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Key West Vacation Rentals

(73 rentals)
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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$314
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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$1,068
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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$362
avg per night
Key West House
Sleeps 8, 3 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

TRANQUIL BEAUTY: 3 BR’s, 2 Baths Private Haven paradise with huge private heated pool and landscaped back yard!ENJOY KEY WEST at its peaceful best in your 3BR, 2 bath private hideaway in a quiet neighborhood near Higgs and Smathers beaches and only a 10 minute bike or Uber ride from Duval Street....

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Featured review

"Wonderful"

Wonderful home, amazing response for any needs, great pool and parking. The covered porch (lanai) expanded the living space. We had an all around great experience. We will be back in the future!

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$283
avg per night
Key West House
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Pool
  • WiFi

About this property

Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to Community PoolWelcome to Coral Hammock, your home away from home in beautiful Key West! Built in 2004 and meticulously maintained, this spacious 3-bedroom, 3-bathroom home...

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Featured review

"Southern Charm with a boat slip!"

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

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$467
avg per night

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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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New
Key West Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

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

"Incredible Ocean View!"

Beautiful Condo Oceanview with beach across the street large heated Pool ! Family Friendly and great location Quiet and centrally located We will be Back!

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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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$500
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 Studio
Sleeps 3, 0 bedrooms, 1 bathroom
7 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!Is no other spot with this...

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Featured review

"A Wonderful vacation stay"

We found the perfect location for our stay in key west. Away from all the hustle and bustle but close enough to visit all the hot spots. Within walking distance to several great restaurants and coffee shops....

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$562
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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$251
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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$710
avg per night
New
Key West House
Sleeps 4, 4 bedrooms, 3 bathrooms

Distance to beach: 2 miles to Smathers

Key Amenities

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

About this property

Available for 28 night stays only, due to Key West regulations so the rate for the month is for 28 nights, not 29 or 30 nights as we need to be able to get people in to do things/maintenance in between guests. In high season If you are renting for one month only the stay would start on the 1st and end...

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$333
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 Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • 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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$162
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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$186
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
New
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom

Distance to beach: 0.4 miles to Fort Zachary Taylor State Park

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Key West is a little piece of the Caribbean, always warm with lovely turquoise waters. It's a short walk to Mallory Square, Hemingway's Home, the Truman White House, Duval Street and Zachary Taylor Park ( do yoga on the beach, swim, snorkel, or hang hammocks between the palms). Walk to...

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$165
avg per night
Key West Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private 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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$690
avg per night
Key West House
Sleeps 10, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, friendly lane with two parking spaces right in the middle of all the action. Four bedrooms (one king and three queens) - each with their own attached bathroom - plus a half bath on the...

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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, June 19, 2026.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 to the unit...

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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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$1,828
avg per night
Key West Condo
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment * King size bed in the bedroom *accommodates 2 adults only * WiFi inlcuded * Parking included *Central AIr Conditioning * Check-out cleaning is $120 * This is not a hotel; it is a privately owned condo facing the...

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Featured review

"The perfect location that has everything..."

Just finished a 2 week stay and I have been renting from Pam for over a decade and she continues to make a great condo even better with her constant upgrades to the unit and she is a wonderful host. The...

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$348
avg per night
Key West Condo
Sleeps 4, 2 bedrooms, 1 bathroom
2 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 GuestsWelcome to Innis-free, our little slice of paradise in Key West—where you're greeted with Céad Míle Fáilte, an Irish expression meaning “a...

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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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$1,323
avg per night
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Key West Weather

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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 73 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 $376.

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 33 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 14 oceanfront rentals in Key West available on FloridaRentals.com. Use our filters to search and book yours today!