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Winter Park Vacation Rentals

Hotels (3)

B&Bs / Inns (1)

Specialty Lodging (0)

Vacation Rentals (716)

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There are no vacation rentals within Winter Park, Florida. We broadened your search to include all rentals within 5 miles.

Contact Owner
Nightly rate from
$150
Management: Verified Plus owner
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 2
Rent an affordable pet friendly kisimmee vacation home rental in the community of Indian Ridge Oaks in Orlando, Florida. You can now bring your family pets ...
  • Nightly
    $150
  • Weekly
    --
  • Monthly
    $3,500
Contact Owner
Nightly rate from
$115
Management: Verified owner
Property: Rental Resort
Bedrooms: 3, sleeps 8
Bathrooms: 4
Min stay:2
Enjoy Orlando at it's best! This beautifully decorated 3 story townhome with 3 bedrooms/3.5 baths is your home away from home for that exciting Orlando ...
  • Nightly
    $115 - $175
  • Weekly
    --
  • Monthly
    --
Contact Owner
Nightly rate from
$98
Management: Verified owner
Property: Rental Resort
Bedrooms: 3, sleeps 6
Bathrooms: 2
Welcome to WorldQuest Resort, a new Italian themed development of luxury condominiums suites located in the center of the world’s most famous holiday ...
  • Nightly
    $98 - $169
  • Weekly
    --
  • Monthly
    --
Management: Verified owner
Property: Rental Home
Bedrooms: 5, sleeps 10
Bathrooms: 4
Looking for superior accommodation, fantastic facilities within a place that you can relax and feel at home, for that special holiday in Orlando, Florida? ...
  • Nightly
    --
  • Weekly
    $1,241 - $1,471
  • Monthly
    --
VC3023, Orlando
Contact Manager
Nightly rate from
$125
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 4
Brand new 3 bedroom, 3-1/2 bath town home with almost 1800 square feet of living space plus a one car garage! Professionally decorated and luxuriously ...
  • Nightly
    $125 - $150
  • Weekly
    $875 - $1,050
  • Monthly
    --
VC3049, Orlando
Contact Manager
Nightly rate from
$130
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
This luxurious 3 bedroom 2 bath condominium is located in Orlando’s newest resort community of Vista Cay at Harbor Square. Tuscan themed Vista Cay offers ...
  • Nightly
    $130 - $199
  • Weekly
    $910 - $1,250
  • Monthly
    --
VC3044, Orlando
Contact Manager
Nightly rate from
$125
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 8
Bathrooms: 4
This deluxe 3 bedroom 3.5 bath townhome is located in Orlando’s newest resort community of Vista Cay at Harbor Square. Tuscan themed Vista Cay offers spacious ...
  • Nightly
    $125 - $150
  • Weekly
    $875 - $1,050
  • Monthly
    --
TI3051, Orlando
Contact Manager
Nightly rate from
$130
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 2
This stunning 3 bedroom 2 bath condominium is located in Orlando’s newest resort community of The Isles at Cay Commons. Tuscan themed Vista Cay & The Isles ...
  • Nightly
    $130 - $175
  • Weekly
    $910 - $1,100
  • Monthly
    --
VC3055, Orlando
Contact Manager
Nightly rate from
$130
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
This luxurious 3 bedroom 2 bath condominium is located in Orlando’s newest resort community of Vista Cay at Harbor Square. Tuscan themed Vista Cay offers ...
  • Nightly
    $130 - $199
  • Weekly
    $910 - $1,250
  • Monthly
    --
Contact Manager
Nightly rate from
$177
Management: Professional
Property: Rental Home
Sleeps: 8
Bathrooms: 2
This beautiful 3 bedroom/ 2-bath condo is located in the brand new, leisure community of Vista Cay, located within walking distance from the Orange County ...
  • Nightly
    $177 - $246
  • Weekly
    --
  • Monthly
    --
Contact Manager
Nightly rate from
$177
Management: Professional
Property: Rental Home
Bedrooms: 3, sleeps 6
Ventura Unit - This beautiful 3 bedroom/ 2-bath condo is located in leisure community of Vista Cay, located within walking distance from the Orange County ...
  • Nightly
    $177 - $246
  • Weekly
    --
  • Monthly
    --
VC3026, Orlando
Contact Manager
Nightly rate from
$130
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 2
This luxurious 3 bedroom 2 bath condominium is located in Orlando’s newest resort community of Vista Cay at Harbor Square. Tuscan themed Vista Cay offers ...
  • Nightly
    $130 - $199
  • Weekly
    $910 - $1,250
  • Monthly
    --
VC3045, Orlando
Contact Manager
Nightly rate from
$130
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
This luxurious 3 bedroom 2 bath condominium is located in Orlando’s newest resort community of Vista Cay at Harbor Square. Tuscan themed Vista Cay offers ...
  • Nightly
    $130 - $199
  • Weekly
    $910 - $1,250
  • Monthly
    --
VC3060, Orlando
Contact Manager
Nightly rate from
$130
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
At Vista Cay, you will enjoy the elegance of a luxury property combined with the cozy comfort of your own home. This luxurious 3 bedroom 2 bath condominium is ...
  • Nightly
    $130 - $199
  • Weekly
    $910 - $1,250
  • Monthly
    --
VC3047, Orlando
Contact Manager
Nightly rate from
$130
Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 8
Bathrooms: 2
This luxurious 3 bedroom 2 bath condominium is located in Orlando’s newest resort community of Vista Cay at Harbor Square. Tuscan themed Vista Cay offers ...
  • Nightly
    $130 - $199
  • Weekly
    $910 - $1,250
  • Monthly
    --
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns