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Winter Park Apartment Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
34 rentals 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, holiday rental in Winter Park

Total Serenity #2, 2 BDRM, 2 Bath

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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Adorable 1 Bedroom in the perfect location!, holiday rental in Winter Park
Adorable 1 Bedroom in the perfect location!, holiday rental in Winter Park
Adorable 1 Bedroom in the perfect location!, holiday rental in Winter Park

Adorable 1 Bedroom in the perfect location!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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Beautiful 2 Story Winter Park Villa, holiday rental in Winter Park
Beautiful 2 Story Winter Park Villa, holiday rental in Winter Park
Beautiful 2 Story Winter Park Villa, holiday rental in Winter Park

Beautiful 2 Story Winter Park Villa

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Condominium/Apartment
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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, Condominium/Apartment
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Cozy Comfort In The Heart of Winter Park!, holiday rental in Winter Park
Cozy Comfort In The Heart of Winter Park!, holiday rental in Winter Park
Cozy Comfort In The Heart of Winter Park!, holiday rental in Winter Park

Cozy Comfort In The Heart of Winter Park!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Condominium/Apartment
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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, Condominium/Apartment
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Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, holiday rental in Winter Park
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, holiday rental in Winter Park
Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths, holiday rental in Winter Park

Modern Elegance In The Heart Of Winter Park - 2 beds/2 baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Condominium/Apartment
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3 Bedroom Apartment (420428) by Houzlet, holiday rental in Winter Park
3 Bedroom Apartment (420428) by Houzlet, holiday rental in Winter Park
3 Bedroom Apartment (420428) by Houzlet, holiday rental in Winter Park

3 Bedroom Apartment (420428) by Houzlet

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Condominium/Apartment
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Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!, holiday rental in Winter Park
Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!, holiday rental in Winter Park
Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!, holiday rental in Winter Park

Just 3 Blocks to Park Ave Shops/ Restaurants, 2 From The Winter Park Village!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Condominium/Apartment
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Queen Room Near All Saints Episcopal Church ORL, holiday rental in Winter Park
Queen Room Near All Saints Episcopal Church ORL, holiday rental in Winter Park
Queen Room Near All Saints Episcopal Church ORL, holiday rental in Winter Park

Queen Room Near All Saints Episcopal Church ORL

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Condominium/Apartment
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4 Bedroom Single_family (420976) by Houzlet, holiday rental in Winter Park
4 Bedroom Single_family (420976) by Houzlet, holiday rental in Winter Park
4 Bedroom Single_family (420976) by Houzlet, holiday rental in Winter Park

4 Bedroom Single_family (420976) by Houzlet

Condo/Apartment
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Condominium/Apartment
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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, Condominium/Apartment
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Luxury Living Just 3 Blocks From Park Ave!!!, holiday rental in Winter Park
Luxury Living Just 3 Blocks From Park Ave!!!, holiday rental in Winter Park
Luxury Living Just 3 Blocks From Park Ave!!!, holiday rental in Winter Park

Luxury Living Just 3 Blocks From Park Ave!!!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Condominium/Apartment
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SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS, holiday rental in Winter Park
SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS, holiday rental in Winter Park
SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS, holiday rental in Winter Park

SPACIOUS CONDO CLOSE TO UCF, FULL SAIL & ROLLINS

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Condominium/Apartment
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Amazing location- walk to everything, holiday rental in Winter Park
Amazing location- walk to everything, holiday rental in Winter Park
Amazing location- walk to everything, holiday rental in Winter Park

Amazing location- walk to everything

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Condominium/Apartment
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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, Condominium/Apartment
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Little gem apartment, holiday rental in Winter Park
Little gem apartment, holiday rental in Winter Park
Little gem apartment, holiday rental in Winter Park

Little gem apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Condominium/Apartment
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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
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Condominium/Apartment
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You're Pampered Here - Just 3 Blocks From Park Avenue!, holiday rental in Winter Park
You're Pampered Here - Just 3 Blocks From Park Avenue!, holiday rental in Winter Park
You're Pampered Here - Just 3 Blocks From Park Avenue!, holiday rental in Winter Park

You're Pampered Here - Just 3 Blocks From Park Avenue!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Condominium/Apartment
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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
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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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, Condominium/Apartment
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The following properties match some of your filters:
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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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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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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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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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
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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
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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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Adorable and espacious, 2 Beds, with great location, holiday rental in Winter Park
Adorable and espacious, 2 Beds, with great location, holiday rental in Winter Park
Adorable and espacious, 2 Beds, with great location, holiday rental in Winter Park

Adorable and espacious, 2 Beds, with great location

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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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Florida Vacation Rental ~ 6 Mi to Downtown Orlando, holiday rental in Winter Park
Florida Vacation Rental ~ 6 Mi to Downtown Orlando, holiday rental in Winter Park
Florida Vacation Rental ~ 6 Mi to Downtown Orlando, holiday rental in Winter Park

Florida Vacation Rental ~ 6 Mi to Downtown Orlando

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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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Charming Clean Home near East End Market - Monthly discounts available, holiday rental in Winter Park
Charming Clean Home near East End Market - Monthly discounts available, holiday rental in Winter Park
Charming Clean Home near East End Market - Monthly discounts available, holiday rental in Winter Park

Charming Clean Home near East End Market - Monthly discounts available

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury Villa, 3bed/2bath Great Location with Pool, holiday rental in Winter Park
Luxury Villa, 3bed/2bath Great Location with Pool, holiday rental in Winter Park
Luxury Villa, 3bed/2bath Great Location with Pool, holiday rental in Winter Park

Luxury Villa, 3bed/2bath Great Location with Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Ideal Location, Charming 4 bedroom home w Lap Pool, fenced yard, month discounts, holiday rental in Winter Park
Ideal Location, Charming 4 bedroom home w Lap Pool, fenced yard, month discounts, holiday rental in Winter Park
Ideal Location, Charming 4 bedroom home w Lap Pool, fenced yard, month discounts, holiday rental in Winter Park

Ideal Location, Charming 4 bedroom home w Lap Pool, fenced yard, month discounts

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Best Home by Winter Park Hospital, Rollins College and Park Ave !, holiday rental in Winter Park
Best Home by Winter Park Hospital, Rollins College and Park Ave !, holiday rental in Winter Park
Best Home by Winter Park Hospital, Rollins College and Park Ave !, holiday rental in Winter Park

Best Home by Winter Park Hospital, Rollins College and Park Ave !

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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