Florida Keys Vacation Rentals

(305 rentals)
Waterfront Get Hooked

4 BR | 3 BA | Sleeps 10 | Quick View

4

$364

per night

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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 View of Sunset,Sunrise

$314

per night

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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 60-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

"Great location"
Reviewed October 14, 2019

Our visit was a two week stay in a really great location. Now first the bad, ok now that that's out of the way let's get on to the great! First off the location to the open water and dock are perfect, ...

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Pearl of Key West

3 BR | 2 BA | Sleeps 6 | Quick View

$141

per night

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Key Amenities

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

About this property

This home is meticulously cared for and will not disappoint! One story living with an open airy feel in all living and entertaining areas while bathrooms are easily accessible and bedrooms are tucked away for privacy and serenity. Indoor entertaining will not be an issue for the kitchen is newly and beautifully ...

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Property Type

Key West House

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Island Living with Gulf Views

2 BR | 2 BA | Sleeps 4 | Quick View

$114

per night

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Key Amenities

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

About this property

Tropically furnished, privately owned condominium at the Futura Yacht Club in the Village of Islamorada. Futura Yacht Club is a gated community located on the Gulf of Mexico and consisting of 70 units. Enjoy your morning coffee watching the boats go out. Relax with a amazing sunset and a glass ...

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Property Type

Islamorada Condo

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Deluxe Key West Condo - Minimum 28 days Rental

$150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Our beautiful deluxe one bedroom condo in Key West Florida on Southard Street is just blocks from the ocean and Duval street. Located in historic old town, the condo is enclosed in a beautiful garden on the ground floor.It is approximately 950 sq ft of air- conditioned luxury. There is a king size ...

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Property Type

Key West Condo

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Palm Breezes

5 BR | 3 BA | Sleeps 12 | Quick View

$549

per night

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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

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Sand in your toes

2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.1 miles to Coco Plum

$243

per night

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Key Amenities

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

About this property

Walk the Beach! Beautiful 2 bedroom, 2 bath Ocean front condo at Coco Plum Beach Villas, nicely decorated and furnished. Leather recliners in the main living area overlooking the Atlantic Ocean. King in master, 2 twins in 2nd. Pull Out couch in living room. Deck, master bedroom and the livingroom overlook ...

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Property Type

Marathon Condo

"OH Well, again"
Reviewed April 7, 2020

With the shutdown of the Keys due to the covid-19 issue, the management of this property called and returned our money for our reservation that we couldn't use due to the shutdown. It is really appreciated ...

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The 6 bedroom Duval Street Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1250

per night

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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

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Cozy Castaway

2 BR | 2 BA | Sleeps 6 | Quick View

2

$225

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Luxurious townhouse condo with 2 bedrooms, 2 and a half baths with Gulf views. Open floor plan with a large living area, dining and kitchen all wide open for great socializing! There is a queen size sofa sleeper in the living area for extra guests. 50 " Flat screen TV in the main living area. There ...

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Property Type

Marathon Condo

"Marathon and Manatee's"
Reviewed January 7, 2020

Oh my goodness, what a lovely home. So tastefully decorated, warm and inviting. We absolutely loved our stay and the home. We were entertained by the amazing manatees in the intercoastal waterway behind ...

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Seaglass-20 feet from the Gulf

2 BR | 2.5 BA | Sleeps 6 | Quick View

2

$185

per night

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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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Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$171

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Rentals by Owner

About this property

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

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Property Type

Islamorada Apartment

"Hidden Gem!!"
Reviewed April 15, 2020

This was such an amazing property. The owners were so friendly and very helpful on local recommendations. The property was very clean. There were high-end touches and details (down to the white robes provided.) ...

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Three Sheets~ Room for 2 boats! 70' dockage - QUICK GULF & OCEAN ACCESS

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 4 miles to Sombrero

$314

per night

View Details

Key Amenities

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

About this property

Trailer parking, newly remodeled, private pool, private bedroom/en suite bath, great outdoor group seating!7 day Minimum Rental During Peak and Holiday weeks Rentals are Saturday-Saturday OnlyTake a break from the hustle and bustle of the daily grind and relax in the calm and serene atmosphere ...

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Property Type

Marathon House

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Luxury Florida Keys Estate

3 BR | 3 BA | Sleeps 8 | Quick View

$714

per night

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Key Amenities

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

About this property

Ocean Front, Lush Gardens, Private Beach, Deep-Water Dockage, Brand new Pool with Spa.This luxurious and newly renovated home is situated on the very desirable Lower Matecumbe Beach in Islamorada. This gated home offers supreme peace and privacy overlooking the Atlantic Ocean. Over 4,000 sq feet of ...

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Property Type

Islamorada House

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Paradise Palms

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 10 miles to Bahia Honda Beach

Inquire for rates

View Details

Key Amenities

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

About this property

This is an open concept and spacious home, (1) King, (1) Queen and (2) Twin Beds, (2) Bathrooms, 6 people accommodation, brightly painted colors, beautifully furnished. Relax in the upper covered porch or down below onto the pool patio area. Outdoor Tiki shower hut. The grounds are landscaped with an ...

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Property Type

Cudjoe Key House

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Deep wide canal, ocean view, unlimited dockage.

$149

per night

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Key Amenities

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

About this property

Sea horse 1: Deep wide unlimited dockage with 50 amp power by the dock, flow through canal, View of Vaca Cut & Atlantic Ocean. Swimming , snorkeling, fishing all right from the dock and swim with beautiful Tropical fishes and manatees! Tastefully decorated & furnished, cute & clean, ...

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Property Type

Marathon House

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MA945 334 Calzada de Bougainville Marathon, FL 33050

$543

per 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

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Chillax

4 BR | 3 BA | Sleeps 10 | Quick View

$321

per night

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Key Amenities

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

About this property

"Chillax" Vacation Rental ~ rent one side or both! It is a gorgeous brand new beautifully decorated 4 bedroom 3 bath canal front Villa (pull out couch)! With a private dock that can accommodate a boat up to 40', private pool, plenty of parking for cars and boat trailer and a two minute drive ...

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Property Type

Marathon Villa

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LUXURY HOME WITH DOCK, POOL, HOT TUB, AND ELEVATOR

3 BR | 3 BA | Sleeps 8 | Quick View

5

Distance to beach: 1 miles to Coco Plum & Sombrero Beach

$329

per night

View Details

Key Amenities

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

About this property

This new gated Marathon home is 2 levels with an elevator. 3 Bedroom / 3 Bathroom , Sleeps 8 people, with all the comforts of home. This home offers nothing but the best in home furnishings and security. Panoramic water views from private decks off the living room and master bedroom. Master / King bed; ...

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Property Type

Marathon House

"EVERYTHING you need for a relaxing vacation!"
Reviewed February 2, 2020

Larry’s place has everything you need and so much more! We did fish right from the pier in front of the house, had fun with a rented boat, went for an amazing snorkelling trip... Also many relaxing days ...

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Cockadoodledo

4 BR | 4 BA | Sleeps 10 | Quick View

$300

per night

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Key Amenities

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

About this property

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

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Property Type

Key West House

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Searenity Canal Front

2 BR | 2 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Coco Plum Beach

$290

per night

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Key Amenities

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

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

"Searenity !"
Reviewed February 15, 2020

One Month of pure bliss ! From the moment we walked in to the Dolphin Drive home we fell in love ! We felt immediately comfortable and at home ! Clean , spacious with every amenity needed for your home ...

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MA876 122nd Street Ocean Marathon, FL

5 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 3 miles to Coco Plum

$583

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Enjoy life at Serenity! Amazing home on the ocean with 137' of deep water protected dockage. Unobstructed views of Vaca Cut from this elegant home. Enjoy breathtaking sunsets, dolphins playing in your backyard, visiting manatees, fishing from your very own The dock has 137' of seawall , with water and ...

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Property Type

Marathon House

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Luxury Home Ocean views(#109) in Key West with Pool, Dock, Kayaks, Bicycles

$300

per night

View Details

Key Amenities

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

About this property

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. I also rent units 111 and 107 on in case you need more than one home. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock ...

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Property Type

Cudjoe Key House

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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

$283

per night

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Key Amenities

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

About this property

Down a very quite lane the house has one off street parking spot.Enter from gate through lush and colorful walk to front door of main house . Enter into the living room with smart tv ,through to the right into the dinning area. The kitchen is off to the left. There is a large working counter with seating ...

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Property Type

Key West House

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**Perfect Paradise - Gorgeous Waterfront *Million $ Views!**

2 BR | 1.5 BA | Sleeps 5 | Quick View

LAST MINUTE DEAL 6/1 - 6/27: Book between now and June 27, for only $1500 TOTAL, per week!! Plus, $200 refundable deposit.

$225

per night

View Details

Key Amenities

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

About this property

Welcome to our Perfect Paradise!! We are proud to share that our condo is one of the very few condos with a county permit which allows for weekly vacation rentals.Please feel free to text me, as well as submit an online inquiry, for a quick response. Provide dates of interest and number of renters. ...

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Property Type

Key Largo Condo

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

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$233

per night

View Details

Key Amenities

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

About this property

COVID-19 UPDATE: Key West and Monroe County are opening to visitors June 1! Restuarants will be open at 50% capacity and bars that do not serve food will remain closed. MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early ...

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Property Type

Key West House

"Beautiful Bougainvillea Villa"
Reviewed February 27, 2018

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

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PARADISE FOUND! BOAT RENTAL/BRING YOUR BOAT! HOME WITH BEACH AND BOAT RAMP!

3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 40 feet to Across the street

$127

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Key Largo House

"Truly paradise found"
Reviewed March 16, 2020

My husband and I with another couple spent the whole month of February here. The location is perfect. We brought our boat and the marina next door let us dock the boat at a reasonable monthly rate. ...

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Waterfront Hideaway. Waterfront Bungalow- Peace and Quiet in the heart of Marathon!

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 3 miles to Sombrero Beach

$92

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly

About this property

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 and is 24' of dock space. There's a BBQ grill, dishwasher, Cable TV, WIFI, dishwasher, washer/dryer, and all the amenities of home. The house was undamaged in the hurricane ...

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Property Type

Marathon House

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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

per night

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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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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

1

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$186

per night

View Details

Key Amenities

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

About this property

This upscale home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval ...

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Property Type

Key West Condo

"Destination Wedding/Honeymoon"
Reviewed January 11, 2020

This was our first experience staying in a condo instead of hotel and we could not have made a better choice! We got married on Smathers Beach December 5th and stayed 6th-12th. This condo is lovely and ...

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Conch Cottage Key West's only real beach house

$414

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

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

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Property Type

Key West House

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Truman Annex - ' Island Queen' End Unit Villa is One-of-a-Kind!

$393

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

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

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Property Type

Key West Townhome

"Great Winter Getaway! Wonderful! 5-Stars!"
Reviewed March 4, 2020

Yes, this end unit is "One of a Kind"! Many thanks to Rosemary & Mark. Their spacious, quiet & immaculate home has been our great winter escape. This was our third stay at this remarkable townhouse in ...

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

View Details

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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South Creek Crab Shack

4 BR | 3 BA | Sleeps 8 | Quick View

$321

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Named for the owners who live in North Creek and love to crab, this beautiful Villa with it's welcoming coastal decor makes for a peaceful vacation home in the perfect location! Enjoy views from the upstairs porch with your coffee in the morning and cooking out on the patio by your private pool with your ...

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Property Type

Marathon House

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Beautiful Key West Home located in Golf Course community

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 2 miles to Smathers Beach

$169

per 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 is a great location to stay with a monthly rental minimum. Yearly rates available. You are close to everything Key West has to offer. Renovated 2019. Our house offers many amenities to make your stay comfortable and convenient. Each Bedroom on the ...

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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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Private House Facing the Ocean with New Heated Swim/Pool/Spa LOC LOC LOC

$357

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Ramrod Key House

"Unbelievable vacation"
Reviewed January 1, 2020

I wish I could give this property more than just 5 stars. Property owner was amazing and helpful. Owner was available to answer all my questions and more. This property was everything described and more. ...

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Breezy Palms

4 BR | 3 BA | Sleeps 10 | Quick View

$414

per 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

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Sombrero Heaven

4 BR | 3 BA | Sleeps 10 | Quick View

$321

per night

View Details

Key Amenities

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

About this property

"SOMBRERO HEAVEN" ~ Rent one side or both! Brand New, Designer Decorated and Perfectly Appointed 4-Bedroom (1 King, 3 Queens), 3-Bath Private Heated Pool Villa with Neighborhood Ocean Front beach and Second Story Screened Balcony that Over Looks Private Pool and Canal! Everything you need for ...

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Property Type

Marathon Villa

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Poolside Paradise @ , beach & Duval St.

$182

per night

View Details

Key Amenities

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

About this property

Location, Location, Location!! Sunrise off Southard is a highly desirable home that has it all! An upscale one bedroom home offers beauty with all the comforts. Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical ...

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Property Type

Key West Condo

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Beautiful Townhouse Awaiting Your Tropical Escape

2 BR | 2.5 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.3 miles to Ft. Zachary Taylor Beach

$264

per night

View Details

Key Amenities

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

About this property

Located in the gated community of Truman Annex: a popular and beautifully landscaped community in Old Town Key West. Enjoy the peaceful tropical landscape and pool while only 2 blocks from the excitement of Duval St. We are just outside the entrance to Ft Zachary Taylor State Park and Beach and so close ...

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Property Type

Key West House

"Great place to stay near everything."
Reviewed October 31, 2019

Beautiful condo in a great part of town. It was exactly as advertised. Wonderful. We visited the fort, beaches, pool, and numerous restaurants, bars, and shops. It was Fantasy Fest week. We ate at Bagtell’s, ...

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Open Water Views from Every Floor! Fabulous Modern Waterfront Home, Private Pool

$500

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Upscale Modern 4 Bedroom 3 Bath Ocean Front Home, Private Pool, Summer Kitchen We are currently not able to take reservations until after May 31 for reservations due to Covid 19.The photos tell everything you need to know about this STUNNING vacation rental home! Gorgeous upscale decor with a modern ...

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Property Type

Marathon House

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MA976 938 92nd Street 0cean Marathon, FL 33050

3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 4 miles to Sombrero

$371

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront

About this property

Single Family Home fully updated with everything you will need for a perfect vacation. The master suite has a king size bed with an ensuite bath. The ensuite bath has his and her sinks, lovely, large shower and bidet. The 1st Guest Bedroom has 2 Queen size beds and it's own ensuite bath. There is also ...

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Property Type

Marathon House

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Waterfront Sgl Family Pool Home:60' Dock: Direct Ocean Access:Kayaks:Ocean

2 BR | 3 BA | Sleeps 6 | Quick View

1

Distance to beach: 1 miles to Sombrerro Beach

$195

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"5 stars go to both the rental home itself as well as the home owners"
Reviewed April 6, 2020

If I were to own an island getaway in the keys, I would design and furnish it exactly as the owners of Lemon Key Cottage have. My wife and I, both retired, found this retreat fulfilled all of our needs ...

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Islamorada Paradise Vacation Home on the Water

$229

per night

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Key Amenities

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

About this property

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

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Property Type

Islamorada House

"Girls Trip"
Reviewed June 5, 2019

We had an awesome time in Islamarada. Loved this rental, it was in a nice area. I would highly recommend this place. Very clean!

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Oceanfront Luxury "Mar Azul"

3 BR | 2.5 BA | Sleeps 6 | Quick View

2

$421

per night

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Key Amenities

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

About this property

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

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Property Type

Marathon Estate

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

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

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Tropical Oasis! Paddle Board, Kayaks, Outdoor TV, Private Heated Pool

$349

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

4/3 with paddle boards, kayaks, private pool, private dock on canal, beach!Everything you want and need for the perfect tropical vacation in the Florida Keys is at Sombrero Breeze including 2 kayaks and 2 paddle boards! The canal has deep water access to the ocean and can accommodate up to a 42' boat. ...

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Property Type

Marathon Villa

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Canal Front Villa with a Tiki Hut, Kayaks, Bikes, Pool, Neighborhood Beach!

$321

per night

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Key Amenities

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

About this property

"Dockside Retreat" ~ rent one side or both! Warm and inviting coastal decor, this 4/3 villa is the perfect vacation home! This beautifully decorated Villa is truly a relaxing retreat and a vacation home that offers you everything you need for a fun filled Keys vacation, including an oceanfront ...

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Property Type

Islamorada House

"Awesome house!!!"
Reviewed January 27, 2020

We recently stayed in the dockside retreat and loved it. We traveled to Marathon with my wife, kids, and mother in law and all thoroughly enjoyed our stay. The house was clean, new, and had everything we ...

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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

$250

per 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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Panoramic Ocean View, Pool, Hot Tub, Tennis & Fishing

2 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Sombrero Beach

$299

per night

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Key Amenities

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

About this property

Entering our luxurious condo, you will be impressed with expansive ocean views, literally from every room. Corner-sited and on the 1st floor (above parking), the wrap around private balcony, with all-new wicker lounge furniture, is but a stone toss to the ocean. Travertine tile floors and granite counters ...

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Property Type

Key Colony Beach Condo

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Canal Front 3/2 with Private Pool and Dock, Beach, Kayaks, Paddle Boards & Bikes

$299

per night

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Key Amenities

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

About this property

"Coastal Key" ~ Georgous brand new home-just down the street from the street from Sombrero Beach. Beautifully decorated brand new home, has a private pool, private dock, fish cleaning station, bait freezer, outdoor TV in covered patio, gas grill, 4 bikes, 2 kayaks, 2 paddle boards! With 3 bedrooms, ...

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Property Type

Marathon House

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Toes in the Water

4 BR | 3 BA | Sleeps 10 | Quick View

$321

per night

View Details

Key Amenities

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

About this property

"Toes in the Water" ~ Rent one side or both! It is a gorgeous brand new beautifully decorated 4 bedroom 3 bath canal front Villa (pull out couch)! With a private dock that can accommodate a boat up to 40', private pool, plenty of parking for cars and boat trailer and a two minute drive to the ...

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Property Type

Marathon Villa

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Florida Keys Vacation Rentals