Key West Vacation Rentals

(73 rentals)
Conch Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$414

per night

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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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Ann Street Tranquility

1 BR | 1 BA | Sleeps 2 | Quick View

$236

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This charming one bedroom cottage is the perfect hideaway.The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy Joe's, ...

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Property Type

Key West House

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$1480 wk. AVAILABLE - NO DAMAGE FROM HURRICANE IRMA

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Smathers Beach

$211

per night

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Key Amenities

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

About this property

'TEE BY THE SEA' vacation rental(we include 7 bikes free for our guests!!!)MY VAC. RENTAL SUSTAINED NO DAMAGE FROM HURRICANE IRMA. ITS DOING FINE AND READY TO ACCOMMODATE GUESTS. OUR CONDO COMPLEX IS FINE TOO AND WE ARE READY TO RECEIVE GUESTS. PLEASE MAKE YOUR RESERVATION.We're less then ...

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Property Type

Key West Condo

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30 night minimum stay, SUNSET KEY, LUXURY UPSCALE HOME RIGHT ON THE BEACH,

$399

per night

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Key Amenities

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

About this property

30 day stay minimum, 3000 SF, 3BDR, 2.5BATHS, SLEEPS 6 Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, private pool, and 2 hot tubs for our guests ...

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Property Type

Key West House

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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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Truman Annex Shipyard Condo-1BR/1BA w/Loft

$185

per night

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Key Amenities

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

About this property

1BR/1BA w/ Loft in Truman Annex close to Ft Zachary Taylor beachThis condo easily accommodates both couples and small families with its unique layout. It features a private bedroom, loft area and sleeper sofa for flexible sleeping accommodations. Located within the gated community of Truman Annex, ...

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Property Type

Key West Condo

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Key West Beach Front Rental! Beach Studio Ocean views

Studio | 1 BA | Sleeps 2 | Quick View

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

$269

per night

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Key Amenities

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

About this property

Ocean View Unit offers, private unit - kitchen/bath, private patio! See calendar before flights! Read base rates before asking rate.Requesting under minimum stay? Just might fly fine! ask new rate. Please {2 person stay} or Add your teen call first. Casa Marina District but ocean side {honestly ...

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Property Type

Key West Studio

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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$178

per night

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Key Amenities

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

About this property

Beautifully Remodeled -1BR/1BA End Unit Shipyard Condo in Truman Annex Location, Beauty and Comfort! Southard Breezes has what you are looking for! This gorgeous home has been meticulously renovated with our guests' complete comfort in mind. Located in the gated community of Truman Annex: a popular and ...

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Property Type

Key West Condo

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

$193

per night

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Key Amenities

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

About this property

Dos Casas can be the answer to your fabulous Old Town Key West vacation. We've been renting to discriminating travelers for over 10 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenitites and ideal location the perfect spot to enjoy all that Key West has to offer.Why ...

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Property Type

Key West House

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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

$167

per night

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Key Amenities

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

About this property

MONTHLY RENTALS ONLY We purchased Bougainvillea Villa in late 2014 as our future retirement home. The villa was built in the early 1960’s and our neighbors tell us that at one time Jimmy Buffett’s manager owned and lived in the home. It has always been a private home, and was renovated and ...

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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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The Duval Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1250

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

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

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Property Type

Key West Villa

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Villa Serena Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Open the door to Villa Serena and find yourself transported to a peaceful sanctuary. Recently renovated in February 2018, Villa Serena is the perfect space for your relaxing vacation.The downstairs living area is decorated in soothing cobalt and beachy sand tones and provides plenty of space for ...

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Property Type

Key West Condo

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Parrot Dice --"MONTHLY," 2 bedroom (+den), 3 bath, Pool & Hot Tub, Private Drive

2 BR | 3 BA | Sleeps 6 | Quick View

Distance to beach: 0.5 miles to Higgs Beach

$150

per night

View Details

Key Amenities

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

About this property

"MONTHLY" RENTAL ONLY: Old Town Tropical Oasis, Private Pool, Hot Tub, Private Driveway. Meticulously restored and maintained home featuring: 2 bedrooms + den with sleep sofa (can be a 3rd bedroom) and 3 full en suite bathrooms. Our favorite part of this property is the lush & extremely ...

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Property Type

Key West House

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Cozy End Unit Condo in Truman Annex

$171

per night

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Key Amenities

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

About this property

Beautifully Remodeled Tropical Sanctuary-1BR/1BA Shipyard Condo in Truman AnnexLocation, Location, Location!! Sunrise off Southard 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 ...

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Property Type

Key West Condo

"Our Stay In Key West"
Reviewed January 11, 2019

This is a great one bedroom rental. Within walking distance to all the restaurants and bars. Tracy was quick to respond when I had any questions. The condo had beach passes, bikes, a cooler, beach towels, ...

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Southard Street - Queen Conch

4 BR | 4 BA | Sleeps 8 | Quick View

$750

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool, or combines for a wonderful four bedroom retreat.Downstairs there is a large, open floor plan with living ...

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Property Type

Key West House

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Casa de Cuba

3 BR | 2 BA | Sleeps 6 | Quick View

$501

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now restored ...

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Property Type

Key West House

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Colony Sunset Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$180

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Sunset is a colorful and relaxing retreat. Walk up the flagstone path and enter the home through the vivid and cheerful living space, accented with cerulean blue walls and splashes of tropical art. A vaulted ceiling with ...

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Property Type

Key West Condo

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Brass Palm Villa -Private Luxury Key West Home with Heated Pool

$200

per night

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Key Amenities

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

About this property

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

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Property Type

Key West House

"“It’s a Magic Kind of Medicine”"
Reviewed December 30, 2017

Now I know where J.Buffett got the inspiration for those lyrics! Just the right blend of tranquility and fun! It was love at first sight. The pool, surrounding outdoor living spaces were just perfect. I ...

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Single Family Home, 3 Bedroom, 2 Bath, Pool and Electric Car, Great Value!

$117

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. Use of bicycles and four passenger electric car provide flexible transportation all over the island. The home features a modern kitchen with all appliances and granite ...

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Property Type

Key West House

"Fabulous house!"
Reviewed October 1, 2018

My family and I had the best time staying at the Edsons' place, and the other reviewer is quite right - the pictures do not do it justice. Jill and her family could not be better hosts and have provided ...

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The Hamilton House

5 BR | 4.5 BA | Sleeps 9 | Quick View

$233

per night

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Key Amenities

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

About this property

Monthly rentals only. 28 day minimum. This single family home is perfectly located in old town two blocks away from the southernmost point and one block away from Duval street. It has 4 bedrooms in the main house and a separate guest cottage with a bedroom and a full bathroom. It has two off street ...

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Property Type

Key West House

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Palm Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$471

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished with central ...

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Property Type

Key West House

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KEY WEST'S SUNSET MARINA CONDOMINIUMS ON THE WATER

$214

per night

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Key Amenities

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

About this property

Everything your would need to assure your Key West Vacation is a success is here at my Sunset Marina Ocean Front Condo. The best value-added feature of this property is it's unique location. Sunset Marina Residences are situated on a very narrow strip of land stretching out into the Gulf of Mexico. My ...

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Property Type

Key West Condo

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"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 1 miles to Fort Zachery Taylor State Park

$153

per night

View Details

Key Amenities

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

About this property

924 Southard Street... an Old Town cottage made famous by Country Home magazine! Featured in Country Home , in June 2001, this one-of-a-kind cottage was formerly owned and decorated by well known decorator Mary Emmerling. Southard Comfort is perfect for the guest who wants to feel like a local and enjoy ...

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Property Type

Key West House

"Great, authentic experience!"
Reviewed October 22, 2018

My husband and I had the best stay here! We loved the location, walkability, and charm of this home. You truly get the sense of what Key West is about by staying here. The owner is awesome and so accommodating- ...

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Private beach estate,gated,dock,and pool

$857

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys. 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 the Florida Keys has to offer. ...

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Property Type

Key West House

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Peaceful 2 BR Condo with All Amenities

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Smathers Beach

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Full 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

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

$193

per 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

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Vista Fresco

2 BR | 2 BA | Sleeps 4 | Quick View

$251

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst friendly neighbors. The 1800 Atlantic complex sits on 400 feet of oceanfront property. An expansive pool and spa sits ocean side, surrounded by a lushly landscaped garden of native Key West plants ...

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Property Type

Key West Condo

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Louisa House

4 BR | 3 BA | Sleeps 8 | Quick View

$551

per night

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Key Amenities

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

About this property

An absolutely perfect location, just a half a block off Duval Street and within walking distance to amazing restaurants, turquoise beaches and the Southernmost Point in the United States. Louisa House has it all for the perfect Key West vacation.A historic home with elegant curb appeal, Louisa House ...

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Property Type

Key West House

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Artist's House Duval Square

2 BR | 2 BA | Sleeps 6 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This 2 bedroom, 2.5 bath rooftop town home is located within the quaint community of Duval Square. Beautifully decorated with bright colors and unique art work, this property will give you a great Key West experience and is perfectly located right in the heart of old town Key West. Park your car in the ...

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Property Type

Key West Condo

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A Touch Of Cuba In Key West

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$250

per night

View Details

Key Amenities

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

About this property

Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque ...

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Property Type

Key West Condo

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La Brisa #403E Ocean Vista

2 BR | 2 BA | Sleeps 4 | Quick View

$203

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

La Brisa Beach Condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly ...

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Property Type

Key West Condo

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Coconut Cabana

3 BR | 2 BA | Sleeps 6 | Quick View

$425

per night

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Key Amenities

  • Air Conditioning
  • Private Pool

About this property

A quintessential "Old Town Key West" home, located in the Historic District and just one half a block off Duval Street.This charming home is within walking distance of dozens of restaurants, the Atlantic Ocean, the Southernmost Point and the sunset pier. Lovingly restored and cared for, ...

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Property Type

Key West House

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Townhouse, 1/2 Block from Duval in Old Town. Monthly Only

$100

per night

View Details

Key Amenities

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

About this property

Available for rent by the month, managed by owner. Located on a side street off Duval and Truman Avenue, this newly remodeled two story townhouse is one in a gated cluster of twelve surrounding a beautiful award winning courtyard. You are within walking distance of all the Key West attractions, yet ...

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Property Type

Key West Townhome

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Dreaming on Duval

5 BR | 4 BA | Sleeps 10 | Quick View

$1150

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Luxury on Duval Street in historic Key West? Luxury is not a word most people associate with Duval Street... until you look at Dreaming On Duval! There are very few private homes on this famous street, let alone a single-family, free-standing vacation rental that is just steps away from everything Key ...

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Property Type

Key West House

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La Brisa 405E Sea Orchid

2 BR | 2 BA | Sleeps 4 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is directly ...

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Property Type

Key West Condo

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Beach Club #408

4 BR | 3 BA | Sleeps 8 | Quick View

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the ocean ...

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Property Type

Key West Condo

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Namaste

1 BR | 2 BA | Sleeps 2 | Quick View

$260

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds: relaxing and taking advantage of all that Key West has to offer. Within 2 blocks ...

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Property Type

Key West House

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Havana Lane

2 BR | 2 BA | Sleeps 4 | Quick View

$352

per night

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Key Amenities

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

About this property

Havana Lane recalls a time in Key West's colorful history when cigar makers populated the neighborhood, gathering on their porch stoops to cool off and socialize with friends. Very close to the colorful Key West Cemetery, this classic Conch cottage embodies the essence of rustic charm while offering modern ...

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Property Type

Key West House

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Casa Atlantica Studio

Studio | 1 BA | Sleeps 2 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will find in ...

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Property Type

Key West Condo

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Southard Horse Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The Horse Conch is a one bedroom one bathroom suite in a house consisting of three vacation suites. Decorated with tropical color palette and has a queen bed. Accessed from the second floor covered porch that overlooks the shared gardens and pool below.

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Property Type

Key West House

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Beach Club #204

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.This is one of the most elegant and colorful 2 bedroom units in the Key ...

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Property Type

Key West Condo

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Simonton Studio, an Old Town get-away for 2

Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$138

per night

View Details

Key Amenities

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

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $45 * WiFi included * King size bed * Check-out cleaning included * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress for free ...

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Property Type

Key West Condo

"Excellent location - would definitely stay there again!"
Reviewed April 7, 2018

This little gem had everything we needed and was just perfect for a getaway for two. We appreciated the tips left by the owner, giving recommendations for dining and activities, and it was fun to have ...

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Duval Square Retreat

2 BR | 2 BA | Sleeps 4 | Quick View

$251

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Located in the heart of Old Town, Duval Square is a charming brick-paved and tree-lined courtyard complex located at the quieter end of Duval Street. The residential units are located upstairs, while quaint shops and restaurants occupy the courtyard below.This recently upgraded unit is tastefully ...

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Property Type

Key West Condo

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Key West Seashell Cottage - private home with spa, located on a quiet lane.

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.5 miles to South Beach

$186

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Forget that 'been there, done that' hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and 'Sunset Celebration'.The original local artwork throughout the ...

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Property Type

Key West Cottage

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Ann Street Cottage

1 BR | 1.5 BA | Sleeps 2 | Quick View

$237

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage, a charming one bedroom cottage.This quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within ...

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Property Type

Key West House

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Duval Square Courtyard Condo

3 BR | 2 BA | Sleeps 6 | Quick View

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

n the heart of Old Town and convenient to just about everything, this condo is set above a quaint brick and tree-lined courtyard that includes shops and restaurants. This three bedroom, two bath unit is in one of the only "stand-alone" buildings in the Duval Square complex. Simply walk down ...

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Property Type

Key West Condo

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Beach Club #104

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Unique oceanfront living only 65 feet from the Atlantic!The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit.The huge oceanfront balcony can be accessed from both the living/dining ...

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Property Type

Key West Condo

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Southard Rooster Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

On a lovely tree-lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. The two one bedroom suites are located on the second floor, ...

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Property Type

Key West House

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Paradise Place Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Open the door to Paradise Place and find yourself transported to a peaceful sanctuary.The downstairs living area is decorated with warm wood floors, blue and sand accents and provides plenty of space for entertaining. French doors lead out to a large covered and private patio area. The kitchen features ...

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Property Type

Key West Condo

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Luxury Shark Key waterfront home with beach 10 minutes from downtown Key West

$253

per night

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Key Amenities

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

About this property

Rentals are per calendar month only. WE HAVE A 28 DAY MINIMUM STAY PER MONROE COUNTY LAW, WE WILL NOT RESPOND TO REQUESTS FOR SHORTER PERIODS! 3 bedrooms 4 bath, sleeps 6 to 8, spectacular open water sunsets Enjoy the amenities of a luxury hotel in the privacy of our home located on the sunset side ...

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Property Type

Key West House

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Key West Vacation Rentals

Key West Weather

 | 

7524°  6518°
JANUARY
Ocean 7122°
7624°  6619°
FEBRUARY
Ocean 7122°
7926°  6921°
MARCH
Ocean 7323°
8228°  7222°
APRIL
Ocean 7825°
8529°  7624°
MAY
Ocean 8127°
8831°  7926°
JUNE
Ocean 8329°
8932°  8027°
JULY
Ocean 8530°
9032°  7926°
AUGUST
Ocean 8731°
8831°  7926°
SEPTEMBER
Ocean 8530°
8529°  7624°
OCTOBER
Ocean 8328°
8127°  7222°
NOVEMBER
Ocean 7826°
7725°  6719°
DECEMBER
Ocean 7524°

Stay steps from the sand in your Key West vacation rental

Relaxing, laid-back Key West calls to beach bums who prefer their landscape pristine and untouched. Key West is famous for watersports, nightlife, beaches and historic sites. Don’t miss Duval Street, one of the most energetic strips of shops, bars and cafes in Florida. Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere.

From a romantic bungalow for a couple to a house that can fit your entire family and more, the Key West house rentals are endless. When staying in one of our Key West vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our condos and villas even come with special amenities like a set of bicycles, chef’s kitchen, and in-home theater. Use the filters to narrow down your choices and choose the property that calls to you, just like Key West does.

Key West, Florida travel advice

Thanks to economic boom and a bustling cigar industry, this area's became quite a hot spot by the turn of the 20th century. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street. Located closer to Cuba than to Miami, Key West offers endless Latin and Cuban cultural influences from the cuisine to the music and art. Running four miles long and about two miles wide at its widest, this is a small island. The popular Old Town makes up about half of this area.

Climate

Abundant sunshine and gentle breezes make Key West one of the most popular tourist destinations in Florida. With over 320 sunny days per year you’ll most likely get the weather you want, no matter when you visit. Be sure to bring plenty of sunscreen and beach umbrellas as the UV rays can be quite strong here. The sea temperature is almost bath water and you’ll love the turquoise-blue color.

Top activities and attractions

Even getting to Key West is an adventure. The Overseas Highway is one of the most beautiful drives in the country. Completed in 1938, it connects a string of cays and coral rock with 113 miles of concrete roadway. The aptly named Seven Mile Bridge is the longest and most scenic of the entire route.

Key West’s diverse and unique ecosystems are a result of the convergence of two major bodies of water. There’s endless entertainment to be had on the ocean. You’ve got the deep blue Atlantic and its Gulf Stream current to the south and the shallow flats of the Gulf of Mexico to the west. From deep sea fishing to parasailing and even just body surfing, you’ll love a day out on the water in Key West.

Hop on the Conch Tour Train for a fun way to see the surrounding area. You’ll get a narration of the city’s past from an experienced tour guide as you cruise around the streets. Walking tours are one of the best ways to see the city, too. Peek in at the area’s intriguing architecture, courtyards, and gardens.

On the presidential side of life, don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset.

Dining and Nightlife

Over 300 restaurants and bars make this city one of the most fun places to be in southern Florida. For those with a sophisticated palate, try the highly-rated Bien restaurant to indulge in Latin & Cuban flavors. For great sandwiches and service, eat at the cleverly named Munch Box to break up your day of adventure. For Korean food that will make you scream “WOW”, pop in to Garbo’s Lunchbox. And lastly, for those who love to brunch, visit Key Plaza Creperie for delicious breakfast foods.

At night, Duval Street is the place to be. The Green Parrot is Key West’s oldest bar but it’s still a rockin’ atmosphere. Famed local Ernest Hemingway loved to get sauced at Sloppy Joe’s bar. (Don’t miss the Ernest Hemingway Home & Museum to get a closer look at what made this famous author tick.) For those who like the legitimate arts, take in a performance at Key West’s Fringe Theater, the Red Barn Theatre, or the Waterfront Playhouse.

For the kids, take the family to Mallory Square, where you’ll find local performers, plenty of fried food, and gorgeous sunset views.

Key West vacation homes on FloridaRentals.com

Vacation rentals in Key West on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!