Vacation Rentals in Upper Florida Keys

Relax in this peaceful, open-water bird and wildlife sanctuary. In a living room only 9 feet from water's edge, you can sit on your sofa and watch fish swim.

Port of Call is a secluded 10 unit oceanfront complex along 'Millionaires Row' on Plantation Key Islamorada. (Mile Marker 88) Unit has intimate setting for your...

Relax in this peaceful, open-water bird & wildlife sanctuary. Private patio views of the State Park. In a living room just a few feet from water's edge, you can sit...

Immaculate 2 bedroom, 2 bathroom condo with breathtaking views of the Atlantic Ocean from the living room balcony. This condo boasts a queen bed in master bedroom, 2...

Islamorada-- Most south-easterly house in USA. Gated property end of Sunset Drive @ MM 74-1/2 The best Private Beach in keys, palm trees, hammocks, fire pit.

Bonefish Bay is a private secluded community of only 12 homes on 5 acres overlooking the Bay with 350 feet of shoreline. The Starfish house sits just steps from the...

Tranquil sunrises and sunsets are yours as you sit on the screened deck of this bay front beauty. Unobstructed bay views abound with over 80' of seawall on the...

'Caddy Corners' is a charming Key West style three-bedroom, two-bath home located in the heart of Islamorada on the Florida Keys.

This 750 square foot one-bedroom/one-bath, oceanfront condo features a balcony overlooking the Atlantic Ocean. It has a small beach area on the water with fishing...

This beautiful and spacious, two-story, three bedroom, three bath home is situated on a huge lot with 100 feet of frontage on a short, crystal clear, bayside canal.

Luxurious one bedroom apartment in home across the charming private street from the long sandy beach. There is a 60 foot deep water dock with quick access to the...

Eagle's Nest, a unique rental for single vacationers or a pair of traveling companions. Upper level, ocean view master suite is a private designer ‘studio’...

Forget cramped condos and hotels, this house is roomy, private and comfortable. This home has also just been completely renovated and is now being offered as a...

This home is the perfect getaway in the Florida Keys, brand new home in the fishing capital of the Islamorada Key, situated in the exclusive community known as ”Port...

Totally remodeled, canal front home, quiet and in the nicest neighborhoods (Plantation Key Colony). Situated on the bayside on mile marker 90.

This adorable 1/1 condominium is located in Seagulls. (Mile marker 90 on the ocean side.) Seagulls is located in a well maintained community.

Tucked away on a gated tropical estate, is our 'Island Breeze Cottage'. This cottage is located in the middle of the Estate and steps away from our white sandy...

Paradise by the bay. Quiet, serene, gorgeous sunsets, crystal clear waters. Tropical setting. Easy and friendly atmosphere and yet very private.

Sun, fun and relaxation, its all here waiting for you. This two bed, two bath oceanfront Condo offers you breathtaking views of the Atlantic Ocean from the second...

Enjoy our PRIVATE BEACH with panoramic views of the Gulf of Mexico ,spectacular sunsets! Excellent Fishing, snorkeling and boating in your backyard.