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Monthly Key West Rentals

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Sunshine House

1 Bedroom
1 Bathroom
Welcome to the Sunshine House - a beautifully renovated 1 bedroom home tucked away in the Bahama Village neighborhood in the heart of Old Town Key West! This adorable home features brand new furnishings, including a new queen sized bed and new queen sized sleeper sofa with a top of the line...

Paradise Palms

2 Bedrooms
2 Bathrooms
5.0000
(1 Review)
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...

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 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...

Bay Harbor View

5 Bedrooms
3 Bathrooms
4.7500
(@ct 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...

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...

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....

Caribbean Fling

2 Bedrooms
1 Bathroom
Ever wish you could spend a month or two in one of those perfect little conch houses set along the streets of Old Town, Key West? Take a look inside this classic little conch house with a Caribbean flair, and you’ll find exactly what you’ve been looking for. Set in the ideal Key West location - on...

Casa 625

2 Bedrooms
2 Bathrooms
4.7500
(@ct 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...

Carriage Courtyard

3 Bedrooms
2 Bathrooms
Carriage courtyard prior to becoming the beautiful modern wonder that it is today was used to store a horse drawn carriage. Newly remodeled, you can now retreat to you very own courtyard paradise.

Located in Historic Bahama Village and only one block away from the World famous Duval St, places...

Tsalta

3 Bedrooms
3 Bathrooms
5.0000
(@ct 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...

Eliza's Escape

4 Bedrooms
3 Bathrooms
Unwind on the wrap around patio, cool off in the pool, explore the wonders of your next vacation. Let Eliza's Escape become your favorite vacation spot!

Surprisingly elegant tropical oasis. Unassuming and hidden by lush mature foliage, in a quite Key West neighborhood. Be swept away by warm...

Beach View Breeze

2 Bedrooms
2 Bathrooms
4.5000
(@ct 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...

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...

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...

Paradise on Sunset Key

2 Bedrooms
2 Bathrooms
5.0000
(1 Review)
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...

Shark Key Chateau

5 Bedrooms
4 Bathrooms
4.7500
(@ct 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...

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...

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...

Whitehead Manor

5 Bedrooms
2 Bathrooms
Located in Bahama Village this 5 Bedroom, 2 Bathroom house sits in a divine location. Just one block from the Historic Duval Street, and minutes from many other attractions. Fenced in yard provides a private, secluded space to relax on your island vacation.

You will be greeted by a open and sunny...

Howe Street Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(@ct 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...

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...

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