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Monthly Key West Rentals

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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...

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...

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...

Shark Key Chateau

5 Bedrooms
4 Bathrooms
4.7500
(8 Reviews)
Château - Merriam-Webster defines it as a "large impressive residence". This does not do the 'Shark Key Chateau' justice! Very impressive, very large, very luxurious! Set apart from any residence you have experienced. But this property does not rest on

Shark Key Chateau is 'Grande' to say the...

Key West Nest

3 Bedrooms
2 Bathrooms
This could be your home away from home… All the comforts you’re used to right here in Key West.

The 3 bedrooms and 2 baths comfortably accommodate up to 6 persons (3 couples, etc). There is a king bed in the master bedroom and queen beds in the other two bedrooms. The kitchen is well stocked with...

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...

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...

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...

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...

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...

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,...

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...

Golf Club Getaway

2 Bedrooms
1 Bathroom
Cute 2 bed 1.5 bath house located in the Key West Golf Club with fenced in yard.

New Furnishings and Appliances. Great location, steps to golf clubhouse and visitor parking, 2 miles from airport, very close to shopping, and 4 miles from Duval. Private setting with no neighbors to back, fenced yard...

Casa Diamante

3 Bedrooms
2 Bathrooms
Casa Diamante is a beautiful three bedroom, two and a half bathroom home in the perfect location of downtown Key West. This newly renovated home is sure to impress and is the perfect island getaway! When you walk through the frosted glass door, you will be welcomed by an expansive living area with...

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...

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...

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...

Cabana Retreat

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

Cabana Retreat 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...

Casa Hueso

4 Bedrooms
3 Bathrooms
**There will be construction in the surrounding developing area on and off for the next year**

Trade in your stressful workdays and chilly weather for a fresh ocean breeze and plenty of sunshine! This Newly Built Key West Home has more than enough space for all your friends and family to share...

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...

Great Egret Escape

2 Bedrooms
2 Bathrooms
As you enter the home through the beautiful stain-glass door, you will be greeted by colorful artwork, high ceilings and rich wooden floors. Just to your left is the immaculate kitchen, fit for a master chef! You will love the brand new appliances, marble counter tops and island, with bar seating...

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...

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