Florida Keys Vacation Rentals

(486 rentals)
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Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Distance to beach: 0.5 miles to White Marlin Beach

$727

avg/night

$727
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Bring your boat and Jet Skis Nestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...

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Property Type

Islamorada House

Featured review

"Fabulous location, off the beaten path, clean, owner available for questions and very responsive."

We stayed in this home for a month, the location is amazing if you love to paddle board, kayak and discover the many mangrove islands that are a five minute paddle from your dock. The outside area has ...

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Key West Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 0.2 miles to Public Beach is Smathers

$429

avg/night

$429
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s not just a place on the map, it’s a frame of mind, an Attitude…… come and let us share that Key West Attitude with you! Fully Renovated This is a Luxury ...

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Property Type

Key West Condo

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 100 feet to Front door

$226

avg/night

$226
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

MINIMUM STAY: 30 days Spacious and beautiful 2 bedroom/2 bath ocean front condo unit with unobstructed ocean views. BOAT SLIP is available upon request for up to a 46 foot boat, low tide draw is 30 inches. There is an additional fee for boat slip. Walk out your front door and go boating. You’ll ...

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Property Type

Islamorada Condo

Featured review

"Ocean Harbor M3 is Fabulous!"

Priceless view of the ocean. Nice marina. Workout room is great with a view. The condo is clean and spacious. Every thing you need is here. Very easy to maintain. During my 3 month stay from May to August ...

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Cudjoe Key House
4 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 2 bathrooms
4 reviews

$419

avg/night

$419
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado's These boats are set up with everything you need to fish the Keys, ...

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Property Type

Cudjoe Key House

Featured review

"SPECTACULAR SOUTHERN SUNSET - 5 STARS"

No need for all the little details - this place is just SPECTACULAR! Our stay was absolutely INCREDIBLE! If you're looking for the PERFECT spot for ALL the Florida Keys activities, then this one is a ...

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Key Colony Beach House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Cabana Beach Club

$232

avg/night

$232
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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

Featured review

"Paradise"

The place is beautiful, spotless on arrival, and I made sure it was spotless when I left. The entire time I was at your property an old late 80's song by David Lee Roth kept running through my mind -"This ...

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Marathon House
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom

Distance to beach: 3 miles to Sombrero Beach

$281

avg/night

$281
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Waterfront Hideaway! Experience tranquil serenity in the heart of Marathon, Florida with this stunning canalfront half duplex. Imagine waking up each morning to the soothing sound of palm trees in the wind, while you bask in the warmth of the Florida sun on your very own screened-in porch ...

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Property Type

Marathon House

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Marathon House | On the beach
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms
2 reviews

$1388

avg/night

$1,388
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Great for Family Reuions, and Large Groups vacationing in the Florida Keys! Fabulous 6500 sq ft. vacation paradise. Includes everything you need for a perfect Family Reunion or large destination vacation. Private Vacation Rental Waterfront Home with 6 Bedroom 5 Baths Private Pool and Spa ~Tiki Hut, ...

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Property Type

Marathon House

Featured review

"Amazing place and hosts"

This place was beautiful and well taken care of. It had anything and everything you could possibly need while on vacation. The hosts Captain Bob and Liz were also very helpful and kind. Thanks for sharing ...

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Key West Yacht
5 BR | 5.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 5.5 bathrooms
3 reviews

$1286

avg/night

$1,286
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

VACATION RENTALS Florida offers amazing opportunities on the water aboard private yacht, Lady Grace, which is available for winter vacation rentals in Key West. Lady Grace provides a relaxing retreat and the thrill of living on your own private 92-foot yacht with plenty of space for enjoying time ...

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Property Type

Key West Yacht

Featured review

"Amazing Week Cruising"

“My family and I just spent an amazing week cruising around the Gulf Of Mexico visiting Key West and the Dry Tortugas onboard The Lady Grace. The accommodations were incredible with spacious staterooms ...

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Islamorada House
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
3 reviews

Distance to beach: 2 miles to Founders Park

$635

avg/night

$635
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios ...

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Property Type

Islamorada House

Featured review

"You found it"

If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...

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Key West House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

$532

avg/night

$532
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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

Key West House

Featured review

"WonderfUll"

The heated pool, tiki bar and view of the ocean was just beautiful as "out of a storybook. The eggs and a home made lime pie from Carol (owner) was a nice surprise. The house was plenty big enough to house ...

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$135

avg/night

$135
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

Featured review

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

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Key West Townhome
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
19 reviews

$464

avg/night

$464
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

Once you see this historic two storey townhouse, you won’t want to stay anywhere else! Filled with natural light, this end unit is ‘tucked away’ in an exclusive, historic Foundry building next to the ‘Truman Little Whitehouse’. There are only 3 residences in our building! There ...

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Property Type

Key West Townhome

Featured review

"Beautiful home. Perfect location."

I almost don’t want to write this as I’d like to keep it for myself! This extra special house is truly one of a kind. It’s beautifully appointed with so much care given to the decor. It’s truly ...

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Islamorada Condo
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$555

avg/night

$555
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful views from this condo! Bay Harbour is a gated community located at MM 77.5 bayside in Islamorada, FL. We are new owners of this condo that has never been in the rental pool. (that is why few reviews) Complete remodel with no expense spared! The location is quiet with the most beautiful ...

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Property Type

Islamorada Condo

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Tavernier Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

$303

avg/night

$303
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to your remodeled 2 - bedroom, 2 - bathroom vacation rental that has everything you need! The Master bedroom features a comfortable king size bed with a private bathroom that has a walk-in shower. The second bedroom has 2 twin beds and a connecting bathroom. The kitchen boasts beautiful granite ...

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Property Type

Tavernier Condo

Featured review

"2 week vacay"

Our trip was wonderful! The condo was clean and nicely decorated. We had plenty of room and the view was priceless!

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Islamorada House | On the beach
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$2250

avg/night

$2,250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool

About this property

$15,000-$17,500 Weekly A world-class oceanfront residence, located in the heart of Islamorada in the Florida Keys. This luxurious residence features unsurpassed vistas of the Atlantic Ocean from the master bedroom, grand room, kitchen & oversized living terraces. Arrive by car ~ just a short 90-minute ...

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Property Type

Islamorada House

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Key West House | On the beach
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
1 review

$987

avg/night

$987
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. 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 ...

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Property Type

Key West House

Featured review

"Wonderful property wonderful hosts!"

I just got back from taking my family and a friend's family to Troy and Carol's property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away ...

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Beautiful oceanfront apartment with easy access to pool, spa, and beach. Dock with boat slips and tiki hut overlooking the Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Condo

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Marathon Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

$211

avg/night

$211
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner

About this property

2 bedrooms, 2 bathrooms ideal getaway in Coco Plum Beach, the Florida Keys Anchors Away is a completely remodeled condo in Coco Plum Terraces that includes updated kitchen with granite, beautiful coastal furnishing and décor. Enjoy views of the canal right from the 2nd floor private balcony. ...

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Property Type

Marathon Condo

Featured review

"Paradise!"

The condo is beautiful and updated with beautiful amenities. The location is excellent for the beach restaurants and all Florida Keys activities! The street is quiet and easy to locate. The condo owner ...

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$485

avg/night

$485
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Ocean Oasis Escape to this newly built, stunning 4-bedroom, 3-bathroom vacation home nestled in the heart of Marathon, FL. Perfectly situated in Coco Plum and boasting a private pool and dock, this retreat offers everything you need for an unforgettable getaway in the Florida Keys. ••• ...

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Property Type

Marathon House

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Marathon House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Our wonderful, Oceanside and waterfront home is just two minutes from the Atlantic Ocean and Vaca Cut. No bridges to the Atlantic and super easy to access the Gulf via Vaca Cut. This home is completely remodeled and features brand new furniture throughout. The 55 foot dock is brand new and awaits your ...

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Property Type

Marathon House

Featured review

"Great Vacation Rental"

We came in by boat and had a wonderful stay in this home. Rooms are large and plenty of space to move around. Sunrises are beautiful. Outside freezer for fish and bait was a great asset. Nice area to take ...

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Marathon Estate
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
14 reviews

$515

avg/night

$515
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Mar Azul is a High-end Oceanfront Residence overlooking the tranquil 'Bonefish Flats' of Marathon. Enjoy a Private, Secluded 3-Story Home with Spectacular Views of the Atlantic Ocean! Densely surrounded by Nature, the Property includes a Private In-Ground Pool Deck featuring an Outdoor Gazebo ...

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Property Type

Marathon Estate

Featured review

"A safe and beautiful haven for my family"

To begin with Lisa is the hot digging bomb The property is amazingly beautiful and immaculately kept They even have a butter dish My husband had a great 60yh Bday, Lisa even had a ballon waiting for ...

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Islamorada Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$209

avg/night

$209
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in one of Islamorada's most prestigious condo complexes. PROPERTY NAME: Beacon Reef #407 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2 DETAILS: ...

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Property Type

Islamorada Condo

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Islamorada House
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
7 reviews

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community ...

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Property Type

Islamorada House

Featured review

"BEST TROPICAL VACATION EVER!!!!!!!!"

Here is the review I am trying to post via for our March 2024 stay. Wonderful! Fantastic! Amazing! Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we ...

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Marathon Villa
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
7 reviews

$624

avg/night

$624
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Reel Life 2 has everything! 4 bedroom 3 bathrooms, canal front, private dock (boat up to 35'), large private pool, Tiki Hut with flat screen TV, large grill, 2 bikes, 2 paddle boards, 1 kayak and a natural landscape view across the canal! Plus, Sombrero Beach is just down the street (1.3 miles). ...

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Property Type

Marathon Villa

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Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 2 miles to Smarthers Beach and Higgs Beach

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Rate reduced for December 2024. This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding ...

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Property Type

Key West House

Featured review

"Great getaway"

This house has everything we need. The best part is the private backyard with lovely gardens and a pool and an outdoor shower. Inside is also wonderful with 3 bedrooms, a big kitchen, a dedicated office, ...

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Summerland Key House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Distance to beach: 6 miles to Baja Honda

$167

avg/night

$167
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Conchcanary is located on Little Torch Key, in the heart of the Florida Keys. Come relax in our hammocks with a tropical beverage or bring your boat for some fantastic fishing. Enjoy your morning coffee with a canal views from the screened balcony. Newly updated kitchen with top of the line appliances, ...

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Property Type

Summerland Key House

Featured review

"Honeymoon in the Keys"

My wife and I spent the first 7 days of our married life living it up in the Keys. We loved it. Kayaking in the bay. Trips to the beach (very different from other beaches). Snorkeling in the ocean! Live ...

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Big Pine Key House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

$125

avg/night

$125
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Welcome to the beautiful Canal-facing newly rebuilt rambler home. Located at Big Pine key that is easily accessible to Key West, Marathon, Bahia Honda State Park, 7 mile Bridge, and many other hidden treasures of the keys. This is a contemporary styled home with amazing views of the Canal from the Master ...

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Property Type

Big Pine Key House

Featured review

"Enjoy Big Pine Key and don't break the bank"

We were very pleased with the house, its location and the price. The kitchen/living room area is open and comfortable. The kitchen is spacious and well equipped. The 2 bedrooms and bathrooms were comfortable ...

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Marathon House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
10 reviews

Distance to beach: 900 yards to Sombrero Beach

$1275

avg/night

$1,275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

"BELLA VISTA" - a Spectacular Oceanfront home in Marathon, Fla. with an Invisible-edge heated salt water pool that overlooks the Atlantic Ocean. Open Water Unobstructed VIEWS. VERY PRIVATE. Newly renovated! This 4 bedroom/3.5 bath home can comfortably sleep 8 people. Three bedrooms have King ...

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Property Type

Marathon House

Featured review

"Exquisite!"

Property is amazing! It was perfectly clean and comfortable. We loved everything about it. The views were unbelievable and the location was great. The hostess was very helpful in advance and we had a lovely. ...

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Key Colony Beach Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 50 feet to Sea Isle private beach

$265

avg/night

$265
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

VIDEO: copy this link, then choose "paste and go" on the address/url line of your browser: /watch?v=rSpVAf6yAq4 Or go to YouTube and search "Sea Isle #8" Triple your vacation memories with unforgettable sunrises, sun drenched ocean views and magical sunsets. Recently renovated ...

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Property Type

Key Colony Beach Condo

Featured review

"Perfect!"

We enjoyed every minute of our vacation here! The entire condominium and the unit was very well maintained. Ed was fantastic and very helpful. The location was perfect! We met a lot of great people staying ...

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Key Largo Condo
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
5 reviews

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Look no further than this perfect place in the Keys for your next vacation! Our cozy condominium provides an ideal location to enjoy the best of the Florida Keys and has some of the best views in all of Key Largo! Located on the 5th floor, you are the top floor of the building with no one above to ...

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Property Type

Key Largo Condo

Featured review

"A Little Slice of Heaven"

We can’t say enough about staying at Moon Bay 507. Great location , attentive hosts, clean and comfy condo, great view, wonderful pool and waterfront. We’ve been there twice and hope to return soon.

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Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
16 reviews

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

''BEAUTIFUL BAYFRONT PROPERTY!!!!''** 2022 Remolded bathrooms, 2021 NEW POOL** Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 8. There is a 1/1 guest suite attached which does have its own separate and private access with full kitchen and bath. Entire house ...

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Property Type

Islamorada House

Featured review

"The BEST of the BEST in every way!"

By far and away, this was the best rental property we have ever stayed! We have been visiting Islamorada for nearly 20 years and have stayed almost everywhere you can imagine, and we have now struck gold ...

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Key Largo House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 40 feet to Across the street

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

FAMILY FRIENDLY GORGEOUS HOME WITH DIRECT WATER VIEW OF LARGO SOUND! WATCH THE SUN RISE FROM THE COMFORT OF YOUR LIVING ROOM! 3 BEDROOMS 2 BATHROOMS BEACH AND BOAT LAUNCH INCLUDED IN RATE! THIS IS THE OPPORTUNITY OF A LIFETIME! KING SIZE BED IN MASTER BEDROOM, Queen bed in 2ND BEDROOM AND TWIN ...

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Property Type

Key Largo House

Featured review

"The perfect getaway spot"

This place is amazing, beautiful beach right out the front door is why we come here. The host is the best, Nancy catered to all our needs. The home is nicely decorated, it had everything we needed. We will ...

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$210

avg/night

$210
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in one of Islamorada's most prestigious condo complexes. PROPERTY NAME: Beacon Reef #414 83201 Old Highway, Islamorada, Florida LOCATION: Ocean side Condo MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 83.2 DETAILS: ...

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Property Type

Islamorada Condo

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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
7 reviews

$851

avg/night

$851
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

‘The Beach House’ at Tarpon Point in Islamorada- DIRECT RENTAL WITH NO ADDITIONAL FEES ‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State ...

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Property Type

Islamorada House

Featured review

"Very peaceful and beautiful accommodations"

Impressive location. View from master bedroom is fantastic. House was clean, comfortable, well furnished and great layout. Area is easy to navigate and lots of great restaurants close bye. Green Turtle ...

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Key Largo Villa
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$555

avg/night

$555
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique ...

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Property Type

Key Largo Villa

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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

$468

avg/night

$468
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside ...

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Property Type

Key West House

Featured review

"A hidden gem in Key West!"

We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage ...

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
3 reviews

Distance to beach: 0.5 miles to Sombrero Beach

$334

avg/night

$334
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

4 Bedrooms, 3 Full bathroom home with a gorgeous pool, covered porch, luxurious granite kitchen, covered parking, private dock (with water & electricity). A new tiki bar in 2023 located in front of pool area- great for the whole family! Located a 1/2 mile from Sombrero beach, located less than 1/2 ...

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Property Type

Marathon House

Featured review

"Clean, comfortable, spacious!"

Great location--close to gorgeous Sombrero Beach. A bit too far to walk, but within comfortable biking distance (fee for parking at beach now). New bikes provided but would prefer 5-speed and will rent ...

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Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Looking to ​ Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

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Property Type

Key West House

Featured review

"Great location!"

We loved this house at the end of a quiet lane. Huge pool! The location was perfect, walking was easy to so many places. Fully fenced and a small backyard made it perfect for our dog. And the shower ...

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Ramrod Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
5 reviews

$267

avg/night

$267
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open from Aug.6th to April 1st. This is a spacious oceanfront home with breathtaking open water views! It is located on beautiful Ramrod Key 85 ft concrete seawall facing the priceless Atlantic ocean teaming ...

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Property Type

Ramrod Key House

Featured review

"Paradise in the Keys!"

Beautiful home with absolutely gorgeous view. All the amenities made for a wonderful stay. Fred & Marilyn were the best to work with. Love this home.

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Key Largo House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

Distance to beach: 6 miles to John Pennekamp State Park

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront

About this property

1 BR/1 Bath Rare Find! Lovely oceanfront home with large private boat basin. This ground-level house has two enclosed sleeping areas - a master bedroom with a king bed, and a private alcove providing sleeping space for up to 4, with 2 bunks and a full-sized bed (separated from the living room by an ...

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Property Type

Key Largo House

Featured review

"Mahalo ocean view"

We loved every minute of our vacation. The sunsets were magnificent. Fun meter is high with a unique blend of restaurants and tiki bars. So convenient having a boat slip. We will be back!

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Marathon House | On the beach
6 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5 bathrooms
4 reviews

Distance to beach: 0.1 miles to Sombrero Beach

$1381

avg/night

$1,381
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Waterfront 6 Bedrooms , 5 Baths, canal views. On the HIGHLY sought after Sombrero Beach !!! (We rent weekly only, and our Check-in is on a Saturday and Check-out is on a Saturday dates only so we can optimize our months.) Our houses are safe and clean because we disinfect them with the highest ...

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Property Type

Marathon House

Featured review

"The house was perfect for our fishing trip."

The house was very clean, and location could not be better. The house was more amazing than the pictures showed. The outside tiki hut, (2) barbeque grills and pool made a perfect end to a day of fishing. ...

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Marathon House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$953

avg/night

$953
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

"This house was very clean and well very well put together. So much to do just at the house alone. Eric was very responsive..." - Bailey Set your compass for Captain's Quarters, your tropical paradise nestled in Marathon. Minutes from the shores of Sombrero Beach, this 4BR/3BA home casts ...

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Property Type

Marathon House

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Marathon House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
18 reviews

$442

avg/night

$442
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

We would love for you to come visit our renovated ground level Florida Keys home! We decided to call our home "TIGHT LINES", because my wife loves to fish. Our conch home consists of 3 bedrooms with king size beds with ensuite bathrooms. A half bath for guests. We have a 60 foot dock with ...

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Property Type

Marathon House

Featured review

"Wonderful experience!"

Everything was just as we had hoped for. Lynn and Freida always make you feel right at home-- only better! Thank you again for your hospitality and the sharing of your beautiful home!

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Key West Townhome
1 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 1 bedroom, 1.5 bathrooms
8 reviews

$262

avg/night

$262
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price is generally half of what you would pay for a daily-rate comparable unit, and it gives you a lot more options and freedom. Located on a side street off Duval and ...

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Property Type

Key West Townhome

Featured review

"Beautiful Stay!"

This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...

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Islamorada House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
14 reviews

$821

avg/night

$821
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumbe so you are mere blocks from several restaurants and breweries that you will love! The home is just 3 years old and WELL apportioned with everything you'd need on vacation and ...

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Property Type

Islamorada House

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Key Colony Beach House
3 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 4 bathrooms

Distance to beach: 1 miles to Coco Plum

$495

avg/night

$495
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Enjoy this 3 bedroom, 4 bathroom treasure in the heart of the Florida Keys. Upon arriving for your stay you will be greeted to a large family room on the first level of this 2 level home that opens to a private pool and poolside kitchen. On this floor you will find a bedroom with a king sized bed and ...

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Property Type

Key Colony Beach House

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Marathon House | On the beach
14 BR | 10 BA | Sleeps 30 | Quick View
Sleeps 30, 14 bedrooms, 10 bathrooms

Distance to beach: 100 yards to Sombrero Beach

$2488

avg/night

$2,488
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home ...

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Property Type

Marathon House

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Key West House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews

$825

avg/night

$825
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny ...

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Property Type

Key West House

Featured review

"Beautifully Appointed Historic Home in Old Town"

I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to ...

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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
3 reviews

$1714

avg/night

$1,714
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Located on the Highly sought after Sombrero Beach area of Marathon, which is the beginning of the lower keys just 50 min from Key West is our Florida Keys Tropical Paradise . Less than a third of a mile to the Sombrero Beach and the Sombrero Beach Park, With a deep water concrete dock with ocean access ...

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Property Type

Marathon House

Featured review

"Great house and location"

Highly recommend this home. My family of 5 just spent the week there and had a fabulous time. It had everything we needed. It was close to some amazing restaurants. Publix was around the corner. The beach ...

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Key Largo Townhome
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

If you want to experience the true meaning of a Key Largo Island vacation, then look no further than our spacious townhouse on the ocean side of the world famous Key Largo, Florida. ... The Dive Capital of the World! This Villa is located inside Kawama Yacht Club, a beautiful Hawaiian Island style resort ...

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Property Type

Key Largo Townhome

Featured review

"Great place"

Nice condo in Key Largo. Owner very responsive. Beds comfortable. Would rent again, for sure. Close to a lot of restaurants & stores.

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