disney World: 4BR/2BA Pool Home + Free Internet, holiday rental in Kissimmee

Special! Near Disney World: 4BR/2BA Pool Home + Free Internet

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 4 Bedroom/3 Bathroom Resort Townhouse w/ Private Pool Close to Disney, holiday rental in Kissimmee
Beautiful 4 Bedroom/3 Bathroom Resort Townhouse w/ Private Pool Close to Disney, holiday rental in Kissimmee
Beautiful 4 Bedroom/3 Bathroom Resort Townhouse w/ Private Pool Close to Disney, holiday rental in Kissimmee

Beautiful 4 Bedroom/3 Bathroom Resort Townhouse w/ Private Pool Close to Disney

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Modern Luxury Villa with Everything in Storey Lake!, holiday rental in Kissimmee
Modern Luxury Villa with Everything in Storey Lake!, holiday rental in Kissimmee
Modern Luxury Villa with Everything in Storey Lake!, holiday rental in Kissimmee

Modern Luxury Villa with Everything in Storey Lake!

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 17
Match: Sleeps
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Dolphin Villa - Doral Woods, 5*Trip Advisor Rated & Inspected. Read our reviews., holiday rental in Kissimmee
Dolphin Villa - Doral Woods, 5*Trip Advisor Rated & Inspected. Read our reviews., holiday rental in Kissimmee
Dolphin Villa - Doral Woods, 5*Trip Advisor Rated & Inspected. Read our reviews., holiday rental in Kissimmee

Dolphin Villa - Doral Woods, 5*Trip Advisor Rated & Inspected. Read our reviews.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ultimate Lakeview Villa with Everything!, holiday rental in Kissimmee
Ultimate Lakeview Villa with Everything!, holiday rental in Kissimmee
Ultimate Lakeview Villa with Everything!, holiday rental in Kissimmee

Ultimate Lakeview Villa with Everything!

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 15
Match: Sleeps
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DISNEY Family Vacation / Lakefront Townhome /  New Bedding / 4 Miles To Disney!, holiday rental in Kissimmee
DISNEY Family Vacation / Lakefront Townhome /  New Bedding / 4 Miles To Disney!, holiday rental in Kissimmee
DISNEY Family Vacation / Lakefront Townhome /  New Bedding / 4 Miles To Disney!, holiday rental in Kissimmee

DISNEY Family Vacation / Lakefront Townhome / New Bedding / 4 Miles To Disney!

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Villa with Security Gate, Sunset Lakes in Kissimmee, holiday rental in Kissimmee
Private Villa with Security Gate, Sunset Lakes in Kissimmee, holiday rental in Kissimmee
Private Villa with Security Gate, Sunset Lakes in Kissimmee, holiday rental in Kissimmee

Private Villa with Security Gate, Sunset Lakes in Kissimmee

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Amazing  Home with Shared Pool on Disneys Doorstep, holiday rental in Kissimmee
Amazing  Home with Shared Pool on Disneys Doorstep, holiday rental in Kissimmee
Amazing  Home with Shared Pool on Disneys Doorstep, holiday rental in Kissimmee

Amazing Home with Shared Pool on Disneys Doorstep

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chris and Sue's Disney Condo at Windsor Palms Resort, holiday rental in Kissimmee
Chris and Sue's Disney Condo at Windsor Palms Resort, holiday rental in Kissimmee
Chris and Sue's Disney Condo at Windsor Palms Resort, holiday rental in Kissimmee

Chris and Sue's Disney Condo at Windsor Palms Resort

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Chris and Elaine's Florida  Home, Near Disney, holiday rental in Kissimmee
Chris and Elaine's Florida  Home, Near Disney, holiday rental in Kissimmee
Chris and Elaine's Florida  Home, Near Disney, holiday rental in Kissimmee

Chris and Elaine's Florida Home, Near Disney

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Lakeside Villa With Pool; WiFi, holiday rental in Kissimmee
Beautiful Lakeside Villa With Pool; WiFi, holiday rental in Kissimmee
Beautiful Lakeside Villa With Pool; WiFi, holiday rental in Kissimmee

Beautiful Lakeside Villa With Pool; WiFi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Florida Villa in Kissimmee, holiday rental in Kissimmee
Luxury Florida Villa in Kissimmee, holiday rental in Kissimmee
Luxury Florida Villa in Kissimmee, holiday rental in Kissimmee

Luxury Florida Villa in Kissimmee

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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