Key West Vacation Rentals

(59 rentals)
Poolside Palms

2 BR | 2 BA | Sleeps 5 | Quick View

$268

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Key West Condo

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The 6 bedroom Duval Street Compound

6 BR | 7 BA | Sleeps 16 | Quick View

2

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1377

avg/night

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Key Amenities

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

About this property

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

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Property Type

Key West Villa

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

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

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2 Bedroom Townhouse Key West 10% off Available Dates Spring/Summer 2021

2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 2 miles to Smathers Beach

$169

avg/night

View Details

Key Amenities

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

About this property

Come stay in a premier development in Key West. This would be a great location to stay with a monthly 29 day rental minimum. Yearly rates available. You would be close to everything Key West has to offer and the peaceful serenity of your temporary home in Paradise. Our house offers many amenities to ...

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Property Type

Key West Townhome

"Three months in Paradise"
Reviewed April 1, 2021

The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific ...

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Beautiful Townhouse Awaiting Your Tropical Escape

2 BR | 2.5 BA | Sleeps 6 | Quick View

2

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

$299

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 ...

View all property information

Property Type

Key West House

"Kokomo Korner"
Reviewed February 1, 2021

Excellent location. Short walk or bike ride to Duval for shops and restaurants. Outdoor patio space is large, private and perfect for morning coffee or evening cocktails. Overall condition of the property ...

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

$393

avg/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

"What a beauty"
Reviewed April 6, 2021

We just got back from a week stay at this beautiful condo! My husband and I brought my daughter and her husband with us, and the private bedroom and bath arrangement was exceptional for 2 couples. Just ...

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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

$190

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 $75 * 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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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

1

$233

avg/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

"Perfect pet-friendly vacation cottage"
Reviewed March 2, 2021

The house is tucked away on a lane in Old Town within walking distance to everywhere. It is very private with lush plantings and a variety of outdoor spaces to sit. The house is well equipped and the owners ...

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Conch Cottage Key West's only real beach house

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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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

3

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$195

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 ...

View all property information

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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Cockadoodledo Vacation Rental. Featured On Hgtv***multiple Month Discount***updated

$319

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

$223

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

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Historic Studio on the Waterfront at the Red Doors

$104

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, and one of the best people watching front porches in Key West. Steps from the water, just 3 blocks from Duval street, and surrounded by ...

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Property Type

Key West Studio

"Key West Gem"
Reviewed April 10, 2019

We stayed at this property for 6 weeks. The location is awesome! It is steps away from the marina, a short walk to a small beach, and just several blocks from Duval Street. The location is also set in close ...

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

$195

avg/night

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Key Amenities

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

About this property

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

View all property information

Property Type

Key West Condo

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Bay Breezes

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Pet Friendly

About this property

Bay Breezes

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Property Type

Key West House

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Ocean Front-Top Rated- $1.5M Property - 90 FT BALCONY- Ocean View Every Room!!

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 30 feet to property 20 yards from ocean, 4 mile white sand be

$349

avg/night

View Details

Key Amenities

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

About this property

Virtual tourIn Key West - Not Islands Away * ** Ocean Front**Ocean View From Every Room *90' Scenic Balcony Huge 2200 Sq Ft under air.Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". (CFAR) /advisor/travel-insurance/cancel-for-any-reason/ In the ...

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Property Type

Key West Apartment

"Simply beautiful, great location!"
Reviewed January 18, 2021

Stunning views, next to a nature preserve; clean, functional, well-appointed condo. Short walk to the beach and easy bicycle ride to Duval. Overall Joe (the owner) was very reachable and helpful. Strongly ...

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

$303

avg/night

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Key Amenities

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

About this property

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

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Property Type

Key West Bungalow

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Beautiful Key West Golf Club -- Paradise Found

$174

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports and ...

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Property Type

Key West Townhome

"Peaceful, great location"
Reviewed January 25, 2021

Lovely house with a beautiful sunset view! Nice and quiet location with easy access to Key West by car, bike or walk. Recommended!

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YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

$171

avg/night

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Key Amenities

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

About this property

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

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Property Type

Key West Yacht

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

3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Higg's Beach

$247

avg/night

View Details

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

"Great home to enjoy Key West!"
Reviewed February 20, 2020

Four of us , and our dog, stayed at Lynda’s beautiful home in Casa Marina area. We had a wonderful month there. The location was great and quiet. We spent most of our time enjoying the covered deck ...

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Keys only real beach front home in the Keys

$536

avg/night

View Details

Key Amenities

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

About this property

Sea Vista EstateStay 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 ...

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Property Type

Key West House

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

$231

avg/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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Deluxe Key West Condo - Minimum 28 days Rental

$150

avg/night

View Details

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 Villa Key West's only real beach house, private and gated.

$393

avg/night

View Details

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

"It was perfect!"
Reviewed June 18, 2020

This is the perfect place for a quiet retreat. We loved the beach view, the house and the pool. The ocean breeze on the porch is heavenly. :)

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Peaceful 2 BR Condo with All Amenities

2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 1 miles to Smathers Beach

$213

avg/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

"Outstanding"
Reviewed August 2, 2020

The service at Sunrise Suites was amazing, everyone was so kind and helpful. The condo was perfect and featured amazing views from every window. The location was the perfect distance from the strip of Key ...

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A Thousand Hidden Hemingways

4 BR | 3 BA | Sleeps 10 | Quick View

$350

avg/night

View Details

Key Amenities

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

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny and bright, ...

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Property Type

Key West House

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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

$285

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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Private beach estate,gated,dock,and pool

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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Private beach estate. Gated, tropical peace and quiet. Dock

$336

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Key West House

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Private beach estate.Dock and pool

$407

avg/night

View Details

Key Amenities

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

About this property

The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just ...

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Property Type

Key West House

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

$117

avg/night

View Details

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

"Perfect vacation!"
Reviewed September 10, 2019

What a lovely stay - I heartily recommend and hope that I will be back in the future. The house was great, but I think the pool was my favorite place to be! Really enjoyed the owners’ thoughtful attention ...

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"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

5

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

$191

avg/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

"I wish I didn't write this review."
Reviewed February 25, 2021

Mainly because it will lessen our chances to get back here. My wife and I used to live in Key West for close to 10 years. We had our house and a couple of rental properties and vacation properties. Then ...

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Key West Old Town Sanctuary- Huge Private Pool- Quiet Lane- Monthly Rental

$217

avg/night

View Details

Key Amenities

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

About this property

Looking to ​ Relax Renew Recharge? We got you. Your own Key West Sanctuary awaits! Escape to a classic Conch family home perfectly tucked away for privacy yet, only 5 Blocks from famous Duval Street. The best of both worlds! Morning yoga class on the deck, late night dip in the pool, and sunset ...

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Property Type

Key West House

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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

$303

avg/night

View Details

Key Amenities

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

About this property

SUMMER/FALL SPECIAL. $ 1850/WK PLUS TAX AUG 14-22. 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 over sized two ...

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Property Type

Key West Condo

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Key West Beach Front Rental! Beach Studios Ocean views

Studio | 1 BA | Sleeps 3 | Quick View

3

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

$425

avg/night

View Details

Key Amenities

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

About this property

Welcome to; Key West Beach Front Rental Ocean view STUDIO See rates first**** save yourself some valuable *****time This is NOT A BUDGET STAY It is a romantic stay for two Ocean view in town of Key West UNMATCHED unless in 5 star resort with tons of faces everywhere!!! Our apartments ...

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Property Type

Key West Studio

"WONDERFUL!!!"
Reviewed August 16, 2020

This place is an ABSOLUTE DREAM!!! The studio is hidden from the street. The view is AWESOME!!! Walk out the door and BOOM your on the beach!!! The bikes are so fun, you are just a few pedals away from ...

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Bougainvillea Villa Key West MONTHLY RENTALS ONLY

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$359

avg/night

View Details

Key Amenities

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

About this property

COVID-19 UPDATE: Key West restaurants and bars are open. Masks are required at all times unless you are seated at a table in a bar or restaurant.MONTHLY RENTALS ONLY We purchased Bougainvillea Villa as our future retirement home. Since we are unable to visit as often as we’d like, we are ...

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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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Seaside Condo, May to November $1950 ( 6 month special)

$80

avg/night

View Details

Key Amenities

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

About this property

This lovely quiet sun filled resort apartment is located just across the street from Smather's beach and a ten minutes walk from Old Town. Artistically furnished and serviced by an elevator the apartment is located on the second floor facing southwest where you can enjoy a lovely view of the enormous ...

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Property Type

Key West Apartment

"Stepping into Paradise"
Reviewed October 17, 2017

I loved my stay in 219c Key West by the Sea! It was across the street from the beach where I could take morning walks seeing gulls and pelicans fishing for their breakfast. The apt. Is light, bright, and ...

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@ Best of the Annex Waterfront with Fantastic Weekly Rates @

$530

avg/night

View Details

Key Amenities

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

About this property

A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old militaryHospital building. In the mid 80's it was purchased by a developer who renovated the entire property in keeping with the existing architecture. ...

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Property Type

Key West Condo

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Keys to Paradise

3 BR | 2 BA | Sleeps 8 | Quick View

$285

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Key West Condo

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Geiger Key Waterfront

2 BR | 2 BA | Sleeps 7 | Quick View

$133

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean. ...

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Property Type

Key West Mobile Home

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Latitude Penthouse Key West B417

$383

avg/night

View Details

Key Amenities

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

About this property

Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently been renovated and features a new kitchen with granite counters, lovely open floor plan with vaulted ceilings. The elegant master bathroom has a spacious walk in shower. The master bedroom ...

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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

3

Distance to beach: 0.5 miles to South Beach

$184

avg/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 $75 * 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

"Highly Recommended!"
Reviewed March 30, 2021

The room was exactly like the photos. The room is airy, very clean, bed is super comfortable, nice roomy shower and has a full kitchen. The small patio was awesome too! The owner is great and available ...

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High Tide @

2 BR | 2 BA | Sleeps 6 | Quick View

$331

avg/night

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Key Amenities

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

About this property

1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 AtlanticPerfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully equipped eat in Kitchen, Washer/Dryer. Expansive private balcony overlooking the lush tropical ...

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Property Type

Key West Condo

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Blue Moonshine on the Atlantic Great Discounts until Feb 11th 2021

$420

avg/night

View Details

Key Amenities

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

About this property

Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full size fully equipped kitchen with a washer/dryer. Both bedrooms and the living room have impact doors open to your private balcony. There is a King bed in the master bedroom and a queen ...

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Property Type

Key West Condo

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Awake to the Morning Reflections OPEN MAY 2021 $3750 PLUS TAX & FEES

$145

avg/night

View Details

Key Amenities

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

About this property

Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk ...

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Property Type

Key West Condo

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Coral Hammock Poolside Home

3 BR | 3 BA | Sleeps 6 | Quick View

1

$379

avg/night

View Details

Key Amenities

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

About this property

This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a nice Kitchen for your use. High speed internet is available. There is a TV in ...

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Property Type

Key West Condo

"Southern Charm with a boat slip!"
Reviewed March 25, 2021

Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This ...

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Historical Tropical Hideaway

4 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 600 yards to Simonton Street Beach

$358

avg/night

View Details

Key Amenities

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

About this property

Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen and ...

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Property Type

Key West House

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Bay Pointe

3 BR | 3 BA | Sleeps 6 | Quick View

1

$161

avg/night

View Details

Key Amenities

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

About this property

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor ...

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Property Type

Key West House

"Soon to be there"
Reviewed January 3, 2021

I have not stayed there yet, but will gladly take $5 for this review. I hope is as nice as it its described

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Townhouse 1/2 block from Duval**

1 BR | 1.5 BA | Sleeps 6 | Quick View

8

$105

avg/night

View Details

Key Amenities

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

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price will generally be the same as for a comparable unit rented by the day for 10-14 days. It does however give you a lot more options and freedom.Located on a side ...

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Property Type

Key West Townhome

"Beautiful Stay!"
Reviewed September 6, 2020

This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...

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Casa Coastal East C231

2 BR | 2 BA | Sleeps 6 | Quick View

$258

avg/night

View Details

Key Amenities

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

About this property

Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its new owners. From new interior design work and furnishings, courtesy of Royal Furniture of Key West, to new closets, drapes and local art, includes works from the gallery of Alan ...

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Property Type

Key West Condo

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Ocean View condo steps to Smathers Beach

$214

avg/night

View Details

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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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!