Florida Keys Vacation Rentals

(450 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...

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Property Type

Islamorada Townhome

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2 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to beach: 7 miles to Sombrero

$205

avg/night

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Key Amenities

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

About this property

There is currently a 17-foot dock, and people have tied up 25 ft boats to our dock. In full disclosure, Hurricane Irma took out the remaining part of the dock, but we are working to fix that.Our indoor upgrades included getting a Tempur Pedic king-size adjustable bed for the master bedroom (raise ...

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Property Type

Marathon House

"Comfortable 2 bedroom"

we LOVED our time here; perfect spot to boat to the reefs and discover Marathon. Beds are comfortable.

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$417

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Three bedroom, two bath attractive concrete stilt home home with an additonal den for extra sleeping. Nice patio facing the canal with 50' of dockage with fish cleaning station and boat water.Very quick ocean access. Decorated throughout by an interior designer, the master bedroom has a king size bed, ...

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Property Type

Marathon House

"Honeymoon"

We rented this house for our Honeymoon, we weren’t disappointed! What an awesome house and experience! This house was perfect and fit all our needs, beautiful and clean. Has everything you need and especially ...

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2 BR | 2 BA | Sleeps 5 | Quick View

$303

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool

About this property

Direct oceanfront condo with stunning views of the Atlantic. Large heated pool, tennis, hi speed wifi. Stroll along the long span of beach or relax at the oceanfront pool. Or just sit on your private balcony and watch the world go by. Large open living area, master bedroom with King size bed, the guest ...

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Property Type

Marathon Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool

About this property

This beautiful 4 bedroom, 3 bath home is less than 2 minutes from Sombrero Beach just down the street (oceanfront) and less than 15 minutes to open water! Private pool with outdoor tv on the patio, private dock, 2 bikes, 2 kayaks, bait freezer, gas grill! The private dock can accommodate up to a 40' boat. ...

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Property Type

Marathon House

"Family reunion"

Excellent stay, everything in the house worked smoothly, nice big pool, kayaks at our disposal, Sombrero beach, groceries in just few minutes of drive. One ctisism: no garbage recycling option.

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3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 50 yards to Private sunning beaches at Anglers

$614

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Vacation Rental License 097. Welcome to Anglers Reef, a very special community of vacation homes with UNOBSTRUCTED OCEAN VIEWS FROM EVERY ROOM!We are new to this site so no reviews yet, BUT MANY AT OUR DIRECT SITE (SEE "LINKS" TAB ON THE LEFT) AND 12 YEARS of top reviews ON VRBO PROPERTY ...

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Property Type

Islamorada Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Beautiful Oceanfront Condo"

Plantation by the Sea is an older condo complex that is beautifully maintained. The condo is located at MM 87.5 just off of U.S. 1 in the heart of Islamorada. Restaurants of various types can be found within ...

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3 BR | 2 BA | Sleeps 8 | Quick View

$425

avg/night

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Key Amenities

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

About this property

Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

We would love for you to come visit our newly 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 ...

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Property Type

Marathon House

"2 weeks in Marathon"

Great house. Great hosts! Nothing left out. Lynn and Freida were great. Super attentive to any need. Already thinking about going back! 10/10!!!!

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4 BR | 4 BA | Sleeps 10 | Quick View

4.9 rating on other travel sites

$667

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

The Blue Turtle Villa, located in Key Colony Beach, in the Marathon area, is a gorgeous, brand new, designer decorated canal front duplex with a modern coastal feel! Each side is rented separately and has 4 bedrooms, 4 bathrooms, a private pool with a heater and a chiller, and all the amenities you would ...

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Property Type

Key Colony Beach Villa

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3 BR | 3 BA | Sleeps 8 | Quick View

55

Distance to beach: 4 miles to Sombrero Beach

$525

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

***Now renting Sunday to Sundays in 2022***WE LOVE THIS PLACE, EVERYONE DOES!!***Our weekly rates for the year are posted here on this site! Our calendar of available dates is also current too***Welcome to the luxurious “Yellowtail” Villa, where luxury meets the Gulf of Mexico! ...

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Property Type

Marathon Villa

"Awesome"

This was an awesome location. Great place in the middle of the keys to access all the things to do. And a wonderful place to hang out and relax too. It was everything it was advertised to be. Highly ...

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4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$700

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Bring your boat and Jet SkisNestled 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

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Key Amenities

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

About this property

2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, ...

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Property Type

Key West House

"Perfect place!"

This house is in the perfect location that is quiet and private. It’s literally in the center of old town and just a short walk to everything. It is very comfortable and has a great layout. The cabana ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

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

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Property Type

Key West House

"Beautiful Paradise"

The owners and property are one of a kind in the Florida Keys. I have stayed in many locations in the Florida Keys and this is one most unique places to stay. We stayed in their other house on the same ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

This is a Waterfront home with 2 Bedrooms and 2 full baths. We also have a 10,000 lb boat lift so you can bring your boat or rent a boat. We have a hot tub for your enjoyment and have 2 brand new kayaks for you to enjoy exploring the waterways. We have a tiki hut overlooking the most beautiful water ...

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Property Type

Little Torch Key House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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

"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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4 BR | 2 BA | Sleeps 8 | Quick View

4

Distance to beach: 3 miles to Bahia Honda Park

$200

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Modern 4 bedroom 2 bath stilt home centrally located in Big Pine. Heated salt water swimming pool. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars ...

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Property Type

Big Pine Key House

"Keys house"

We just completed our month long rental and what a wonderful home. We loved the layout of the home, pool and location. We look forward to renting next year if possible and appreciate how attentive Rich ...

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3 BR | 2 BA | Sleeps 6 | Quick View

9

Distance to beach: 0.5 miles to White Marlin Beach

$643

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6 Pure High End Luxury with all the Bells and Whistles Boat Friendly Vacation Rental with DockVilla 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. ...

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Property Type

Islamorada House

"Perfect, quiet, and secluded"

This was a spectacular vacation! The house was clean and comfortable, and the location was quiet and the setting perfect. I could write a novel about the host and the house, but in a few words the host ...

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3 BR | 3 BA | Sleeps 8 | Quick View

2

Distance to beach: 3 miles to Sombrero Beach

$697

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

UNDER NEW MANAGEMENTThis Spacious 3 Bedrooms and 3 Baths 1,600 sq ft Luxury Home overlooking a canal with a brand new dock that spans the width of the property complete with a fish cleaning station and private pool. The Open Concept Living and Kitchen Area Allow The Family to Gather Without Being ...

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Property Type

Marathon House

"An endlessly relaxing, luxurious vacation that made me feel like I never wanted to leave!"

Our stay at Yellowtail Cove is a testament to the ultimate luxurious vacation experience. No detail is left out in this lovely home centrally located to all Marathon attractions including beaches, restaurants/tiki ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"Awesome"

We had a wonderful time!! The house is beautifully decorated and we had everything needed in the kitchen to cook our Thanksgiving dinner. We used the kayaks and bikes provided almost everyday for trips ...

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$450

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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

"Waterfront Paradise"

This was a terrific location and home. The house and amenities were excellent. The backyard was the standout for our group with the pool, dock and Tiki area....this felt like a true resort get away. The ...

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3 BR | 2 BA | Sleeps 8 | Quick View

9

Distance to beach: 2 miles to Sombrero Beach

$435

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

For real time availability, instant quote and booking with confirmation visit our direct websiteOUTDOORS at LUNA BAY BREEZE We invite you to enjoy tropical tranquil breezes from the Atlantic Ocean side of Marathon and Boot Key Harbor sweeping through the grounds of this spacious DUPLEX property ...

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Property Type

Marathon House

"Could not have asked for a better stay!"

Our stay was amazing! From the gorgeous balconey views, to the convenient location, and the small touches like the welcome basket and coffee bar, we were floored with all aspects of our visit. I have rented ...

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1 BR | 2 BA | Sleeps 4 | Quick View

4.5 rating on other travel sites

$180

avg/night

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Key Amenities

  • Kitchen
  • Pool

About this property

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the back yard ...

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Property Type

Key West Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

9

Distance to beach: 3 miles to Sombrero Beach

$470

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Location matters!"

This was our 2nd vacation at Villa Nena, our family had a wonderful time once again at this amazing property! Boaters' paradise, with easy, breathtaking acces to the ocean and great, well equipped dock. ...

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4 BR | 3 BA | Sleeps 10 | Quick View

5.0 rating on other travel sites

$700

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Upscale Modern 4 Bedroom 3 Bath Ocean Front Home, Private Pool, Summer Kitchen! Gorgeous upscale decor with a modern coastal feel offers SPECTACULAR oceanfront views and the advantage of the canal for dockage! Direct open water access!This property is a Saturday to Saturday booking only.Three ...

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Property Type

Marathon House

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2 BR | 2 BA | Sleeps 6 | Quick View

9

Distance to beach: 2 miles to Sombrero Beach

$223

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

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

"Great views"

Spent much time sitting along the dock taking in the calm, restful atmosphere as the view was amazing. We even had a manatee come swim up to dock. Duplex was very spacious. Good communication with both ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Sailfish Villa, unit #6, is a brand new gorgeous, professionally decorated 5 bedroom 4 bath Villa with open water views on Vaca Cut! Enjoy sunrise and sunset colors and direct ocean and Gulf access! It has a private pool (can be heated for a fee of $ 125/7 days) and boat slip for a boat up to 35' including ...

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Property Type

Marathon Villa

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

The Space Y Knot is a 44 foot trawler yacht with 2 staterooms, a full head with walk in shower, a complete galley complimented by 2 refrigerators, freezer, stove/oven and microwave. Dining booth sits 6 adults. The v-berth stateroom has 3 double berths and 1 single birth. The small stateroom has 2 single ...

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Property Type

Key West Yacht

"Didn't stay here"

I did not stay at this property, but had inquired about it and would have loved to check it out. Sadly, we only hit Key West once while we stayed in Key Largo. This site believe I did stay there, so I ...

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2 BR | 3 BA | Sleeps 6 | Quick View

14

Distance to beach: 1 miles to Sombrerro Beach

$459

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring, ...

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Property Type

Marathon House

"Christmas Vacay"

10 ️ Rating! I called Florida Rentals. I Booked. Counted Down the days until our Christmas vacation began. We were able to take homemade cookies to the USCG base on Christmas Day. We were able to see ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

Relax in Key Largo and enjoy the many adventures that the Florida Keys has to offer! This home is perfect for large/multi families or friends. This newly remodeled 4/3 mobile home has wood laminate flooring and textured walls and ceilings. It has 4 bedrooms. Room 1: Master bedroom with queen bed, ...

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Property Type

Key Largo Mobile Home

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3 BR | 3.5 BA | Sleeps 6 | Quick View

$539

avg/night

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Key Amenities

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

About this property

VACA-22-238 BRAND NEW BUILD! 3- bedrooms with king beds and full size bathrooms, and 1/2 bath for guests. Large common area living room and open kitchen. Located on canal three houses from the ocean, with great open water views. Pool with sitting area under the house. Our home offers a 60' dock ...

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Property Type

Marathon House

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2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 2 miles to Smathers Beach

$163

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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 29 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

"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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5 BR | 4 BA | Sleeps 10 | Quick View

2

Distance to beach: 1 miles to In the Key Colony Beach walking distance

$1429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

Waterfront 5 Beds 4 Bath Heated Private Pool, Dock, Spa, Outdoor Kitchen, Bar,Waterfront Florida Keys Home in Key Colony Beach. Heated Pool & Jacuzzi 5 Bedrooms 4 Baths. HIGHLY sought after near the beach. Great for fishermen - 100 ft. Deep Water Dock. BBQ, Pool Table.We rent Friday to Friday ...

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Property Type

Key Colony Beach Villa

"Group Vacation"

Stayed with a group of friends from around the country. The house was very clean and well provisioned Kitchen, bedrooms, bathrooms, outdoor cooking area. Met the host and hostess, who were very pleasant. ...

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1 BR | 2 BA | Sleeps 2 | Quick View

1

$302

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history that befits its esteemed place along one of the most elegant streets in Key West. Unit # 6 is a second floor, 1BR/2BA unit that is entered on the left side of the building. The condo ...

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Property Type

Key West Condo

"Perfect place for a warm-weather couple!"

The location is perfect! Close to Duval Street, Mallory Square and many fabulous shops. We rode our bikes every morning to Higgs Beach to play tennis then enjoyed the white sand and cool morning breeze ...

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2 BR | 1 BA | Sleeps 6 | Quick View

1

Distance to beach: 3 miles to Sombrero Beach

$263

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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

"Faro Blanco Condo"

We absolutely loved our condo. It was spacious, beautifully decorated and very comfortable, as well as very well stocked. Our large lanai, which overlooked the lovely grounds, the marina, and the Gulf, ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. ...

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Property Type

Key West Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.9 miles to Rest Beach

$417

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Totally restored furnished pool home. On site parking, one bedroom, den, two baths, deck, loft and pool. High quality renovation. Available monthly. Pool heater, central AC, Viking appliances, sleeps 6. King bed in bedroom, den has a pull out couch, living room has a pull out couch. Unit is available ...

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Property Type

Key West House

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6 BR | 7 BA | Sleeps 16 | Quick View

2

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1771

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • 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!"

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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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool

About this property

Minimum 28-day rental.Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property....two cottages (each two-bedroom) and a main house overlooking the ocean. Located between the houses is a breathtaking resort-style pool, diving pool, and ...

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Property Type

Summerland Key House

"Peaceful and beautiful"

The location is fabulous, you can sit under the tiki hut by the water and just take in the gorgeous views. Pool was awesome. It was only a short drive to Key West where you can walk Duval street and take ...

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2 BR | 2 BA | Sleeps 6 | Quick View

9

Distance to beach: 1 miles to Smathers Beach

$386

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

About this property

Enjoy the comforts of home in the midst of paradise.Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by ...

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Property Type

Key West Condo

"hurricane ian"

Lourdes was so helpful as our reservation was the day of the storm and she kept us updated as well.The condo is very comfortable and everything one would need to cook a meal or relax with a drink. We took ...

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4 BR | 3 BA | Sleeps 10 | Quick View

4.9 rating on other travel sites

$579

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

MARATHON ANGLER'S RETREAT in Marathon is a brand new property with every modern convenience and warm coastal decor! Located right on a canal (just 15-20 minutes from open water) it has its own private dock (can accommodate up to a 35' boat on a 32' dock), fish cleaning station, private pool, hot tub, ...

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Property Type

Marathon Villa

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$175

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

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

"Casa Coco - a worthy stay"

A wonderful place, with canal and sea view at a few blocks away and centerally located to all the key places. The in-house amenities are best. Felt like home away from home. Experience it! I am not in to ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Baja Breeze , a freshly updated, family-friendly, resort-style villa in the of the Keys.Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others!Waterfront canal view Gated Resort Area Private spa pool Halfway ...

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Property Type

Duck Key Villa

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1 BR | 1 BA | Sleeps 2 | Quick View

3

Distance to beach: 12 miles to Founders Park

$150

avg/night

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Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

Secluded Waterfront Studio with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this listing. ...

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Property Type

Islamorada Apartment

"Little piece of paradise!"

We stayed two weeks in the beautiful apartment and it was the best vacation ever! Chris is a wonderful host, very friendly and a wealth of information about the area! We will be back next year!

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Key Amenities

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

About this property

Scuba diver and angler’s dream on canal within minutes of ocean access in Key Largo. Dive Capital of the World!! Just outside of world famous John Pennekamp State Park and Molasses Reef. Scuba dive, fish, or relax at the sandbar, in our canal or pool. Space to park boat, trailer and 40 ft RV. Ice ...

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Property Type

Key Largo House

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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

"It was a wonderful Florida keys vacation"

Andy was a wonderful host and his property was gorgeous. My family, including kids and grandkids took full advantage of the water access and all of the fun amenities. There was plenty of room for our two ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner

About this property

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

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Property Type

Islamorada Apartment

"Easy to Work With"

Although we had to cancel our trip due to a medical issue, Jerry was extremely helpful during the booking process. He answered all of my many questions and offered suggestions and activities. Based on how ...

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2 BR | 2 BA | Sleeps 6 | Quick View

11

Distance to beach: 2 miles to Sombrero Beach

$314

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

A beautiful waterfront half duplex home in a tropical setting with views of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround ...

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Property Type

Marathon House

"Enjoyed our stay!"

This was our first time renting a private property and I was a little nervous and had lots of questions. The owner took the time to answer all my questions and explain the process to me. Booking was easy. ...

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1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 6 miles to John Pennekamp State Park

$147

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

This charming little cabin sits right on its own protected harbor with right on the Atlantic Ocean. The bedroom has a king bed while the living area offers a few choices to sleep two adults and two children. Prepare your meals in the cozy kitchen and then enjoy your meals at the large family table located ...

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Property Type

Key Largo Cottage

"Great"

Enjoyed my alone time here. I love to fish, and fishing was great. Kayaking was fun right out the back door. I felt safe in the neighborhood. Quiet. Close to everything. Saw many beautiful sun rises. Next ...

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$941

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

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

"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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