Key West Vacation Rentals

(70 rentals)
Dos Casas - 2 Houses 2 blocks from Duval in beautiful Old Town -- Monthly Rental

$193

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Managed by Owner
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Bougainvillea Villa Key West-monthly rental on water with private pool & dock

Bougainvillea Villa Key West-monthly rental on water with private pool & dock

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$167

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Non-Smoking
  • Managed 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 ...

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Location Information

Key West, Florida, 33040

Property Type

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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Conch Cottage

Conch Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$414

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • 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 ...

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Location Information

Key West, Florida, 33042

Property Type

House

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SUNSET KEY, Villa Ambriana, LUXURY UPSCALE HOME RIGHT ON THE BEACH, 30 day stay

SUNSET KEY, Villa Ambriana, LUXURY UPSCALE HOME RIGHT ON THE BEACH, 30 day stay

3 BR | 2.5 BA | Sleeps 6 | Quick View

LAST MINUTE DEAL 12/1 - 12/29: Celebrate Christmas by the Ocean! Last minute, rent month of December at a discounted rate!

$399

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Beachfront
  • Oceanfront
  • Kid Friendly

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

House

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DEAL
Casa de Cuba

Casa de Cuba

3 BR | 2 BA | Sleeps 6 | Quick View

$501

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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The Duval Compound

The Duval Compound

6 BR | 6.5 BA | Sleeps 16 | Quick View

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1250

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

Villa

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Villa Serena Duval Square

Villa Serena Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Colony Sunset Suite

Colony Sunset Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$180

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Non-Smoking
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Townhouse, 1/2 Block from Duval Street in Old Town Key West

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Managed by Owner
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Town Home

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$1480 wk. AVAILABLE - NO DAMAGE FROM HURRICANE IRMA

$1480 wk. AVAILABLE - NO DAMAGE FROM HURRICANE IRMA

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Smathers Beach

$211

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Kid Friendly
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Southard Street - Queen Conch

Southard Street - Queen Conch

4 BR | 4 BA | Sleeps 8 | Quick View

$750

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Seaside Paradise monthly rentals- 2 pools, close to Old Town

$82

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Pet Friendly
  • Oceanfront
  • Communal Pool
  • Kid Friendly

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 ...

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Location Information

Key West, Florida, 33040

Property Type

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

A Touch Of Cuba In Key West

2 BR | 1 BA | Sleeps 4 | Quick View

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

$250

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Ann Street Tranquility

Ann Street Tranquility

1 BR | 1 BA | Sleeps 2 | Quick View

$236

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Smoking Allowed
  • Managed by Owner
  • Free WiFi

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” ...

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Location Information

Key West, Florida, 33040

Property Type

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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Beach Studio Key west Beach front rental! Ocean views

Beach Studio Key west Beach front rental! Ocean views

Studio | 1 BA | Sleeps 2 | Quick View

Distance to beach: 22 yards to Public and Resort

$249

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Oceanfront
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner

About this property

base rate Please {2 person stay} call for clarity, availability, ...under minimum stay, might fly fine! ask rate. Casa Marina District but ocean side {honestly a very rare find} Beach Studio Ocean views Ask what is avail for unit is available- go ...

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Location Information

Key West, Florida, 33040

Property Type

Studio

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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
  • Linens Provided
  • 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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

"Fabulous house!"
Reviewed October 1, 2018

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

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"Southard Comfort"

"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

3

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

$157

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed 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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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

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

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Private beach estate,gated,dock,and pool

$857

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool

About this property

2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of ...

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Location Information

Key West, Florida, USA

Property Type

House

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KEY WEST'S SUNSET MARINA CONDOMINIUMS ON THE WATER

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Oceanfront
  • Communal Pool
  • Managed by Owner
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Condo

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The Hamilton House

The Hamilton House

5 BR | 4.5 BA | Sleeps 9 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Owner

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

House

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Palm Villa

Palm Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$471

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • 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 ...

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Location Information

Key West, Florida, USA

Property Type

House

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Peaceful 2 BR Condo with All Amenities *** Free shuttle service ***

Peaceful 2 BR Condo with All Amenities *** Free shuttle service ***

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Smathers Beach

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Wheelchair Accessible
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Non-Smoking

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. ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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

$193

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed 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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Pete's West Cottage

Pete's West Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$236

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Deluxe Key West Condo - Minimum 28 days Rental

$150

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • 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 ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Havana Lane

Havana Lane

2 BR | 2 BA | Sleeps 4 | Quick View

$352

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Non-Smoking
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Simonton Studio, an Old Town get-away for 2

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

$152

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Non-Smoking
  • Managed by Owner
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

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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Villa Paradiso

Villa Paradiso

3 BR | 3 BA | Sleeps 6 | Quick View

$425

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

This mid-town Key West home is beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Southard Rooster Conch Suite

Southard Rooster Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

House

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CasaBella Duval Square

CasaBella Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

Located just steps from famous Duval street, this two-story town home is located in quaint, cobble stoned Duval Square. You are within the heart of the historic district and can walk almost everywhere. Although close to Duval, the home is a quiet escape ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Bali Hideaway

Bali Hideaway

Studio | 1 BA | Sleeps 2 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location.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 ...

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Location Information

Key West, Florida, 33040

Property Type

Studio

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Catherine House

Catherine House

2 BR | 2 BA | Sleeps 4 | Quick View

$309

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Non-Smoking
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Namaste

Namaste

1 BR | 2 BA | Sleeps 2 | Quick View

$260

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

House

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Vista Fresco

Vista Fresco

2 BR | 2 BA | Sleeps 4 | Quick View

$251

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Pete's East Cottage

Pete's East Cottage

2 BR | 1 BA | Sleeps 4 | Quick View

$233

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

View all property information

Location Information

Key West, Florida, 33040

Property Type

House

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Beach Club #408

Beach Club #408

4 BR | 3 BA | Sleeps 8 | Quick View

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Paradise Place Duval Square

Paradise Place Duval Square

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Beach Club #103

Beach Club #103

2 BR | 2 BA | Sleeps 6 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Oceanfront
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Coconut Cabana

Coconut Cabana

3 BR | 2 BA | Sleeps 6 | Quick View

$425

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

House

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La Brisa #403E Ocean Vista

La Brisa #403E Ocean Vista

2 BR | 2 BA | Sleeps 4 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Southard Queen Conch Suite

Southard Queen Conch Suite

2 BR | 2 BA | Sleeps 4 | Quick View

$280

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

Southard Street Downstairs Queen Conch is a two bedroom two bathroom retreat in a house consisting of three vacation suites. Open floor plan with French doors that open to the large shared sunny pool surrounded by beautiful landscaped garden.

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Location Information

Key West, Florida, 33040

Property Type

House

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A Touch of Bermuda at Truman Annex

$257

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • Managed 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 ...

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Location Information

Key West, Florida, USA

Property Type

Cottage

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Louisa's Hideaway

Louisa's Hideaway

3 BR | 3 BA | Sleeps 6 | Quick View

$551

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

Tucked away near the quite end of Duval Street, you'll find this stylish, newly renovated, three bedroom, three bath home. Thoughtful details are luxuriously appointed to appeal to the traveler looking for privacy, style and elegant design.Walk up ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Pete's Cottages

Pete's Cottages

4 BR | 2 BA | Sleeps 8 | Quick View

$477

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

House

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Southard Horse Conch Suite

Southard Horse Conch Suite

1 BR | 1 BA | Sleeps 2 | Quick View

$202

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

House

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Beach Club #304

Beach Club #304

2 BR | 2 BA | Sleeps 4 | Quick View

$275

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water as few do in Key West. The breathtaking view can be seen as soon as you enter this spacious 2 bedroom ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Ann Street Cottage

Ann Street Cottage

1 BR | 1.5 BA | Sleeps 2 | Quick View

$237

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Free WiFi

About this property

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

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Location Information

Key West, Florida, 33040

Property Type

House

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Historic Studio on the Waterfront at the Red Doors

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Free WiFi

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 ...

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Location Information

Key West, Florida, 33040

Property Type

Studio

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Shipyard Palms

Shipyard Palms

2 BR | 1.5 BA | Sleeps 4 | Quick View

$203

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

In the heart of old town Key West, nestled within the secluded and lush community of private homes and condominiums of Truman Annex, this Shipyard Condominium has convenient access to both the gorgeous Fort Zachary State Park Beach and historic old town ...

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Location Information

Key West, Florida, 33040

Property Type

Condo

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Key West Vacation Rentals

Local Weather

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7524°  6518°
JANUARY
Ocean 7122°
7624°  6619°
FEBRUARY
Ocean 7122°
7926°  6921°
MARCH
Ocean 7323°
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APRIL
Ocean 7825°
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MAY
Ocean 8127°
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JUNE
Ocean 8329°
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JULY
Ocean 8530°
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AUGUST
Ocean 8731°
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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!