Key West Vacation Rentals with Private Pool

(29 rentals)
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Key West Villa
6 BR | 7 BA | Sleeps 16 | Quick View
Sleeps 16, 6 bedrooms, 7 bathrooms
3 reviews

Distance to beach: 0.3 miles to Ft Zachary Taylor

$1805

avg/night

$1,805
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theaters and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a huge, fabulous decks that overlooks the action on ...

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Property Type

Key West Villa

Featured review

"Glenn dinner group get away"

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

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

$533

avg/night

$533
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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 | On the beach
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
1 review

$989

avg/night

$989
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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

Featured review

"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 West Condo | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 0.2 miles to Public Beach is Smathers

$430

avg/night

$430
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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

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Property Type

Key West Condo

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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

$470

avg/night

$470
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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
1 review

$402

avg/night

$402
avg per night
View Details

Key Amenities

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

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 House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4 reviews

$827

avg/night

$827
avg per night
View Details

Key Amenities

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

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
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
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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 House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
6 reviews

$317

avg/night

$317
avg per night
View Details

Key Amenities

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

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 House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$608

avg/night

$608
avg per night
View Details

Key Amenities

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

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
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

$817

avg/night

$817
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

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 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
  • Private pool
  • Rentals by owner
  • WiFi

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
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

$459

avg/night

$459
avg per night
View Details

Key Amenities

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

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 House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$495

avg/night

$495
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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 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
  • Private pool
  • Rentals by owner
  • WiFi

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

$483

avg/night

$483
avg per night
View Details

Key Amenities

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

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
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

$413

avg/night

$413
avg per night
View Details

Key Amenities

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

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 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

$1314

avg/night

$1,314
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • 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 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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 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
  • Private pool
  • WiFi

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 Condo | On the beach
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$1409

avg/night

$1,409
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

This is a spectacular 3 bedroom 2 bath ocean front unit in a premier location in the complex. Conveniently located close to the elevator with covered secure parking in the garage for a vehicle under 6ft 4 inches. Around 2000 sq feet, each bedroom and living room have sliding glass doors that open onto ...

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Property Type

Key West Condo

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Key West House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

$202

avg/night

$202
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$342

avg/night

$342
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

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

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Property Type

Key West Condo

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Key West 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
  • 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 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
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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 themselves. My over sized two bedroom, one bathroom condominium end unit (cross ...

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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 House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

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

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 | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
4 reviews

$376

avg/night

$376
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$301

avg/night

$301
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

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 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

$281

avg/night

$281
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 Vacation Rentals