Key West Vacation Rentals

(86 rentals)
2 BR, 2 BA Oceanfront Oasis On The Beach in Key West

$714

per night

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Key Amenities

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

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Spectacular 2 BR Luxury Villa On The Beach with Spectacular Open Water View of ...

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Property Type

Key West Villa

"great vacation spot"
Reviewed February 24, 2018

This condo was wonderful. It was clean, very well equipped, the complex had great amenities and the agent was very attentive. the location was convenient to beaches and town via bike path. The pool and ...

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4 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$681

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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Sea Watch 3 BR Open Water Luxury Penthouse - Ask About Our Specials!

3 BR | 3 BA | Sleeps 7 | Quick View

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$714

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.These 2 BR and 3 BR Open Water View Villas boast the single Finest Location in ...

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Property Type

Key West Villa

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3 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$633

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval Street and just 5 tiny tropical island sized ...

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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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Cockadoodledo

4 BR | 4 BA | Sleeps 10 | Quick View

$300

per night

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Key Amenities

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

About this property

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

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Property Type

Key West House

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

$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

"Paradise in the Keys!!"
Reviewed April 7, 2019

Our vacation to Sugarloaf Key was amazing!! The location is perfect with stunning views of the water. The fishing off the pier was good. You could catch all the Snapper you wanted. The beach area was ...

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Historic Studio on the Waterfront at the Red Doors

$100

per 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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2 BR, 2 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$425

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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3 BR, 2 BA Oceanfront Oasis On The Beach in Key West

$964

per night

View Details

Key Amenities

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

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Spectacular 3 BR Luxury Villa On The Beach with Spectacular Open Water View of ...

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Property Type

Key West Villa

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Sea Watch 2 BR Open Water Luxury Penthouse - Ask About Our Specials!

2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$500

per night

View Details

Key Amenities

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

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.These 2 BR and 3 BR Open Water View Villas boast the single Finest Location in ...

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Property Type

Key West Villa

"Sundown Refuge"
Reviewed November 18, 2019

We had a great family vacation. The condo had everything you would need. Just like being at home but with much better weather.

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Pearl of Key West

3 BR | 2 BA | Sleeps 6 | Quick View

$1

per night

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Key Amenities

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

About this property

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

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Property Type

Key West House

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The 6 bedroom Duval Street Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1250

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals by Owner

About this property

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

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Property Type

Key West Villa

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2 BR, 1 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$393

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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Conch Cottage Key West's only real beach house

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

$1

per night

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Key Amenities

  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

Located within the gated community of Truman Annex, you are just steps away from the new Truman Waterfront Park and only 2 blocks from the famous Duval St. Enjoy the heart of Old Town Key West and all its charms! Stroll or bike to many of the historic sites such as Hemingway House and Little Truman White ...

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Property Type

Key West Condo

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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

$160

per night

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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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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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4 BR, 3 BA Margaritavilla Beach Cottage in Old Town - Ask About Our Specials!

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 0.2 miles to Fort Zachary Taylor Park & Beach

$697

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts.Located just 2 blocks off Duval Street and just 5 tiny tropical island sized ...

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Property Type

Key West Villa

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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

$233

per night

View Details

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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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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1 BR Margaritavilla Beach Cottage at Fort Zachary Taylor - Discounts Available!

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$236

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

IMPORTANT: A Phone Number Is Required for service. By providing your phone number, we can offer you a weekly stay at a rate equivalent to 5 nights rent. Inquiries without a phone number will not qualify for any discounts. Located just 2 blocks off Duval Street and just 5 tiny tropical island sized ...

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Property Type

Key West Cottage

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

$393

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

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

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Property Type

Key West Townhome

"Another Wonderful Week at the Island Queen!!"
Reviewed June 27, 2019

I believe this was our 5th or 6th year we've stayed at the Island Queen and we are never disappointed. Thanks to Rosemary and Mark's meticulous care of their home, there are never any surprises. This ...

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Beautiful Key West Home located in Golf Course community

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 2 miles to Smathers Beach

$169

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Key West Townhome

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

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

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Upscale Home in Truman Annex!

1 BR | 1 BA | Sleeps 3 | Quick View

1

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$1

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Key West Condo

"Destination Wedding/Honeymoon"
Reviewed January 11, 2020

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

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6 BR, 5.5 BA Luxury Key West Beach House in Old Town at Fort Zachary Taylor

6 BR | 5.5 BA | Sleeps 10 | Quick View

Distance to beach: 0.1 miles to Fort Zachary Taylor Park & Beach

$1929

per night

View Details

Key Amenities

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

About this property

This Luxury 6 BR, 5.5 BA Ocean View Private Pool Home is one of the finest rentals to ever become available in Key West and is crawling distance to everything you are coming to Key West for, including just one home away from entering Fort Zachary Taylor Park & Beach. Duval Street is just 3 blocks ...

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Property Type

Key West House

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"RARE CANCELLATION -FEB.-MARCH OPEN !" -OCEAN FRONT! 90 FT BALCONY- Ocean View!!

3 BR | 2 BA | Sleeps 6 | Quick View

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

$206

per night

View Details

Key Amenities

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

About this property

Military Vouchers Welcome! In 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 ****OCEANFRONT… There is nothing like it. To me, it means being directly ...

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Property Type

Key West Apartment

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Ann Street Tranquility

1 BR | 1 BA | Sleeps 2 | Quick View

1

$236

per night

View Details

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

"Charming and Cozy Villa"
Reviewed December 16, 2019

We are so glad we chose Ann Street Tranquility to stay in during our week long vacation the first week in December. It was a very peaceful villa with all the amenities one needs, and on top of that, within ...

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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

$4

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Key West House

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

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

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Private beach estate,gated,dock,and pool

$743

per 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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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

$283

per night

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Key Amenities

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

About this property

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

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Property Type

Key West House

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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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YKNOT CHARTERS, ON AND OFF DOCK CHARTERS

$171

per night

View Details

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

1

Distance to beach: 0.5 miles to Higg's Beach

$213

per 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

"“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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Beautiful Key West Golf Club -- Paradise Found

$180

per 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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Peaceful 2 BR Condo with All Amenities

2 BR | 2 BA | Sleeps 6 | Quick View

1

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

"Key west vaca"
Reviewed March 8, 2019

We enjoyed our stay. The condo was very comfortable and met our needs. Thanks Lordes for all your help locating an available unit.

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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

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

$193

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

$183

per 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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Deluxe Key West Condo - Minimum 28 days Rental

$150

per 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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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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Havana Lane

2 BR | 2 BA | Sleeps 4 | Quick View

1

$352

per night

View Details

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

"Best hidden treasure in Key West!"
Reviewed July 11, 2019

We absolutely LOVED it! One Havana Lane will be forever in our best memories of our time spent in the Keys! The pool was perfect and we enjoyed the few entertaining iguanas. The house was laid out so that ...

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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

$142

per 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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Colony Poolside

1 BR | 1 BA | Sleeps 2 | Quick View

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Poolside is a peaceful retreat. Enter the home through the serene and inviting living space, accented with blue and white decor, wood floors and pops of color from nautical-themed accents and artwork. A vaulted ceiling with ...

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Property Type

Key West House

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Pete's Cottages

4 BR | 2 BA | Sleeps 8 | Quick View

$477

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

These twin homes have the charming original style of the Key West "shot gun" cottages and have been restored with a beautiful natural cypress exterior. Each cottage opens to it's own semi-private deck and lounge area with access to a large free-form pool with waterfall.Inside, the comfortable ...

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Property Type

Key West House

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Catherine House

2 BR | 2 BA | Sleeps 4 | Quick View

$309

per night

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Key Amenities

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

About this property

This charming Key West cottage is just a short walk to a selection of great restaurants, art galleries, and shopping.Catherine House is located only ½ block from the quieter end of Duval Street, and better yet, just three blocks to a beach (Duval & South Streets). The house can comfortably ...

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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

$300

per 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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Dreaming on Duval

5 BR | 4 BA | Sleeps 10 | Quick View

$1150

per night

View Details

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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Colony Calypso

1 BR | 1 BA | Sleeps 2 | Quick View

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Located in The Colony, a secluded compound just steps from Duval Street, Colony Calypso is a peaceful retreat. Enter the home through the tranquil and inviting living space, accented with sage green walls, new tile floors and pops of color from local artwork and photography. A vaulted ceiling with exposed ...

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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!