Luxury Vacation Rentals in Key West

(51 rentals)
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Private beach estate,gated,dock,and pool

$911

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!"
Reviewed March 15, 2021

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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Mar Y Sol Ocean Front A101

3 BR | 2 BA | Sleeps 8 | Quick View

$639

avg/night

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Key Amenities

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

About this property

MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breezes from your 60 foot private wrap around balcony with a fabulous view of the Atlantic ocean.Mar Y Sol has renovated kitchen and bathrooms. Mar y Sol is in high demand so during we ...

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Property Type

Key West Condo

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A Thousand Hidden Hemingways

4 BR | 3 BA | Sleeps 10 | Quick View

1

$623

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • 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

"Perfection in every way"
Reviewed May 4, 2021

This home is beautifully appointed, spacious, quiet, comfortable and perfectly located. The pool is a haven on hot afternoons, the upper deck is amazing on warm nights for stargazing and the kitchen has ...

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C425- Atlantic Sunrise Penthouse

$602

avg/night

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Key Amenities

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

About this property

3 Bedroom 3 bath Partial Ocean View This 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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@ Best of the Annex Waterfront with Fantastic Weekly Rates @

$595

avg/night

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Key Amenities

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

About this property

A beautifully appointed Gulf front Condo in the heart of Truman Annex. Mills place features a walkway flanked by Royal Palms. Mills place was the old militaryHospital building. In the mid 80's it was purchased by a developer who renovated the entire property in keeping with the existing architecture. ...

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Property Type

Key West Condo

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Keys to Paradise

3 BR | 2 BA | Sleeps 8 | Quick View

$573

avg/night

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Key Amenities

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

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Sunrise on the Atlantic

2 BR | 2 BA | Sleeps 6 | Quick View

$570

avg/night

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Key Amenities

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

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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C232 – Atlantic Paradise Found

$547

avg/night

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Key Amenities

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

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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C339- Hemingway’s Atlantic Retreat

$543

avg/night

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Key Amenities

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

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 from ...

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Property Type

Key West Condo

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C224 – Moonlight Paradise

2 BR | 2 BA | Sleeps 6 | Quick View

$525

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private 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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Private beach estate.Dock and pool

$515

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

"Loved it!!!!"
Reviewed April 21, 2021

We thought the accommodations were great, there were some minor things that could have helped but overall we give a glowing review. The pool and outdoor tiki bar were amazing and the owners were wonderful. ...

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Key West Beach Front Rental Beach Studios Ocean views

Studio | 1 BA | Sleeps 3 | Quick View

5

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

$510

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

This is Key West Beach Front Rental Welcome to; Ocean view STUDIO See rates first**** save yourself some valuable ***time This is NOT A BUDGET STAY! This is truly a romantic Ocean View stay for two adults. Opposite of most Ocean View destination experiences of huge buildings, long ...

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Property Type

Key West Studio

"Amazing place to stay- spectacular view"
Reviewed June 8, 2021

This was our second time staying at here and we love it! The views and sound of the ocean are amazing! Place is clean and cozy. Host Holly is fantastic! We will definitely be returning again next year. ...

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25% DISCOUNT FOR SEPTEMBER ONLY "OCEAN FRONT! 90 FT BALCONY-Spectacular View"

3 BR | 2 BA | Sleeps 6 | Quick View

1

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

$505

avg/night

View Details

Key Amenities

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

About this property

Notice: Due to Corona Virus We suggest you purchase "Cancel For Any Reason Insurance". (CFAR) CSA Insurance In the event you purchase the insurance and cancel,It costs a little over 10% of the total trip costs. Great for people with health problems or in this case "Pandemics"Here ...

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Property Type

Key West Condo

"Simply beautiful, great location!"
Reviewed January 18, 2021

Stunning views, next to a nature preserve; clean, functional, well-appointed condo. Short walk to the beach and easy bicycle ride to Duval. Overall Joe (the owner) was very reachable and helpful. Strongly ...

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Blue Moonshine on the Atlantic Great Discounts until Feb 11th 2021

$500

avg/night

View Details

Key Amenities

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

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Bougainvillea Villa Key West MONTHLY RENTALS ONLY

3 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 4 miles to Smathers

$494

avg/night

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Key Amenities

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

About this property

COVID-19 UPDATE: Key West restaurants and bars are open. Masks are required at all times unless you are seated at a table in a bar or restaurant.MONTHLY RENTALS ONLY We purchased Bougainvillea Villa as our future retirement home. Since we are unable to visit as often as we’d like, we are ...

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Property Type

Key West House

"Beautiful Bougainvillea Villa"
Reviewed February 27, 2018

Nothing is missing from this very clean and very well organized beautiful home situated on a wide lagoon. For us, the highlight is the superb view of the wide lagoon from the window wall across the entire ...

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Hidden Cottage

3 BR | 3 BA | Sleeps 6 | Quick View

1

$466

avg/night

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Key Amenities

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

About this property

Down a very quite lane the house has one off street parking spot.Enter from gate through lush and colorful walk to front door of main house . Enter into the living room with smart tv ,through to the right into the dinning area. The kitchen is off to the left. There is a large working counter with seating ...

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Property Type

Key West House

"Perfect pet-friendly vacation cottage"
Reviewed March 2, 2021

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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High Tide @

2 BR | 2 BA | Sleeps 6 | Quick View

2

$465

avg/night

View Details

Key Amenities

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

"Amazing!!!"
Reviewed September 10, 2021

Our stay was terrific the pool fabulous and the staff couldn’t have been more helpful! The gardens were incredible and the sand area was just the best!

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Private beach estate. Gated, tropical peace and quiet. Dock

$459

avg/night

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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

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Cockadoodledo Vacation Rental. Featured On Hgtv***multiple Month Discount***updated

$457

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

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

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Property Type

Key West House

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Latitude Penthouse Key West B417

$433

avg/night

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Key Amenities

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

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Coral Hammock Poolside Home

3 BR | 3 BA | Sleeps 6 | Quick View

1

$416

avg/night

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Key Amenities

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

About this property

This 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 Kitchen for your use. High speed internet is available. There is a TV in ...

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Property Type

Key West Condo

"Southern Charm with a boat slip!"
Reviewed March 25, 2021

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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Truman Annex - ' Island Queen' End Unit Villa is One-of-a-Kind!

$414

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

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

"Amazing visit"
Reviewed October 17, 2021

Island Queen is the perfect space for two couples we had an awesome time and the place is set up for a longer stay. Had some great dinners and enjoyed our stay

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Nautical Adventure in Paradise C126

$403

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Private 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"
Reviewed March 23, 2021

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

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Peaceful 2 BR Condo with All Amenities

2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 1 miles to Smathers Beach

$388

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Pool

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

"AWESOME AWESOME AWESOME AWESOME"
Reviewed July 9, 2021

Couldn't ask for more. Everything is at your fingertips. The location is awesome, the beach, shopping, and restaurants is right at your doorstep. We took this trip for our 30th anniversary and my granddaughter's ...

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A Touch of Bermuda at Truman Annex

2 BR | 2 BA | Sleeps 6 | Quick View

2

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

$353

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • 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"
Reviewed March 25, 2021

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

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Truman Annex, Lrg In/Outdoors Beautiful 1st Flr, 2BR KING/twins, Pool

2 BR | 1 BA | Sleeps 5 | Quick View

1

Distance to beach: 0.2 miles to Fort Zachary Beach

$351

avg/night

View Details

Key Amenities

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

About this property

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.58 5-STAR REVIEWS!!! (on our primary site on VRBO #595903)Our fantastic cleaner has been ...

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Property Type

Key West Condo

"Perfect condo for our needs"
Reviewed March 16, 2021

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

$335

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 LaneHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping, the main 2/2 house features an indoor/outdoor ...

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Property Type

Key West House

"Perfect place!"
Reviewed August 21, 2021

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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Dos Casas - A 2 House Compound in Old Town -- A Monthly Rental

$331

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • 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.Why ...

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Property Type

Key West House

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A Touch Of Cuba In Key West

2 BR | 1 BA | Sleeps 4 | Quick View

1

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

$327

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • 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…"
Reviewed September 10, 2021

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

3 BR | 2.5 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Higg's Beach

$326

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • 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!"
Reviewed February 20, 2020

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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Beautiful Downtown Truman Annex Condo

$325

avg/night

View Details

Key Amenities

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

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 you come ...

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Property Type

Key West Condo

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Beautiful Downtown Truman Annex Condo

$322

avg/night

View Details

Key Amenities

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

About this property

Best Deal in Truman Annex - Cead Mile Failte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5Here's Caad Mile Failte 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 you come from, whosoever you be. Welcome to our home ...

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Property Type

Key West Condo

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Nassau Suite Downtown Key West

$308

avg/night

View Details

Key Amenities

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

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Key West Old Town Sanctuary- Huge Private Pool- Quiet Lane- Monthly Rental

$293

avg/night

View Details

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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"Southard Comfort"

2 BR | 2 BA | Sleeps 6 | Quick View

5

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

$289

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed
  • 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

"I wish I didn't write this review."
Reviewed February 25, 2021

Mainly because it will lessen our chances to get back here. My wife and I used to live in Key West for close to 10 years. We had our house and a couple of rental properties and vacation properties. Then ...

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Cockadoodledo Condo. Historic Caroline Street Condo!

$283

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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

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Sunset on Southard

1 BR | 1 BA | Sleeps 4 | Quick View

1

$280

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

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Property Type

Key West Condo

"Sunset on Southard"
Reviewed April 25, 2021

We arrived to a wonderful and super clean condo in a great location. We had everything we needed plus! It was great having a cooler and beach towels provided for our use to the beach, 2 bicycles, loved ...

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Ocean View condo steps to Smathers Beach

$276

avg/night

View Details

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 included * This is not a hotel; it is a privately owned condo facing the ...

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Property Type

Key West Condo

"AMAZING"
Reviewed January 30, 2019

There truly aren't enough adjectives to describe the level of service Pam provided. At the very beginning, she answered all my questions, in less than an hour. Her customer service was amazing. She provided ...

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Southard Breezes

1 BR | 1 BA | Sleeps 3 | Quick View

3

Distance to beach: 0.3 miles to Ft. Zachary Taylor

$273

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We inspect our homes multiple times each month and follow the AHLA Stay Safe Guidelines to ensure your stay is safe and comfortable. You will also find an initial supply of cleaning and ...

View all property information

Property Type

Key West Condo

"Paradise"
Reviewed September 29, 2020

We loved the location of this rental. Everything inside the rental was as should be. I could not complain about anything but only say that i cant wait to return. We were a couple of blocks away from everywhere ...

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Joe's Place. A+ Location in Old Town Key West

$264

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This beautiful house is a two bedroom, two bath with a pullout sofa. The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor and an outdoor shower. The kitchen and living room area is open. Very well air conditioned for those hot days. A nice ...

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Property Type

Key West House

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Old Town! Spacious Condo in Historic Home with Pool, Porch and Two Bikes!

$259

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

Beautiful One Bedroom Condo with Sleeper Sofa in Old Town! Close to Everything!This 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 ...

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Property Type

Key West Condo

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A114- Island Time Hideaway

2 BR | 2 BA | Sleeps 4 | Quick View

$259

avg/night

View Details

Key Amenities

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

About this property

Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed and plenty of closet space. Both have access to the private balcony that faces the nature preserve in a quiet tranquil location at the property. The unit is located across from the Elevator ...

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Property Type

Key West Condo

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Olivia House-Downtown Historic District

$256

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pets allowed

About this property

This home has been beautifully upgraded with attention to detail. In it's day it was a well known flower shop to the locals. This historic home living room is wider than most "conch homes" with traditional wood floors and vaulted ceilings. The kitchen is a cooks dream with nicely stocked cookware, ...

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Property Type

Key West House

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Awake to the Morning Reflections OPEN MAY 2021 $3750 PLUS TAX & FEES

$248

avg/night

View Details

Key Amenities

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

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"
Reviewed July 26, 2021

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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Casa Coastal East C231

2 BR | 2 BA | Sleeps 6 | Quick View

$241

avg/night

View Details

Key Amenities

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

About this property

Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its new owners. From new interior design work and furnishings, courtesy of Royal Furniture of Key West, to new closets, drapes and local art, includes works from the gallery of Alan ...

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Property Type

Key West Condo

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Superb Location, Affordably Priced - The TwoSim Suite

Studio | 1 BA | Sleeps 2 | Quick View

1

Distance to beach: 0.5 miles to South Beach

$239

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • 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 included * 2 wall AC units * flat screen TV * Shared gas grill * porch with ...

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Property Type

Key West Condo

"Perfect Place to Stay"
Reviewed September 9, 2020

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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Simonton Studio, an Old Town get-away for 2

Studio | 1 BA | Sleeps 2 | Quick View

4

Distance to beach: 0.5 miles to South Beach

$239

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pets allowed
  • Rentals by owner

About this property

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

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Property Type

Key West Condo

"A perfect stay"
Reviewed September 7, 2021

This little piece of paradise was everything we expected and then some. Perfect for the two of us during our week long stay. Within walking distance to Duval and a beautiful church where mass is offered ...

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Julia's Secret. Julia's Secret in Old Town Key West

$239

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This beautiful house is a two bedroom, two bathroom located in the best area in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are so many great attractions nearby like the Hemingway House, Light House Museum, Southernmost Point. The bedrooms each have ...

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Property Type

Key West House

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2 Bedroom Townhouse Key West 10% off Available Dates Spring/Summer 2021

2 BR | 1.5 BA | Sleeps 4 | Quick View

2

Distance to beach: 2 miles to Smathers Beach

$226

avg/night

View Details

Key Amenities

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

About this property

Come stay in a premier development in Key West. This would be a great location to stay with a monthly 29 day rental minimum. Yearly rates available. You would be close to everything Key West has to offer and the peaceful serenity of your temporary home in Paradise. Our house offers many amenities to ...

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Property Type

Key West Townhome

"Three months in Paradise"
Reviewed April 1, 2021

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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Beautiful Key West Golf Club -- Paradise Found

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Private pool

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 and ...

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Property Type

Key West Townhome

"Peaceful, great location"
Reviewed January 25, 2021

Lovely house with a beautiful sunset view! Nice and quiet location with easy access to Key West by car, bike or walk. Recommended!

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