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Holiday Rentals in Winter Park

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
97 rentals in Winter Park.
3 Bed 1.5 Bath Spacious house in Winter Park Orlando, holiday rental in Winter Park
3 Bed 1.5 Bath Spacious house in Winter Park Orlando, holiday rental in Winter Park
3 Bed 1.5 Bath Spacious house in Winter Park Orlando, holiday rental in Winter Park

3 Bed 1.5 Bath Spacious house in Winter Park Orlando

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Ocean Guest House !, holiday rental in Winter Park
Ocean Guest House !, holiday rental in Winter Park
Ocean Guest House !, holiday rental in Winter Park

Ocean Guest House !

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Breezy Pool Home!, holiday rental in Winter Park
Breezy Pool Home!, holiday rental in Winter Park
Breezy Pool Home!, holiday rental in Winter Park

Breezy Pool Home!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stylish Boutique Guest house in Winter Park, holiday rental in Winter Park
Stylish Boutique Guest house in Winter Park, holiday rental in Winter Park
Stylish Boutique Guest house in Winter Park, holiday rental in Winter Park

Stylish Boutique Guest house in Winter Park

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Casa Winter Park, holiday rental in Winter Park
Casa Winter Park, holiday rental in Winter Park
Casa Winter Park, holiday rental in Winter Park

Casa Winter Park

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow, holiday rental in Winter Park
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow, holiday rental in Winter Park
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow, holiday rental in Winter Park

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CHARMING - Cozy Retreat Near Lake Killarney in Winter Park, holiday rental in Winter Park
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park, holiday rental in Winter Park
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park, holiday rental in Winter Park

CHARMING - Cozy Retreat Near Lake Killarney in Winter Park

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly, holiday rental in Winter Park
Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly, holiday rental in Winter Park
Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly, holiday rental in Winter Park

Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !, holiday rental in Winter Park
Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !, holiday rental in Winter Park
Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !, holiday rental in Winter Park

Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cozy 2BR Duplex w/ Garden, Patio & Pet-Friendly, holiday rental in Winter Park
Cozy 2BR Duplex w/ Garden, Patio & Pet-Friendly, holiday rental in Winter Park
Cozy 2BR Duplex w/ Garden, Patio & Pet-Friendly, holiday rental in Winter Park

Cozy 2BR Duplex w/ Garden, Patio & Pet-Friendly

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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A DEAL By The Month! Walk to Rollins & Park Ave, holiday rental in Winter Park
A DEAL By The Month! Walk to Rollins & Park Ave, holiday rental in Winter Park
A DEAL By The Month! Walk to Rollins & Park Ave, holiday rental in Winter Park

A DEAL By The Month! Walk to Rollins & Park Ave

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter Park charm. Close to Park Ave, holiday rental in Winter Park
Winter Park charm. Close to Park Ave, holiday rental in Winter Park
Winter Park charm. Close to Park Ave, holiday rental in Winter Park

Winter Park charm. Close to Park Ave

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cottage on Cornell - Quaint & Cozy w/Outdoor Kitchen, holiday rental in Winter Park
Cottage on Cornell - Quaint & Cozy w/Outdoor Kitchen, holiday rental in Winter Park
Cottage on Cornell - Quaint & Cozy w/Outdoor Kitchen, holiday rental in Winter Park

Cottage on Cornell - Quaint & Cozy w/Outdoor Kitchen

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Quaint Key West Pool Home, holiday rental in Winter Park
Quaint Key West Pool Home, holiday rental in Winter Park
Quaint Key West Pool Home, holiday rental in Winter Park

Quaint Key West Pool Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy 1BR Duplex|Winter Park|Close to Attractions, holiday rental in Winter Park
Cozy 1BR Duplex|Winter Park|Close to Attractions, holiday rental in Winter Park
Cozy 1BR Duplex|Winter Park|Close to Attractions, holiday rental in Winter Park

Cozy 1BR Duplex|Winter Park|Close to Attractions

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Mid Century Luxury, 1 block from Park Ave (#3), holiday rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#3), holiday rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#3), holiday rental in Winter Park

Mid Century Luxury, 1 block from Park Ave (#3)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Winter Park Getaway, holiday rental in Winter Park
Winter Park Getaway, holiday rental in Winter Park
Winter Park Getaway, holiday rental in Winter Park

Winter Park Getaway

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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THE CLOUD 9 SUITE, holiday rental in Winter Park
THE CLOUD 9 SUITE, holiday rental in Winter Park
THE CLOUD 9 SUITE, holiday rental in Winter Park

THE CLOUD 9 SUITE

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Private Balcony - Award Winning Accommodations w/Rooftop Pool, Close to Parks!, holiday rental in Winter Park
Private Balcony - Award Winning Accommodations w/Rooftop Pool, Close to Parks!, holiday rental in Winter Park
Private Balcony - Award Winning Accommodations w/Rooftop Pool, Close to Parks!, holiday rental in Winter Park

Private Balcony - Award Winning Accommodations w/Rooftop Pool, Close to Parks!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks, holiday rental in Winter Park
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks, holiday rental in Winter Park
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks, holiday rental in Winter Park

ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cute Guest House In Winter Park Minutes From Downtown in Car, holiday rental in Winter Park
Cute Guest House In Winter Park Minutes From Downtown in Car, holiday rental in Winter Park
Cute Guest House In Winter Park Minutes From Downtown in Car, holiday rental in Winter Park

Cute Guest House In Winter Park Minutes From Downtown in Car

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College, holiday rental in Winter Park
Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College, holiday rental in Winter Park
Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College, holiday rental in Winter Park

Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College, holiday rental in Winter Park
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College, holiday rental in Winter Park
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College, holiday rental in Winter Park

Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins, holiday rental in Winter Park
Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins, holiday rental in Winter Park
Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins, holiday rental in Winter Park

Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private Poolside Guest House In Winter Park/Orlando, holiday rental in Winter Park
Private Poolside Guest House In Winter Park/Orlando, holiday rental in Winter Park
Private Poolside Guest House In Winter Park/Orlando, holiday rental in Winter Park

Private Poolside Guest House In Winter Park/Orlando

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations, holiday rental in Winter Park
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations, holiday rental in Winter Park
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations, holiday rental in Winter Park

Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!, holiday rental in Winter Park
ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!, holiday rental in Winter Park
ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!, holiday rental in Winter Park

ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool, holiday rental in Winter Park
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool, holiday rental in Winter Park
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool, holiday rental in Winter Park

Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Winter Park Oasis, holiday rental in Winter Park
Winter Park Oasis, holiday rental in Winter Park
Winter Park Oasis, holiday rental in Winter Park

Winter Park Oasis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! ☀Bungalow+Patio+FirePit! Close to Everything!, holiday rental in Winter Park
NEW! ☀Bungalow+Patio+FirePit! Close to Everything!, holiday rental in Winter Park
NEW! ☀Bungalow+Patio+FirePit! Close to Everything!, holiday rental in Winter Park

NEW! ☀Bungalow+Patio+FirePit! Close to Everything!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Condo w/ Sunroom, Office, & Lakeside Pool, holiday rental in Winter Park
Lakefront Condo w/ Sunroom, Office, & Lakeside Pool, holiday rental in Winter Park
Lakefront Condo w/ Sunroom, Office, & Lakeside Pool, holiday rental in Winter Park

Lakefront Condo w/ Sunroom, Office, & Lakeside Pool

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quaint Winter Park East End Market Home, holiday rental in Winter Park
Quaint Winter Park East End Market Home, holiday rental in Winter Park
Quaint Winter Park East End Market Home, holiday rental in Winter Park

Quaint Winter Park East End Market Home

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Mid Century Luxury, 1 block from Park Ave (#2), holiday rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#2), holiday rental in Winter Park
Mid Century Luxury, 1 block from Park Ave (#2), holiday rental in Winter Park

Mid Century Luxury, 1 block from Park Ave (#2)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Winter Park
☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Winter Park
☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park, holiday rental in Winter Park

☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Winter Park Oasis, holiday rental in Winter Park
Winter Park Oasis, holiday rental in Winter Park
Winter Park Oasis, holiday rental in Winter Park

Winter Park Oasis

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Cozy Comfort Just 2 Blocks From Park Ave!, holiday rental in Winter Park
Cozy Comfort Just 2 Blocks From Park Ave!, holiday rental in Winter Park
Cozy Comfort Just 2 Blocks From Park Ave!, holiday rental in Winter Park

Cozy Comfort Just 2 Blocks From Park Ave!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Private Winter Park Getaway Near Theme Parks!, holiday rental in Winter Park
Perfect Private Winter Park Getaway Near Theme Parks!, holiday rental in Winter Park
Perfect Private Winter Park Getaway Near Theme Parks!, holiday rental in Winter Park

Perfect Private Winter Park Getaway Near Theme Parks!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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6 Mi to Downtown Orlando: Quiet Home w/ Sunroom, holiday rental in Winter Park
6 Mi to Downtown Orlando: Quiet Home w/ Sunroom, holiday rental in Winter Park
6 Mi to Downtown Orlando: Quiet Home w/ Sunroom, holiday rental in Winter Park

6 Mi to Downtown Orlando: Quiet Home w/ Sunroom

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Light, Bright and Full of Delight! 2 Blocks to Park Ave, holiday rental in Winter Park
Light, Bright and Full of Delight! 2 Blocks to Park Ave, holiday rental in Winter Park
Light, Bright and Full of Delight! 2 Blocks to Park Ave, holiday rental in Winter Park

Light, Bright and Full of Delight! 2 Blocks to Park Ave

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mid Century Modern Cottage in The Heart of Winter Park, holiday rental in Winter Park
Mid Century Modern Cottage in The Heart of Winter Park, holiday rental in Winter Park
Mid Century Modern Cottage in The Heart of Winter Park, holiday rental in Winter Park

Mid Century Modern Cottage in The Heart of Winter Park

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Three Blocks to Park Ave, 2 Blocks to WP Village!!!, holiday rental in Winter Park
Three Blocks to Park Ave, 2 Blocks to WP Village!!!, holiday rental in Winter Park
Three Blocks to Park Ave, 2 Blocks to WP Village!!!, holiday rental in Winter Park

Three Blocks to Park Ave, 2 Blocks to WP Village!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stroll to Park Avenue from Vintage Lake-View House, holiday rental in Winter Park
Stroll to Park Avenue from Vintage Lake-View House, holiday rental in Winter Park
Stroll to Park Avenue from Vintage Lake-View House, holiday rental in Winter Park

Stroll to Park Avenue from Vintage Lake-View House

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Home Away from Home- Winter Park, holiday rental in Winter Park
Home Away from Home- Winter Park, holiday rental in Winter Park
Home Away from Home- Winter Park, holiday rental in Winter Park

Home Away from Home- Winter Park

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Charming 2BR/2BA Winter Park Cottage, steps from Park Ave, holiday rental in Winter Park
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave, holiday rental in Winter Park
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave, holiday rental in Winter Park

Charming 2BR/2BA Winter Park Cottage, steps from Park Ave

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk The Downtown Village of Winter Park!!!, holiday rental in Winter Park
Walk The Downtown Village of Winter Park!!!, holiday rental in Winter Park
Walk The Downtown Village of Winter Park!!!, holiday rental in Winter Park

Walk The Downtown Village of Winter Park!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Greatest location! Condo with private yard!, holiday rental in Winter Park
Greatest location! Condo with private yard!, holiday rental in Winter Park
Greatest location! Condo with private yard!, holiday rental in Winter Park

Greatest location! Condo with private yard!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!, holiday rental in Winter Park
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!, holiday rental in Winter Park
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!, holiday rental in Winter Park

LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!, holiday rental in Winter Park
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!, holiday rental in Winter Park
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!, holiday rental in Winter Park

Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Stay near Winter Park action at our 2-bedroom apartment, holiday rental in Winter Park
Stay near Winter Park action at our 2-bedroom apartment, holiday rental in Winter Park
Stay near Winter Park action at our 2-bedroom apartment, holiday rental in Winter Park

Stay near Winter Park action at our 2-bedroom apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia, holiday rental in Winter Park
Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia, holiday rental in Winter Park
Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia, holiday rental in Winter Park

Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Showing results 1-50 of 97
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