Florida Keys Vacation Rentals

(273 rentals)
Summertime in the Fabulous Florida Keys !

$207

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

Duplex, 2 Bedrooms + Convertible bed (Sleeps 4-5), 2 baths, Wi-fi, all amenitiesGround level with back yard for BBQ and relaxing. Dock your own boat or a rental boat at this canal front home. Easy access from dock to the ocean or bay for fishing, snorkeling, sightseeing, or just floating. There are ...

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Property Type

Key Colony Beach House

"I would rent again"
Reviewed July 30, 2018

The place was very clean and as described. The owner was very helpful with recommending local activities and provided guidance from public boat ramp to the house. She was very responsive and friendly. We ...

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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

$269

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...

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Property Type

Islamorada Condo

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Private beach estate,gated,dock,and pool

$857

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants the Florida Keys has to offer. ...

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Property Type

Key West House

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Hemingway's Retreat

3 BR | 2 BA | Sleeps 6 | Quick View

$686

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Sea Vista EstateStay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free ...

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Property Type

Sugarloaf Key House

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Private beach estate.Dock and pool

$283

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just ...

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Property Type

Sugarloaf Key House

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Colony Sunset Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$180

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with ...

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Property Type

Key West Condo

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Bougainvillea Villa Key West-monthly rental on water with private pool & dock

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$167

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early 1960’s and our neighbors tell us that at one time Jimmy Buffett’s manager owned and lived in the home. It has always been a private home, and was renovated and ...

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Property Type

Key West House

"Beautiful Bougainvillea Villa"
Reviewed February 27, 2018

Nothing is missing from this very clean and very well organized beautiful home situated on a wide lagoon. For us, the highlight is the superb view of the wide lagoon from the window wall across the entire ...

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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$178

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Beautifully Remodeled -1BR/1BA End Unit Shipyard Condo in Truman Annex Location, Beauty and Comfort! Southard Breezes has what you are looking for! This gorgeous home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and ...

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Property Type

Key West Condo

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Mosaic House - A Charming 3 bed/3 bath Waterfront Home with Ocean Views

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

About this property

The MOSAIC HOUSE as it is named is located on one of Lower Matecumbe's (Islamorada) most popular streets and features a very unique floor plan. This home "lives" in the back of the house with glass walls overlooking a tropical paradise. There's an outdoor "play" area which includes ...

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Property Type

Islamorada House

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Moon Bay A206 - Totally Remodeled Condo with Pool and Dock in Key Largo

$150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Minimum Rental: 7 DaysSATURDAY to SATURDAY "Moon Bay A206" is calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal ...

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Property Type

Key Largo Condo

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Little Bay Lower Duplex - Gated Bayfront Property Shared w/ 2 Other Rental Units

$357

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Minimum Rental: 7 DaysLittle Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...

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Property Type

Islamorada House

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The Key's only real beach house Dock and pool

$471

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island.Enjoy full use of direct TV channels, free current video library ...

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Property Type

Sugarloaf Key House

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Bayside Breeze - Beautiful Home with open living, gourmet kitchen and boat lift.

$165

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Bayside Breeze" is a wonderful 2013 built stilt home. Features include an open living area with gourmet kitchen, stainless steel appliances, including a wine refrigerator and granite counters. The oversized center island in the kitchen makes a perfect snack ...

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Property Type

Plantation Key House

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Cozy End Unit Condo in Truman Annex

$171

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

Beautifully Remodeled Tropical Sanctuary-1BR/1BA Shipyard Condo in Truman AnnexLocation, Location, Location!! Sunrise off Southard has it all! An upscale one bedroom home offers beauty with all the comforts. Located in the gated community of Truman Annex: a popular and beautifully landscaped community ...

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Property Type

Key West Condo

"Our Stay In Key West"
Reviewed January 11, 2019

This is a great one bedroom rental. Within walking distance to all the restaurants and bars. Tracy was quick to respond when I had any questions. The condo had beach passes, bikes, a cooler, beach towels, ...

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Matecumbe Jewel - 3 bedroom home with pool and dockage is a jewel of a home!

$158

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days"Matecumbe Jewel" is a jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. ...

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Property Type

Islamorada House

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Lovely, oceanfront 4 bedroom, 3 bath home

4 BR | 3 BA | Sleeps 10 | Quick View

2

Distance to beach: 4 miles to Sombrero

$536

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool

About this property

Lovely, oceanfront 4 bedroom, 3 bath home. The main house is three bedroom, two bath with the kitchen, living and dining area. The master bedroom has a king size bed, the first guest bedroom has a queen and the 3rd bedroom has two sets of bunk beds with full size on the bottom and twins on the top. Then ...

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Property Type

Marathon House

"Wonderful property"
Reviewed February 26, 2019

We spent a week at this property with our extended family. It is a beautiful home with a great amount of outdoor space. There are so many options, from fishing on the dock to swimming in the heated pool, ...

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Private beach estate. Gated, tropical peace and quiet. Dock

$464

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is ...

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Property Type

Sugarloaf Key House

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Palm Harbor - Fabulous Home with Privacy Gate, Pool, Dock and Outdoor Enter

$333

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Palm Harbor" is a spacious elegant home with pool and dock. Gently swaying palm trees greet you at the gated entrance to this wonderful home. The ground level entry features a billiard/game room, bedroom and full bath. An open curved staircase leads to the 2nd ...

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Property Type

Plantation Key House

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Palms #301 - Darling condo with panoramic views of the Atlantic Ocean.

$77

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

About this property

Minimum Rental: 28 Days"The Palms #301" is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure ...

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Property Type

Islamorada Condo

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Cockadoodledo

4 BR | 4 BA | Sleeps 10 | Quick View

$300

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Cock-a-doodle-do Vacation Rental, named for Key West's beloved chicken population, is a mid-town oasis! 5 minute drive to Old Town or take Uber for just $ 10!A meticulously updated pool home with beautifully lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, ...

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Property Type

Key West House

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Oceanfront Luxury "Mar Azul"

3 BR | 2.5 BA | Sleeps 6 | Quick View

2

$400

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

A relaxing executives delight -High-end Estate overlooking tranquil 'Bonefish Flats' in picturesque Marathon. Designer decorated with contemporary colors, loads of fine architectural details, Crema Marfil marble, Granite, Hardwood floors, open air porches and balconies. This is a superb, secluded estate, ...

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Property Type

Marathon Estate

"Nature Paradise. 30 mins to Reef by boat, private mangrove walkway from pool to dock, great team running the place."
Reviewed June 24, 2018

This is both a unique and well-run property. Lisa is very accessible and responsive. I left something very valuable here, and before I even realized it Lisa had told me it was found and wanted to know where ...

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Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$82

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen ...

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Property Type

Islamorada Condo

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Plantation Adventure - Sensational remodeled home awaits your arrival.

$217

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Plantation Adventure" is a sensational remodeled single family home on Plantation Key awaits your arrival. The gorgeous POOL, HOT TUB, and TIKI BAR are ready and waiting. Imagine fun filled days and evenings relaxing in the patio and yard area! The patio is spacious ...

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Property Type

Plantation Key House

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KLYC#20 - 3 BR Townhouse Oceanside with 30' Dock and Boat Lift

$127

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Minimum Rental: 1 MONTH This is a gorgeous 3 bedroom townhouse in a private upscale ocean front condominium community! Everything you could want is located within the community - heated pool; hot tub; covered seating area; tennis court; children's playground; basketball court; boat ramp; boat slip ...

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Property Type

Key Largo House

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Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling ...

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Property Type

Islamorada House

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

3 BR | 2 BA | Sleeps 6 | Quick View

4
Owner special: Last minute cancellation, April 4th to April 13th. Special pricing !

Distance to beach: 0.5 miles to White Marlin Beach

$457

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three bedrooms, two bath, private home totally renovated and remodeled, new furniture ...

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Property Type

Islamorada House

"Beautiful Home on the channel to the Gulf"
Reviewed January 27, 2019

My friends and I (total 6 adults) rented this beautiful home for a birthday celebration. The home is absolutely beautiful and in close proximity too many features within the Keys. The house has water craft ...

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Best Marathon House

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Completely remodeled 3 bedrooms, 2 bath house in Marathon - the middle of the Florida Keys, on Mile Marker 51, only one hour to Key West. OUR WEEKS ARE SATURDAY - SATURDAY. Beautiful place in a quiet neighborhood. Direct access to the ocean, with 37 feet of dockage. House set up for fishing and relaxing. ...

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Property Type

Marathon House

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Beacon Reef #222 - Gorgeous condo with panoramic views of the Atlantic Ocean.

$147

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. ...

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Property Type

Islamorada Condo

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Blue Water Retreat - Location!!!! Gorgeous house with Pool and Ocean Views.

$183

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from ...

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Property Type

Islamorada House

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Palms #407 - Beautiful condo with panoramic views of the Atlantic Ocean.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. ...

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Property Type

Islamorada Condo

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A Touch of Bermuda at Truman Annex

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private townhome (one of only seven available for ...

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Property Type

Key West Cottage

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Waterfront / Pool / Two Tiki Huts!

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 5 miles to Bahia Honda State Park

$167

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Sorry NO SMOKING or PETS!Minimum 28 days / Please check availabilityGround level 4 bedroom, 2 bath waterfront home on a double lot with a saltwater pool with hot and cold shower, large pool deck and two Tiki Huts. 180 ft of waterfront and 90 feet of dock space with a double fish cleaning table. ...

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Property Type

Big Pine Key House

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Waterfront Property - Key Colony Beach

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.2 miles to Cabana Beach Club

$196

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

This is a large stilted duplex located in a tropical paradise. The water view property is located on the island City of Key Colony Beach in the Middle Keys (near Marathon). This is a canal-front unit with a 37.5 step down concrete dock with quick easy access to ocean. Dock comes with ladder access and ...

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Property Type

Key Colony Beach House

"What a way to start off the New Year!"
Reviewed January 29, 2019

Key Colony Beach is indeed "the gem of the Florida Keys." It offers shops, restaurants, beach and pool access, golf, tennis, and really friendly people. I enjoyed a phenomenal jazz concert and a hilarious ...

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Key Colony Vacation Rental by Owner

$114

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Tads Place has everything you need for your Keys Vacation. 30ft of boat dockage,ample parking for your boat trailer and vehicles.Full kitchen all towels and linens provided.Great out door sitting area and grill. Walk in freezer. Washer and Dryer and Cabana Club membership for pool.

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Property Type

Key Colony Beach Condo

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Dos Casas - 2 Houses 2 blocks from Duval in beautiful Old Town -- Monthly Rental

$193

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 10 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenitites and ideal location the perfect spot to enjoy all that Key West has to offer.Why ...

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Property Type

Key West House

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Barry Beach - Waterfront Cozy House with Dock & Heated Pool!

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 9 miles to Bahia Honda State Park & Beach

$490

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to paradise! Come experience the amazing Keys and beautiful open water home with 200 foot long dock for your boat. Exclusive heated pool to relax and enjoy the surrounding ocean view - just breath taking! The private lot is .81 acre with one other rental and still very spacious. Stunning panoramic ...

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Property Type

Little Torch Key House

"Barry Beach"
Reviewed November 1, 2018

Enjoyed every minute....great layout and even better for the watercraft...thank you.

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Islamorada Paradise Vacation Home on the Water

$229

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Great house! Great location!House On Canal… 40 foot concrete dock with fish cleaning stand, water, electricity and dock ladder. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. ...

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Property Type

Islamorada House

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Florida Vacation Home, Great View Over Cudjoe Bay. Private heated POOL

$364

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Vacation home sits close to the water and has a view over Cudjoe Bay to the Atlantic. Has a private heated pool, 4 bedrooms and 2 bathrooms. Large deck with water access for a boat. Vacation home sits far off of the main road for a great quiet vacation. We have 3 Florida Keys vacation homes on this property. ...

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Property Type

Cudjoe Key House

"A Perfect Vacation"
Reviewed January 22, 2019

Our stay was perfect! The scenery was beautiful, and the house was very well cleaned and decorated. The manager Steve was very friendly and helpful as well! I would highly recommend this rental to anyone ...

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Direct Oceanfront Views at Sea Gulls

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Harry Harris Park

$229

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

Sea Gulls 511 is one of the nicest condos in the Islamorada area. It has been completely rebuilt following Hurricane Irma so everything about it is new, upscale, and extremely clean.The living area is open plan with a large island, full kitchen, and most importantly, a fabulous direct ocean view ...

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Property Type

Tavernier Condo

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**BEST VALUE IN KEY WEST**OCEAN FRONT! Ocean view every room. 90ft Balcony

$221

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Military Vouchers Welcome! In Key West - Not Islands Away * ** Ocean Front**Ocean View From Every Room *90' Scenic Balcony Huge 2200 Sq Ft under air. ***SPECIAL REDUCED RATES FOR ANNUAL, OR OTHER LONG TERM RENTALS ***OCEANFRONT… There is nothing like it. To me, it means being directly on ...

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Property Type

Key West Apartment

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TORCHVIEW SECLUDED PARADISE /FAMILY & PET FRIENDLY

3 BR | 2 BA | Sleeps 6 | Quick View

6
Owner special: SPECIAL $300 DISCOUNT FOR EACH WEEK MAY 4-25, 2019 ---SEASON RATE $2500 WEEK "NOW $2200 WEEK"

Distance to beach: 8 miles to BAHIA HONDA

$328

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

Big Torch Key is reminiscent of the Keys 40 years ago, seclusion and peace invade your senses immediately, sunset views will take your breathe away. Located on 1.4 acres on Niles Channel, in National Key Deer Refuge, the best boating access to the Atlantic (2 miles) and the Gulf (6 miles) in the lower ...

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Property Type

Big Torch Key House

"Absolutely relaxing"
Reviewed March 12, 2019

My son and I spent a wonderful week at torchview. It was very relaxing had everything we needed. The house was very clean and has a well equipped kitchen. We we're able to bring our puppy with us which ...

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5 Bedroom 4 Bath Canal Front Home Sleeps 12. (28 day min. rental)

$233

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Large home located on a double lot with plenty of parking and 200 feet of seawall. Quiet neighborhood with convenient access to grocery stores and other services. Large master bedroom upstairs with big screen TV. Large living room with big screen TV and shuffle board table. Large porch balcony for watching ...

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Property Type

Big Pine Key House

"Excellent House with Space for Big Family"
Reviewed February 19, 2019

This house is so great and continues to be perfect for our big family at Christmas time! We have had 10 adults staying in the house at one time with kiddos too and it never feels cramped. The pool is perfect ...

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Luxury Home with Dock, Waterfall Pool, HotTub, Wi-Fi deep water dock up to 60 ft

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Venetian Shores 4-Bed/4-Bath Luxury Pool Home with 100' Dock & Opt. ElevatorMINIMUM STAY: 29 DAYS Dreaming of a Florida Keys vacation where you can boat, fish, dive, snorkel, or stay home and swim in your own private heated pool? This is it. This home offers a professionally-designed living environment ...

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Property Type

Islamorada House

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Southern Diversion Islamorada

5 BR | 3.5 BA | Sleeps 17 | Quick View

$857

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat ...

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Property Type

Islamorada Estate

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Gulfview Getaway - Bayfront Home with Private Beach

$400

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on ...

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Property Type

Islamorada House

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Southard Street - Queen Conch

4 BR | 4 BA | Sleeps 8 | Quick View

$750

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.Downstairs there is a large, open floor plan with living ...

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Property Type

Key West House

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Sunrise on Sunset

3 BR | 3 BA | Sleeps 12 | Quick View

$300

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

**AMAZING SPECIAL! 25% OFF RENT MARCH THROUGH AUGUST 2019!** MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level ...

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Property Type

Islamorada House

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Lobster Lounge II

5 BR | 4 BA | Sleeps 12 | Quick View

1

Distance to beach: 4 miles to Sombrero

$457

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Stunning waterfront single family, ground level with brand new private pool. Fish cleaning table, bait freezer, 75' of dockage, 60' wide canal. Completely remodeled inside and out July of 2018. All new and custom, inside and out. All new tile floors, kitchen w/stainless appliances, quartz counter tops ...

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Property Type

Marathon House

"BEAUTIFUL PROPERTY AND LOCATION"
Reviewed March 18, 2019

I would highly recommend this property to anybody who wants to have a great fishing experience and be able to relax in a gorgeous home when they return

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NEW Listing, 4Bed/3bath, Tiki Hut, Canal,Cabana Club After Hurricane Photos

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 0.9 miles to Cabana Club

$207

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

ENJOY OUR HOME with 5 STAR REVIEWS & New TIKI HUT, Open Water Access 5 minutes NEW WHITE kitchen with QUARTZ COUNTERTOPS, NEW STAINLESS STEEL APPLIANCES (photos coming soon),Perfect home for a Family Gathering, or Extended Family Get Together, or Families traveling together. Boater's perfect ...

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Property Type

Key Colony Beach House

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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$120

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Rentals by Owner

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...

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Property Type

Islamorada Apartment

"Incredible views and water."
Reviewed February 18, 2019

Lower Matecumbe Key is beautiful and secluded. You need to be a boater with a boat or enjoy water sports, or just like the quiet. This unit is small, regular bed. There are plenty of items on the property ...

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