Key West House Rentals

(29 rentals)
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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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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
  • 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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3 BR | 3 BA | Sleeps 6 | Quick View

2

$300

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

"A hidden gem in Key West!"

We loved our stay at Hidden Cottage! Located on a perfect bike loop with bike-lane to Duval (one way on Southard to Duval and one way on Fleming home)! Also very close to the boat docks. Hidden Cottage ...

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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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$867

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
  • 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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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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$468

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

"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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3 BR | 2.5 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.5 miles to Higg's Beach

$342

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

"Stunning Private Villa in Key West - Fabulous Location!"

We were so impressed with this Key West hidden gem. Along with it's beauty, you feel the love and care the owners have for this private home, as they provided you with all the amenities, plus so much more. ...

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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 BA | Sleeps 4 | Quick View

Distance to beach: 0.4 miles to Higgs Beach

$333

avg/night

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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 | 2.5 BA | Sleeps 8 | Quick View

2

Distance to beach: 600 yards to Simonton Street Beach

$235

avg/night

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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
  • 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
  • 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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4 BR | 4.5 BA | Sleeps 8 | Quick View

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

$740

avg/night

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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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2 BR | 2 BA | Sleeps 4 | Quick View

6

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

$204

avg/night

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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
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

This 4 bed 3 bath home with spectacular ocean views is the perfect spot for your vacation. 1 King and 3 queen beds. There are 2 kayaks provided for your enjoyment. You may bring up to a 25' boat and dock at the seawall. The kitchen is fully stocked with all the essentials. Linens, towels and ...

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Property Type

Key West House

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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
  • 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
  • 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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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

"Highly Recommend!"

My husband and I recently rented this home for a month and we couldn’t have enjoyed it more! Let me start with our favorite space… the backyard. From the heated pool, to the outdoor shower, guest house, ...

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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

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

3 Bedroom 1 & half bath Historic Conch House in the Heart of Old Town Key West Queen in the Master, 1 Queen in 1st guest bedroom and 2 queen's in the 2nd guest bedroom. Nicely renovated Kitchen & Wonderful Outside Living Area with Hot Tub & Sun Deck. There is an outside shower and full ...

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Property Type

Key West House

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3 BR | 2 BA | Sleeps 8 | Quick View

2

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

$172

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Key West House

"Great getaway"

This house has everything we need. The best part is the private backyard with lovely gardens and a pool and an outdoor shower. Inside is also wonderful with 3 bedrooms, a big kitchen, a dedicated office, ...

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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 ...

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Property Type

Key West House

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3 BR | 2 BA | Sleeps 6 | Quick View

$193

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

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

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Property Type

Key West House

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2 BR | 2 BA | Sleeps 6 | Quick View

$242

avg/night

View Details

Key Amenities

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

About this property

Welcome to our paradise please enjoy our modern 1400 square foot 2 bedroom 2 bathroom totally renovated condo. This condo is one of the nicest you will find in the complex. There is music available in every room even the master bathroom. We have thought of everything there is even a flat screen tv in ...

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Property Type

Key West House

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