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Winter Springs Holiday Rentals

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49 rentals in Winter Springs.
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Tranquil, Spacious property in a gated Community, holiday rental in Winter Springs

Tranquil, Spacious property in a gated Community

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog, holiday rental in Winter Springs

Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!, holiday rental in Winter Springs

NOT YOUR TYPICAL HOUSEBOAT: 60 FEET OF FUN!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming Home Located Between Theme Parks and Beaches., holiday rental in Winter Springs

Charming Home Located Between Theme Parks and Beaches.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Historic Cottage, super clean, comfortable and well equipped., holiday rental in Winter Springs

Historic Cottage, super clean, comfortable and well equipped.

2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Cozy and picture perfect Little house on the Lake, holiday rental in Winter Springs

Cozy and picture perfect Little house on the Lake

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Fresh & Modern Home, Sweet Home  DISCOUNTS AVAILABLE, holiday rental in Winter Springs

Fresh & Modern Home, Sweet Home DISCOUNTS AVAILABLE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Carriage House In Sanford's Historic District, holiday rental in Winter Springs

Charming Carriage House In Sanford's Historic District

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Just Like Home... With A Pool!, holiday rental in Winter Springs

Just Like Home... With A Pool!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Orlando/Sanford Lake-front home near SFB Airport, holiday rental in Winter Springs

Orlando/Sanford Lake-front home near SFB Airport

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Quiet Home Families Teams Seniors Business, holiday rental in Winter Springs

Cozy Quiet Home Families Teams Seniors Business

2 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The Orlando perfect villa, holiday rental in Winter Springs

The Orlando perfect villa

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Oviedo Charmer!! - Minutes from Everything!, holiday rental in Winter Springs

Oviedo Charmer!! - Minutes from Everything!

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The Cottage at Oviedo, holiday rental in Winter Springs

The Cottage at Oviedo

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Historic Craftsman, holiday rental in Winter Springs

The Historic Craftsman

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Three-Bedroom Two Bath Lake Jesup Home at Gator Den, holiday rental in Winter Springs

Three-Bedroom Two Bath Lake Jesup Home at Gator Den

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy Sanford Home near Orlando Resorts & Airport!, holiday rental in Winter Springs

Cozy Sanford Home near Orlando Resorts & Airport!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Charming & Chic Suite, holiday rental in Winter Springs

The Charming & Chic Suite

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Modern Tropical Pool Home East Orlando, holiday rental in Winter Springs

Modern Tropical Pool Home East Orlando

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Two-Bedroom Gator Cottage, holiday rental in Winter Springs

Two-Bedroom Gator Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Home, Sweet Home Orlando, holiday rental in Winter Springs

Home, Sweet Home Orlando

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Chef's Suite, holiday rental in Winter Springs

The Chef's Suite

1 bedroom
1 bathroom
Sleeps 2
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The Coastal Cottage, holiday rental in Winter Springs

The Coastal Cottage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Ivy Cottage, holiday rental in Winter Springs

The Ivy Cottage

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

3 bed/2 both Lake Front home

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Warm and Inviting. Ideally located, 3BR/2BA Home, holiday rental in Winter Springs

Warm and Inviting. Ideally located, 3BR/2BA Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Gator Nest - Three-Bedroom Two Bath Lake View House, holiday rental in Winter Springs

Gator Nest - Three-Bedroom Two Bath Lake View House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fern Park House w/Pool - New Patio & Fire Pit!, holiday rental in Winter Springs

Fern Park House w/Pool - New Patio & Fire Pit!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Luxury Furnished  Split Floor Plan First Floor Condo, holiday rental in Winter Springs

Lakefront Luxury Furnished Split Floor Plan First Floor Condo

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Eagles Nest - North of Orlando, holiday rental in Winter Springs

Eagles Nest - North of Orlando

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

Five-Bedroom House at Gator Palace

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

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Bedroom for renting near UCF . 1 or 2 people., holiday rental in Winter Springs

Bedroom for renting near UCF . 1 or 2 people.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Guest Suite; Pool Access by Seminole Wekiva Trail, holiday rental in Winter Springs

Guest Suite; Pool Access by Seminole Wekiva Trail

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Storey Lake Resort 21 - townhouse with private pool near Disney, holiday rental in Winter Springs

Storey Lake Resort 21 - townhouse with private pool near Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Family Home w/ Shared Pool < 7 Mi to Wekiva Island, holiday rental in Winter Springs

Family Home w/ Shared Pool < 7 Mi to Wekiva Island

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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2965fs Luxury Lake View 8 BEDROOMS, holiday rental in Winter Springs

2965fs Luxury Lake View 8 BEDROOMS

8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Gator Mansion, holiday rental in Winter Springs

Gator Mansion

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

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

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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GOLDEN SUNRISE:Contact-Free Stay & Covid Cleaning Precautions! Pool & Spa!, holiday rental in Winter Springs

GOLDEN SUNRISE:Contact-Free Stay & Covid Cleaning Precautions! Pool & Spa!

9 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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GOLDEN LAKE: Contact-Free Stay & Covid Cleaning Precautions! Pool & Spa!, holiday rental in Winter Springs

GOLDEN LAKE: Contact-Free Stay & Covid Cleaning Precautions! Pool & Spa!

9 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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3 Bedroom, 1.5 Bathroom perfect for 4 p in the middle of Black Hammock Fish Camp, holiday rental in Winter Springs

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

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Altamonte Springs Home w/Canoe on Lake Marion, holiday rental in Winter Springs

Altamonte Springs Home w/Canoe on Lake Marion

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Ideal Orlando Getaway -Entire Home, holiday rental in Winter Springs

Ideal Orlando Getaway -Entire Home

4 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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1922 Garden Flat in the Sanford Historic District on the park by Venue 1902, holiday rental in Winter Springs

1922 Garden Flat in the Sanford Historic District on the park by Venue 1902

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful 3 Bedroom 2 full bath 2 car � garage., holiday rental in Winter Springs

Beautiful 3 Bedroom 2 full bath 2 car � garage.

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Affordable, convenient and private family space, holiday rental in Winter Springs

Affordable, convenient and private family space

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Private Room Master Suite, holiday rental in Winter Springs

Amazing Private Room Master Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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New Sanford Hideaway Studio Apartment + Free Parking, holiday rental in Winter Springs

New Sanford Hideaway Studio Apartment + Free Parking

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bedroom for 1. Orlando East. Near UCF ., holiday rental in Winter Springs

Bedroom for 1. Orlando East. Near UCF .

1 bedroom
1 bathroom
Sleeps 1
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