Florida Keys Vacation Rentals

(360 rentals)
Kens Conch Key Cottage - Optional motor boat rental - Pay direct to owner site

2 BR | 2 BA | Sleeps 5 | Quick View

1

Distance to beach: 4 miles to Long Key or Curry Hammock

$286

avg/night

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Key Amenities

  • Air Conditioning

About this property

*****Booking on Pay Direct to Owner sites save you the most money!*******Kens Conch Key Cottage is a small romantic cottage in a quaint Old Florida Keys style Lobster fishing village, on a tropical island named Conch Key. We are located about 10 miles from Marathon and close to various state parks ...

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Property Type

Marathon Cottage

"Relaxation vacation"
Reviewed January 27, 2019

Our first visit to the keys was stress free with this cottage rental. From first inquiry to end of vacation, Ken made this so easy. The cottage had everything we needed. After a day of exploring it was ...

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Privacy On Sombrero Beach With Heated Pool, Deep Water Dock, Ocean View

$633

avg/night

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Key Amenities

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

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

"Great house and location"
Reviewed September 22, 2020

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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LITTLE BAY - Lower Duplex - Ground Level Unit on Gated Bayfront Shared Property

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

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Key Amenities

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

About this property

Minimum Rental: 7 Days Little 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 Apartment

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Casa del Sol Resort

4 BR | 5.5 BA | Sleeps 12 | Quick View

3

$500

avg/night

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Key Amenities

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

About this property

The best the Keys has to offer is right here at Casa Del Sol... This stunning house has 4 bedrooms, all with incredible views of the bay from your bed. It also has 5 1/2 bathrooms with unlimited hot water to all but one bathroom. The house also is gated out by the road for privacy and has a brand new ...

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Property Type

Tavernier House

"summer"
Reviewed July 23, 2019

Every year we stay at this home it is the most beautiful home we have stayed in since the past 14 years we have been going great location great owner. great areas to fish and lobster by the house close ...

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4Bed/3bath, Tiki Hut, Canal,Cabana Club &INCH BEACH

4 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to beach: 0.9 miles to Cabana Club

$267

avg/night

View Details

Key Amenities

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

About this property

ENJOY OUR HOME with 5 STAR REVIEWS & TIKI HUT, Open Water Access 5 minutes NEW WHITE kitchen with QUARTZ COUNTERTOPS, NEW STAINLESS STEEL APPLIANCES (photos coming soon),TOTALLY REDONE AFTER HURRICANE IRMAPerfect home for a Family Gathering, or Extended Family Get Together, or Families ...

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Property Type

Key Colony Beach House

"Great and comfortable stay!"
Reviewed December 30, 2019

The home was well equipped and comfortable! Homeowner very easy to work with and eager to help in any way possible to make stay perfect!

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Modern Tropical Home in Lower Sugarloaf Key

$268

avg/night

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Key Amenities

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

About this property

Enjoy the quiet beauty of life in the Keys from this waterfront gem located in upscale South Point, Sugarloaf Key on an extra-wide swimming canal. At Mile marker 16.5, this beautiful home offers indoor/outdoor living in an updated and beautifully furnished setting. The extra-large pool with spacious pool ...

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Property Type

Sugarloaf Key House

"Spacious relaxing home!"
Reviewed August 16, 2020

It was very spacious! It had a very well stocked kitchen.The pool very nice with a large downstairs shaded area! The yard had space for the traveler & cars! It was a quiet neighborhood and neighbors were ...

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MA923 101st St Ocean Street Marathon, FL 33050

6 BR | 6 BA | Sleeps 14 | Quick View

1

Distance to beach: 5 miles to Sombrero

$714

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

The Pelican's Nest………New six bedroom, six bath completely remodeled in 2018. This is truly PARADISE. There is 150' of concrete step down dockage, with instant ocean access. The house is one lot in from the ocean, views are outstanding, while affording protected dockage. Fish right ...

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Property Type

Marathon House

"Nice!"
Reviewed December 24, 2020

Wonderful location for a fishing excursion, only 5 minute drive to the marina and twenty minute cruise to the fishing grounds!

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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$214

avg/night

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Key Amenities

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

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...

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Property Type

Islamorada Condo

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Villa Abre el Aqua. Modern Pool Home with STUNNING Open Water Views!

$640

avg/night

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Key Amenities

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

About this property

Please note that construction is taking place on the empty lot next door. Not all views are blocked but some are. We are working on getting updated pictures. Please reach out with questions!Upscale Modern 4 Bedroom 3 Bath Ocean Front Home, Private Pool, Summer Kitchen! Gorgeous upscale decor with ...

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Property Type

Marathon House

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MA945 334 Calzada de Bougainville Marathon, FL 33050

$543

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

The view over the lagoon will take your breath away. Lovely Sombrero Beach neighborhood, just a short walk to the beach (less than 1/2 mile). Very quiet residential area. Large lot with ample of parking for all your needs. Deep water 40' dock also has a kayak and jet ski dock. Fish cleaning table, fish ...

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Property Type

Marathon House

"Great property and location"
Reviewed July 17, 2020

We loved everything about this place. The home, the view, and the location. Sombrero beach is right around the corner and Publix is right off Sombrero Rd. We would definitely visit this location again.

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Sombrero Heaven. Sombrero Heaven - Private Pool and Dock, Canal Front, Beach!

$425

avg/night

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Key Amenities

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

About this property

"SOMBRERO HEAVEN" ~ Updated Villa with neighborhood Ocean Front beach and Second Story Screened Balcony that Over Looks Private Heated Pool and Canal! Everything you need for the perfect keys vacation ~ private dock, fish cleaning station, bikes, beach towels, beach chairs, beach umbrella, beach ...

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Property Type

Marathon Villa

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Snowscape - Clean and Tropical 3/2 Home - you will love to stay in!

$128

avg/night

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Key Amenities

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

About this property

Clean, Tropical 3/2 on open canal in quiet residential neighborhood on a cul-de-sac. House is on Gulfside with quick access to Miles Channel Bridge towards ocean or bayside. 50’ concrete dock with fish cleaning station and shower.Master Bedroom has a queen size bed, shower and indoor jacuzzi ...

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Property Type

Ramrod Key House

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Ocean Harbour Condo with breath taking views!

$208

avg/night

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Key Amenities

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

About this property

Wake up to the sun rising over the ocean and relax by the pool, in the spa or on the sandy beach in a safe gated community. This nicely appointed 2 bed (one king, two twins, also has sofa bed), 2 bath condo is fully furnished with everything you need to enjoy your stay in the Keys. Amenities include a ...

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Property Type

Islamorada Condo

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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

3

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$269

avg/night

View Details

Key Amenities

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

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

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Property Type

Key West Condo

"Paradise"
Reviewed September 29, 2020

We loved the location of this rental. Everything inside the rental was as should be. I could not complain about anything but only say that i cant wait to return. We were a couple of blocks away from everywhere ...

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PALMS 301 - 2 Bedroom Condo with Lovely Ocean Views from Balcony

$125

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • 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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Breezy Palms

4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 3 miles to Sombrero

$450

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This spectacular home has everything you will need to enjoy paradise! Situated in a very quiet and desirable neighborhood close to the beach and shopping. This home is a private oasis with mature landscaping on both sides, the golf course on the street side and only mangrove fringe across the canal. private ...

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Property Type

Marathon House

"Great house!"
Reviewed December 4, 2020

Everything from the location to the layout of bedrooms was perfect! The house is walking distance to a cute little coffee shop, fishing bait, snorkeling, gas station, shops, etc. We fished off the dock ...

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Coastal Key. Flexible Cancellation on Future Bookings! Private Pool - Dock

$371

avg/night

View Details

Key Amenities

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

About this property

Beautifully decorated brand new home, located down the street from oceanfront Sombrero Beach, has a private pool, private dock, fish cleaning station, bait freezer, outdoor TV in covered patio, gas grill, 4 bikes, 2 kayaks, 1 paddle board! With 3 bedrooms, 2 bathrooms, a pull out couch, a pack n play ...

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Property Type

Marathon House

"Best Vacation Ever."
Reviewed November 6, 2020

We decided last minute to cancel our Disney trip & head to the keys. With thousands of options i was overwhelmed to say the least. After weeks of researching reading reviews really digging deep i came across ...

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Waterfront Keys Home - Spectacular View, 37' Dock

2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 2 miles to Sombrero Beach

Key Amenities

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

About this property

Gorgeous crystal clear, open water views of the Gulf of Mexico, incredible sunsets. Deep Water Dockage for your boat, snorkel, fish or dive right from the dock.This is not your typical canal home that are rented throughout Marathon. This one has open water, privacy and an un-obstructed view. This ...

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Property Type

Marathon House

"Lobster season"
Reviewed August 11, 2020

This is the second time I have rented from Joe, absolutely fabulous experience, the house was great the view was spectacular the home was clean and well kept and well-equipped look forward to staying in ...

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Key Colony Vacation Rental by Owner

$171

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid 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

"Great place to stay"
Reviewed January 6, 2021

Susan and Tad keep the place in great shape, a great experience. An the location is perfect, wide canal, safe neighborhood, pleasant people.

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Brand New Luxury Waterfront Pool Home - 6 Beds, 6.5 Baths

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Brand new construction built in 2019. Be one of the first to stay in this luxury home.6 Bedrooms 6.5 BathroomsWelcome to paradise! Escape to this luxurious six bedroom home designed for VIP guests. Across the street from open water, with beautiful views! Each bedroom includes an en suite bathroom. ...

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Property Type

Marathon House

"Great"
Reviewed December 3, 2020

Enjoyed the stay Was a great house Had a great time The weather was great It was all of what we were told it was

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Chillax. "Chillax" Private Pool and Dock, Canal Front, Beach!

$425

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Rent one side or both of this gorgeous, brand new, updated canal front Villa! Each side is a 4 bedroom, 3 bath home (pull out couches) with its own private pool, private dock and delegated parking (covered parking for 2 cars with additional parking for cars and/or boat trailer) and gated back yard with ...

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Property Type

Marathon Villa

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Waterfront Hideaway: Quiet Locals Experience with Dockage!. Waterfront Hideaway

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 3 miles to Sombrero Beach

$184

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Peace and Quiet in the heart of Marathon!This house is a 2 bedroom, 1 bathroom waterfront half duplex. There's a screened in porch, so you can relax in comfort on the water. The house has 24' of dock space that you can leave your boat parked at and room for a trailer in the driveway. There's a BBQ ...

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Property Type

Marathon House

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Waterfront Get Hooked

4 BR | 3 BA | Sleeps 10 | Quick View

4

$390

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

Waterfront Home in the heart of the Florida Keyes. Come relax and enjoy the beautiful waters of Sombrero and Bahia Honda Beaches. Both nearby. There is plenty of room and comfort in our 4 bedroom, 3 bath home. Two King Master Suites with attached baths. Satellite Flat Screen TV's in each bedroom. Fully ...

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Property Type

Marathon House

"Perfect Getaway"
Reviewed March 8, 2020

What a great place! Has everything you need to feel at home! We stayed the entire month of February 2020 and had an absolutely wonderful time. George is awesome and so responsive to any of the questions ...

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Waterfront/Open Gulf Access/Dock/Pool/Spa/Wraparound Deck

$314

avg/night

View Details

Key Amenities

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

About this property

With quick, easy access to the Gulf and Atlantic Ocean, this home is perfect for fishing, snorkeling and boating. This three-bedroom, two-bath home, which sleeps eight, has a 45-foot dock with ample room for your boat. It is only one house away from the mouth of a deep-water canal that leads directly ...

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Property Type

Marathon House

"Quiet and cozy"
Reviewed September 21, 2020

House had plenty of parking. Dock was great for our boat. Easy access on and off boat. The hot tub and pool is where we were if we were not on the boat. House was very clean. Will stay here again.

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Toes in the Water. Toes in the Water - Private Pool and Dock, Canal Front

$425

avg/night

View Details

Key Amenities

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

About this property

Rent one side or both of this gorgeous, brand new, updated canal front Villa! Each side is a 4 bedroom, 3 bath home (pull out couches) with its own private pool, private dock and delegated parking (covered parking for 2 cars with additional parking for cars and/or boat trailer) and gated back yard with ...

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Property Type

Marathon Villa

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Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$249

avg/night

View Details

Key Amenities

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

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $45 * King size bed * WiFi included * check-out cleaning included * 2 wall AC units * flat screen TV * Shared gas grill * porch with ...

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Property Type

Key West Condo

"Perfect Place to Stay"
Reviewed September 9, 2020

This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...

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Poolside Paradise @ , beach & Duval St.

$371

avg/night

View Details

Key Amenities

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

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

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Property Type

Key West Condo

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks Kayaks

3 BR | 2 BA | Sleeps 6 | Quick View

7

Distance to beach: 0.5 miles to White Marlin Beach

$523

avg/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

"Just what we were looking for"
Reviewed December 18, 2020

EXTREMELY COMFORTABLE, CLEAN, CHEERFUL AND LOVELY HOME. Beautiful layout with lots of windows allowing natural lighting in. Loved the furniture layout with plenty of seating. Beds very comfortable ...

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The Blue Turtle Villa. Direct Ocean & Gulf, Bayfront! Brand New! Private

$683

avg/night

View Details

Key Amenities

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

About this property

The Blue Turtle Villa on Vaca Cut at The Tides (unit #4) is a brand new 5 bedroom 4 bath home with a private pool, boat slip, all the toys for the perfect vacation ~ paddle boards, kayak, giant Jenga, ping pong and more! Perfectly situated on the water with stunning views, sunrise and sunset colors and ...

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Property Type

Marathon House

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The 6 bedroom Duval Street Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

2

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1616

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

"Best place we have ever stayed!"
Reviewed August 1, 2020

What an amazing 6 bedroom property in the heart of Old Town Key West. We did not move the car once, We would not rent one next time as you can walk to everything. It is all so close. The pools were simply ...

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

$354

avg/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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Ma984 93 Coral Lane Marathon, Fl 33050

$225

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pool

About this property

The Coral Escape is located on Coral Lane in the City of key Colony Beach. This hidden gem is a beautiful, GROUND level 1570 sq ft single family home. 3 bedroom’s, 3 bath’s with plenty of parking. Lots of room for your boat trailer as well. This is the ultimate fishing, diving, and relaxation ...

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Property Type

Key Colony Beach House

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Seaglass-20 feet from the Gulf

2 BR | 2.5 BA | Sleeps 6 | Quick View

2

$290

avg/night

View Details

Key Amenities

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

About this property

Seaglass-Paradise on the Gulf is located in the heart of the the beautiful Florida Keys. The Keys are a series of 40 islands connected by 40 bridges , off the southern most tip of Florida. The chain of islands extends 120 miles into the Atlantic Ocean and Gulf of Mexico. The area is famous for its Caribbean ...

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Property Type

Marathon Condo

"Xmas get away"
Reviewed January 4, 2020

THis condo is beautiful, so many pretty views, very clean an d easy access to restaurants. My husband and I visitied for the first time and we were not disappointed, Ed was so easy to work with. Loved Sea ...

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

Key Amenities

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

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

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Property Type

Islamorada Condo

"Wonderful location and hosts."
Reviewed January 10, 2019

This home was perfect for our family of five. Spacious bedrooms, living area and bathrooms. We also had use of the storage unit for our fishing gear and coolers. The pier is breathtaking. Our thoughtful ...

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Keys Spectacular Gulf of Mexico Views

3 BR | 3 BA | Sleeps 8 | Quick View

3

Distance to beach: 2 miles to Sombrero Beach

$318

avg/night

View Details

Key Amenities

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

About this property

Waterfront Keys home with wide open view of the Gulf of Mexico. 3 Bedroom 3 bath, half-duplex home with private pool, dock with great amenities - perfect for three couples or a family. Great location that's walk-able to the 7-Mile bridge and some of Marathon's best restaurants and bars. Incredible open ...

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Property Type

Marathon House

"Another great family vacation"
Reviewed August 19, 2019

Our family has been going to the Florida Keys since 1977 We have always stayed close to the Seven Mile Bridge This is our third time We have been staying here in Marathon at this Duplex it’s very roomy ...

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LUXURIOUS GULF FRONT VILLA~TIKI BAR-ELEVATOR-BOAT SLIP-30' ROOF TOP PARTY DECK!

3 BR | 3 BA | Sleeps 8 | Quick View

34

Distance to beach: 4 miles to Sombrero Beach

$390

avg/night

View Details

Key Amenities

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

About this property

What's better now then to create some Social distance while staring endlessly out to the Gulf of Mexico? Gorgeous views here in this small gated community. Escape the crowds and isolate yourself in an incredible Luxury Gulf front Villa for peace and relaxation. No crowds in this small, secluded, gated ...

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Property Type

Marathon Villa

"Whimsical, Relaxing, and Great Amenities"
Reviewed January 1, 2021

We had such an amazing time at the Yellow Tail Villa! We can't decide if our favorite part of staying here were the nights in the hot tub, making s'mores in the fire pit on the roof, grilling at our private ...

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Serenity at 1st Avenue Gulf Unit # 1

$571

avg/night

View Details

Key Amenities

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

About this property

Brand new 5 bedroom, 4 bath single family home with 30′ of assigned dockage, 11 X 22 private pool that goes from 3.5′ to 5′ in depth. 2293 square feet of living area. Stunning views, with balconies to capture the breezes and the views. Lots of parking for your vehicles and boat trailer. ...

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Property Type

Marathon House

"Family Christmas"
Reviewed December 28, 2020

Great property. 6 adults and Five kids. The pool and dock made this a great week. Had a couple of minor problems which were handed very quickly.

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Sanctuary in Paradise Featured on H G T V

$571

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront

About this property

Sanctuary in paradise. Unique property featuring: ~1BR 1BA main house ~2BR 2BA downstairs apt. ~1BR 1BA cottage ~3 Full KitchensWheather you are planning your very first visit to the Florida Keys or are a returning guest, we'd like to welcome you to our paradise. Islamorada, meaning purple isle, ...

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Property Type

Plantation Key House

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Ma1000 235 Sombrero Beach Road Marathon, Fl 33050

$434

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Newer and nicer than most. This lovely 4 bedroom, 3 bath will be a very comfortable spot for you to call home away from home. Pleasantly decorated with large covered porches, hi-speed wireless internet, 4 flat screen TVs, fish cleaning table and bait freezer. There are two complimentary kayaks (two-man) ...

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Property Type

Marathon House

"Plush enough for the workaholic"
Reviewed January 15, 2021

The house was very well decorated, it gave you a feeling of newness and class. Everything was taken care of down to the last detail of having spices in the cabinet. My family would recommend this place ...

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Paradise Cozy Home

3 BR | 2 BA | Sleeps 8 | Quick View

$266

avg/night

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Key Amenities

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

About this property

Elegant Florida Keys direct ocean access and some open water views from the dock and balcony. This property is single family elevated home. All rooms and bathrooms are upstairs. 40 foot dock with 4 cleats. Large driveway, parking for at least 6 cars, trailer and RV. 75' of waterfront with wood dock. ...

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Property Type

Marathon House

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Unique Layout! Truman Annex Shipyard Condo-1BR/1BA w/Loft

$270

avg/night

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Key Amenities

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

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

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Property Type

Key West Condo

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Beautiful 3BD 3BA Villa in the Exclusive Flamingo Island

3 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 3 miles to Sombrero Beach

$489

avg/night

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Key Amenities

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

About this property

Welcome to Villa Nena!Stay in a beautiful villa in the exclusive Flamingo Island in Marathon, FL, located on a lagoon close to the famous Sombrero Beach and many well-known local restaurants. With the home just 10 min from the ocean by boat, you can enjoy the Florida Key's world class fishing, snorkeling, ...

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Property Type

Marathon House

"Fabulous private retreat with amazing water and wildlife views"
Reviewed January 3, 2021

We booked Villa Nena for the week in between Christmas and New Years - it was a week in paradise. Not only was the house spotlessly clean, comfortable and spacious, the location is divine - every room ...

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Tropical Old Town Bungalow - Great Location to Beaches and Duval!

$286

avg/night

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Key Amenities

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

About this property

Great Location*Private Hot Tub*Close to Duval Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Key West Historic District, ...

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Property Type

Key West Bungalow

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January available Waterfront / Pool / Two Tiki Huts!

4 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Bahia Honda State Park

$185

avg/night

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Key Amenities

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

About this property

Big Pine Key favorite since 2013. Once you book an available month, it's yours for future bookings. No one can book that month until you advise you no longer want to return. No more searching, you never want to leave!Sorry (NO SMOKING) or (PETS)!Minimum 27 nights / 28 days / Please check availability!Ground ...

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Property Type

Big Pine Key House

"Just Perfect"
Reviewed March 31, 2019

This was a repeat visit for us. We love Big Pine Key and enjoy staying in a quiet neighborhood that's close to fishing, the grocery store and nature trails. The house is very comfortable and the outdoor ...

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Ma761

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to Coco Plum Beach

$214

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Fishing Paradise……Two bedroom, two bath home in a great boating location! Just one canal in from the Gulf and very close to Vaca Cut. Fish cleaning table, bait freezer, 75' of dockage, hi speed internet, washer/dryer.Cute home with a King size bed in the master, 1 Queen and 1 twin in ...

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Property Type

Marathon House

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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$181

avg/night

View Details

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

"Wonderful Winter Mini Vacation"
Reviewed January 1, 2021

The location was absolutely beautiful. Quiet and safe. The owner, Jerry, was very friendly and helpful with many restaurant recommendations. The small apartment was spotless, and amenities adequate for ...

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Tingler Retreat. 100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

$526

avg/night

View Details

Key Amenities

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

About this property

This newly renovated tastefully decorated 3 bedroom 3 bath home (pull out couch) has a peek a boo view of the ocean and is seconds to open water in your boat! It has an open floor plan and is ground level with plenty of natural light and a fully fenced yard! Available for guest use are 2 bikes, 3 kayaks ...

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Property Type

Marathon House

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Palm Breezes

5 BR | 3 BA | Sleeps 12 | Quick View

1

$620

avg/night

View Details

Key Amenities

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

About this property

This 5 bedroom 3 bath house with pool on Ocean front property on Highway 1. Located just 20 miles away from Key West. This lovely home has its own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill, Jacuzzi. Full WiFi. TVs in every ...

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Property Type

Cudjoe Key House

"Amazing find!!!"
Reviewed November 24, 2020

Amazing home in Cudjoe Key!! Only 20 minutes from Key West! Prime location, wonderful home with all the amenities. We had 9 of us and loved having the pool, jacuzzi and kayaks to use! Great restaurants ...

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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada ...

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Property Type

Islamorada House

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Paradise is Calling...We have monthly availability still left for 2021 & Beyond

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 2 miles to Smathers Beach

$204

avg/night

View Details

Key Amenities

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

About this property

Come stay in a premier development in Key West. This would be a great location to stay with a monthly 28 day rental minimum. Yearly rates available. You would be close to everything Key West has to offer and the peaceful serenity of your temporary home in Paradise. Our house offers many amenities to ...

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Property Type

Key West Townhome

"The best of the best!!"
Reviewed January 20, 2020

The owners are amazing to work with. The house is newly remodeled and furnished. It was just perfect for 4 people and we had a wonderful time! We were just a few minutes to great restaurants on Stock Island ...

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Florida Keys Vacation Rentals