Key West Vacation Rentals

Key West Florida Vacation Rentals with Pool Amenities

Key West Florida vacation rentals have all the comforts of home including plush beach towels that are ready for some fun in the sun. Beach towels can be bulky and take up a lot of room when packing for a vacation. These rentals have a stocked and ready supply of beach towels so you can pack lighter and have a great towel to lie on or dry off with at one of the many area beaches or the private pool at your vacation rental.  There are plenty of beach towels to go around for all guests in the house.
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5 Bedrooms
5½ Baths
Sleeps 12
Type of property: Home
Area: Old Town

CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street, you'll spend most of your time in the magnificent pool in your private backyard. Duval Street, pool and sunshine - a perfect recipe for Key West living.


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2 Bedrooms
1 Bath
Sleeps 4
Type of property: Condo
Area: Old Town

SIESTA BAY: Beautiful 2 bedroom 1 bath 2nd floor condo in Truman Annex, just steps away from the shared pool and a short walk to Fort Zachary Taylor State Park. Anything you want to do on our island paradise is within a few blocks. Enjoy quiet solitude in this home in between visits to chaotic Duval Street, then do it again and again.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

Breezy Bungalow - Weekly Rental When a name says it all you know you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and Fench doors open to allow sunshine and seaside breezes to flow openly.


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3 Bedrooms
2 Baths
Sleeps 8
Type of property: Home
Area: Mid Town

FLAGLER STATION (monthly rental): This one just arrived and it is a true gem! Flagler Station was just remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after year.


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1 Bedroom
2 Baths
Sleeps 2
Type of property: Home
Area: Old Town

TROPICAL CASITA: It is rare you find a true jewel like Tropical Casita, nestled in a sweet little spot amid lush landscaping and secluded tranquility.  Languish in the grandiose bedroom on the second level, unwind around the pool, dine under the stars and sunbathe on the private upper level deck.  Decadence at its best.


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2 Bedrooms
2½ Baths
Sleeps 6
Type of property: Townhouse
Area: Old Town

DUVAL ON THE SQUARE (monthly rental):  Located at the Duval Square townhomes directly on Duval but above all the hubbub. The townhomes are built on the second and third story of the complex with community pool overlooking Duval Street. This lovely 2 bedroom 2.5 bath townhome is available for a relaxing, luxurious month in Paradise.


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2 Bedrooms
1 Bath
Sleeps 3
Type of property: Cottage
Area: Old Town

William's Loft (Monthly Rental)
Located in Old Town in a small, quiet compound of cottages sits William's Loft in one of Key West's most desirable neighborhoods. A secluded compound surrounded by lush tropical foliage make this the idyllic escape. The cottage is exactly as you envision in Key West with distressed wood floors and Dade County Pine plus all the modern amenities of home.


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2 Bedrooms
1½ Baths
Sleeps 5
Type of property: Townhouse
Area: Old Town

BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West:  sunset celebration, beach, bars, restaurants, galleries, theater.  This will be the place you'll return to again and again.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

Shrimp Party (MONTHLY RENTAL) Key West Pinks, Parties and Drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway pack your gear and settle in for a month or longer.


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3 Bedrooms
3 Baths
Sleeps 6
Type of property: Home
Area: Old Town

CONCH CORNER: Here's a little gem in a long-established local residential neighborhood just across from the Key West historic cemetery (quiet neighbors).


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Cottage
Area: Old Town

GREEN ORCHID (monthly rental): Dreaming of living like a local in Key West? Dream no more. Green Orchid offers a true Conch Cottage experience situated on a narrow lane in one of the last historic Old Town neighborhoods. Inside you'll live with all the modern conveniences and furnishings; outside you'll feel you've been transported to years gone by.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Townhouse
Area: Old Town

THE HEMINGWAY: A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. Just steps away from the community pool and only 2 blocks from famous Duval Street and historic Old Town Key West. Relax on your back porch, take a dip in the pool, and check out the sights that you have heard so much about on our Island paradise.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse

THE GALLERY - This is a very unique home where the original owner has kept this little treasure all to herself and now wants to share it with you!  An accomplished artist, the home is filled with her original artwork of favorite things in Key West.  Excellent location in Key West Golf Club with the community pool just outside the back steps with easy access to the clubhouse and library.


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2 Bedrooms
2½ Baths
Sleeps 4
Type of property: Townhouse
Area: Stock Island

KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo.  Located in the exclusive Key West Golf Club Community you will enjoy a beautifully manicured landscaped grounds, a fabulous pool with waterfall and access to the fitness facility.


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2 Bedrooms
2 Baths
Sleeps 4
Type of property: Cottage
Area: Old Town

KEY LIME PIE (monthly rental): A little slice of paradise located one block from the Historic Seaport on a tiny lane. Close enough to bike to all the sights and attractions of Old Town; far enough away to forget you are staying right in the middle of the action. 2 bedrooms 2 baths with private swim spa, this home will give you a reason to say, Ahhh...


 

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