Key West Vacation Rentals

(83 rentals)
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Key Amenities

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

About this property

The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroom. It is light and airy, with gorgeous and comfortable indoor and outdoor living spaces. It's perfect for family gatherings, or just a quiet escape. Each room is sunny ...

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Property Type

Key West House

"Beautifully Appointed Historic Home in Old Town"

I really can't rave enough about this home and the hospitality of the owners. The house is a beautiful historic home in old town that has been lovingly restored. The outdoor living space and the open to ...

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2 BR | 2.5 BA | Sleeps 4 | Quick View

$450

avg/night

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Key Amenities

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

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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Property Type

Key West Condo

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$477

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just ...

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Property Type

Key West House

"WonderfUll"

The heated pool, tiki bar and view of the ocean was just beautiful as "out of a storybook. The eggs and a home made lime pie from Carol (owner) was a nice surprise. The house was plenty big enough to house ...

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2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.8 miles to Fort Zachary Taylor State Park and Beach

$310

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Our condo has always received great reviews on cleanliness and the bright citrus pallet is welcoming, there are 2 bedrooms (1 King & 1 Queen), one bathroom with couples walk in shower, The small but ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Great location!"

We loved this house at the end of a quiet lane. Huge pool! The location was perfect, walking was easy to so many places. Fully fenced and a small backyard made it perfect for our dog. And the shower ...

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4 BR | 2 BA | Sleeps 8 | Quick View

last minute deal
LAST MINUTE DEAL 4/4 - 5/16: 15% OFF Monthly Stay - Steal Sept in Old Town Key West

$376

avg/night

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Key Amenities

  • Air conditioning
  • 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 discerning travelers for over 15 years. Our guests come back over and over, finding the comfortable spaces, stocked with amenities and ideal location the perfect spot to enjoy all that Key West has to offer.Dos ...

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Property Type

Key West House

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DEAL

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Public Beach is Smathers

$388

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

Here in Key West we believe in One Human Family where everyone is welcome and treated like family.Key West! .....it’s not just a place on the map, it’s a frame of mind, an Attitude…… come and let us share that Key West Attitude with you!Fully Renovated This is a Luxury ...

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Property Type

Key West Condo

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Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$241

avg/night

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Key Amenities

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

About this property

This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill ...

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Property Type

Key West Condo

"Perfect Place to Stay"

This was our 3rd time staying in Pam's wonderful little cottage. My husband and I really love this place. Pam is awesome to work with, she always answers all my questions quickly. It was great being close ...

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3 BR | 3 BA | Sleeps 6 | Quick View

1

$306

avg/night

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Key Amenities

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

About this property

Down a very quite lane the house has one off street parking spot. If you are familiar with Key West you understand what a treat it is to have off street Parkin !Enter from gate through lush and colorful walk to front door of main house . Walking over the front porch is the typical Key West style outside ...

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Property Type

Key West House

"Perfect pet-friendly vacation cottage"

The house is tucked away on a lane in Old Town within walking distance to everywhere. It is very private with lush plantings and a variety of outdoor spaces to sit. The house is well equipped and the owners ...

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3 BR | 3 BA | Sleeps 6 | Quick View

1

$197

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second floor. The second floor ...

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Property Type

Key West House

"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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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

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

"Year After Year ..... Island Queen Is Simply An Outstanding Vacation Rental!"

For years, Island Queen never disappoints. This is like no other rental in Key West. Perfect location. Outstanding historic home and amenities. Wonderful owners to work with. What more do you need? ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Overlooking the Historic Key West Bight Seaport, this large 1/1 with King sized bed features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, new split unit AC, high speed internet, right in the middle of it all! Steps from the water, just 3 blocks from Duval street, ...

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Property Type

Key West Apartment

"This Space is a true Key West Gem, location can not be beat!"

We have stayed with this host numerous times and can not say enough about them as well as this particular space and location. If you are looking for a true taste of Key West look no further. This building ...

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3 BR | 2 BA | Sleeps 6 | Quick View

$203

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

About this space Built in 2022, this vibrant, 1400 sq ft stilted home brims with personalized art and touches inspired by The Keys history, landscapes and local artisans. From this luxurious retreat you will enjoy a crystal-clear canal access, a private dock, a tropical micro pool, a stocked chef's ...

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Property Type

Key West House

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1 BR | 2 BA | Sleeps 2 | Quick View

1

$275

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The gracious building at 616 Caroline Street, exquisitely renovated into 6 condominiums, claims a long and proud history that befits its esteemed place along one of the most elegant streets in Key West. Unit # 6 is a second floor, 1BR/2BA unit that is entered on the left side of the building. The condo ...

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Property Type

Key West Condo

"Perfect place for a warm-weather couple!"

The location is perfect! Close to Duval Street, Mallory Square and many fabulous shops. We rode our bikes every morning to Higgs Beach to play tennis then enjoyed the white sand and cool morning breeze ...

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$872

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • 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

"Wonderful property wonderful hosts!"

I just got back from taking my family and a friend's family to Troy and Carol's property for a week. The houses were just as described, the location was just what we wanted, quiet and peaceful and away ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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 home with beautiful lush landscaped grounds and plenty of space for everyone! The main house is a 3/3 (1 King, 2 ...

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Property Type

Key West House

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Key Amenities

  • Air conditioning
  • 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 LaneMulti-month Discounts availableHidden 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, ...

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Property Type

Key West House

"A little slice of heaven on earth"

The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is ...

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Property Type

Key West House

"The Perfect Relaxing week!!"

My family booked Seaview Estates for our 25th Anniversary trip! We rented both houses so we had the property to ourselves. Upon arrival, Carol met us at the gate and began our tour of the property. The ...

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Key Amenities

  • Air conditioning
  • 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"

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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Key Amenities

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

About this property

Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the ...

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Property Type

Key West House

"Key West paradise"

Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the ...

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6 BR | 7 BA | Sleeps 16 | Quick View

3

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1526

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • 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

"Glenn dinner group get away"

We had 6 couples visiting key west for a week to celebrate milestone birthdays and get away. The houses were perfect for our group. Beautifully decorated,plenty of space for everyone to enjoy and not ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Blue Haven: An Exquisite Oceanfront Penthouse – Complete Remodel with Direct Ocean Views and Massage Chair – Premier Unit on Property Blue Haven is the premiere property in this complex. This luxury penthouse condominium is unbelievable. You will not want to leave. Nestled on the shore of ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

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 ...

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Property Type

Key West Townhome

"our vacation at Key West Golf Club"

We had wonderful time enjoying the beautiful weather and the beauty of all the attractions at Key West. Our condo was all we needed to fulfill our stay. It was clean and we enjoyed being right on the golf ...

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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Higg's Beach

$360

avg/night

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Key Amenities

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

About this property

Private Luxury Key West Home with Private Pool, surrounded by lush tropical landscaping in the Casa Marina neighborhood of Old Town.The fusion of a mid-century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district ...

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Property Type

Key West House

"Great home to enjoy Key West!"

Four of us , and our dog, stayed at Lynda’s beautiful home in Casa Marina area. We had a wonderful month there. The location was great and quiet. We spent most of our time enjoying the covered deck ...

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2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 2 miles to Smathers Beach

$183

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Come stay in a premier development in Key West. If you're looking for a monthly stay of 28 days or more then this is the place. You would be close to everything Key West has to offer stay at our peaceful serenity of your temporary home in Paradise. Our house offers many amenities to make your stay ...

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Property Type

Key West Townhome

"Three months in Paradise"

The townhouse and grounds are exactly as pictured and described! Staying on Stock Island was a great experience. Close enough to beaches and downtown Key West and the island itself offers a number of terrific ...

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3 BR | 2 BA | Sleeps 6 | Quick View

2

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

$582

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

Please contact the owner for stays less than 28 days before you try to book . In Key West - Not Islands Away *** Ocean Front**Ocean View from Every Room *90' Scenic Balcony Huge 2200 Sq Ft under air. This is a $1.5 Million Dollar Property with priceless View!***SPECIAL REDUCED RATES FOR ...

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Property Type

Key West Condo

"Great Escape"

Love these condos !! Second time to same place!! Great escape from Seattle. Family friendly. Great food.

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2 BR | 2 BA | Sleeps 4 | Quick View

3

$229

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Welcome to Key West Getaway in Old Town!This three-story townhome offers a great layout to enjoy your monthly stay. Enter the ground level just steps away from your dedicated parking spot to a den with a convenient workstation and television. The couch in the den pulls out to a queen sleeper. Level ...

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Property Type

Key West Townhome

"Fantastic location and unit!"

We stayed at Holly's Key West Getaway from October 2022 through May 2023, and it was absolutely fantastic. The unit is in a complex perfectly located in Key West, within blocks of great restaurants, attractions, ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Location Location Location....Close to Duval and Beaches! Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Key West Historic ...

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Property Type

Key West Bungalow

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.4 miles to Higgs Beach

$333

avg/night

View Details

Key Amenities

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

About this property

Tiki Tango - Your Key West Oasis in the Coveted Casa Marina District!Welcome to Tiki Tango, a grand 2-bedroom, 2-bathroom home that blends island ambiance with modern luxury. Located in the coveted Casa Marina District of Key West, this vacation rental promises a memorable stay with its private pool, ...

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Property Type

Key West House

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4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 50 yards to One block from fantastic beach

$758

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

This one of a kind beautiful home was built in 1912 by one of the first cigar makers. It is listed on the National registry of historic homes and has been showcased in the Holiday Parade of Homes. The home was restored and expanded in 2002 Key West contractor Richard Manley with the highest level of ...

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Property Type

Key West House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

2

Distance to beach: 600 yards to Simonton Street Beach

$302

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Enjoy an unforgettable stay at a one-of-a-kind ship-builder's home in the heart of Old Town Key West. You will be on a quiet lane in the most desirable neighborhood, just a few short blocks from dining, boating, fishing, galleries, theatre and entertainment. Unique features include open air kitchen ...

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Property Type

Key West House

"Tropical Paradise"

This property was absolutely amazing! Being in Old Town and just steps away from Caroline St and a few blocks from Duval was so convenient. We were traveling with our adult children and everyone could come ...

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Key Amenities

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

About this property

Private home located in New Town available for 28 day minimum rental. Beautifully landscaped yard with secure private back yard and pool. The home features a kitchen with all appliances and granite counter top. The master suite opens onto the pool deck and is furnished with a king size bed and walk-in ...

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Property Type

Key West House

"Excellent location,beautiful house,outstanding owners!"

We stayed a month in December(2022),had everything we needed,close to shopping,sightseeing, nightlife,beaches and airport. House is completely furnished and nothing is lacking.Pool was heated and had all ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Suncatcher on the ocean is new to the rental pool at 1800 Atlantic. A fabulous property with many upgrades throughout. Totally renovated from top to bottom with high end finishes and no attention to detail spared. We are excited to offer it for rent for the first time. Tastefully decorated in Island ...

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Property Type

Key West Condo

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2 BR | 1 BA | Sleeps 5 | Quick View

1

Distance to beach: 0.2 miles to Fort Zachary Beach

$345

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

DISCOUNTED MONTHLY RATES. AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all. Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors. POOL within 1 walk of condo108!! 5-STAR ...

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Property Type

Key West Condo

"Perfect condo for our needs"

Location was perfect as it is closer to the entrance of Truman Annex and in turn only steps away from Duval, Mallory Square and Truman Waterfront park. Owner's were very friendly, extremely responsive ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This estate has it all waterfront, large sun-filled pool and seawall dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and entertain your guests. The home was recently rented ...

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Property Type

Key West House

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Key Amenities

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

About this property

**Available for rent by the month. Although you rent it for a month, you may of course come late and/or leave early. The monthly price is generally half of what you would pay for a daily-rate comparable unit, and it gives you a lot more options and freedom.Located on a side street off Duval and ...

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Property Type

Key West Townhome

"Beautiful Stay!"

This unit is in a tucked away little oasis one street over from all the action on Duval street. If is a very peaceful and unique spot. The unit itself is exceptionally clean and well appointed. It has ...

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2 BR | 2 BA | Sleeps 4 | Quick View

6

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

$231

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Just Perfect"

Southard Comfort is perfectly appointed and comfortable. There is nothing I can suggest to improve the experience. The house is nicely decorated, the kitchen is completely outfitted, the location is great ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and travels of “Papa” Earnest Hemingway. This is a beautiful top floor two-bedroom ocean-view unit at 1800 Atlantic condos. It has pristine ocean-views from all rooms ...

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Property Type

Key West Condo

"SIMPLY DIVINE"

BEST PLACE WE EVER STAYED AT. THERE WERE FOUR OF US. BEAUTIFUL LOCATION. SO COMFORTABLE. KIRK WAS SO HELPFUL TO HELP US GET SETTLED IN. ALL THE TREATS OF HOME. VIEW INCREDIBLE. WANTED OUR TIME THERE TO ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride to all that Key West has to offer. Keys to Paradise will not disappoint. Direct ocean front condo that features 1 master suite with a king size bed, jacuzzi and luxurious walk in shower. ...

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Property Type

Key West Condo

"Amazing, Heaven, Can't wait to go back"

THE KEYS TO PARADISE CONDO IS SO WONDERFUL. The view is Breathtaking. The condo is well kept and clean. It has beautiful furnishings and distinctive artwork on the walls. The condo is in the perfect location,facing ...

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Key Amenities

  • Air conditioning
  • Kid friendly

About this property

This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedroom suite has a king size bed. The renovated bathroom ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. "Moonlight" ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an extra large floor plan with a nice ocean view. This property features 2 queen beds in the master bedroom and a king in the guest bedroom. Full size washer/ dryer and 1 assigned private ...

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Property Type

Key West Condo

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2 BR | 1 BA | Sleeps 4 | Quick View

1

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

$376

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

LAST MINUTE CANCELLATION. WEEK OF APRIL 6-13 NOW OPEN Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My over sized two ...

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Property Type

Key West Condo

"A touch is all you need…"

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area ...

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever ...

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Property Type

Key West Condo

"Perfect location! Beautiful property!"

This was an amazing spot for a vacation! The condo was walking distance to everything! Beautiful beaches, amazing parks, Hemingway House, Duval Street, the aquarium. The property within the gated community ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the master bedroom, 2 twins in the guest bedroom (which can also be converted to a King bed upon request) and a queen sleeper sofa in the living room.Anchor Drop is beautifully renovated ...

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Property Type

Key West Condo

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1 BR | 1 BA | Sleeps 2 | Quick View

2

$257

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

We specialize in amazing vacations and honeymoon and extended stays for two guests, aboard a yacht that stays dockside without the chance of seasickness allowing you to come and go according to your own schedule. Our pedigree Hatteras, a custom 60' motor yacht, a timeless classic designed for elegant ...

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Property Type

Key West Yacht

"Great experience!"

The Paradise is a grogerous yacht. The woodworking is amazingly beautiful. The bed is very comfortable. We really enjoyed our stay and was very pleased. Captain Berry & Tamara were very tentative and superior ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open onto the 40 ft private balcony that has views of the nature preserve and Atlantic ocean. Fully equipped with all the modern conveniences you would need for an enjoyable vacation. This ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower.Downstairs in ...

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Property Type

Key West House

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2 BR | 2 BA | Sleeps 4 | Quick View

$158

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

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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Property Type

Key West Condo

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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's vacation rentals call to beach bums and other likeminded travelers 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!


FAQ

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

There are 83 Key West acation rentals available on FloridaRentals.com. From condo rentals to house 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 $117 per night with an average price per night of $400.

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 29 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 20 oceanfront rentals in Key West available on FloridaRentals.com. Use our filters to search and book yours today!