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Winter Park, FL Holiday Rentals & Apartments
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Winter Park, FL Holiday Rentals & Apartments
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Internet or Wifi (112)
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Kid friendly (97)
Pet friendly (50)
Elder access (5)
Smoking allowed (1)
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Holiday Rental House (70)
Condominium/Apartment (45)
Cabin Holiday Rental (0)
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Waterfront (1)
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Distance from
5 km
Charles Hosmer Morse Museum of American Art
Albin Polasek Museum & Sculpture Gardens
Rollins College
Central Park
Kraft Azalea Gardens
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115 rentals
in Winter Park.
Ocean Guest House !
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Breezy Pool Home!
5 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Stylish Boutique Guest house in Historic Winter Park.
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Casa Winter Park
18 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Sunset Cove Luxury 2BR/2BA Condo Winter Park! FREE GARAGE, Wi-Fi
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 5
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Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
16 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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The Mid-Century Modern Gem
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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NEW - Cozy Retreat Near Lake Killarney in Winter Park
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Newly renovated Cottage in the heart of Winter Park's most desired neighborhood.
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Relaxing, lake-view home near Park Avenue
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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A curated stay in the Historic College Quarter
8 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Total Serenity #2, 2 BDRM, 2 Bath
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
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Hidden Oasis #4 2 BDRM, 2 Bath
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Modern apartment w/ enclosed yard & kitchenette
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 6
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Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !
2 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
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Sweet Sunshine house is available now!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Peaceful Retreat #1 -2B /2B Apartment
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 8
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★Quiet Location House➠Minutes Away from Everything
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Million Dollar View on the Lake!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Winter Park charm. Close to Park Ave
38 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Cottage on Cornell - Quaint & Cozy w/Outdoor Kitchen
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
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Modern Apartment in Prime Location (ID1019X387)
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Tranquil & Tiny house
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
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Modern Apartment in Prime Location (ID8210X91)
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Modern Apartment in Prime Location (ID4310X2)
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Quaint Key West Pool Home
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Modern Apartment in Prime Location (ID8201X09)
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Modern Apartment in Prime Location (ID4310X3)
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Quiet Location, 1BR/1BA APT in Duplex House
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Modern and Romantiv Villa
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
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Comfy and Charming -A 1 Bedroom Duplex Apartment
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Mid Century Luxury, 1 block from Park Ave (#3)
3 reviews
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Winter Park Getaway
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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THE CLOUD 9 SUITE
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Private Balcony - Award Winning Accommodations w/Rooftop Pool, Close to Parks!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Cute Guest House In Winter Park Minutes From Downtown in Car
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Contemporary Award Winning Hotel w/Rooftop Close to Parks & Rollins College
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins College
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Cute and Cozy Apartment-B 1 Bedroom Duplex
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Private Poolside Guest House In Winter Park/Orlando
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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As seen on
Modern Apartment in Prime Location (ID8201X11)
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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As seen on
ADA Compliant Room in Award Winning Hotel w/Rooftop Pool - Close to Parks!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 6
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As seen on
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 6
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As seen on
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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As seen on
Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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2br - 1000ft2 - Winter Park House
2 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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Winter Park Oasis
9 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Luxury King Condo min from everything!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Showing results 1-50 of 115
Frequently Asked Questions about Winter Park
Do any holiday rentals in Winter Park have a pool?
Yes, here are some popular holiday rentals in Winter Park that have a pool:
Ocean Guest House !
Breezy Pool Home!
Stylish Boutique Guest house in Historic Winter Park.
See all holiday rentals with a pool in Winter Park on Tripadvisor
Do any holiday rentals in Winter Park have internet access?
Yes, here are some popular holiday rentals in Winter Park that have internet access:
Ocean Guest House !
Breezy Pool Home!
Stylish Boutique Guest house in Historic Winter Park.
See all holiday rentals in Winter Park on Tripadvisor
What are the best pet friendly rentals in Winter Park?
The best pet friendly rentals in Winter Park are:
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
NEW - Cozy Retreat Near Lake Killarney in Winter Park
A curated stay in the Historic College Quarter
See all pet friendly holiday rentals in Winter Park on Tripadvisor
What are some great rentals in Winter Park that are kid friendly?
Some of the most popular kid friendly rentals in Winter Park are:
Stylish Boutique Guest house in Historic Winter Park.
Casa Winter Park
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
See all kid friendly holiday rentals in Winter Park on Tripadvisor