Key West Vacation Rentals

(48 rentals)
Beautiful Key West Home located in Golf Course community

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 2 miles to Smathers Beach

$214

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

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Property Type

Key West Townhome

"The best of the best!!"
Reviewed January 20, 2020

The owners are amazing to work with. The house is newly remodeled and furnished. It was just perfect for 4 people and we had a wonderful time! We were just a few minutes to great restaurants on Stock Island ...

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

$270

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 ...

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Property Type

Key West Condo

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

$278

avg/night

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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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Cockadoodledo

4 BR | 4 BA | Sleeps 10 | Quick View

$439

avg/night

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Key Amenities

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

About this property

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

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Property Type

Key West House

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Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$242

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 $45 * 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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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

3

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$276

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 ...

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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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The 6 bedroom Duval Street Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

2

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1820

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

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

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Property Type

Key West Villa

"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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Key West Luxury Resort Home with pool

4 BR | 3 BA | Sleeps 10 | Quick View

1

Distance to beach: 2 miles to Smarthers Beach

$300

avg/night

View Details

Key Amenities

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

About this property

Large 4 bedroom home in the center of Key West, only minimum 28 days stay, walk to shopping center, restaurant and water sports.1/1 in the first floor with a large gourmet kitchen, a very large master bedroom with a large balcony overlooking the pool, 2 bedrooms in the other side sharing a bathroom.Very ...

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Property Type

Key West House

"Loved everything about this place !!!"
Reviewed February 2, 2020

Wonderful place !! Our family had the best Christmas in Summerland keys! Loved all the wall art so we purchased the same ones

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Bluegrass Seabattical oceanfront retreat

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 150 yards to Smathers Beach

$454

avg/night

View Details

Key Amenities

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

About this property

Bluegrass Seabbatical is a Spectacular 3 bedroom 2 bath oceanfront condominium at 1800 Atlantic. Enjoy the incredible ocean front view from all 3 bedrooms and the living room. This property is close to 2000 sq feet and can be your fantastic home away from home. Available for extended stays during the ...

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Property Type

Key West Condo

"Amazing Views"
Reviewed March 4, 2020

This condo has the most beautiful views. I also love the full kitchen and ammenities. Perfect for a relaxing getaway with a huge balcony overlooking the ocean.

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Poolside Paradise @ , beach & Duval St.

$387

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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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

$285

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

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Property Type

Key West House

"Beautiful Bougainvillea Villa"
Reviewed February 27, 2018

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

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Paradise Awaits! Enjoy you stay in our spacious Shipyard Condo!

$267

avg/night

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Key Amenities

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

About this property

This second floor 920 sq ft condo is unique to the Shipyard community in that it is larger if not the largest condo there. It is an end unit so it is bright and airy. The great room has 25’ cathedral ceiling, two sets french doors to the balcony that overlook the community pool. Kitchen, dining ...

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Property Type

Key West Condo

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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

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

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

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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

$433

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

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Conch Cottage Key West's only real beach house

$414

avg/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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Ocean Front with Ocean View. Across from Smathers beach. Sleeps 5, 2/2 baths.

$338

avg/night

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Key Amenities

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

About this property

"Kokomo" is what we have named our unit. It is a 2 bedroom 2 baths with queen sleeper sofa in living room. Central AC in unit, clean unit, living/dinning is open concept. Master bedroom with a king bed, with private bathroom and access to balcony. W/D in unit, full kitchen, beach towels, reg ...

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Property Type

Key West Condo

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Beautiful Townhouse Awaiting Your Tropical Escape

2 BR | 2.5 BA | Sleeps 6 | Quick View

1

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

$417

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

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

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

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Pearl of Key West

3 BR | 2 BA | Sleeps 6 | Quick View

$141

avg/night

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Key Amenities

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

About this property

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

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Property Type

Key West House

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

$370

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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Duval Balcony Rentals - Suite Mischief

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 1 miles to Fort Zachary Taylor, Higgs Beach, Smathers Beach

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

Located in the heart of Key West, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. For Fantasy Fest, this property offers an ideal location from where you can enjoy ...

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Property Type

Key West Apartment

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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

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

$605

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. **SPECIAL REDUCED RATES FOR ANNUAL, OR OTHER LONG TERM RENTALS **** Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". ...

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Property Type

Key West Apartment

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YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

$171

avg/night

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Key Amenities

  • Beachfront
  • Oceanfront
  • Private Pool

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

$319

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

1 BR | 1 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 11/29 - 12/1: 3 night minimum stay $160.00 a night plus taxes and cleaning fee!

$278

avg/night

View Details

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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DEAL
Deluxe Key West Condo - Minimum 28 days Rental

$217

avg/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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Private beach estate,gated,dock,and pool

$847

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

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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

$315

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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Private beach estate.Dock and pool

$460

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

$367

avg/night

View Details

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

$471

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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Beautiful Key West Golf Club -- Paradise Found

$180

avg/night

View Details

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

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

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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Keys only real beach front home in the Keys

$686

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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"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

4

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

$301

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

"Loved It"
Reviewed February 20, 2019

We've been coming to Key West almost every year since 1986, staying for longer visits as we've left more and more of work behind. We spent a month here in 2018 and loved it. Due back this April. The front ...

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Historic Studio on the Waterfront at the Red Doors

$148

avg/night

View Details

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

$394

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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Bay Pointe

3 BR | 3 BA | Sleeps 6 | Quick View

$160

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

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A Touch of Bermuda at Truman Annex

2 BR | 2 BA | Sleeps 6 | Quick View

1

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

$350

avg/night

View Details

Key Amenities

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

About this property

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 town home (one of only seven available for ...

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Property Type

Key West Cottage

"A Touch of Bermuda"
Reviewed August 19, 2019

Jack is an excellent host! We were there all week and had a great time with the location of this house. We were able to walk everywhere.

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Seaside Condo, DECEMBER SPECIAL

1 BR | 1 BA | Sleeps 2 | Quick View

1

$125

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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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

$307

avg/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 over sized two bedroom, one bathroom condominium is located on picturesque ...

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Property Type

Key West Condo

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Ocean View condo steps to Smathers Beach

$284

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • 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 * queen size sleeper sofa in the living area *accommodates 2 adults of family of 4 * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning included * This ...

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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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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

$242

avg/night

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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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MV Coconuts

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 20 yards to Private beach at Marina

$300

avg/night

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Key Amenities

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

About this property

Beautiful fully furnished floating home. Coconuts is a sturdy steel hull Florida Bay Coaster. She is safely located at the Stock Island Yacht Club and Marina. In a convenient slip. Full marina amenities including pool, grounds, gated and free parking, laundry steps nearby. Full size refrigerator, dishwasher, ...

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Property Type

Key West Houseboat

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Spend January in townhouse 1/2 block from Duval**

$202

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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Geiger Key Waterfront

2 BR | 2 BA | Sleeps 7 | Quick View

$133

avg/night

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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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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

$416

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 Ocean view in town is next to nil unless in 5 star resort with full house!!! come enjoy serenity views pelicans - beach and people watch ...

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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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Truman Annex, Large Outdoors Beautiful Spacious 1st Flr, 2BR KING/twins, Pool

$332

avg/night

View Details

Key Amenities

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

About this property

Hello out there: KEY WEST IS OPEN! TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors. Our fantastic cleaner has been with us for years. We are following CDC guidelines for ...

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Property Type

Key West Condo

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Heart of Downtown Key West Cottage With Off-Street Parking

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

A Historic Cigar-Makers Conch Home, privately owned by a native hospitable family in the heart of Downtown, a few minutes walk from Duval St. Accommodates 1-2 couples. Your car will be safe in this parking spot, nowhere near the street. The Cottage is set back from the sidewalk so you are not subjected ...

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Property Type

Key West Cottage

"Perfect for our stay"
Reviewed September 10, 2020

Thank you to our hosts, Hugh and Yaya, were so sweet. They went out of their way to make us feel welcome. The location was perfect. We loved the back porch that we spent time relaxing in the morning and ...

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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!