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.
Listed since Aug 2015

Freewheeler Vacations, Inc. has 47 rentals in Islamorada, Key Largo, Matecumbe 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.
Languages spoken:
English
Member on:
FlipKey
Listed since :
Aug 2015
1 / 20
Studio, 1 Bathroom, Sleeps 2 | Quick View
From
$1,600
Per Month
View Details
1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$900
Per Week
View Details
1 / 46
3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
From
$2,000
Per Week
View Details
1 / 21
2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
From
$3,200
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 35
5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
From
$3,000
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 24
5 of 5 bubbles (2) Excellent
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$3,000
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 19
3.5 of 5 bubbles (4) Average
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$850
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
From
$3,800
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 38
3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
From
$5,500
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 47
3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
From
$5,000
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 28
2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
From
$1,325
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 26
Studio, 2 Bathrooms, Sleeps 4 | Quick View
From
$800
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 31
1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
From
$900
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$3,000
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 40
Studio, 2 Bathrooms, Sleeps 8 | Quick View
From
$7,000
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 23
3.5 of 5 bubbles (2) Average
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$3,000
Per Month
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 20
3 Bedrooms, Sleeps 6 | Quick View
From
$1,700
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 25
2 of 5 bubbles (2) Poor
2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
From
$1,325
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 27
4.5 of 5 bubbles (2) Very good
2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
From
$3,000
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
1 / 30
4.5 of 5 bubbles (7) Very good
3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
From
$2,300
Per Week
View Details
Suitability
  • Pets allowed
  • Smoking allowed
  • Kid friendly
  • ?
  • ?
  • ?
Property Summary Rating
4.5 of 5
Very good
24 rated properties
  • Excellent
    17
  • Very good
    6
  • Average
    0
  • 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 »