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Holiday Homes in Winter Park

Destination
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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
115 rentals in Winter Park.
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 Historic Winter Park., holiday rental in Winter Park
Stylish Boutique Guest house in Historic Winter Park., holiday rental in Winter Park
Stylish Boutique Guest house in Historic Winter Park., holiday rental in Winter Park

Stylish Boutique Guest house in Historic Winter Park.

Condo/Apartment
2 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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Sunset Cove Luxury 2BR/2BA  Condo Winter Park! FREE GARAGE, Wi-Fi, holiday rental in Winter Park
Sunset Cove Luxury 2BR/2BA  Condo Winter Park! FREE GARAGE, Wi-Fi, holiday rental in Winter Park
Sunset Cove Luxury 2BR/2BA  Condo Winter Park! FREE GARAGE, Wi-Fi, holiday rental in Winter Park

Sunset Cove Luxury 2BR/2BA Condo Winter Park! FREE GARAGE, Wi-Fi

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Mid-Century Modern Gem, holiday rental in Winter Park
The Mid-Century Modern Gem, holiday rental in Winter Park
The Mid-Century Modern Gem, holiday rental in Winter Park

The Mid-Century Modern Gem

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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NEW - Cozy Retreat Near Lake Killarney in Winter Park, holiday rental in Winter Park
NEW - Cozy Retreat Near Lake Killarney in Winter Park, holiday rental in Winter Park
NEW - Cozy Retreat Near Lake Killarney in Winter Park, holiday rental in Winter Park

NEW - Cozy Retreat Near Lake Killarney in Winter Park

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly renovated Cottage in the heart of Winter Park's most desired neighborhood., holiday rental in Winter Park
Newly renovated Cottage in the heart of Winter Park's most desired neighborhood., holiday rental in Winter Park
Newly renovated Cottage in the heart of Winter Park's most desired neighborhood., holiday rental in Winter Park

Newly renovated Cottage in the heart of Winter Park's most desired neighborhood.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Relaxing, lake-view home near Park Avenue, holiday rental in Winter Park
Relaxing, lake-view home near Park Avenue, holiday rental in Winter Park
Relaxing, lake-view home near Park Avenue, holiday rental in Winter Park

Relaxing, lake-view home near Park Avenue

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A curated stay in the Historic College Quarter, holiday rental in Winter Park
A curated stay in the Historic College Quarter, holiday rental in Winter Park
A curated stay in the Historic College Quarter, holiday rental in Winter Park

A curated stay in the Historic College Quarter

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Total Serenity #2, 2 BDRM, 2 Bath, holiday rental in Winter Park
Total Serenity #2, 2 BDRM, 2 Bath, holiday rental in Winter Park
Total Serenity #2, 2 BDRM, 2 Bath, holiday rental in Winter Park

Total Serenity #2, 2 BDRM, 2 Bath

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Hidden Oasis #4  2 BDRM, 2 Bath, holiday rental in Winter Park
Hidden Oasis #4  2 BDRM, 2 Bath, holiday rental in Winter Park
Hidden Oasis #4  2 BDRM, 2 Bath, holiday rental in Winter Park

Hidden Oasis #4 2 BDRM, 2 Bath

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Modern apartment w/ enclosed yard & kitchenette, holiday rental in Winter Park
Modern apartment w/ enclosed yard & kitchenette, holiday rental in Winter Park
Modern apartment w/ enclosed yard & kitchenette, holiday rental in Winter Park

Modern apartment w/ enclosed yard & kitchenette

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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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Sweet Sunshine house is available now!, holiday rental in Winter Park
Sweet Sunshine house is available now!, holiday rental in Winter Park
Sweet Sunshine house is available now!, holiday rental in Winter Park

Sweet Sunshine house is available now!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Peaceful Retreat #1    -2B /2B Apartment, holiday rental in Winter Park
Peaceful Retreat #1    -2B /2B Apartment, holiday rental in Winter Park
Peaceful Retreat #1    -2B /2B Apartment, holiday rental in Winter Park

Peaceful Retreat #1 -2B /2B Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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★Quiet Location House➠Minutes Away from Everything, holiday rental in Winter Park
★Quiet Location House➠Minutes Away from Everything, holiday rental in Winter Park
★Quiet Location House➠Minutes Away from Everything, holiday rental in Winter Park

★Quiet Location House➠Minutes Away from Everything

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Million Dollar View on the Lake!, holiday rental in Winter Park
Million Dollar View on the Lake!, holiday rental in Winter Park
Million Dollar View on the Lake!, holiday rental in Winter Park

Million Dollar View on the Lake!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
More info
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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
More info
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Modern Apartment in Prime Location (ID1019X387), holiday rental in Winter Park
Modern Apartment in Prime Location (ID1019X387), holiday rental in Winter Park
Modern Apartment in Prime Location (ID1019X387), holiday rental in Winter Park

Modern Apartment in Prime Location (ID1019X387)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Tranquil & Tiny house, holiday rental in Winter Park
Tranquil & Tiny house, holiday rental in Winter Park
Tranquil & Tiny house, holiday rental in Winter Park

Tranquil & Tiny house

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Modern Apartment in Prime Location (ID8210X91), holiday rental in Winter Park
Modern Apartment in Prime Location (ID8210X91), holiday rental in Winter Park
Modern Apartment in Prime Location (ID8210X91), holiday rental in Winter Park

Modern Apartment in Prime Location (ID8210X91)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern Apartment in Prime Location (ID4310X2), holiday rental in Winter Park
Modern Apartment in Prime Location (ID4310X2), holiday rental in Winter Park
Modern Apartment in Prime Location (ID4310X2), holiday rental in Winter Park

Modern Apartment in Prime Location (ID4310X2)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
More info
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Modern Apartment in Prime Location (ID8201X09), holiday rental in Winter Park
Modern Apartment in Prime Location (ID8201X09), holiday rental in Winter Park
Modern Apartment in Prime Location (ID8201X09), holiday rental in Winter Park

Modern Apartment in Prime Location (ID8201X09)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern Apartment in Prime Location (ID4310X3), holiday rental in Winter Park
Modern Apartment in Prime Location (ID4310X3), holiday rental in Winter Park
Modern Apartment in Prime Location (ID4310X3), holiday rental in Winter Park

Modern Apartment in Prime Location (ID4310X3)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Quiet Location, 1BR/1BA APT in Duplex House, holiday rental in Winter Park
Quiet Location, 1BR/1BA APT in Duplex House, holiday rental in Winter Park
Quiet Location, 1BR/1BA APT in Duplex House, holiday rental in Winter Park

Quiet Location, 1BR/1BA APT in Duplex House

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Modern and Romantiv Villa, holiday rental in Winter Park
Modern and Romantiv Villa, holiday rental in Winter Park
Modern and Romantiv Villa, holiday rental in Winter Park

Modern and Romantiv Villa

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Comfy and Charming -A 1 Bedroom Duplex Apartment, holiday rental in Winter Park
Comfy and Charming -A 1 Bedroom Duplex Apartment, holiday rental in Winter Park
Comfy and Charming -A 1 Bedroom Duplex Apartment, holiday rental in Winter Park

Comfy and Charming -A 1 Bedroom Duplex Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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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
More info
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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
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
More info
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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
More info
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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
More info
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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
More info
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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 College, holiday rental in Winter Park
Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins College, holiday rental in Winter Park
Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins College, holiday rental in Winter Park

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cute and Cozy Apartment-B     1 Bedroom Duplex, holiday rental in Winter Park
Cute and Cozy Apartment-B     1 Bedroom Duplex, holiday rental in Winter Park
Cute and Cozy Apartment-B     1 Bedroom Duplex, holiday rental in Winter Park

Cute and Cozy Apartment-B 1 Bedroom Duplex

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
More info
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Modern Apartment in Prime Location (ID8201X11), holiday rental in Winter Park
Modern Apartment in Prime Location (ID8201X11), holiday rental in Winter Park
Modern Apartment in Prime Location (ID8201X11), holiday rental in Winter Park

Modern Apartment in Prime Location (ID8201X11)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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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
More info
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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
More info
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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
More info
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Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen, holiday rental in Winter Park
Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen, holiday rental in Winter Park
Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen, holiday rental in Winter Park

Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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2br - 1000ft2 - Winter Park House, holiday rental in Winter Park
2br - 1000ft2 - Winter Park House, holiday rental in Winter Park
2br - 1000ft2 - Winter Park House, holiday rental in Winter Park

2br - 1000ft2 - Winter Park House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Payment Protection
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
More info
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Luxury King Condo min from everything!, holiday rental in Winter Park
Luxury King Condo min from everything!, holiday rental in Winter Park
Luxury King Condo min from everything!, holiday rental in Winter Park

Luxury King Condo min from everything!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Showing results 1-50 of 115
Frequently Asked Questions about Winter Park