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Winter Park, FL Holiday Rentals
Holiday Rentals
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Florida (FL)
Central Florida
Winter Park, FL Holiday Rentals
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Internet or Wifi (95)
Air Conditioning (94)
Washer/Dryer (73)
Other outdoor space (60)
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Suitability
Kid friendly (84)
Pet friendly (59)
Elder access (1)
Smoking allowed (1)
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Holiday Rental House (71)
Condominium/Apartment (26)
Cabin Holiday Rental (0)
Private Room (0)
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Private Chef (0)
Private Beach (0)
Waterfront (0)
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Distance from
5 km
The Charles Hosmer Morse Museum Of American Art
Kraft Azalea Gardens
Albin Polasek Museum & Sculpture Gardens
Central Park
Rollins College
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97 rentals
in Winter Park.
3 Bed 1.5 Bath Spacious house in Winter Park Orlando
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
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Ocean Guest House !
36
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Breezy Pool Home!
5
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Stylish Boutique Guest house in Winter Park
60
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Casa Winter Park
33
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
42
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
14
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Modern apartment with enclosed yard, central AC, & kitchenette - dog-friendly
19
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Best Winter Park Home close to Rollins College, Advent Health & Park Avenue !
19
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 12
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Sleeps
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Cozy 2BR Duplex w/ Garden, Patio & Pet-Friendly
5
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Sleeps
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A DEAL By The Month! Walk to Rollins & Park Ave
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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Winter Park charm. Close to Park Ave
1
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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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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Sleeps
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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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Cozy 1BR Duplex|Winter Park|Close to Attractions
3
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 3
Match:
Sleeps
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Mid Century Luxury, 1 block from Park Ave (#3)
11
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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Winter Park Getaway
3
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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THE CLOUD 9 SUITE
Holiday Rental House
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2 bedrooms
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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Sleeps
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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
Match:
Sleeps
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Cute Guest House In Winter Park Minutes From Downtown in Car
2
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Sleeps
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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
Match:
Sleeps
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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
Match:
Sleeps
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Large Room Award Winning Hotel w/Rooftop Pool - Close to Parks & Rollins
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Private Poolside Guest House In Winter Park/Orlando
2
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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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
Match:
Sleeps
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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
Match:
Sleeps
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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
Match:
Sleeps
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As seen on
Winter Park Oasis
11
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
NEW! ☀Bungalow+Patio+FirePit! Close to Everything!
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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Lakefront Condo w/ Sunroom, Office, & Lakeside Pool
1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Quaint Winter Park East End Market Home
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Mid Century Luxury, 1 block from Park Ave (#2)
11
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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☀️ King Condo w/ Sunroom, Lakeside Pool and Waterfront Park
1
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Winter Park Oasis
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 8
Match:
Sleeps
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As seen on
Cozy Comfort Just 2 Blocks From Park Ave!
4
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Perfect Private Winter Park Getaway Near Theme Parks!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
6 Mi to Downtown Orlando: Quiet Home w/ Sunroom
2
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Light, Bright and Full of Delight! 2 Blocks to Park Ave
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Mid Century Modern Cottage in The Heart of Winter Park
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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Three Blocks to Park Ave, 2 Blocks to WP Village!!!
3
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Stroll to Park Avenue from Vintage Lake-View House
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Home Away from Home- Winter Park
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Charming 2BR/2BA Winter Park Cottage, steps from Park Ave
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Walk The Downtown Village of Winter Park!!!
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Sleeps
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Greatest location! Condo with private yard!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Sleeps
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LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
1
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
1
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Stay near Winter Park action at our 2-bedroom apartment
2
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Charming home 3 blocks from historic Park Avenue & one block from Lake Virginia
2
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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1
2
Showing results 1-50 of 97
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 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 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:
Casa Winter Park
Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow
CHARMING - Cozy Retreat Near Lake Killarney in Winter Park
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 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
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Holiday Rentals near Harry P. Leu Gardens
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