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Freewheeler Vacations

Freewheeler Vacations

Member since 2025
9 rentals
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New
Islamorada House
Sleeps 6, 3 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Tucked away on a quiet street in Lower Matecumbe, this beautifully furnished canalfront home is everything you imagine when you think of a laid-back Keys escape. Surrounded by lush, tropical landscaping and offering total privacy, this 3-bedroom, 3.5-bath getaway has all the extras—100 feet of dockage,...

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$550
avg per night
Islamorada House
Sleeps 14, 5 bedrooms, 4 bathrooms

Distance to beach: 3 miles to Founders Park

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...

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$1,000
avg per night
New
Islamorada Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The Artist's Cottage at Anglers Reef #136 - This beautiful home is located in Angler's Reef, a gated oceanfront community located in Islamorada. The owner has shared his own personal artwork throughout the unit for guests to enjoy. Angler's Reef is known for its beautiful tropical landscaping...

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$338
avg per night
New
Islamorada House
Sleeps 8, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle...

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$604
avg per night
New
Islamorada Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to this laid-back, oceanfront townhouse in Angler's Reef, where coastal vibes and easy living come together in the perfect Keys getaway. With three bedrooms, three baths, and plenty of charm, this spot is all about kicking back and enjoying the island life.The space has a cool, beachy...

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$615
avg per night
New
Islamorada House
Sleeps 12, 5 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Kara Pan - Islamorada's Premier Oceanfront Estate Home... Kara Pan 1. Discreet Key West style home is situated on a four-acre parcel surrounded by lush landscaping and a natural white sand beach dotted with palm trees. When entering the winding driveway, you will be intrigued with anticipation of...

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$2,071
avg per night
New
Islamorada Estate
Sleeps 16, 7 bedrooms, 7 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that...

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$2,009
avg per night
New
Islamorada Cottage
Sleeps 5, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Green Cottage - The Green Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards...

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$457
avg per night
New
Islamorada Condo
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Hot tub
  • Private pool

About this property

Welcome to Bay Harbour A-304, a waterfront penthouse in Islamorada featuring a private 50 feet deep water boat slip in a protected harbor with direct views of the marina and Atlantic Ocean. Atlantic Ocean views are visible directly beyond the protected harbor. Enjoy immediate Florida Bay access and quick...

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$411
avg per night
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