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Winter Springs Vacation Rentals

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50 rentals in Winter Springs.
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Tranquil, Spacious property within an gated Community, vacation rental in Winter Springs
Tranquil, Spacious property within an gated Community, vacation rental in Winter Springs
Tranquil, Spacious property within an gated Community, vacation rental in Winter Springs

Tranquil, Spacious property within an gated Community

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Robin's Nest (Rent the whole house), vacation rental in Winter Springs
Robin's Nest (Rent the whole house), vacation rental in Winter Springs
Robin's Nest (Rent the whole house), vacation rental in Winter Springs

Robin's Nest (Rent the whole house)

Rental Home
5 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Tranquil, Spacious property in a gated Community, vacation rental in Winter Springs
Tranquil, Spacious property in a gated Community, vacation rental in Winter Springs
Tranquil, Spacious property in a gated Community, vacation rental in Winter Springs

Tranquil, Spacious property in a gated Community

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New townhome with plenty of outdoor space., vacation rental in Winter Springs
New townhome with plenty of outdoor space., vacation rental in Winter Springs
New townhome with plenty of outdoor space., vacation rental in Winter Springs

New townhome with plenty of outdoor space.

Rental Home
2 bedrooms
6 bathrooms
Sleeps 4
Match: Sleeps
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3B/2Ba Home with Commmunity Pool. 30min from Universal Studios, vacation rental in Winter Springs
3B/2Ba Home with Commmunity Pool. 30min from Universal Studios, vacation rental in Winter Springs
3B/2Ba Home with Commmunity Pool. 30min from Universal Studios, vacation rental in Winter Springs

3B/2Ba Home with Commmunity Pool. 30min from Universal Studios

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stylish & Comfy Private Bedroom, vacation rental in Winter Springs
Stylish & Comfy Private Bedroom, vacation rental in Winter Springs
Stylish & Comfy Private Bedroom, vacation rental in Winter Springs

Stylish & Comfy Private Bedroom

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful two bedroom two bath, vacation rental in Winter Springs
Beautiful two bedroom two bath, vacation rental in Winter Springs
Beautiful two bedroom two bath, vacation rental in Winter Springs

Beautiful two bedroom two bath

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy and picture perfect Little house on the Lake, vacation rental in Winter Springs
Cozy and picture perfect Little house on the Lake, vacation rental in Winter Springs
Cozy and picture perfect Little house on the Lake, vacation rental in Winter Springs

Cozy and picture perfect Little house on the Lake

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Alderwood lake house Sanford/Orlando near SFB, vacation rental in Winter Springs
Alderwood lake house Sanford/Orlando near SFB, vacation rental in Winter Springs
Alderwood lake house Sanford/Orlando near SFB, vacation rental in Winter Springs

Alderwood lake house Sanford/Orlando near SFB

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Two-Bedroom, 1 Bath Cottage Near Lake Jesup in Oviedo, vacation rental in Winter Springs
Beautiful Two-Bedroom, 1 Bath Cottage Near Lake Jesup in Oviedo, vacation rental in Winter Springs
Beautiful Two-Bedroom, 1 Bath Cottage Near Lake Jesup in Oviedo, vacation rental in Winter Springs

Beautiful Two-Bedroom, 1 Bath Cottage Near Lake Jesup in Oviedo

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Lakeside Cottage, vacation rental in Winter Springs
Cozy Lakeside Cottage, vacation rental in Winter Springs
Cozy Lakeside Cottage, vacation rental in Winter Springs

Cozy Lakeside Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Edgewater lake house Sanford/Orlando near SFB, vacation rental in Winter Springs
Edgewater lake house Sanford/Orlando near SFB, vacation rental in Winter Springs
Edgewater lake house Sanford/Orlando near SFB, vacation rental in Winter Springs

Edgewater lake house Sanford/Orlando near SFB

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cozy Sanford Home near Orlando Resorts & Airport!, vacation rental in Winter Springs
Cozy Sanford Home near Orlando Resorts & Airport!, vacation rental in Winter Springs
Cozy Sanford Home near Orlando Resorts & Airport!, vacation rental in Winter Springs

Cozy Sanford Home near Orlando Resorts & Airport!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded 3 Bedroom Home on Lake with Gorgeous Sunsets, vacation rental in Winter Springs
Secluded 3 Bedroom Home on Lake with Gorgeous Sunsets, vacation rental in Winter Springs
Secluded 3 Bedroom Home on Lake with Gorgeous Sunsets, vacation rental in Winter Springs

Secluded 3 Bedroom Home on Lake with Gorgeous Sunsets

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gator Mansion -Brand New 6 Bedroom, 5-Baths next to the lake, vacation rental in Winter Springs
Gator Mansion -Brand New 6 Bedroom, 5-Baths next to the lake, vacation rental in Winter Springs
Gator Mansion -Brand New 6 Bedroom, 5-Baths next to the lake, vacation rental in Winter Springs

Gator Mansion -Brand New 6 Bedroom, 5-Baths next to the lake

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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2 Bedroom, 1.5 Bath perfect for 4 in the middle of Black Hammock Fish Camp, vacation rental in Winter Springs
2 Bedroom, 1.5 Bath perfect for 4 in the middle of Black Hammock Fish Camp, vacation rental in Winter Springs
2 Bedroom, 1.5 Bath perfect for 4 in the middle of Black Hammock Fish Camp, vacation rental in Winter Springs

2 Bedroom, 1.5 Bath perfect for 4 in the middle of Black Hammock Fish Camp

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Entire House For Rent - North Of Orlando In Longwood, Florida, vacation rental in Winter Springs
Entire House For Rent - North Of Orlando In Longwood, Florida, vacation rental in Winter Springs
Entire House For Rent - North Of Orlando In Longwood, Florida, vacation rental in Winter Springs

Entire House For Rent - North Of Orlando In Longwood, Florida

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Brand New 2-Bedroom Cottage With a Large Yard, vacation rental in Winter Springs
Brand New 2-Bedroom Cottage With a Large Yard, vacation rental in Winter Springs
Brand New 2-Bedroom Cottage With a Large Yard, vacation rental in Winter Springs

Brand New 2-Bedroom Cottage With a Large Yard

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Orlando perfect villa, vacation rental in Winter Springs
The Orlando perfect villa, vacation rental in Winter Springs
The Orlando perfect villa, vacation rental in Winter Springs

The Orlando perfect villa

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Lakeside and Beautiful, vacation rental in Winter Springs
Lakeside and Beautiful, vacation rental in Winter Springs
Lakeside and Beautiful, vacation rental in Winter Springs

Lakeside and Beautiful

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Three-bedroom, Two-Bathroom Lakeview House - Gator Nest, vacation rental in Winter Springs
Three-bedroom, Two-Bathroom Lakeview House - Gator Nest, vacation rental in Winter Springs
Three-bedroom, Two-Bathroom Lakeview House - Gator Nest, vacation rental in Winter Springs

Three-bedroom, Two-Bathroom Lakeview House - Gator Nest

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sportsman's Paradise- Near Lake With Boat Slip and Trailer Parking, vacation rental in Winter Springs
Sportsman's Paradise- Near Lake With Boat Slip and Trailer Parking, vacation rental in Winter Springs
Sportsman's Paradise- Near Lake With Boat Slip and Trailer Parking, vacation rental in Winter Springs

Sportsman's Paradise- Near Lake With Boat Slip and Trailer Parking

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront cottage beautiful !, vacation rental in Winter Springs
Lakefront cottage beautiful !, vacation rental in Winter Springs
Lakefront cottage beautiful !, vacation rental in Winter Springs

Lakefront cottage beautiful !

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Chic Farmhouse - Sleeps 8 - near Orlando, vacation rental in Winter Springs
Chic Farmhouse - Sleeps 8 - near Orlando, vacation rental in Winter Springs
Chic Farmhouse - Sleeps 8 - near Orlando, vacation rental in Winter Springs

Chic Farmhouse - Sleeps 8 - near Orlando

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Three-Bedroom Two Bath Lake Jesup Home at Gator Den, vacation rental in Winter Springs
Three-Bedroom Two Bath Lake Jesup Home at Gator Den, vacation rental in Winter Springs
Three-Bedroom Two Bath Lake Jesup Home at Gator Den, vacation rental in Winter Springs

Three-Bedroom Two Bath Lake Jesup Home at Gator Den

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Two-Bedroom Gator Cottage, vacation rental in Winter Springs
Two-Bedroom Gator Cottage, vacation rental in Winter Springs
Two-Bedroom Gator Cottage, vacation rental in Winter Springs

Two-Bedroom Gator Cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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3 bed/2 both Lake Front home, vacation rental in Winter Springs
3 bed/2 both Lake Front home, vacation rental in Winter Springs
3 bed/2 both Lake Front home, vacation rental in Winter Springs

3 bed/2 both Lake Front home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gator Nest - Three-Bedroom Two Bath Lake View House, vacation rental in Winter Springs
Gator Nest - Three-Bedroom Two Bath Lake View House, vacation rental in Winter Springs
Gator Nest - Three-Bedroom Two Bath Lake View House, vacation rental in Winter Springs

Gator Nest - Three-Bedroom Two Bath Lake View House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Eagles Nest - North of Orlando, vacation rental in Winter Springs
Eagles Nest - North of Orlando, vacation rental in Winter Springs
Eagles Nest - North of Orlando, vacation rental in Winter Springs

Eagles Nest - North of Orlando

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Five-Bedroom House at Gator Palace, vacation rental in Winter Springs
Five-Bedroom House at Gator Palace, vacation rental in Winter Springs
Five-Bedroom House at Gator Palace, vacation rental in Winter Springs

Five-Bedroom House at Gator Palace

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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2 Bedroom 1 Bathroom Near Lake With Boat Slip and Trailer Parking, vacation rental in Winter Springs
2 Bedroom 1 Bathroom Near Lake With Boat Slip and Trailer Parking, vacation rental in Winter Springs
2 Bedroom 1 Bathroom Near Lake With Boat Slip and Trailer Parking, vacation rental in Winter Springs

2 Bedroom 1 Bathroom Near Lake With Boat Slip and Trailer Parking

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Gator Mansion, vacation rental in Winter Springs
Gator Mansion, vacation rental in Winter Springs
Gator Mansion, vacation rental in Winter Springs

Gator Mansion

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Gator Cove Brand New 2-bedroom, 1-bathroom cottage, vacation rental in Winter Springs
Gator Cove Brand New 2-bedroom, 1-bathroom cottage, vacation rental in Winter Springs
Gator Cove Brand New 2-bedroom, 1-bathroom cottage, vacation rental in Winter Springs

Gator Cove Brand New 2-bedroom, 1-bathroom cottage

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Paradise in a country setting . ( Note this an upstairs apartment 1100 sq ft ), vacation rental in Winter Springs
Paradise in a country setting . ( Note this an upstairs apartment 1100 sq ft ), vacation rental in Winter Springs
Paradise in a country setting . ( Note this an upstairs apartment 1100 sq ft ), vacation rental in Winter Springs

Paradise in a country setting . ( Note this an upstairs apartment 1100 sq ft )

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2 Bedroom, 1.5 Bathroom perfect for 4 p in the middle of Black Hammock Fish Camp, vacation rental in Winter Springs
2 Bedroom, 1.5 Bathroom perfect for 4 p in the middle of Black Hammock Fish Camp, vacation rental in Winter Springs
2 Bedroom, 1.5 Bathroom perfect for 4 p in the middle of Black Hammock Fish Camp, vacation rental in Winter Springs

2 Bedroom, 1.5 Bathroom perfect for 4 p in the middle of Black Hammock Fish Camp

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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NEAR THEME  PARKS UNIVERSAL - DISNEY  AND DOWNTOWN ORLANDO, vacation rental in Winter Springs
NEAR THEME  PARKS UNIVERSAL - DISNEY  AND DOWNTOWN ORLANDO, vacation rental in Winter Springs
NEAR THEME  PARKS UNIVERSAL - DISNEY  AND DOWNTOWN ORLANDO, vacation rental in Winter Springs

NEAR THEME PARKS UNIVERSAL - DISNEY AND DOWNTOWN ORLANDO

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Villa with  Pool, Guest House and fantastic patio, vacation rental in Winter Springs
Villa with  Pool, Guest House and fantastic patio, vacation rental in Winter Springs
Villa with  Pool, Guest House and fantastic patio, vacation rental in Winter Springs

Villa with Pool, Guest House and fantastic patio

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Florida Vacation with pool fun for families, vacation rental in Winter Springs
Florida Vacation with pool fun for families, vacation rental in Winter Springs
Florida Vacation with pool fun for families, vacation rental in Winter Springs

Florida Vacation with pool fun for families

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Peaceful and Private Orlando Getaway | Game Garage, vacation rental in Winter Springs
Peaceful and Private Orlando Getaway | Game Garage, vacation rental in Winter Springs
Peaceful and Private Orlando Getaway | Game Garage, vacation rental in Winter Springs

Peaceful and Private Orlando Getaway | Game Garage

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious 4 bedroom home in Sanford/Orlando!, vacation rental in Winter Springs
Spacious 4 bedroom home in Sanford/Orlando!, vacation rental in Winter Springs
Spacious 4 bedroom home in Sanford/Orlando!, vacation rental in Winter Springs

Spacious 4 bedroom home in Sanford/Orlando!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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New Modern Home- Perfect for your next vacation.66, vacation rental in Winter Springs
New Modern Home- Perfect for your next vacation.66, vacation rental in Winter Springs
New Modern Home- Perfect for your next vacation.66, vacation rental in Winter Springs

New Modern Home- Perfect for your next vacation.66

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beautiful Renovated Home - Peaceful Location60, vacation rental in Winter Springs
Beautiful Renovated Home - Peaceful Location60, vacation rental in Winter Springs
Beautiful Renovated Home - Peaceful Location60, vacation rental in Winter Springs

Beautiful Renovated Home - Peaceful Location60

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Eagle Nest II - North of Orlando, vacation rental in Winter Springs
Eagle Nest II - North of Orlando, vacation rental in Winter Springs
Eagle Nest II - North of Orlando, vacation rental in Winter Springs

Eagle Nest II - North of Orlando

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Get away Lake House, vacation rental in Winter Springs
Get away Lake House, vacation rental in Winter Springs
Get away Lake House, vacation rental in Winter Springs

Get away Lake House

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Clear Lake home near Orlando / Sanford SFB, vacation rental in Winter Springs
Clear Lake home near Orlando / Sanford SFB, vacation rental in Winter Springs
Clear Lake home near Orlando / Sanford SFB, vacation rental in Winter Springs

Clear Lake home near Orlando / Sanford SFB

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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“Harmony”_, vacation rental in Winter Springs
“Harmony”_, vacation rental in Winter Springs
“Harmony”_, vacation rental in Winter Springs

“Harmony”_

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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1910 Farmhouse Charm in Orlando Area, vacation rental in Winter Springs
1910 Farmhouse Charm in Orlando Area, vacation rental in Winter Springs
1910 Farmhouse Charm in Orlando Area, vacation rental in Winter Springs

1910 Farmhouse Charm in Orlando Area

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Condo, vacation rental in Winter Springs
Beautiful Condo, vacation rental in Winter Springs
Beautiful Condo, vacation rental in Winter Springs

Beautiful Condo

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Country Quiet | 1.05 Protected Acres | All-New Interior | Gas Grill & Firepit, vacation rental in Winter Springs
Country Quiet | 1.05 Protected Acres | All-New Interior | Gas Grill & Firepit, vacation rental in Winter Springs
Country Quiet | 1.05 Protected Acres | All-New Interior | Gas Grill & Firepit, vacation rental in Winter Springs

Country Quiet | 1.05 Protected Acres | All-New Interior | Gas Grill & Firepit

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Downtown Historic Longwood steps to City park & SunRail, vacation rental in Winter Springs
Downtown Historic Longwood steps to City park & SunRail, vacation rental in Winter Springs
Downtown Historic Longwood steps to City park & SunRail, vacation rental in Winter Springs

Downtown Historic Longwood steps to City park & SunRail

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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