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Monthly Key West Rentals

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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...

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...

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...

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....

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...

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,...

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...

Sunset Marina View

2 Bedrooms
2 Bathrooms
Gorgeous monthly rental next to the golf course on stock island in Key West! This spacious condo is located next to the best dining and water activities the island has to offer!

When you walk into the condo, you will be fall in love with the island feel of the home. The breeze hits the palm trees...

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...

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...

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...

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 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...

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...

Club Clark

3 Bedrooms
3 Bathrooms
4.7500
(8 Reviews)
The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a tub and full vanity, and an open, spacious living room with beautiful furnishings...

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...

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...

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
(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...

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...

Villa Azul

3 Bedrooms
3 Bathrooms
5.0000
(2 Reviews)
You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old Town, just 4 blocks to the Historic Seaport District or the Art Gallery District on White...

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...

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