Florida Keys Vacation Rentals

(388 rentals)
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W09 - 2394 Coco Plum Dr Unit 3

6 BR | 6 BA | Sleeps 14 | Quick View

$849

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Be one of the first to stay in this luxury home.This home is a 7 night minimum rental.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 ...

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Property Type

Marathon House

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Beacon Reef Condominium 205

2 BR | 2 BA | Sleeps 4 | Quick View

$167

avg/night

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Key Amenities

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

About this property

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

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Property Type

Islamorada Apartment

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Luxury Home #109-pool,dock,kayaks,bikes,on Ocean Near Key West,free Trailer Keep

$337

avg/night

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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. We are 80 feet the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of ...

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Property Type

Cudjoe Key House

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Key West Beach Front Rental Beach Studios Ocean views

Studio | 1 BA | Sleeps 3 | Quick View

5

Distance to beach: 22 yards to Public use + Private views Waldorf Astoria Resort

$470

avg/night

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Key Amenities

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

About this property

This is Key West Beach Front Rental Welcome to; Ocean view STUDIO See rates first**** save yourself some valuable ***time This is NOT A BUDGET STAY! This is truly a romantic Ocean View stay for two adults. Opposite of most Ocean View destination experiences of huge buildings, long ...

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Property Type

Key West Studio

"Amazing place to stay- spectacular view"
Reviewed June 8, 2021

This was our second time staying at here and we love it! The views and sound of the ocean are amazing! Place is clean and cozy. Host Holly is fantastic! We will definitely be returning again next year. ...

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MA923 101st St Ocean Street Marathon, FL 33050

6 BR | 6 BA | Sleeps 14 | Quick View

3

Distance to beach: 5 miles to Sombrero

$807

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

"It was paradise"
Reviewed September 9, 2021

Very Clean home. The bedrooms were large with a bathroom in it and sliding doors to the terrace, the beds were clean and very comfortable. There is a pool table, poker table for entertainment , the out ...

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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

$216

avg/night

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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 $90 * 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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Tropical Seclusion On Old Town Lane With Pool And Detached Bungalow.

$294

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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 LaneHidden 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, the main 2/2 house features an indoor/outdoor ...

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Property Type

Key West House

"Perfect place!"
Reviewed August 21, 2021

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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Ocean View condo steps to Smathers Beach

$243

avg/night

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Key Amenities

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

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * King size bed in the bedroom *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning included * This is not a hotel; it is a privately owned condo facing the ...

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Property Type

Key West Condo

"AMAZING"
Reviewed January 30, 2019

There truly aren't enough adjectives to describe the level of service Pam provided. At the very beginning, she answered all my questions, in less than an hour. Her customer service was amazing. She provided ...

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Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks Kayaks

3 BR | 2 BA | Sleeps 6 | Quick View

9
LAST MINUTE DEAL 9/20 - 10/30: Just had a cancellation for October.

Distance to beach: 0.5 miles to White Marlin Beach

$571

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 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"
Reviewed April 6, 2021

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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DEAL
Truman Annex, Lrg In/Outdoors Beautiful 1st Flr, 2BR KING/twins, Pool

2 BR | 1 BA | Sleeps 5 | Quick View

1

Distance to beach: 0.2 miles to Fort Zachary Beach

$333

avg/night

View Details

Key Amenities

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

About this property

TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all. Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors.58 5-STAR REVIEWS!!! (on our primary site on VRBO #595903)Our fantastic cleaner has been ...

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Property Type

Key West Condo

"Perfect condo for our needs"
Reviewed March 16, 2021

Location was perfect as it is closer to the entrance of Truman Annex and in turn only steps away from Duval, Mallory Square and Truman Waterfront park. Owner's were very friendly, extremely responsive ...

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

$676

avg/night

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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

"Family Vacation 2021"
Reviewed July 4, 2021

This was the best vacation of our lives! Quality time together. The house was fabulous, pictures don't do it justice! Spotless tastefully decorated high-end appliances stocked with everything you'd need. ...

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Bikini Bottom (MA1013)

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Sombrero

$414

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Bikini Bottom – 4-bedroom, 3-bath coastal getaway, with all the amenities the whole family will enjoy. Enjoy outdoor dining on a wrap around deck that overlooks the private pool, and canal. Pool heat is an additional $200 plus taxes. This home is perfect for relaxing and enjoying the Middle Keys. ...

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Property Type

Marathon House

"Awesome Trip!!"
Reviewed September 9, 2021

We had such a great time this week. If Bikini Bottom is available for our next vacation we would definitely come back here. It’s located conveniently to anything you could possibly want. Very comfortable ...

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POOL, Waterfront, 75ft dock, Sombrero Beach 2.3mi, WALK to stores & restaurants

3 BR | 2 BA | Sleeps 8 | Quick View

5
Owner special: SEPTEMBER SPECIAL Book a reservation during September for a stay anytime in the future and SAVE 10%

Distance to beach: 2 miles to Sombrero Beach

$362

avg/night

View Details

Key Amenities

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

About this property

OUTDOORS @ 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 on a 7,500sq ft lot . The warm sunrise welcomes your morning as you wake and take in the views from the rear/ east ...

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Property Type

Marathon House

"Vacation"
Reviewed July 27, 2021

Really loved it but like any New business it’s not perfect for everyone, Good easy private location in the Heart of Marathon. Like us the owners are Very Hard working people who are VERY accommodating ...

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Waterfront, oceanview renovated pvt. 3 bedroom, 3.5 bath with pool and dockage.

$398

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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

"Perfect lobstering and fishing getaway for our family."
Reviewed August 21, 2021

This was our first stay at this location but definitely now our favorite rental location on Marathon. The boating access was easy and very convenient to the reefs. The house was set up great with a bathroom ...

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Gorgeous waterfront home

3 BR | 2.5 BA | Sleeps 8 | Quick View

$650

avg/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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Palm Breezes

5 BR | 3 BA | Sleeps 12 | Quick View

1

$619

avg/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

"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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Sunset on Southard

1 BR | 1 BA | Sleeps 4 | Quick View

1

$273

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

"Sunset on Southard"
Reviewed April 25, 2021

We arrived to a wonderful and super clean condo in a great location. We had everything we needed plus! It was great having a cooler and beach towels provided for our use to the beach, 2 bicycles, loved ...

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Bayside Paradise in the Heart of Islamorada *Private Boat Dockage Upon Request*

$692

avg/night

View Details

Key Amenities

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

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and ...

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Property Type

Islamorada House

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Coconut Palm - Beautiful Canalfront 4BR Home with Pool & Dock w/Boat lift

$392

avg/night

View Details

Key Amenities

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

About this property

*25% OFF Rent for AUG, SEPT, OCT, and/or NOV 2021*BRAND NEW TO RENTAL MARKETMINIMUM STAY: 28 DAYS Exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. New owners have purchased all new linens and added many new amenities. ...

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Property Type

Tavernier House

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BEACON REEF #503 - Stunning Newly Renovated Condo in Oceanfront Complex

$164

avg/night

View Details

Key Amenities

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

About this property

MINIMUM STAY: 28 DAYS This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit everyone's preference. Dine in the ...

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Property Type

Islamorada Condo

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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

$284

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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West Plaza del Lago - Gorgeous Waterfront Home with Boat Lift and Beach Access!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$160

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

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Property Type

Islamorada House

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Private beach estate,gated,dock,and pool

$775

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full 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!"
Reviewed March 15, 2021

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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MA876 122nd Street Ocean Marathon, FL

5 BR | 4 BA | Sleeps 12 | Quick View

1

Distance to beach: 3 miles to Coco Plum

$645

avg/night

View Details

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

"Marathon House"
Reviewed December 15, 2020

The view at this house was amazing and the sunsets stunning! The kitchen is large and stocked with everything you need to cook. The Master bedroom is very spacious.

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Desiderata

3 BR | 2 BA | Sleeps 6 | Quick View

$202

avg/night

View Details

Key Amenities

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

About this property

Beautiful ,3 year new home on deep water canal in desirable Breezeswept Estates is your private resort for a minimum of 28 days . Heated, saltwater pool adjoins huge ground level great-room with living area, dining area, shower , gas grill, pingpong table and so much more contained in private setting ...

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Property Type

Ramrod Key House

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Mobile Home, 2 Bedrooms, 2 Baths, (Sleeps 2-4)

$120

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

This property is located on a very unique spot. Very private. Too perfect to describe.During the day you could sunbathe while fishing for snappers, tarpon and lobsters from your private dock. Later on you may want to jump in for a swim or cruise the area on the kayak At early evening you may enjoy ...

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Property Type

Tavernier Mobile Home

"Awesome Beautiful Waterfront Home"
Reviewed August 25, 2020

This was are first stay at Hammer Point and it will not be are last, Our stay was perfect, The house is clean and immaculate with all the amenities you would ever need. The sunsets are just amazing.The ...

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

$1025

avg/night

View Details

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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A Touch of Bermuda at Truman Annex

2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$354

avg/night

View Details

Key Amenities

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

About this property

KEY WEST SAMPLER OCT 5-9 AVAILABLE FOR $ 999. Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private ...

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Property Type

Key West Cottage

"Island Magic"
Reviewed March 25, 2021

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

avg/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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Beautiful Downtown Truman Annex Condo

$308

avg/night

View Details

Key Amenities

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

About this property

Best Deal in Truman Annex - Cead Mile Failte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5Here's Caad Mile Failte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our home ...

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Property Type

Key West Condo

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Luxury Home #107 - pool, dock, kayaks, bikes, on ocean near Key West

$317

avg/night

View Details

Key Amenities

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

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. Our home is third from the waters edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on ...

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Property Type

Cudjoe Key House

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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

3

Distance to beach: 40 feet to Across the street

$153

avg/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

"Very cool!"
Reviewed August 1, 2021

Very good, comfort condo with all you need for a stress free holiday. The pool is great! location is excellent because is half way to ether north or south of the keys so what ever you you exploring home ...

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Luxury Oceanfront Home, Views, Pool, Sandy Beach

$620

avg/night

View Details

Key Amenities

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

About this property

‘The Beach House’ at Tarpon Point in Islamorada‘The Beach House’ is a luxurious oceanfront home in a private gated enclave of only 12 houses. This end home offers privacy and beautiful ocean views including of Indian Key Historic State Park. Enjoy morning coffee and a phenomenal ...

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Property Type

Islamorada House

"Highly Recommended"
Reviewed August 19, 2021

This home is stunning from top to bottom and all around. Our family, ranging from 18-75 years of age, found this home to be spacious, comfortable, and well equipped for cooking, relaxing, and having fun ...

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Twice the Charm - Canal Home with Pool, Dock and Fish Cleaning Station

$232

avg/night

View Details

Key Amenities

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

About this property

Minimum Rental: 28 Days "Twice the Charm" is a gorgeous newly remodeled single family home. You’ll love the convenient location in the Ocean Shores area of Key Largo. There’s easy ocean access from the dock which accommodates a boat up to 30' and includes davits, water, electricity, ...

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Property Type

Key Largo House

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BEACON REEF 501 - Updated Condo in Oceanfront Complex in Islamorada

$133

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

MINIMUM STAY: ONE MONTH. Exceptional 5th floor (top floor) 2 bedroom 2 bath condo at Beacon Reef. Ocean views from the open air balcony. You’ll be so glad you have chosen to spend your holiday here. The kitchen was remodeled in 2013 – granite counters, stainless steel appliances, and ...

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Property Type

Islamorada Condo

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The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip

$654

avg/night

View Details

Key Amenities

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

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs ...

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Property Type

Islamorada House

"Great place!"
Reviewed April 22, 2019

Arlene was wonderful to work with. The home more than accommodated our mix of four couples. Thanks.

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Ocean Harbour K31 - 3 Bedroom Oceanfront Condo in Islamorada

$233

avg/night

View Details

Key Amenities

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

About this property

MINIMUM STAY: One Month Gorgeous 3 bedroom ocean front condo with unobstructed ocean views NEW to the rental market and available now! Be the first to rent this unit and establish your annual winter rental getaway. New owners have refurnished and upgraded this spacious end unit in Ocean Harbour. ...

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Property Type

Plantation Key Condo

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Waterfront Hideaway: Quiet Locals Experience with Dockage!

2 BR | 1 BA | Sleeps 6 | Quick View

1

Distance to beach: 3 miles to Sombrero Beach

$213

avg/night

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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

"Faro Blanco Condo"
Reviewed April 5, 2021

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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Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

$223

avg/night

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Key Amenities

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

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove ...

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Property Type

Islamorada Cottage

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Way to Go (MA1011)

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 4 miles to Sombrero

$521

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Nautical bedroom 2 full size beds King in master Palm Tree bedroom 2 Queens Green Bunk Room two bunks with twin, full and full trundle Casa Paisan You’ll Never Want To Leave! This Mediterranean-inspired waterfront estate nestled on Sombrero Lagoon offers an open interior, phenomenal outdoor space, ...

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Property Type

Marathon House

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Tropical Waterfront - Incredible View, Dock, Kayak

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Sombrero Beach

$177

avg/night

View Details

Key Amenities

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

About this property

Waterfront Home with Dock located on quiet saltwater cove with Gulf ViewLush Tropical Lagoon half duplex home with panoramic views of the Gulf of Mexico. Spacious and comfortable interior with all the amenities you'd expect. Brick pavers surround lush tropic landscaping surrounded by palm trees ...

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Property Type

Marathon House

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Sailfish Villa. Direct Water Front!Gulf & Ocean Access! Pool, Dock, Paddleboards

$676

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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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Southard Breezes

1 BR | 1 BA | Sleeps 3 | Quick View

3

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$251

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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Waterfront Pet-Friendly Single Home - Cabana Club Included

$308

avg/night

View Details

Key Amenities

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

About this property

Beautifully updated single home on wide canal with boat slip. Plenty of parking for boat trailer and multiple vehicles. Beautifully landscaped. Large backyard with Tiki Hut that includes an over-the-water bar plus seating. The yard provides plenty of seating, lounging and dining space overlooking ...

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Property Type

Key Colony Beach House

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Directly OceanFRONT, Panoramic Oceanviews, Wraparound Decks, Optional Boat slip

3 BR | 2.5 BA | Sleeps 8 | Quick View

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

$511

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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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Cockadoodledo Vacation Rental. Featured On Hgtv***multiple Month Discount***updated

$403

avg/night

View Details

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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Palms 314 - Waterfront 2 Bedroom Condo in Islamorada with Private Balcony

$127

avg/night

View Details

Key Amenities

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

About this property

MINIMUM STAY: 30 DAYS This condo offers breathtaking oceanfront views. Imagine watching the sun rise as you lay comfortably in your bed or have your morning beverage on the balcony and enjoy watching the fishing boats leave for their day's adventure. You'll be able to see cruise ships as they ...

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Property Type

Key Largo Condo

"Beautiful location stunning home."
Reviewed January 11, 2020

Beautifully decorated and fabulous location! I highly recommend this home. We had a great time and wonderful experience here in Key Largo FL.

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Conch Bar South - 4 Bedroom Waterfront Home with Swimming Pool

4 BR | 3 BA | Sleeps 10 | Quick View

2

Distance to beach: 3 miles to Founders Park Beach

$390

avg/night

View Details

Key Amenities

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

About this property

Minimum Rental: 1 Month"Conch Bar South" is a magnificent home is located at the mouth of a wide canal in Plantation Key and offers phenomenal open water views. The furnishings are new and provide a comfortable and extremely inviting living environment. This 4 bedroom 3 bath single family ...

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Property Type

Tavernier House

"The view is incredible!!"
Reviewed February 17, 2021

We stayed at Conch Bar South the month of January and It was amazing! Chantree and Courtney were so helpful. Any questions or concerns that we had were taken care of immediately. The kitchen is fully stocked ...

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Ma870

3 BR | 2 BA | Sleeps 8 | Quick View

2

$343

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Have a truly blissful vacation at this charming, Gulf Front home that sits on one acre of pristine property on exclusive Morton St. Enjoy the magnificent open Gulf views from nearly every room. This unique home is reminiscent of the way the Keys used to be…..charming! Perfect area for walking, ...

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Property Type

Marathon House

"Wedding vacation with family and friends what a great house to stay"
Reviewed June 25, 2021

Beautiful home we had a great time in a great area the rooms are beautiful with a bathroom in every bedroom. The pool was big and fun to play volleyball and laying out my granddaughter had so much fun. ...

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Starfish House

3 BR | 2 BA | Sleeps 6 | Quick View

$486

avg/night

View Details

Key Amenities

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

About this property

***We are taking the recommended steps as presented by the Center for Disease Control and Prevention (CDC) for cleaning, disinfecting, and preparing this home for your arrival. We are following the protocols laid out by the CDC and using the EPA-approved disinfectants for Hard (non-porous) Surfaces, Soft ...

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Property Type

Little Torch Key House

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