We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified 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
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Freewheeler Vacations, Inc.

Freewheeler Vacations, Inc. has 66 rentals in Islamorada, Key Largo, Long Key, and more

Freewheeler Vacations is the largest and oldest vacation rental company in the Upper Florida Keys. Our reservationists are extremely knowledgeable of our large inventory of Florida Keys vacation rentals including estates, homes, condos, and villas on the beach, bay, ocean and canals. From efficiencies to oceanfront estates with up to 10 bedrooms, Freewheeler Vacations will locate the perfect Florida Keys vacation rental for you and your family at rates below most hotels. Bring a boat or bring a pet – we have homes that will accommodate both.
Response Rate:
100%
Languages spoken:
English
Response Time:
Within a day
Member on:
FlipKey
1 / 65
4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
From
$300
Per Night
Payment Protection
View Details
1 / 22
3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
From
$160
Per Night
Payment Protection
View Details
1 / 29
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$108
Per Night
Payment Protection
View Details
1 / 30
3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
From
$285
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 18
(4) Average
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$108
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 36
4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
From
$216
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 16
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$106
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 27
3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
From
$150
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 17
2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
From
$175
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$114
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 13
1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
From
$117
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 26
1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
From
$83
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 31
(7) Very good
3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
From
$328
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$110
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 44
(2) Poor
2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
From
$175
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 29
(3) Excellent
5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
From
$785
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 18
(4) Excellent
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$165
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 24
(16) Very good
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$214
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 26
(8) Very good
5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
From
$428
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 25
(9) Very good
3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
From
$171
Per Night
Payment Protection
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
Property Summary Rating
4.5 of 5
Very good
13 rated properties
  • Excellent
    5
  • Very good
    6
  • Average
    1
  • Poor
    1
  • Terrible
    0
The safest rental experience online
Rent from verified owners and managers, and read reviews before you book.
Find out what to expect »