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Key West Vacation Rentals

(74 rentals)
Key West Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy the ocean views from this beautifully appointed condo in the exclusive Key West Beach Club.This two-bedroom, two and half-bath waterfront condo that has been newly renovated with casual furnishing and all the comforts of home: central air conditioning, cable TV, washer/dryer, Wi-Fi, and a fully-equipped...

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$400
avg per night
Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through the Spring of 2026. This construction WILL impact your stay if you are staying during the week days. Please contact All Florida Keys Property Management for more detailed information....

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$163
avg per night
Key West Condo
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

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$606
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

Construction Notice – La Brisa Condominium March 2, 2026 through, May 1, 2026 (East Building) Construction is underway in the East Building to repair walkway spalling. Some construction noise may occur during your stay.Elevators are currently unavailable due to repairs and modernization. Access...

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Featured review

"Vacation"

Very thing was good the condo was perfect and the pool was great the parking was close to the elevator

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$200
avg per night
Key West Cottage
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Charming Pool Cottage in the Heart of Old Town Key WestPerfectly situated in historic Old Town Key West, this quaint and inviting pool cottage offers the ideal island escape for a couple, with room for occasional guests. Thoughtfully decorated and impeccably maintained, the home features a newly renovated...

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$200
avg per night

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Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Shipyard Pool Closure The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. We expect the project to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026.Best Deal in Truman Annex – Céad Míle...

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Featured review

"Great vacation rental!"

We really enjoyed the unit at Shipyard Condos. Very clean and well equipped. Walking distance to local restaurants and very convenient with a dedicated parking place. Pool was nice too. There were only...

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$285
avg per night
Key West Cottage
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.As...

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$231
avg per night
Key West House
Sleeps 8, 3 bedrooms, 2 bathrooms
3 reviews

Distance to beach: 2 miles to Smarthers Beach and Higgs Beach

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding trim. Open living room and...

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Featured review

"Island Paradise in Beautiful Key West"

Sunshine House on Harris Street, Key West is a Home away from Home. We enjoyed 2 months of comfort and convenience at this home. The home is furnished with tasteful Island Decor. The layout is 3 bdrms...

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$167
avg per night
Key West House
Sleeps 8, 2 bedrooms, 2 bathrooms

Distance to beach: 0.8 miles to Simonton Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

AboutClassic Old Key West HomeThis home offers a rare combination of location, charm, and character. With a beautiful mix of historic details and modern updates throughout, it’s perfect for couples traveling together or anyone hosting visitors during their stay in paradise.Primary guest...

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$258
avg per night
New
Key West Cottage
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 0.5 miles to Simonton Street Beach

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Welcome to the Dancing Rooster, your charming retreat just 2 blocks from Duval Street in the heart of downtown Key West! Nestled within the historic Simonton Cottage enclave, our recently renovated 3-bedroom, 2-bath home offers the perfect blend of comfort and convenience. You’ll be surrounded by...

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$475
avg per night
Key West Condo
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

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$537
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen...

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$172
avg per night
Key West House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

Very good location in Big Pine, deer paradise, a very quiet place to relax and rest if what you want is incredible peace to relax, believe me, this is your place, lots of outdoor space, the house is on a corner, very cozy inside and out, outdoor hammocks, many places to sit and spend a lovely afternoon...

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$183
avg per night
Key West Condo
Sleeps 2, 0 bedrooms, 1 bathroom
7 reviews

Distance to beach: 0.5 miles to South Beach

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 *Cleaning fee of $90 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress...

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Featured review

"Perfect little getaway for two!"

Fabulous location, great host. Awesome little getaway just big enough for two. Pam is great to work with.

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$201
avg per night
Key West House
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This nicely appointed home is located in Key Haven subdivision of fine homes. It offers an expansive living room with upgraded kitchen and appliances. The kitchen is nicely stocked with plenty of room for multiple cooks. The house can accommodate up to six people with 3 bedrooms and 2 full bathrooms....

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Featured review

"Serene and comfortable"

We absolutely love this home! The interior features plenty of space and storage. The kitchen is well equipped with everything you need and more. The bedrooms very comfortable. The shower in the master has...

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$183
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Hot tub
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

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$158
avg per night
Key West Apartment
Sleeps 2, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. Everything you will need for your perfect Key West extended stay. 1 assigned parking space with the apartment. Full kitchen and washer dryer, Central AC and wifi access. The owners have...

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$125
avg per night
Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 Please be advised that a balcony restoration project will be underway at 1800 Atlantic from May 2025 through Spring 2026. Important Notes: -Units available for booking will...

View all property information

$524
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom

Distance to beach: 0.4 miles to Fort Zachary

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Escape the winter and settle into this beautifully renovated 2-bedroom, 1-bath condo in the heart of Old Town Key West — perfect for snowbirds and monthly renters seeking the ideal balance of tranquility and convenience. Located in the prestigious gated community of Truman Annex at the Shipyard...

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$175
avg per night
Key West House
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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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Featured review

"Soon to be there"

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

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$212
avg per night
Key West Studio
Sleeps 3, 0 bedrooms, 1 bathroom
8 reviews

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

Key Amenities

  • Air conditioning
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

This beach view is beautiful and apartment in town can be yours! Just Blocks from downtown Key West? Yes! LIKE NO-WHERE ELSE! Like no where else in Key West, do Come + have YOUR, OWN OCEAN VIEWS! Yes! Secluded but not isolated? Yes! HURRY Check Calendar BOOK SOON! MARCH DISCOUNT LAST OPENING!...

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Featured review

"Amazing location!"

Our stay at the studio was lovely. The proximity to the ocean and beach cannot be beat. The place was very clean, well appointed, comfortable, and creatively decorated too. Our host was very responsive...

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$536
avg per night
New
Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Sammy's Hideaway is located in a gated community with easy beach access. This 2 bedroom/2 bath condo faces the Atlantic Ocean offering wonderful ocean breezes and an oversized balcony with dining set. The open style living room has glass slider doors that invite in mother nature's hues. Full...

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Featured review

"Beautiful Apartment"

We stayed at 102 S at LaBrisa for Halloween. The apartment was clean and absolutely gorgeous. The view of the Atlantic Ocean was breathtaking. The pool was clean with warm salt water. The grounds were very...

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$160
avg per night
Key West Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to your Key West escape! Nestled in the heart of 'Old Town', this charming townhouse is part of a wonderful twelve townhouse community with a lush, tropical garden courtyard that provides a tranquil, resort-like feel. You're just a half-block from the quiet end of Duval Street,...

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$150
avg per night
Key West Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

The Mile Zero House is a MONTLY VACATION RENTAL. Rent one or more months comes completely furnished. Charming conch home with true Key West character. Fenced for privacy with a open style front porch to enjoy the local flavor along with a passing Conch Train. Full size kitchen that is nicely stocked with...

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Featured review

"Amazing Location!"

Historic Conch House Located Downtown Key West near Duval St and restaurants beach and many attractions ! Private Yard fully locked and fenced with beautiful plants Sitting on the front Porch you feel...

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$150
avg per night
Full map
Map

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°

FAQ

How many vacation rentals are there in/around Key West?

There are 74 Key West acation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Key West?

There are vacation rentals available in Key West for as low as $120 per night with an average price per night of $258.

Can I find a vacation rental in Key West?

Yes, you can find vacation rentals in Key West close to Dry Tortugas National Park, Ernest Hemingway Home, and Ley West Butterly and Nature Conservatory. Don't forget to stop in to Mallory Squrre or Duval Street.

Do any vacation rentals in Key West have a pool?

Yes, there are 32 vacation rentals with a pool in Key West on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Key West vacation rentals on the ocean?

There are 13 oceanfront rentals in Key West available on FloridaRentals.com. Use our filters to search and book yours today!