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Special Deals for Vacation Homes in the Florida Keys and Key West

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We have partnered with a major provider of vacation rentals, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida Keys. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Islamorada apartment

Bay Harbour D114

Stunning 3 Bedroom Condo with Oceanviews Located in Lower Matecumbe - Bay Harbour D114

Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi. The Bay Harbour Complex comes complete with two tennis courts, weight room, ....

3 Bedroom(s) 3 Bath(s) Apartment
Islamorada, FL

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Big Pine Key house

Reel Paradise

Reel Paradise - A Waterfront Boating Excape

Reel Paradise offer a large open format Keys retreat with vaulted ceilings, 3 bedrooms, 3 baths, dining room, large family room, sitting area, large screen plasma TV in the family room & private TV in each bedroom, 200 channel cable TV, DVD player, W ....

3 Bedroom(s) 3 Bath(s) Vacation Rentals - Sleeps 6
Big Pine Key, FL

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Marathon house

"Villa Sombrero "

Ocean Side Waterfront Exclusive Affordable Home - Pool , Tennis, Fishing & Golf

Villa Sombrero is an exclusive and private waterfront destination in the heart of the fabulous Florida Keys. This unique retreat is perfectly positioned overlooking a natural preserve on a serene protected deep waterway- providing easy boat access t ....

5 Bedroom(s) 5 Bath(s) Vacation Rentals - Sleeps 10
Marathon, FL

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Key West house

Archipelago II

Archipelago ll @ the Truman Annex

This newer renovation is a gorgeous 2 bedroom, 2.5 bath townhouse. The kitchen and baths are new and living room, dining area, and back patio are all updated and beautiful. The bedrooms have a queen size bed and 2 twin beds that can be converted to a ....

2 Bedroom(s) 3 Bath(s) Vacation Rentals - Sleeps 6
Key West, FL

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Islamorada house

151 Anglers Way

Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach

This magnificent home with amazing direct ocean views from the master bedroom, living room and balconies is located in Islamorada at Mile Marker 85 in the exclusive gated community of Angler's Reef. Home also overlooks the community pool. Anglers Ree ....

2 Bedroom(s) 3 Bath(s) Vacation Rentals - Sleeps 6
Islamorada, FL

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Big Pine Key house

Palm Ave 3/3

Experience the Keys like a Local at this Spacious Canal Front Home with Dock!

This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 40 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to enjoy the party atmosphere of Key West! Dock your boat o ....

3 Bedroom(s) 3 Bath(s) Vacation Rentals
Big Pine Key, FL

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Islamorada house

Alligator Reef - Conch Home

Alligator Reef - Conch Home

Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean bre ....

3 Bedroom(s) 3 Bath(s) Vacation Rentals
Islamorada, FL

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Islamorada house

83003 Old Highway

Beautiful Oceanfront Oasis with Pool - 83003 Old Hwy.

Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in ....

4 Bedroom(s) 3 Bath(s) Vacation Rentals
Islamorada, FL

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Key Largo house boat

The Shark Pup

A Peaceful Solar Houseboat at Anchor in the Keys

***This Anchored Houseboat is for Adventurous Campers*** Welcome to The Shark Pup houseboat, a floating retreat anchored in calm Key Largo waters. Enjoy the slow down of boat life as you bob calmly in the still waters. Fish and swim from your privat ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 2
Key Largo, FL

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Key West townhome

"CORAL CABANA" ~ Tropical Comfort!

"CORAL CABANA" ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

GATED COMMUNITY, CLOSE TO BOATING AND GOLFING... Coral Cabana, in the Coral Hammock Community is a gorgeous three bedroom, three bath townhome with over 2,000 square feet of indoor/outdoor living space. A tranquil pool view can be easily appreciated ....

3 Bedroom(s) 3 Bath(s) Townhome
Key West, FL

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Key Largo townhome

Kawama Yatch Club B7

Welcome to Key Largo - Newly Remodeled, clean and cozy with WIFI

Located in Kawama Yacht Club on MM 100 Oceanside 2 Bedrooms, each with a Queen size bed, 1-1/2 bathrooms - (full bathroom upstairs and half bath in first floor), full kitchen with brand new kitchen appliances and complete to make your own meals at h ....

2 Bedroom(s) 2 Bath(s) Townhome - Sleeps 4
Key Largo, FL

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Tavernier condo

Ocean Pointe - 2/2 (D) Partial Ocean View Suite

2 Bedroom Tropical Partial Ocean View Suites - Short Drive to John Pennekamp Coral Reef State Park

Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to su ....

2 Bedroom(s) 2 Bath(s) Condo
Tavernier, FL

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Big Pine Key house

Nichols Key

Gorgeous 2 bedroom 2 bath canal front pool home

Gorgeous canal front 2 bedroom 2 bath pool home located on Big Pine Key. Excellent boating to the Gulf or the Atlantic with over 70' of concrete seawall. Mature landscaping surrounds the pool and tiki hut making it a tropical paradise The home featur ....

2 Bedroom(s) 2 Bath(s) Vacation Rentals
Big Pine Key, FL

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Big Pine Key house

Time To Fish

Fisherman's Paradise in the Heart of Big Pine Key Deer Reserve

This waterfront vacation home is located in a quiet nature reserve, surrounded by several open undeveloped lots for extra privacy. 3 bedroom, 2 bath home with screen porch, and plenty of outdoor living area underneath. Master bedroom features king b ....

3 Bedroom(s) 2 Bath(s) Vacation Rentals - Sleeps 6
Big Pine Key, FL

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Islamorada house

Tarpon Bay Castaway

Brand New / Totally Renovated Luxurious Home New To Rental Market.

PLEASE inquire directly with us about the specific rate based on the length of stay (SHORTER or LONGER)! Located in Islamorada the premier Key of the Florida Keys, which is known as the Sports Fishing Capital of the world. Islamorada is actually mad ....

3 Bedroom(s) 2 Bath(s) Vacation Rentals - Sleeps 9
Islamorada, FL

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Islamorada house

132 Atlantic Lane

Beautifully Renovated 2 Bedroom Oceanfront Home - 132 Columbus

Looking for your next Home away from Home? You can not go wrong in this recently renovated 2 bedroom and 2 bath canal home in Lower Matecumbe at the 76 Mile Marker. This home has everything you need for your next get-away in Islamorada. Only one pr ....

2 Bedroom(s) 2 Bath(s) Vacation Rentals
Islamorada, FL

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Key West house

Island Dreaming

Extraordinary Beach Cottage... Spectacular Ocean Views..10 minutes from Key West

Enjoy the best open ocean views in all of the Florida Keys, with water on 3 sides of the property and no adjacent neighbors. This 1920 sq. ft. beach home was built in 2004 and has an open floor plan with high ceilings. It has all new appliances. Fish ....

3 Bedroom(s) 2 Bath(s) Vacation Rentals - Sleeps 8
Key West, FL

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Key West house

Away from it All

Away from it All @ The Truman Annex

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fo ....

2 Bedroom(s) 1 Bath(s) Vacation Rentals - Sleeps 4
Key West, FL

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Marathon townhome

Indigo Reef

Indigo Reef Resort, Villa 9 with Complimentary Dockage - Lacking Vitamin Sea?

Get lost in the grandeur of this impressive townhome, conveniently located in Marathon, Florida. Featuring only the most tropical of furnishings, a dazzling sunset view patio and a well equipped dining area ready to take on your next kitchen escapade ....

3 Bedroom(s) 3 Bath(s) Townhome - Sleeps 6
Marathon, FL

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Key Largo house

Villa Mirasol

Rent a FULL month for less than 1 week at a hotel.

You Will Never Want to Leave this Key Largo Vacation Home! The beach house is yours to enjoy for a minimum of 28 nights, (per Monroe County Code). The entire month will cost less than most weekly rentals. Home Features: • The large Master Bedr ....

3 Bedroom(s) 2 Bath(s) Vacation Rentals - Sleeps 7
Key Largo, FL

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Islamorada house

2 bedroom 2 bath home in the HEART of Islamorada, Florida Keys-- walk festivals & more!

2 bedroom 2 bath home in the HEART of Islamorada, Florida Keys-- walk festivals & more!

Mile Marker 81. Cute and cozy two bedroom, two bathroom home located off the main streets, in the heart of Islamorada. A full porch wraps around the front and back yard, for relaxing and entertaining in the Florida Keys weather. Natural sunlight ....

2 Bedroom(s) 2 Bath(s) Vacation Rentals
Islamorada, FL

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Tavernier house

Vacation Home

Beautiful Home Conveniently Located in Islamorada, Florida Keys. Amazing dock

3 bedroom 3 bathroom ground level home with central air conditioning. Mother-in-law suite with kitchenette. 2 bedrooms have easy access to a beautiful deck, equipped with a grill, and canal views. 70 ft Spacious dock with capacity for two boats. Also ....

3 Bedroom(s) 3 Bath(s) Vacation Rentals - Sleeps 6
Tavernier, FL

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Key West condo

Vacation Home

COCONUT COTTAGE CONDO at SUNSET MARINA RESIDENCES

Kick your shoes off and enjoy this laid back two bedrooms, two bath spacious condo. Watch glorious sunsets from your balcony overlooking the marina and Florida Bay. The perfect Key West retreat with a large community pool and hot tub that are well ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 4
Key West, FL

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Tavernier house

Plantation Key Paradise

You Don't Need a Passport To Enjoy Our Islands At Plantation Key Paradise

Enjoy this pristine waterfront paradise located in the elite Village of Islamorada in the Fl Keys. Drive into the shady tree lined driveway and the water will lap up to greet you. A large wrap around deck and dock will welcome you with lots of spot ....

2 Bedroom(s) 2 Bath(s) Vacation Rentals - Sleeps 6
Tavernier, FL

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Key Largo apartment

1/1 Cabanas Key Largo #5

Cabanas Key Largo Unit 5

Oceanside apartment with Boat Dock for Pick up and Drop-Off only, The Pilot House Marina and Restaurant is just a few properties down on the same canal where you can dock any size boat overnight. Completely remodeled, spacious and spotless with Priva ....

2 Bedroom(s) 1 Bath(s) Apartment
Key Largo, FL

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Key West house

Treehouse Island

Treehouse Island @ The Truman Annex

Treehouse Island is a traditional Key West eyebrow house. Inside it's spacious and up-to-date, yet as comfortable as you would expect a personal residence to be. Living areas include a large great room, a front sitting room and dining room. A well-fu ....

3 Bedroom(s) 4 Bath(s) Vacation Rentals - Sleeps 8
Key West, FL

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Islamorada house

Vacation Home

ISLAMORADA PARADISE - Welcome to Heaven On Earth!

Built in 2012 and designed by well-known Miami architect to mirror the curved shoreline of the beach, this private custom contemporary beach home is a one of a kind, unique design with gated entry, large private beach, and gorgeous panoramic ocean vi ....

3 Bedroom(s) 4 Bath(s) Vacation Rentals
Islamorada, FL

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Key Largo townhome

Kawama Yacht Club G3

KAWAMA YACHT CLUB - SUN AND FUN IN FABULOUS KEY LARGO. *WiFi, Golf Cart & kayak!

This townhome is located Oceanside in Kawama Yacht Club, in the very heart of Key Largo, minutes away from John Pennekamp State Park, known worldwide for its' excellent scuba diving, snorkeling, and fishing. With great restaurants within walking dist ....

2 Bedroom(s) 2 Bath(s) Townhome - Sleeps 8
Key Largo, FL

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Key West apartment

Suite Blu

Suite Blu - A monthly rental apartment in a great location

Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West. This monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided ....

1 Bedroom(s) 1 Bath(s) Apartment - Sleeps 2
Key West, FL

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Big Pine Key house

Vacation Home

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3 Bedroom(s) 2 Bath(s) Vacation Rentals - Sleeps 6
Big Pine Key, FL

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