Monthly Rentals in Key West

(47 rentals)
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Key West Condo
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 2 Bathrooms
2 reviews

$246

avg/night

$246
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

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

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Property Type

Key West Condo

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Key West House | On the beach
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom
3 reviews

$434

avg/night

$434
avg per night
View Details

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

Featured review

"The Perfect Relaxing week!!"

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

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Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
2 reviews

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

$248

avg/night

$248
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Rate reduced for December 2024. 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 ...

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Property Type

Key West House

Featured review

"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 West House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$466

avg/night

$466
avg per night
View Details

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 West Condo
2 BR | 1 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 1 Bathroom
2 reviews

Distance to beach: 0.2 miles to Fort Zachary Beach

$459

avg/night

$459
avg per night
View Details

Key Amenities

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

About this property

AMAZING LOCATION in TRUMAN ANNEX: SHABBY CHICKEN - come stay with the large & proud bird in town!! She's not too shabby after all. Large front yard and porch to watch Key West pass by. Beautiful and spacious in/out doors. POOL within 1 walk of condo. We rent for 7 days or more, monthly113 ...

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Property Type

Key West Condo

Featured review

"Lovely condo, great location!"

My husband and I enjoyed 8 nights in July at the Shabby Chicken. The condo had everything we needed and couldn’t ask for a better location!

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Key West Mobile home
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 Bedrooms, 2 Bathrooms
1 review

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean. ...

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Property Type

Key West Mobile Home

Featured review

"Awesome Key West Getaway-We'll be back!"

This location is amazing just minutes to downtown Key West and a few minute idle by Boat to the Ocean(we brought our own boat and docked out back!) Had fun Snorkeling in crystal clear water, and even tried ...

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Key West House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
1 review

$374

avg/night

$374
avg per 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

Featured review

"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 West Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1.5 Bathrooms
2 reviews

Distance to beach: 2 miles to Smathers Beach

$228

avg/night

$228
avg per 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. If you're looking for a monthly stay of 28 days or more then this is the place. You would be close to everything Key West has to offer stay at our peaceful serenity of your temporary home in Paradise. Our house offers many amenities to make your stay ...

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Property Type

Key West Townhome

Featured review

"Three months in Paradise"

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

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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
2 reviews

$438

avg/night

$438
avg per 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

Featured review

"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 West House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
6 reviews

$309

avg/night

$309
avg per night
View Details

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

Featured review

"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 West Cottage
2 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 2 Bedrooms, 1 Bathroom

$380

avg/night

$380
avg per night
View Details

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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Key West House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2 Bathrooms

$528

avg/night

$528
avg per night
View Details

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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Key West House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
6 reviews

$511

avg/night

$511
avg per 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

Featured review

"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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Key West House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2.5 Bathrooms

$533

avg/night

$533
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

AMAZING FURNISHED LARGE POOL HOME FOR RENT! This charming 1896 Conch 3 bed, 2 1/2 bath house nestled within the lushly landscaped grounds of the Meadows in Old Town Key West offers a unique blend of character and modern comfort. Lovingly maintained on a private 5860 square foot corner lot, this restored ...

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Property Type

Key West House

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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
5 reviews

$655

avg/night

$655
avg per night
View Details

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

Featured review

"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 West House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 Bedrooms, 3 Bathrooms
4 reviews

$776

avg/night

$776
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • 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

Featured review

"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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Key West House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2.5 Bathrooms
3 reviews

Distance to beach: 0.5 miles to Higg's Beach

$426

avg/night

$426
avg per 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

Featured review

"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 West Townhome
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 Bedrooms, 3 Bathrooms
2 reviews

$200

avg/night

$200
avg per night
View Details

Key Amenities

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

About this property

Relax with family and friends in your own tropical paradise at this spacious townhome in Key West's beautifully landscaped & maintained Golf Club. Located in a private gated community with resort style amenities, it is just minutes away from the beaches, world class restaurants, water sports ...

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Property Type

Key West Townhome

Featured review

"our vacation at Key West Golf Club"

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

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Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

Distance to beach: 0.4 miles to Higgs Beach

$500

avg/night

$500
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Key West House

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Key West Townhome
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
4 reviews

$249

avg/night

$249
avg per 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!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying ...

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Property Type

Key West Townhome

Featured review

"Old Town Getaway"

Excellent property; highly recommended. Holly is an amazing host: very responsive and accommodating. She provided detailed check in/out instructions, descriptions of the property amenities, and a tour guide ...

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Key West Studio
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 Bedrooms, 1 Bathroom
1 review

$197

avg/night

$197
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Overlooking the Historic Key West Bight, this bright and clean studio features a fully equipped kitchen, renovated bathroom, front loading washer/dryer, 4K smart TV, and one of the best people watching front porches in Key West. Steps from the water, just 3 blocks from Duval street, and surrounded by ...

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Property Type

Key West Studio

Featured review

"Key West Gem"

We stayed at this property for 6 weeks. The location is awesome! It is steps away from the marina, a short walk to a small beach, and just several blocks from Duval Street. The location is also set in close ...

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Key West Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
1 review

$214

avg/night

$214
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

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

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Property Type

Key West Apartment

Featured review

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

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

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Key West House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 4.5 Bathrooms

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

$1308

avg/night

$1,308
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Key West House

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Key West House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
6 reviews

$183

avg/night

$183
avg per night
View Details

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

Featured review

"Excellent location,beautiful house,outstanding owners!"

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

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Key West House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 2.5 Bathrooms
3 reviews

Distance to beach: 600 yards to Simonton Street Beach

$447

avg/night

$447
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Key West House

Featured review

"Excellent experience"

Management was informative and responsive. The home was perfect for our needs. Everything was pristine and well cared for. I would give this rental and the management the highest recommendation.

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Key West House | On the beach
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3 Bathrooms

$268

avg/night

$268
avg per night
View Details

Key Amenities

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

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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Key West Townhome
1 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 1 Bedroom, 1.5 Bathrooms
8 reviews

$233

avg/night

$233
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Key West Townhome

Featured review

"Beautiful Stay!"

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

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Key West House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
6 reviews

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

$367

avg/night

$367
avg per 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

Featured review

"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 West Cottage
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

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

$429

avg/night

$429
avg per 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

Featured review

"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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Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom
1 review

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

$397

avg/night

$397
avg per night
View Details

Key Amenities

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

About this property

$250/WEEK DISCOUNT NOVEMBER 30 to DECEMBER 7 DUE TO AN UNEXPECTED CANCELLATION. So 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 ...

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Property Type

Key West Condo

Featured review

"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 West Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$650

avg/night

$650
avg per night
View Details

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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Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
4 reviews

$324

avg/night

$324
avg per night
View Details

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

Featured review

"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 West House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 3.5 Bathrooms

$497

avg/night

$497
avg per night
View Details

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 West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms
1 review

$198

avg/night

$198
avg per night
View Details

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

Featured review

"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 West Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom

$191

avg/night

$191
avg per night
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. Everything you will need for your perfect Key West extended stay. 1 assigned parking space with the apartment. Full kitchen and washer dryer, Central AC and wifi access. The owners have ...

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Property Type

Key West Apartment

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$500

avg/night

$500
avg per night
View Details

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 West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

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

Featured review

"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 West Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$450

avg/night

$450
avg per night
View Details

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 West House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$258

avg/night

$258
avg per night
View Details

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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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
1 review

$425

avg/night

$425
avg per night
View Details

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

Featured review

"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 West House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$587

avg/night

$587
avg per night
View Details

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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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 3 Bathrooms

$600

avg/night

$600
avg per night
View Details

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 West Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$445

avg/night

$445
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

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

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Property Type

Key West Condo

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Key West House | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$259

avg/night

$259
avg per 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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Key West Cottage
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom

$360

avg/night

$360
avg per night
View Details

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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Key West Yacht
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 Bedroom, 1 Bathroom
2 reviews

$242

avg/night

$242
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Key West Yacht

Featured review

"Great experience!"

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

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$318

avg/night

$318
avg per night
View Details

Key Amenities

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

About this property

Luxury island resort style living in Key West. 1800 Atlantic offers a private sandy sunning beach, Olympic style pool, gym, three tennis courts (one is clay), fitness center, community clubhouse, picnic areas and more. This condominium is updated and turnkey . Open living and dining spaces, eat-in kitchen ...

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Property Type

Key West Condo

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