Florida Keys Vacation Rentals

(486 rentals)
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Islamorada House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 0.3 miles to Anne's Beach

$144

avg/night

$144
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner

About this property

Enjoy this modern lagoon front ground-level one-bedroom apartment in a single-family home with exclusive use of backyard, pool, dock, and carport. Located on the Gulf side of Lower Matecumbe (Islamorada MM 73.5), minutes from the Channel 2 and Channel 5 Bridges, offering immediate access to the Oceanside. ...

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Property Type

Islamorada House

Featured review

"Overall excellent .... very comfortable for two with great outdoor ammenities."

this property was great for us as an older couple....park under cover steps from the front door..beautiful pool and canal front and a quiet location. the home is clean and easy to care for and the owner ...

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Tavernier House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$286

avg/night

$286
avg per night
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Key Amenities

  • Air conditioning
  • Private pool

About this property

Swim. Sleep. Repeat., at Manatee Manor. This 3-bedroom, 2.5-bath home on Plantation Key has something for everyone. Enjoy a drink by the tiki bar, rack ‘em up at the billiard table, or soak up some vitamin D next to the pool. With an entrance just off the carport, the downstairs offers a comfortable ...

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Property Type

Tavernier House

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

Distance to beach: 1 miles to Sombrero Beach

$200

avg/night

$200
avg per night
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Key Amenities

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

About this property

Welcome to your tropical escape! Immerse yourself in the beauty and convenience of Marathon Key in our stunning 2 bedroom 2 bath condo at the intimate 20 unit Coral Club Condominiums. Remodeled kitchen contains all amenities including the convenience of in unit washer and dryer. Spend the day at nearby ...

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Property Type

Marathon Condo

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

$5536

avg/night

$5,536
avg per night
View Details

Key Amenities

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

About this property

Welcome to Caribee Beach House!Discover the enchanting charm of Caribee Beach House, where the timeless allure of old-school Islamorada beautifully melds with stylish comforts. Tucked away in the heart of downtown Islamorada, this hidden gem offers an extraordinary retreat with 200 feet of private ...

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Property Type

Islamorada House

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

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Gorgeous views over Largo Sound in Key Largo Florida. You will be very comfortable in the 2 bedroom 1 bath home with brand new bathroom and updated kitchen. The kitchen has all you need to prepare meals and prepare your favorite frozen drinks, all appliances are brand new. Nautical decor gets in the beachy ...

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Property Type

Key Largo House

Featured review

"Visit to Paradise"

We loved the house! It had everything we needed! It is close to all activities & right across the road from the sound! The outdoor deck was a great place for kicking back for happy hour! We'll be back!!

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Lower Matecumbe Key House
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
6 reviews

Distance to beach: 0.5 miles to Anne Beach

$225

avg/night

$225
avg per night
View Details

Key Amenities

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

About this property

Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ of canal frontage located on an extra wide canal ...

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Property Type

Lower Matecumbe Key House

Featured review

"ANOTHER GREAT EXPERIENCE !!!"

This is my fourth year visiting Islamorada. Something that I look forward to each year. And every year I book this Cottage , I won't stay anywhere else!! It's always clean. If there is anything you need ...

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Islamorada Townhome
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

Distance to beach: 0.5 miles to Port Antigua Private Beach

$440

avg/night

$440
avg per night
View Details

Key Amenities

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

About this property

This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...

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Property Type

Islamorada Townhome

Featured review

"A Spectacular Spot"

We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...

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Key Largo Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

$295

avg/night

$295
avg per night
View Details

Key Amenities

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

About this property

Enjoy the panoramic view this tropically decorated, fifth-story unit has to offer of the Atlantic Ocean and the adjacent Wildlife Sanctuary. The unit affords its guests the spectacular sunsets the Florida Keys are famous for, right from your balcony and living room.Kawama Yacht Club is situated at ...

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Property Type

Key Largo Condo

Featured review

"Kawama tower condo"

My husband and i had a wonderfyl trip to Key Largo! The Kawana condo was perfect for us, it had everything we needed! Great location, pool was fabulous, sunsets at the jetty or right on the balcony were ...

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Marathon Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
2 reviews

$250

avg/night

$250
avg per night
View Details

Key Amenities

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

About this property

Newly Remodeled 1 Bedroom 1 Bathroom unit, Marina, Pool, Paddle Boats, Kayaks, Tennis Courts, Bicycles. Fun and Sun. Great amenities, close to everything. Boat slips available on first come basis with fee.Outdoor bar b q grills, great Sunsets from the Dock. Fish from the Dock.

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Property Type

Marathon Condo

Featured review

"Cozy, Comfortable Marina Condo"

Neat, clean and very comfortable condo for the two of us. The pool, gazebo, sheltered deck and marina provided a variety of areas to lounge, swim and read during the wonderful 80 degree weather. Plenty ...

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

Distance to beach: 5 miles to Coco Plum Beach

$374

avg/night

$374
avg per night
View Details

Key Amenities

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

About this property

Searenity was just recently renovated and is a brand new ground level vacation rental! A direct shot to the Gulf in about two minutes and nestled in a nice quiet neighborhood on Dolphin Drive in Marathon, this home is in a great central location, not far from Publix Supermarket, all the restaurants and ...

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Property Type

Marathon House

Featured review

"Home away from Home"

I can’t stay enough. This place felt like home. Definitely coming back! Beds were so comfy, pool was definitely a plus after a day on the water - Neighbors were respectful-location is right on & owners ...

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

$391

avg/night

$391
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • 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

Featured review

"Great Home Away From Home!"

Perfect location! Our family had a great week and we will definitely come back. Condo is well furnished, clean and plenty of space. Kitchen is well stocked with essentials. Pool was very refreshing. The ...

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Islamorada House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

$1483

avg/night

$1,483
avg per night
View Details

Key Amenities

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

About this property

Magnificent brand new home nestled between Cheeca Lodge Resort and Caribbean Resort with its own private beach offering a unique and luxurious experience for those looking for a private getaway. This 4 bedroom/4.5 bath home services from small to a larger family of 8 . Has it own private salt water pool, ...

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Property Type

Islamorada House

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Tavernier House
6 BR | 4 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 4 bathrooms

$550

avg/night

$550
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to Morada Breeze! This 6-bedroom, 4-bath bayside slice of paradise is ready to make your next vacation an enjoyable one. Located on Plantation Key in Islamorada, Morada Breeze has the amenities to elevate your trip to the Keys.Step inside to discover an expansive kitchen perfect for preparing ...

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Property Type

Tavernier House

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Key West Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

Distance to beach: 2 miles to Smathers Beach

$228

avg/night

$228
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Come stay in a premier development in Key West. If you're looking for a monthly stay of 28 days or more then this is the place. You would be close to everything Key West has to offer stay at our peaceful serenity of your temporary home in Paradise. Our house offers many amenities to make your stay ...

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Property Type

Key West Townhome

Featured review

"Three months in Paradise"

The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific ...

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Big Pine Key House
5 BR | 5 BA | Sleeps 13 | Quick View
Sleeps 13, 5 bedrooms, 5 bathrooms
3 reviews

$390

avg/night

$390
avg per night
View Details

Key Amenities

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

About this property

Welcome to our home, “Reel’em Inn” Big Pine Key, an excellent location for a relaxing vacation with family and friends 31 miles from Key West’s Mile Marker 0. This spacious 5 bedroom home is located on a double lot with plenty of parking and 150 feet of seawall. There is a step ...

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Property Type

Big Pine Key House

Featured review

"Great place to stay, especially for fisherman"

Lots of rooms and places to spread out large families. Great facilities, particularly well suited to fisherman. The owner is very helpful and flexible.

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Key Colony Beach Condo | On the beach
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms
3 reviews

$314

avg/night

$314
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

We are a 50 unit Oceanfront Condominium located on our own private beach, with a heated pool in our center courtyard, protected from the North wind. We have a huge tiki hut on our private beach and plenty of lounge chairs and palm trees for shade. We also have a huge deck on our beach for great sunsets, ...

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Property Type

Key Colony Beach Condo

Featured review

"Absolutely Perfect!"

Cay Condominiums had everything we could possibly want. The beach was beautiful with a great view and plenty of chairs. The pool and the grounds were extremely well cared for. We are already planning a ...

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Key West Townhome
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms
2 reviews

$200

avg/night

$200
avg per night
View Details

Key Amenities

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

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports ...

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Property Type

Key West Townhome

Featured review

"our vacation at Key West Golf Club"

We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf ...

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

$267

avg/night

$267
avg per night
View Details

Key Amenities

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

About this property

Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying ...

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Property Type

Key West Townhome

Featured review

"Old Town Getaway"

Excellent property; highly recommended. Holly is an amazing host: very responsive and accommodating. She provided detailed check in/out instructions, descriptions of the property amenities, and a tour guide ...

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

$206

avg/night

$206
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to Blue Haven! This immaculate 3 bedroom / 2.5 bathroom home provides the perfect home base for your next Florida Keys vacation! Tucked away from the main highway you will experience peace and quiet while still being in the heart of Islamorada. Sitting on a large corner lot, this home is surrounded ...

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Property Type

Islamorada House

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Little Torch Key House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
8 reviews

Distance to beach: 10 miles to Bahia Honda

$380

avg/night

$380
avg per night
View Details

Key Amenities

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

About this property

Paradise awaits in the Lower Keys! Situated on a large corner lot, you have over 200 feet of concrete dockage so BIG BOATS are welcome! Featured on " American Dream Home," this vacation home will not disapoint. Whether you're looking to fish the Atlantic or Gulf, snorkel at Looe Key Reef, ...

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Property Type

Little Torch Key House

Featured review

"WOW! WOW! WOW!"

This place was perfect! Serenity abounds. Hanging out by the pool or eating in the beautiful sun porch - it was true relaxation with views of water and palm trees. With the set up of a separate guest ...

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

Distance to beach: 4 miles to Anne's Beach

$313

avg/night

$313
avg per night
View Details

Key Amenities

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

About this property

Enjoy the sunrise from the balcony or from in the condo through 50 ft of glass sliding doors. You can also see the sunset from our walkway on bayside. We have a full kitchen from dishwasher to microwave, washer/dryer, even beach towels. We have wifi, cable TV, and a Master Bath with whirlpool tub, ...

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Property Type

Islamorada Condo

Featured review

"EXCELLENT CONDO"

We had a fabulous time at this condo. Spectacular views, great fishing. Close to EVERYTHING. The condo was spacious and VERY CLEAN. EVERYTHING you would need for a fun time was here.. will be back again ...

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Key West House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
3 reviews

Distance to beach: 0.5 miles to Higg's Beach

$459

avg/night

$459
avg per night
View Details

Key Amenities

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

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district ...

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Property Type

Key West House

Featured review

"Stunning Private Villa in Key West - Fabulous Location!"

We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more. ...

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Key Largo Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$345

avg/night

$345
avg per night
View Details

Key Amenities

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

About this property

Experience the relaxed lifestyle of the Florida Keys. CLEANED AND SANITIZED TO THE NEW CDC STANDARDS. 3 Bedrooms + Loft, 2 Baths, Sleeps up to 8 comfortably. There are 2 large bedrooms on the 3rd floor, each with queen size beds. The first floor bedroom is small with 2 bunk beds. The 4th floor loft ...

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Property Type

Key Largo Condo

Featured review

"Bit chaotic but overall very nice"

Property is very nice, we liked it lots. Resort is laid back & has lots of activities. I haven't done a resort holiday before so it was pleasant surprise to have free access to equipment like kayaks, ...

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Key Largo Villa | On the beach
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
4 reviews

$537

avg/night

$537
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool
  • WiFi

About this property

3 bedroom, 3 bathroom Ocean Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2020. It has dockage for boats up to 45 feet. This Villa is 20 feet from the Ocean and has a private beach 50 feet from the patio. We provide a golf cart, Kayaks, fishing equipment, tennis equipment, pool ...

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Property Type

Key Largo Villa

Featured review

"Perfect view and great place"

We loved our stay here. The views are incredible, the beds comfy and the golf cart made it so easy to haul kids toys and towels to the pool and lagoon every day. We enjoyed 9 nights and wished we had 9 ...

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

$580

avg/night

$580
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Welcome to “At The Sandbar!”This newly built oceanside villa in Islamorada is a wonderful choice for those seeking a serene retreat and an opportunity to immerse themselves in the relaxed nature of the Florida Keys. Situated within the Peaceful Palms community on Windley Key, this three-bedroom, ...

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Property Type

Islamorada Villa

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Key Largo Villa | On the beach
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
6 reviews

Distance to beach: 0.0 miles to 4 small beaches on site

$555

avg/night

$555
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool
  • WiFi

About this property

3 bedroom, 3 bathroom Ocean Front / Beach Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2020. It has dockage for boats up to 38 feet. This Villa is 35 feet from the Ocean and has a private beach 5 feet from the patio. I provide a Golf Cart, Kayaks, PaddleBoards, Fishing equipment, ...

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Property Type

Key Largo Villa

Featured review

"Beautiful views"

We loved our stay and will be coming back. So enjoyed fishing off the jetty.such beautiful views from the place .

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Islamorada Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

$210

avg/night

$210
avg per night
View Details

Key Amenities

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

About this property

This condo is located in a tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yacht Club. FYC is a private 70-unit, gated community with a 53-slip marina and accommodations available for that tranquil tropical getaway you've always imagined. This condo offers ...

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Property Type

Islamorada Condo

Featured review

"Location"

We have been searching for a unit in this area and found this. Islamorada has many restaurants, from fast food to white tablecloths, from waterfront dining to sports bars.

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Islamorada House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$285

avg/night

$285
avg per night
View Details

Key Amenities

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

About this property

4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family-friendly and a fisherman's dream. Our home sleeps 8 with every comfort you would want while on vacation in the keys...Large ...

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Property Type

Islamorada House

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Marathon House
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
4 reviews

$666

avg/night

$666
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Villa overlooks Boot Key Harbor with its beautiful sunsets to the West and refreshing breezes from the East that travel down Sisters Creek, a natural waterway that leads to great diving and fishing grounds of the Atlantic. Across Sisters Creek there is a natural preserve and no neighbors. It is private, ...

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Property Type

Marathon House

Featured review

"Great place to stay!"

We really enjoyed the house, very well appointed! 5 kayaks for you to use anytime , and believe me we used them and had a blast! Debra the owner is a dream even had a Bottlle of Champaign and a cake waiting ...

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

Distance to beach: 100 feet to 4 on site

$310

avg/night

$310
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex.WE FOLLOW THE CDC GUIDELINES FOR CLEANING AND SANITIZING THIS PROPERTY.Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling ...

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Property Type

Key Largo Townhome

Featured review

"Tremendous Resort / Hotel"

What a great place you WONT be disappointed…Staff, entire operation was just perfect. Great food Great beach. Great restaurants right adjacent as well. It’s a 10

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

Distance to beach: 17 miles to Bahia Honda

$360

avg/night

$360
avg per night
View Details

Key Amenities

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

About this property

Looking for a vacation rental to get away from it all in the Fabulous Florida Keys? Look no further than our beautifully renovated home with open water and sunset views! This home has three bedrooms and two full bathrooms, open floor plan with designer kitchen and views from every room! You can enjoy ...

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Property Type

Cudjoe Key House

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

$267

avg/night

$267
avg per night
View Details

Key Amenities

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

About this property

Come enjoy this newly listed property on Beautiful Ramord Key house with a southern view of Newfound Harbor and the Atlantic !! House has a 60 ft+ dock for your water toys. Enjoy lobster season, fishing (back water and deep sea great snorkeling and dining all minutes away. Ramrod is easy boating ...

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Property Type

Ramrod Key House

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Key West Apartment
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$363

avg/night

$363
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Just a few houses off Duval, this wonderful retreat occupies the ground level of an almost 100-year-old home in one of the most desired locations in Old Town Key West. A large covered front porch welcomes you to sit and watch the Key West world go by, imagining what life was like in the early days of ...

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Property Type

Key West Apartment

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Islamorada Townhome | On the beach
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms
2 reviews

$348

avg/night

$348
avg per night
View Details

Key Amenities

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

About this property

Lazy Daze Beach House is a piece of paradise literally on the Beach! Gorgeous and all new! One King plus set of Full/Twin bunk beds, spacious gourmet kitchen with glass atrium dining. Completely renovated, designer finished, all new gorgeous home, no expense spared! Private oceanfront townhouse located ...

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Property Type

Islamorada Townhome

Featured review

"Lazy Daz Beac House"

Excellent couple to work with. Great communication. The rental was beautiful and clean. We had a problem with the rental and they communicated with us and together we solved the problem. They went over ...

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Key Largo Estate
6 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 6 bedrooms, 6 bathrooms

Distance to beach: 6 miles to Pennekamp

$833

avg/night

$833
avg per night
View Details

Key Amenities

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

About this property

Recently renovated large 6 bedroom, 7 bathroom Ocean Front House on 5 Acres. Gated from the main road. It can comfortably sleep up to 16 people. Covered parking for up to 6 vehicles and outside parking for several more. This estate is surrounded on 3 sides by park lands and the Atlantic ocean. If ...

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Property Type

Key Largo Estate

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

$341

avg/night

$341
avg per night
View Details

Key Amenities

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

About this property

Beautiful , home on deep water canal in desirable Breezeswept Estates is your private resort for a minimum of 28 days . Heated, saltwater pool adjoins huge ground level great-room with living area, dining area, shower , gas grill, pingpong table and so much more contained in private setting ! 40 ft dock ...

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Property Type

Ramrod Key House

Featured review

"Desiderata"

Very nice pool & dock area. Neighbors very friendly. Downstairs area very nice for socializing near pool area. House was comfy for family with adults & children. A great location for restaurants ...

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Key Largo Apartment | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 100 feet to On Site

$343

avg/night

$343
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This recently remodeled and upgraded, this 2 bedroom, 2 bathroom, Ocean Front Condo has spectacular Ocean, Marina, Beach & Park views from the Living Room, Dining Room, Kitchen, Master Bedroom, Balcony and even the master bathroom.THIS CONDO IS CLEANED & SANITIZED TO THE NEW CDC STANDARDS.Included ...

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Property Type

Key Largo Apartment

Featured review

"Schöne sanierte Wohnung in einem ruhigen Viertel in Key Largo ..."

... in einer separaten Anlage, Fahrräder und Kajaks sind mit dabei, genug Parkplätze, Restaurants in der Nähe, unkomplizierter Check-in, ...

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

$879

avg/night

$879
avg per night
View Details

Key Amenities

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

About this property

5 Star Modern New Construction Bayfront Home With Private Dock and PoolIsland Dreamz Bay House is a piece of paradise on the Vaca Cut waterway in Marathon. Gorgeous and brand new 5 bedroom, designer decorated, 4 bath single-family home with 36 ft. of assigned dockage. Private pool can be heated upon ...

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Property Type

Marathon House

Featured review

"Island Dreamz a stunning home, lovely view and perfect location in the Keys!"

This was our second stay at Vaca Cut at The Tides. We loved this gorgeous home with its exquisite design and comfort. The house was immaculate ~ kudos to the pros who keep this home clean and well stocked ...

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
owner special
Owner special: We're renting December at a reduced price!

Distance to beach: 100 yards to Port Antigua Private Beach

$351

avg/night

$351
avg per night
Owner special:
We're renting December at a reduced price!

View Details

Key Amenities

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

About this property

Book Your Winter Getaway! This spectacular 3/Bed 2/Bath canal front home is located in Lower Matecumbe Key, a part of Islamorada island. Enjoy the exclusive neighborhood of Port Antigua—just a 5 minute walk to our private beach.The house is nautically designed, with a spacious and open floor ...

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Property Type

Islamorada House

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Key Largo Mobile home
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

$140

avg/night

$140
avg per night
View Details

Key Amenities

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

About this property

***SERIOUS INQUIRIES ONLY**** This house can only be rented for a minimum of 28 days, as per city of Key Largo rules.This cozy and spacious home located in the heart of Key Largo has available water access in the backyard. Located centrally in the Cross Kay Waterways neighborhood near shops, restaurants, ...

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Property Type

Key Largo Mobile Home

Featured review

"Very nice stay"

Beautiful home, giant kitchen open to living room and deck beyond that. We really enjoyed our stay for February '24. Spacious, close to 2 major grocery stores plus Pennekamp park. Grettel was very responsive ...

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Key Colony Beach Condo | On the beach
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms
4 reviews

Distance to beach: 0.0 miles to Walk downstairs!

$641

avg/night

$641
avg per night
View Details

Key Amenities

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

About this property

Located at the southernmost point on Key Colony Beach, Suite 16 is virtually surrounded by the beautiful turquoise waters of the Atlantic Ocean. This spectacular Key Colony Point condo offers panoramic views of Florida Keys ocean waters and sunshine from almost every room. Floor to ceiling windows in ...

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Property Type

Key Colony Beach Condo

Featured review

"Lovely condo, except for the carpeting."

Elizabeth and Michelle are wonderful and helpful. Don in maintenance was really nice. Our condo was great, except for the carpeting, which was not installed well and was difficult to walk on. Other than ...

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

Distance to beach: 100 feet to 4 on site

$310

avg/night

$310
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This is a 2 story, 2 bedroom, 2 bathroom townhouse that comfortably sleeps 6 in a 24 acre Resort / Condo complex.WE FOLLOW THE CDC GUIDELINES FOR CLEANING AND SANITIZING THIS PROPERTY.Included in the price are Taxes, Cleaning, WiFi, a Golf Cart, Kayaks, Paddle Boards, Bikes, Fishing Gear, Snorkeling ...

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Property Type

Key Largo Townhome

Featured review

"Good times"

Our stay at Kawana was perfect. Norman our host/owner was very attentive to our stay and was very responsive If we had any questions. The resort itself was well kept with fun things to do for 10 your old ...

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Big Pine Key House
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms
3 reviews

$250

avg/night

$250
avg per night
View Details

Key Amenities

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

About this property

Introducing "Turtle Cove" - Your Serene Florida Keys Retreat with Water Access and Pool!Escape to a world of tranquility and indulgence at "Turtle Cove," where the allure of the Florida Keys' vibrant tropical paradise meets the luxurious charm of a newly renovated vacation ...

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Property Type

Big Pine Key House

Featured review

"Great Family Visit"

Had a great trip with the family. House was very clean and well stocked. Canal access was perfect for daily trips out exploring the water! Hoping we can make the time to go back next year.

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Ramrod Key House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
1 review

$379

avg/night

$379
avg per night
View Details

Key Amenities

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

About this property

Mermaid House was just recently renovated and is a brand new second level vacation rental! This home is in a great central location, not far from Winn-Dixie, Bahia Honda State Park and Key West!Decorated with a warm coastal feel, this home has an open floor plan with large glass windows! The home ...

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Property Type

Ramrod Key House

Featured review

"Just book it!"

I cannot say enough good things about our month-long stay at Mermaid House, so I'll keep it simple, just book it!!! The outside living area was our most favorable spot. (There is one caveat... be VERY ...

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Islamorada House
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
4 reviews
last minute deal
LAST MINUTE DEAL 11/13 - 12/25: January Special!! Please contact for special monthly rate!

$450

avg/night

$450
avg per night
Offer for: Nov 13 - Dec 25:
January Special!! Please contact for special monthly rate!

View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Newly renovated 3/2 Canal front home with brand new pool, deck and front gates for privacy!The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, ...

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Property Type

Islamorada House

Featured review

"We love this house!"

2022 was our 2nd time renting this wonderful home. The location is fantastic, and the house and property offer everything you can imagine. Outside is a paradise with a refreshing pool (with fun lights ...

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DEAL
Key Largo Townhome
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
8 reviews

Distance to beach: 100 feet to 4 on site

$345

avg/night

$345
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

This 3 story, 3 bedroom + den, 3 bathroom, 4 balcony waterfront (Salt water Lagoon with tropical fish that you may hand feed) townhouse in Key Largo can comfortably sleep 8 people.This property is cleaned and sanitized to the current CDC standards.Included at no extra charge are free WiFi internet, ...

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Property Type

Key Largo Townhome

Featured review

"Fantastic"

Norman is a really great guy. The property was spotless and modern and had every conceivable amenity including a large inventory of sporting equipment. The price, for what we got, was bottom dollar and ...

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

$778

avg/night

$778
avg per night
View Details

Key Amenities

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

About this property

Come have your first sunset drinks compliments on us at Island Fish Company. $100 Gift Certificate to Island Fish Company Included. No Expense Spared! New Construction Bayfront Home With Private Dock and Pool.5 O'Clock Somewhere Bay House is a piece of paradise on the Vaca Cut waterway in Marathon. ...

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Property Type

Marathon House

Featured review

"Fabulous vacation rental for our family celebration with all the amenities and comforts of home plus a fabulous view!"

This vacation getaway home had everything we needed plus Lauri was an extremely responsive host. The location was excellent. We could walk to the Aquarium that was across the canal or drive ten minutes ...

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Key Largo Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 0.0 miles to On Site

$331

avg/night

$331
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

This 2 bedroom, 2 bathroom, Ocean Front Condo has spectacular Ocean, Marina, Beach & Park views from the Living Room, Dining Room, Kitchen, Master Bedroom, Balcony and even the master bathroom.THIS CONDO IS CLEANED & SANITIZED TO THE NEW CDC STANDARDS.Included at no extra charge are free ...

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Property Type

Key Largo Condo

Featured review

"Wonderful location"

Great place to stay. Easy drive to attractions on the other Florida Keys and not too far from the Miami airport. The lagoon is a good place to practice snorkeling. We saw many different species of fish ...

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Islamorada Cottage
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1 bathroom

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the "Keys Life Cottage!"This beautifully updated and spacious two bedroom, one bath home is tucked away on a large landscaped lot in the heart of Islamorada and within walking or biking distance to Islamorada's famed Arts and Cultural district and to some of the most renowned ...

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Property Type

Islamorada Cottage

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Marathon House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 1 miles to Sombrero Beach

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

This beautifully updated, canal front home offers a dock for up to a 40' boat! This home also offers 3 Bedrooms, 2 Full Bathrooms, 1(2 person) Kayak, 1 Paddleboard, 3 Bikes, 6 Beach Chairs, Grill, Fish Cutting Table, outdoor freezer, Covered Porch, Lower-Level Lounge Area and all of this is less ...

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Property Type

Marathon House

Featured review

"Perfect Location"

Great Home!! Perfect location, close to everything. We took our boat and it took about half hour to get out of the canals to ocean. The beds were super comfortable. Everything was nice and CLEAN! Plenty ...

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