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Winter Springs Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
47 rentals in Winter Springs.
Modern Guest Studio 15 mins from SFB Airport, vacation rental in Winter Springs
Modern Guest Studio 15 mins from SFB Airport, vacation rental in Winter Springs
Modern Guest Studio 15 mins from SFB Airport, vacation rental in Winter Springs

Modern Guest Studio 15 mins from SFB Airport

Condo/Apartment
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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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
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Home 4 bedroom 5 bed with Hot Tub. Pet Friendly, vacation rental in Winter Springs
Cozy Home 4 bedroom 5 bed with Hot Tub. Pet Friendly, vacation rental in Winter Springs
Cozy Home 4 bedroom 5 bed with Hot Tub. Pet Friendly, vacation rental in Winter Springs

Cozy Home 4 bedroom 5 bed with Hot Tub. Pet Friendly

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

New two story townhome with plenty of outdoor space.

Rental Home
2 bedrooms
6 bathrooms
Sleeps 4
Match: Sleeps
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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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The following properties within 20 miles of Winter Springs match all your filters:
Luxury 1 bedroom Cottage w/ pool & WiFi Lake Mary, Fl, vacation rental in Winter Springs
Luxury 1 bedroom Cottage w/ pool & WiFi Lake Mary, Fl, vacation rental in Winter Springs
Luxury 1 bedroom Cottage w/ pool & WiFi Lake Mary, Fl, vacation rental in Winter Springs

Luxury 1 bedroom Cottage w/ pool & WiFi Lake Mary, Fl

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious 4 Bed Home near Orlando Gated+Pool Access, vacation rental in Winter Springs
Spacious 4 Bed Home near Orlando Gated+Pool Access, vacation rental in Winter Springs
Spacious 4 Bed Home near Orlando Gated+Pool Access, vacation rental in Winter Springs

Spacious 4 Bed Home near Orlando Gated+Pool Access

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
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 4
Match: Sleeps
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5-Bedroom 4-Bath with Upstairs Loft, vacation rental in Winter Springs
5-Bedroom 4-Bath with Upstairs Loft, vacation rental in Winter Springs
5-Bedroom 4-Bath with Upstairs Loft, vacation rental in Winter Springs

5-Bedroom 4-Bath with Upstairs Loft

Rental Home
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Tiny remodel mobile home close to Orlando and Sanford Airport., vacation rental in Winter Springs
Tiny remodel mobile home close to Orlando and Sanford Airport., vacation rental in Winter Springs
Tiny remodel mobile home close to Orlando and Sanford Airport., vacation rental in Winter Springs

Tiny remodel mobile home close to Orlando and Sanford Airport.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Gaming Room, Hot Tub and a Relaxing Massage Chair., vacation rental in Winter Springs
Gaming Room, Hot Tub and a Relaxing Massage Chair., vacation rental in Winter Springs
Gaming Room, Hot Tub and a Relaxing Massage Chair., vacation rental in Winter Springs

Gaming Room, Hot Tub and a Relaxing Massage Chair.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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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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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 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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Centrally located home with a firepit, large yard, vacation rental in Winter Springs
Centrally located home with a firepit, large yard, vacation rental in Winter Springs
Centrally located home with a firepit, large yard, vacation rental in Winter Springs

Centrally located home with a firepit, large yard

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Lake life house, vacation rental in Winter Springs
Lake life house, vacation rental in Winter Springs
Lake life house, vacation rental in Winter Springs

Lake life house

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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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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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Sportsman's Paradise Near Lake With Nearby Access to Boat Slip & Trailer Parking, vacation rental in Winter Springs
Sportsman's Paradise Near Lake With Nearby Access to Boat Slip & Trailer Parking, vacation rental in Winter Springs
Sportsman's Paradise Near Lake With Nearby Access to Boat Slip & Trailer Parking, vacation rental in Winter Springs

Sportsman's Paradise Near Lake With Nearby Access to Boat Slip & Trailer Parking

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
1 bedroom
1 bathroom
Sleeps 4
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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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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Cheerful & Peaceful 3 Bedroom 1 Bathroom Home, vacation rental in Winter Springs
Cheerful & Peaceful 3 Bedroom 1 Bathroom Home, vacation rental in Winter Springs
Cheerful & Peaceful 3 Bedroom 1 Bathroom Home, vacation rental in Winter Springs

Cheerful & Peaceful 3 Bedroom 1 Bathroom Home

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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The Suite at Lake Mary, vacation rental in Winter Springs
The Suite at Lake Mary, vacation rental in Winter Springs
The Suite at Lake Mary, vacation rental in Winter Springs

The Suite at Lake Mary

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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 5
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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Cozy Oviedo Cottage for 2 Couples or Small Family of 4 with Nearby Attraction, vacation rental in Winter Springs
Cozy Oviedo Cottage for 2 Couples or Small Family of 4 with Nearby Attraction, vacation rental in Winter Springs
Cozy Oviedo Cottage for 2 Couples or Small Family of 4 with Nearby Attraction, vacation rental in Winter Springs

Cozy Oviedo Cottage for 2 Couples or Small Family of 4 with Nearby Attraction

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Memorial Getaway!! Cottage w/queen bed & private lanai Orlando, Florida, vacation rental in Winter Springs
Memorial Getaway!! Cottage w/queen bed & private lanai Orlando, Florida, vacation rental in Winter Springs
Memorial Getaway!! Cottage w/queen bed & private lanai Orlando, Florida, vacation rental in Winter Springs

Memorial Getaway!! Cottage w/queen bed & private lanai Orlando, Florida

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Peace and quiet, vacation rental in Winter Springs
Peace and quiet, vacation rental in Winter Springs
Peace and quiet, vacation rental in Winter Springs

Peace and quiet

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tiny Home - Sanford, FL -3beds, vacation rental in Winter Springs
Tiny Home - Sanford, FL -3beds, vacation rental in Winter Springs
Tiny Home - Sanford, FL -3beds, vacation rental in Winter Springs

Tiny Home - Sanford, FL -3beds

Rental Home
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Tiny House in Sanford, FL - 3 beds: 45 mins to Disneyworld, vacation rental in Winter Springs
Tiny House in Sanford, FL - 3 beds: 45 mins to Disneyworld, vacation rental in Winter Springs
Tiny House in Sanford, FL - 3 beds: 45 mins to Disneyworld, vacation rental in Winter Springs

Tiny House in Sanford, FL - 3 beds: 45 mins to Disneyworld

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
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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Beautiful 2 bed townhome 35 minutes from Disney, vacation rental in Winter Springs
Beautiful 2 bed townhome 35 minutes from Disney, vacation rental in Winter Springs
Beautiful 2 bed townhome 35 minutes from Disney, vacation rental in Winter Springs

Beautiful 2 bed townhome 35 minutes from Disney

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 Bed 2 Bath on the Lake, Surrounded by Nature in Rural Oviedo, vacation rental in Winter Springs
3 Bed 2 Bath on the Lake, Surrounded by Nature in Rural Oviedo, vacation rental in Winter Springs
3 Bed 2 Bath on the Lake, Surrounded by Nature in Rural Oviedo, vacation rental in Winter Springs

3 Bed 2 Bath on the Lake, Surrounded by Nature in Rural Oviedo

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 Bed, 1.5 Bath Lake Front Old-Florida style home at Black Hammock, vacation rental in Winter Springs
3 Bed, 1.5 Bath Lake Front Old-Florida style home at Black Hammock, vacation rental in Winter Springs
3 Bed, 1.5 Bath Lake Front Old-Florida style home at Black Hammock, vacation rental in Winter Springs

3 Bed, 1.5 Bath Lake Front Old-Florida style home at Black Hammock

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
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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Luxurious Lake Front 3 Bed Ranch-Style Home with Jacuzzi Bathtub, vacation rental in Winter Springs
Luxurious Lake Front 3 Bed Ranch-Style Home with Jacuzzi Bathtub, vacation rental in Winter Springs
Luxurious Lake Front 3 Bed Ranch-Style Home with Jacuzzi Bathtub, vacation rental in Winter Springs

Luxurious Lake Front 3 Bed Ranch-Style Home with Jacuzzi Bathtub

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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House with  Pool  and fantastic patio, vacation rental in Winter Springs
House with  Pool  and fantastic patio, vacation rental in Winter Springs
House with  Pool  and fantastic patio, vacation rental in Winter Springs

House with Pool and fantastic patio

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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The Ultimate Lakeside Getaway!, vacation rental in Winter Springs
The Ultimate Lakeside Getaway!, vacation rental in Winter Springs
The Ultimate Lakeside Getaway!, vacation rental in Winter Springs

The Ultimate Lakeside Getaway!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 14
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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6 Bedroom, 5-Bath Villa Perfect for Large Families or Traveling Groups, vacation rental in Winter Springs
6 Bedroom, 5-Bath Villa Perfect for Large Families or Traveling Groups, vacation rental in Winter Springs
6 Bedroom, 5-Bath Villa Perfect for Large Families or Traveling Groups, vacation rental in Winter Springs

6 Bedroom, 5-Bath Villa Perfect for Large Families or Traveling Groups

Rental Home
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Luxurious 6 Bedroom including Master Suite with Wet Room, vacation rental in Winter Springs
Luxurious 6 Bedroom including Master Suite with Wet Room, vacation rental in Winter Springs
Luxurious 6 Bedroom including Master Suite with Wet Room, vacation rental in Winter Springs

Luxurious 6 Bedroom including Master Suite with Wet Room

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
More info
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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
More info
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Beautiful Townhouse awaits you. Pet friendly!, vacation rental in Winter Springs
Beautiful Townhouse awaits you. Pet friendly!, vacation rental in Winter Springs
Beautiful Townhouse awaits you. Pet friendly!, vacation rental in Winter Springs

Beautiful Townhouse awaits you. Pet friendly!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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House of Blues, vacation rental in Winter Springs
House of Blues, vacation rental in Winter Springs
House of Blues, vacation rental in Winter Springs

House of Blues

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Showing results 1-47 of 47
Frequently Asked Questions about Winter Springs