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Longwood Vacation Rentals

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50 rentals in Longwood.
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Gorgeous 2BR/2BA Rental - Close to Disney, vacation rental in Longwood

Gorgeous 2BR/2BA Rental - Close to Disney

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Family Home w/Shared Pool - 6.5Mi to Wekiva Island, vacation rental in Longwood

Family Home w/Shared Pool - 6.5Mi to Wekiva Island

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Eagles Nest - North of Orlando, vacation rental in Longwood

Eagles Nest - North of Orlando

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Storey Lake - 4819 Brier Rose Lane, vacation rental in Longwood

Storey Lake - 4819 Brier Rose Lane

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Guest Suite w/ Pool, Walk to Seminole Wekiva Trail, vacation rental in Longwood

Guest Suite w/ Pool, Walk to Seminole Wekiva Trail

0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Temporary living that feels like home where you can relax and be yourself., vacation rental in Longwood

Temporary living that feels like home where you can relax and be yourself.

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly updated! Great Location*Grill*Free WiFi*AC*Baby Equipment*Pet-Friendly/dog, vacation rental in Longwood

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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Casa Bella, vacation rental in Longwood

Casa Bella

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Orlando Luxury Lakefront Ski Home (Family Friendly Estate), vacation rental in Longwood

Orlando Luxury Lakefront Ski Home (Family Friendly Estate)

6 bedrooms
5 bathrooms
Sleeps 25
Match: Sleeps
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Charming Home Located Between Theme Parks and Beaches., vacation rental in Longwood

Charming Home Located Between Theme Parks and Beaches.

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Just Like Home... With A Pool!, vacation rental in Longwood

Just Like Home... With A Pool!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy and picture perfect Little house on the Lake, vacation rental in Longwood

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, vacation rental in Longwood

Fresh & Modern Home, Sweet Home DISCOUNTS AVAILABLE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Large living area, tropical backyard with swimming pool & covered  back porch, vacation rental in Longwood

Large living area, tropical backyard with swimming pool & covered back porch

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow, vacation rental in Longwood

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

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

Orlando/Sanford Lake-front home near SFB Airport

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely, Spacious, Comfortable house in Altamonte Springs. Very clean ., vacation rental in Longwood

Lovely, Spacious, Comfortable house in Altamonte Springs. Very clean .

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Powerhouse Luxury Privacy Entertainment Location, vacation rental in Longwood

Powerhouse Luxury Privacy Entertainment Location

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Winter Park charm. Close to Park Ave, vacation rental in Longwood

Winter Park charm. Close to Park Ave

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Relax by the pool at this retreat near parks, kayaking, and downtown., vacation rental in Longwood

Relax by the pool at this retreat near parks, kayaking, and downtown.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Quiet Home Families Teams Seniors Business, vacation rental in Longwood

Cozy Quiet Home Families Teams Seniors Business

2 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Airy Stylish Apartment- Near Attractions, vacation rental in Longwood

Airy Stylish Apartment- Near Attractions

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury MidCentury Winter Park/Maitland/Orlando, vacation rental in Longwood

Luxury MidCentury Winter Park/Maitland/Orlando

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Home, Sweet Home Orlando, vacation rental in Longwood

Home, Sweet Home Orlando

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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3 bed/2 both Lake Front home, vacation rental in Longwood

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, vacation rental in Longwood

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Orlando area pool hame in Maitland, vacation rental in Longwood

Orlando area pool hame in Maitland

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Fern Park House w/Pool - New Patio & Fire Pit!, vacation rental in Longwood

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, vacation rental in Longwood

Lakefront Luxury Furnished Split Floor Plan First Floor Condo

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quiet Home Near Shopping & 15 Miles From Orlando!, vacation rental in Longwood

Quiet Home Near Shopping & 15 Miles From Orlando!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect home for a family getaway!!, vacation rental in Longwood

Perfect home for a family getaway!!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Vista Verde I Dream House & Vacation Paradise Orlando Area 5/2 Pool Disney, vacation rental in Longwood

Casa Vista Verde I Dream House & Vacation Paradise Orlando Area 5/2 Pool Disney

5 bedrooms
2 bathrooms
Sleeps 20
Match: Sleeps
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Casa Vista Verde II Orlando Area 1/1 Pool Disney Daytona Universal Dream House &, vacation rental in Longwood

Casa Vista Verde II Orlando Area 1/1 Pool Disney Daytona Universal Dream House &

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Storey Lake Resort 21 - townhouse with private pool near Disney, vacation rental in Longwood

Storey Lake Resort 21 - townhouse with private pool near Disney

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Apopka Family Home Near Downtown - 30 Mi to Disney, vacation rental in Longwood

Apopka Family Home Near Downtown - 30 Mi to Disney

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Orlando Area 5BR/2BA Home w/ Jacuzzi!, vacation rental in Longwood

Orlando Area 5BR/2BA Home w/ Jacuzzi!

5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Heathrow Rentals LLC. Fully Renovated House Orlando, Lake Mary/Sanford ,Florida, vacation rental in Longwood

Heathrow Rentals LLC. Fully Renovated House Orlando, Lake Mary/Sanford ,Florida

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Orlando Group Cottage Sleep 14 Guests, vacation rental in Longwood

Orlando Group Cottage Sleep 14 Guests

5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Tranquil, Spacious property in a gated Community, vacation rental in Longwood

Tranquil, Spacious property in a gated Community

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Longwood Home w/ Pool & Theater Room!, vacation rental in Longwood

Charming Longwood Home w/ Pool & Theater Room!

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Orlando Area 4BR/2BA Home w/Jacuzzi & communal pool Disney Unioversal Daytona, vacation rental in Longwood

Orlando Area 4BR/2BA Home w/Jacuzzi & communal pool Disney Unioversal Daytona

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Altamonte Springs Home w/Canoe on Lake Marion, vacation rental in Longwood

Altamonte Springs Home w/Canoe on Lake Marion

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bijzonder overnachten in de natuur van Orlando, vacation rental in Longwood

Bijzonder overnachten in de natuur van Orlando

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Orlando Area 3BR/2BA/2Ki nearby New City pool, Jacuzzi Disney Universal Daytona, vacation rental in Longwood

Orlando Area 3BR/2BA/2Ki nearby New City pool, Jacuzzi Disney Universal Daytona

3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Affordable, convenient and private family space, vacation rental in Longwood

Affordable, convenient and private family space

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Amazing Private Room Master Suite, vacation rental in Longwood

Amazing Private Room Master Suite

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lounge on Blue Velvet Couches at a Charming Hideaway, vacation rental in Longwood

Lounge on Blue Velvet Couches at a Charming Hideaway

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sanitized & Super Clean North Orlando Family Home, vacation rental in Longwood

Sanitized & Super Clean North Orlando Family Home

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Orlando Area 4/2 Pool Disney Universal Daytona, vacation rental in Longwood

Orlando Area 4/2 Pool Disney Universal Daytona

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Winter Park, Florida Luxury Vacation Rental, vacation rental in Longwood

Winter Park, Florida Luxury Vacation Rental

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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