Luxury Vacation Rentals in Key West

(56 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

3 Bedroom 3 bath Partial Ocean Viewhis is the only 3 bedroom 3 bath unit in the complex. The unit is about 2000 sq feet. It will accommodate 8. 2 Master suites each with a king bed, The 3rd bedroom has 2 twin beds and there is a queen sleeper sofa in the living room. Large private balcony opens off ...

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Property Type

Key West Condo

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Key Amenities

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

About this property

Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full size fully equipped kitchen with a washer/dryer. Both bedrooms and the living room have impact doors open to your private balcony. There is a King bed in the master bedroom and a queen ...

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Property Type

Key West Condo

"New Year’s vacation"

Wanted to go to the Florida Keys, but this place popped up several times during my search. I’m so glad I chose this place. Breathe taking is the best word to use. Beautiful beach (7miles of it), nice ...

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$905

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
  • 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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely view of the Atlantic OceanAtlantic Paradise Found is one of the premium rental properties Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end furnishings. ...

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Property Type

Key West Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the master bedroom, 2 twins in the guest bedroom and a queen size sleeper sofa in the living room.. Totally renovated fall of 2017, Custom Kitchen and bathrooms. Tiled throughout.All ...

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Property Type

Key West Condo

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Key Amenities

  • Kid friendly
  • Kitchen
  • Pool

About this property

3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a nice ...

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Property Type

Key West House

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master bedroom, 2 twins in the 2nd bedroom that can be converted to a King .memory foam luxury queen sleeper in the living room will comfortably accommodate your party.Watch the sunrise ...

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Property Type

Key West Condo

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Key Amenities

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

About this property

Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently been renovated and features a new kitchen with granite counters, lovely open floor plan with vaulted ceilings. The elegant master bathroom has a spacious walk in shower. The master bedroom ...

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Property Type

Key West Condo

"Great location!"

The house was so cute! We loved the location. It was just a few houses down from the main area so we walked almost everywhere. Shana, the property manager was super sweet and helpful !

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Key Amenities

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

About this property

The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropical landscaping with your very own backyard poolside sandy beach. Tiki hut bar, outside cabana living room, zen outdoor shower and sun deck enhance this Centrally located Key West retreat. ...

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Property Type

Key West House

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Key Amenities

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

About this property

1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 AtlanticPerfect for a family get-away or a group of friends looking to relax in Key West with all the amenities of home. Full size fully equipped eat in Kitchen, Washer/Dryer. Expansive private balcony overlooking the lush tropical ...

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Property Type

Key West Condo

"Fabulous from day 1!"

Our vacation at 1800 Atlantic’s high tide was beyond what we expected!! Clean, stocked and beautiful!! We used the Luxury kitchen everyday, the beds were terrific and garden view was the best:) The pool ...

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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

$695

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 ANNUAL, ...

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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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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" is ...

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Property Type

Key West Condo

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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
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper sofa in the living room. This unit has high speed wireless and will accommodate up to 6 people. Just a short walk to the pool and Jacuzzi. For the Sports enthusiast there are 3 lighted ...

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Property Type

Key West Condo

"Loved it"

Great location. Beautiful. A little far from downtown but we worked out. Unit was stocked very well.

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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 and bright, ...

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Property Type

Key West House

"1000 Hidden Hemingways - A true Key West gem!"

We booked this property in the month of April 2023 to be our home base while we got married in Key West!We cannot express how perfect this historic home is! All the Key West charm with modern amenities. ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$645

avg/night

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Key Amenities

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

About this property

When they say it's all about the location, this home says it all!By city ordinance, you must rent this property for 29 days or longer!!Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.A stairway decorated with wainscoting will lead you to the ...

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Property Type

Key West House

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Key Amenities

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

About this property

Bluegrass Seabbatical is a Spectacular 3 bedroom 2 bath oceanfront condominium at 1800 Atlantic. Enjoy the incredible ocean front view from all 3 bedrooms and the living room. This property is close to 2000 sq feet and can be your fantastic home away from home. Available for extended stays during the ...

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Property Type

Key West Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

4
Owner special: Price reduction due to Cancellation! $6,000 off for Dec 2023

$514

avg/night

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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

"Perfect place!"

This house is in the perfect location that is quiet and private. It’s literally in the center of old town and just a short walk to everything. It is very comfortable and has a great layout. The cabana ...

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$501

avg/night

View Details

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

"A little piece of paradise."

The grounds are beautiful and well-maintained. Troy and Carol are delightful... It was the perfect place for our family vacation. We'll visit again!!!

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Key Amenities

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

About this property

Beautifully renovated 2 bedroom 2 bath ocean view condo at 1800 Atlantic available for monthly rentals. King in the master, queen in the second bedroom and a double pull out in the living room. The unit is tiled throughout. The bathrooms have been nicely upgraded and did we mention the view from Poolside ...

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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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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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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 discriminating 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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Studio | 1 BA | Sleeps 3 | Quick View

6

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

$457

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

The beach is beautiful ! OCEAN VIEWS! in town no car needed!reserve before others! TEXT or EMAIL Only ThnxCheck availability - don't miss an opportunity, book soon. I am the Host within management, Hol cru since 2004. If you need more concise info PLEASE SEE OUR FANTASTIC FEEDBACKERS! ...

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Property Type

Key West Studio

"Perfect Private Key West Rental"

Location for this rental is perfect! You can sit out on the front patio and watch the waves roll in from the ocean. We had the downstairs rental. It has a full kitchen, bathroom, dining room, living ...

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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
  • Kid friendly
  • Kitchen

About this property

Fantastic Location in the heart of Old Town Key West. This beautiful 3 bedroom 3 bath property is the perfect place to stay to be in the heart of the buzz of Key West. The main level of the house features living room, dining room, kitchen and full bath on the first floor The Master suite & both guest ...

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Property Type

Key West House

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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 Queens) ...

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Property Type

Key West House

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4 BR | 2.5 BA | Sleeps 8 | Quick View

1

Distance to beach: 600 yards to Simonton Street Beach

$446

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 and ...

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Property Type

Key West House

"Paradise"

This tropical home is stunning. My husband and I spent most of our time in the open air space surrounded by beautiful foliage and flowers when we were not out and about exploring. We floated in the pool, ...

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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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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$424

avg/night

View Details

Key Amenities

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

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for ...

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Property Type

Key West Cottage

"Island Magic"

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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3 BR | 3 BA | Sleeps 6 | Quick View

1

$424

avg/night

View Details

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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2 BR | 1 BA | Sleeps 4 | Quick View

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

$406

avg/night

View Details

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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3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Higg's Beach

$402

avg/night

View Details

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Perfectly situated in Old Town Key West. This quaint pool cottage is perfect for a couple with occasional visitors. beautifully decorated with amazing outside space to enjoy our island breezes and cool off in our pool. This beautiful property has been well maintained with a newly renovated Kitchen. Queen ...

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Property Type

Key West Cottage

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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

$377

avg/night

View Details

Key Amenities

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

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 over sized two bedroom, one bathroom condominium end unit (cross ventilation) ...

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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
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious walk ...

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Property Type

Key West Condo

"beautiful ocean view condo"

condo was very clean and on the top floor with vault ceilings. Check in process was seamless as well as checkout.

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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

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2 BR | 2 BA | Sleeps 6 | Quick View

10

Distance to beach: 1 miles to Smathers Beach

$364

avg/night

View Details

Key Amenities

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

About this property

Enjoy the comforts of home in the midst of paradise.Comfortable, reasonably priced 2-bedroom condominium in Sunrise Suites Resort. The Resort offers concierge service, heated swimming pool, outdoor spa, gym facilities, tennis court and Internet service. The unit is on the 3rd floor, accessible by ...

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Property Type

Key West Condo

"Nice room for two couples"

The room was close to the trolley parking. The room was clean. It was a very quiet area. The bed was comfortable.

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Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

A beautiful historic cottage, in the complex of Sirena Blue=Blue Mermaid, located in a great area of old town Key West, within walking distance of Duval St. and beaches, available to rent for short term. Recently fully remodeled May of 2023. High end furnishings. 2 bedrooms or an office and bedroom, ...

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Property Type

Key West Cottage

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2 BR | 2 BA | Sleeps 4 | Quick View

6

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

$340

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
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Key West Condo

"Beautiful view and a great host."

Pam, thank you so much for making this a great stay in Key West. You had everything we needed and more. The place was awesome, clean and beautiful.Thanks so much for having us!

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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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the famous ...

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Property Type

Key West Apartment

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Key Amenities

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

About this property

Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap around porch, a pool deck and a heated dipping pool/large ...

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Property Type

Key West House

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1 BR | 2 BA | Sleeps 2 | Quick View

1

$299

avg/night

View Details

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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

A gorgeous 3 bedroom / 2 bathroom vacation rental home with high vaulted ceilings and french doors that bring the outside in. The backyard features a large covered patio and an in-ground heated swimming pool, perfect for relaxing anytime of the year. New outside table with seating and gas bbq grill ...

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Property Type

Key West House

"Wonderful Retreat"

This house was truly a private haven. It was so quiet and peaceful but yet so centrally located in the island. Quick golf cart rides to Duval and local shops plus near beaches. The house was very neat and ...

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1 BR | 1 BA | Sleeps 2 | Quick View

1

$275

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 seasickson allowing you to come and go according to your own schecule. Our pedigree Hatteras, a custom 60' motor yacht, a timeless classic designed for elegant entertaining ...

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Property Type

Key West Yacht

"Paradise"

Enjoyed our stay onboard "Paradise" M/Y in Key West. Beautiful yacht with excellent accommodations and plenty of room to roam about. Two popular restaurants just a few steps away from the yacht. Key West ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$266

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

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Key West Vacation Rentals