Upper Florida Keys Rentals

Upper Keys Florida vacation rentals by owner offer a variety of amenities to enjoy your vacation in Upper Keys Florida. Select a Upper Keys Florida Rental below and start planning your Florida Keys Vacation!

 Waterfront Beachside Tropical Paradise in the Upper Keys

House

2 Bed 3 Bath Sleeps 10

Waterfront Beachside Tropical Paradise in the Upper Keys Tavernier

This oceanside tropical estate is perfect for your family vacation or romantic get away. We are cent

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Escape to Paradise in a Gated Tropical Bayfront Estate   (FREE WIFI)

Cottage

2 Bed 2 Bath Sleeps 4

Escape to Paradise in a Gated Tropical Bayfront Estate (FREE WIFI) Tavernier

Tucked away on a gated tropical estate, is our 'Island Breeze Cottage'. This cottage is located in

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Paradise Found modern canal home,pool, hot tub, row boat, great outdoor space

House

2 Bed 2 Bath Sleeps 6

Paradise Found modern canal home,pool, hot tub, row boat, great outdoor space Key Largo

Paradise Found in Key Largo is a beautiful and modern canal front manufactured home convenienty lo

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Oceanfront Angler's Reef, Islamorada, Florida Keys, SLIDESHOW TOUR!

House

2 Bed 2 Bath Sleeps 6

Oceanfront Angler's Reef, Islamorada, Florida Keys, SLIDESHOW TOUR! Islamorada

This relaxing private home, known as "Windley Cottage" is located at 129 Anglers Way in Angler's Ree

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Paradise for Rent (Condo and Private Boat Slip)

Condo

2 Bed 1 Bath Sleeps 6

Paradise for Rent (Condo and Private Boat Slip) Key Largo

Tropical settings, beautiful sunset views, do as much as you want to do. Just lay by the pool and ca

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Luxury 3 story pool home with wonderful ocean views, a piece of paradise.

House

3 Bed 3 Bath Sleeps 6

Luxury 3 story pool home with wonderful ocean views, a piece of paradise. Key Largo

Luxury ocean view home featuring:- Gated home located in the heart of Key Largo- Sleeps 6, 3 bedroom

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Kawama Yacht Club- Oceanfront Private Beach - Sunsets! Two Bedroom Two Bathroom!

Condo

2 Bed 2 Bath Sleeps 8

Kawama Yacht Club- Oceanfront Private Beach - Sunsets! Two Bedroom Two Bathroom! Key Largo

Unit bought in 2012, all new furnishings and fixings purchased then. A true comfort, our little slic

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Paradise found... Relax and enjoy

Condo

1 Bed 1 Bath Sleeps 4

Paradise found... Relax and enjoy Tavernier

Spacious one bedroom condo located in beautiful Islamorada Fl. Oceanfront pool, tennis courts, priv

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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

Condo

1 Bed 2 Bath Sleeps 4

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay Islamorada

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort prope

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Luxury Keys Home at Oceanfront Anglers Reef, Dock, Pool, Tommy Bahama Furniture

House

2 Bed 2 Bath Sleeps 4

Luxury Keys Home at Oceanfront Anglers Reef, Dock, Pool, Tommy Bahama Furniture Islamorada

This property is fully insured for rentals and licensed by Village of Islamorada, license #VR-212.Ch

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John Pennekamp State Park - Beautiful Key Largo Oceanside Townhouse  (Free WiFi

Condo

3 Bed 2 Bath Sleeps 7

John Pennekamp State Park - Beautiful Key Largo Oceanside Townhouse (Free WiFi Key Largo

It’s just what you need. Minutes from Miami, yet seemingly a world away.The vacation you deserve i

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Spectacular Panoramic Views! Oceanfront Resort/Marina End Unit

Condo

2 Bed 2 Bath Sleeps 6

Spectacular Panoramic Views! Oceanfront Resort/Marina End Unit Tavernier

Gorgeous ocean views from this beautifully furnished end unit in a luxury gated community are waitin

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Brand New Unique Deep Water Gulf Front Estate.  Beach, Pool, Hot tub and docks

House

4 Bed 4 Bath Sleeps 10

Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks Islamorada

This is a brand new house. Just completed August 2014 This unique Gulf Front property is located am

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Oceanfront Paradise W/ Large Screened Porch & Cable Internet

Condo

2 Bed 2 Bath Sleeps 5

Oceanfront Paradise W/ Large Screened Porch & Cable Internet Tavernier

Oceanfront 90 mm Plantation Key , full screened in terrace 6.5 ft by 28.5 ft. Newly decorated whit

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Mariner's Club by KeysCaribbean - Spectacular Views

Condo

4 Bed 3 Bath Sleeps 10

Mariner's Club by KeysCaribbean - Spectacular Views Key Largo

This 4 bedroom Elevated Villa is on an island paradise situated at the gateway to the Florida Keys -

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Stunning Lakefront Home Was Designed By Distinguished Architect Robert S. Bennet

House

4 Bed 4 Bath Sleeps 12

Stunning Lakefront Home Was Designed By Distinguished Architect Robert S. Bennet Key Largo

This Ocean Reef two-story home offers stunning details throughout the open floor plan featuring four

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Ocean Reef®  Pool 36' Seawall Beach Golf Tennis

Condo

2 Bed 1 Bath Sleeps 4

Ocean Reef® Pool 36' Seawall Beach Golf Tennis North Key Largo

Ocean Reef® is a 2,500 acre private resort community located on the northern tip of Key Largo, Flor

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Anglers Reef Vacation Paradise Islamorada Florida Keys

House

2 Bed 2 Bath Sleeps 6

Anglers Reef Vacation Paradise Islamorada Florida Keys Islamorada

Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85

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Enjoy Sunrise By The Seashore! Luxuriously Appointed Sanctuary In Angler's Reef

House

2 Bed 2 Bath Sleeps 5

Enjoy Sunrise By The Seashore! Luxuriously Appointed Sanctuary In Angler's Reef Islamorada

Welcome to Anglers Reef, a quiet upscale gated community consisting of 52 single family homes built

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Meagan's Beach House - Bayfront Home with spectacular Sunrises and Sunsets

House

2 Bed 2 Bath Sleeps 6

Meagan's Beach House - Bayfront Home with spectacular Sunrises and Sunsets Key Largo

Beautiful and peaceful bayfront home with casual coastal living décor. A charming piece of paradise

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