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Monthly Key West Rentals

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Fishtail Hideaway

1 Bedroom
2 Bathrooms
5.0000
(6 Reviews)
Fishtail Hideaway will make you feel like you may never want to return home with its intimate, private garden from all the fun and beauty Key West has to offer.

Your living area offers a brand new, large, comfortable couch; which also serves as a sleeper sofa. Unique art hangings and decorative...

Bay Harbor View

5 Bedrooms
3 Bathrooms
4.7500
(8 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.***

a passport tucked away off of mile marker 15.

While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island.

Around the back of the...

Paradise on Sunset Key

2 Bedrooms
2 Bathrooms
5.0000
(2 Reviews)
Paradise at its finest is exactly what you can expect from this immaculate and unique home. Sunset Paradise is a stunning two bedroom, two and a half bathroom house on the private island of Sunset Key, in Key West. Enjoy access to private owner’s beach on western facing side of island with...

Howe Street Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(10 Reviews)
The neighborhood is complete with conch style homes, little lanes, corner gardens and yes our famous Key West Roosters watching their chicks. Featuring a classic front porch for greeting the neighbors as they go about their day.

Entering into this lovely home you are surrounded with light, beauty...

Garden of Roses

3 Bedrooms
2 Bathrooms

Originally built in 1933, this fully renovated, three-bedroom home has a yard, a cozy front porch where you can sit back and watch the day go by, and room for up to eight guests (six comfortably). Stroll to shopping, entertainment, and beaches, all within a few blocks of this rental....

Tobago House

2 Bedrooms
2 Bathrooms
4.7500
(8 Reviews)
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.***

Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,...

Casa Hermosa

2 Bedrooms
2 Bathrooms
Secluded yet conveniently located near great attractions, it's perfect for a relaxing getaway to the island of Key West. Plus, it comes complete with a fully fenced-in yard and perfect patio so that you can enjoy the indoor and outdoor living spaces. And there's a Pool!

Bright and inviting open...

Casa Atlantic

3 Bedrooms
3 Bathrooms
This three bedroom, three bathroom home is an absolute dream! From its perfect location to the picturesque street and impeccable interior, Casa Atlantic is just what you need to enjoy an extended stay on our beautiful island.

You will enjoy strolls to the beach and to dinner at Salute and the...

Salt Pond Hideaway

2 Bedrooms
2 Bathrooms
4.0000
(4 Reviews)
Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex.

It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic right across the street. Taking a walk or bike ride down the oceanfront stretch right outside of...

Mermaid Manor

4 Bedrooms
3 Bathrooms
In one of the most desirable lanes in Old Town Key West. The perfect location for walking to Duval Street and the historic Seaport. Situated at the end of a quiet lane on a lush tropical lot. This 4 bedroom home is in one of the most sought after neighborhoods on the island. High ceilings, hardwood...

Hemingway's Shadow

1 Bedroom
1 Bathroom
4.6667
(6 Reviews)
Hemingway's Shadow is a well-appointed, 1 bedroom home located on Thomas Street, directly behind the Key West Lighthouse Museum.

The living room, dining area and kitchen form an L-shape open area. The kitchen also has a counter with seating for those times you don't care to use the dining table...

The Headquarters

2 Bedrooms
1 Bathroom
Walk into to The Headquarters and experience purer paradise! The living area has gorgeous, light wooden, vaulted ceilings and a plush couch that offers ultimate comfort.

Just off the kitchen, you will find a state of the art kitchen with stainless steel appliances and granite countertops. The...

La Brisa - Beach View Breeze

2 Bedrooms
2 Bathrooms
4.5000
(8 Reviews)
Beachfront Breeze is located on S. Roosevelt Blvd., directly across from world famous Smathers Beach on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the pool, tennis courts and gardens or make your own at the pool, hot tub, saunas, under the tropical...

Sweet Serenity

2 Bedrooms
3 Bathrooms
Welcome to Sweet Serenity, a newly constructed monthly rental located in the brand new Southernmost Cabana Town Home Complex.

Sweet Serenity is nothing short of pure perfection. A complete turnkey, fully accommodating monthly vacation rental is hard to come by. Located in the heart of 'Old Town...

Tsalta

3 Bedrooms
3 Bathrooms
5.0000
(4 Reviews)
At last, a magnificent 3-bedroom home in the middle of Old Town with room for all. This home is a BIG secret but not for long! Lushly landscaped grounds with meandering brick walkways leading to the main house, pool and guest cottage. New owners with new furnishings and linens, breathing new life...

Paradise Palms

2 Bedrooms
2 Bathrooms
5.0000
(2 Reviews)
Paradise Palms is located in a cute, quiet neighborhood on the edge of Old Town Key West. The exterior features of this home include one off street parking spot, a small courtyard with seating, a side deck which includes an outdoor shower and gas grill!

The master bedroom features a king-size bed...

Duval Dreamin'

2 Bedrooms
2 Bathrooms
This property is quite the hidden gem! Located on the second story of one of the most famous streets in the world, you will find Duval Dreamin'. The home over looks Duval Street and features TWO living areas, TWO bedrooms and TWO bathrooms. This is the perfect pad for couples, friends or family...

Paradise Suite

1 Bedroom
1 Bathroom
4.2000
(10 Reviews)
Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite.

Paradise Suite is a bi-level suite with one bedroom upstairs. The bedroom features a king bed and is decorated in rich tropical colors with local Key West hand colored...

Casa 625

2 Bedrooms
2 Bathrooms
4.7500
(16 Reviews)
The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to detail! Sit on the front porch and watch the world go by or enjoy the totally private...

Flagler's Crossing

2 Bedrooms
2 Bathrooms
Flagler's Crossing is a stunning 3 story condo with 2 bedrooms and 2 1/2 bathrooms. This home is one of the very few in Key West with a backyard ocean view! There is off-street covered parking, boat dockage, shared pool, multiple balconies, and an outdoor living area.

The backyard haven includes a...

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