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Key West Rentals

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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...

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...

Saint Lucia Suite #201

2 Bedrooms
2 Bathrooms
4.6842
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Duval Canopy

Studio
1 Bathroom
4.5714
(@ct Reviews)
Cozy Condo in Prime Location! Right off of Duval Street! Located just steps off of world famous Duval Street, Duval Canopy is the perfect blend of comfort, location and value.

Just a few blocks from The Southernmost Beach, the Southernmost Point, and other favorites like The Butterfly Conservatory...

Duval Street Retreat

4 Bedrooms
2 Bathrooms
4.7500
(@ct Reviews)
Welcome to "Duval Street Retreat" - The perfect vacation rental for large groups looking to be around all the Duval St action!

Duval St. Retreat consists of two separate two-bed, one-bath condos located at 1124 Duval St. The property is only a couple steps (or stumbles) away from fine dining, bars...

Saint Barts Suite #303

2 Bedrooms
2 Bathrooms
4.5581
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and...

Cayo Coco Suite #208

2 Bedrooms
2 Bathrooms
4.7436
(@ct Reviews)
(Recently updated!)

*** 1 Private, covered parking spot is included when you rent this particular vacation condo

Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make...

Antigua Suite #312

2 Bedrooms
2 Bathrooms
4.4706
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Wahoo Way On Duval

1 Bedroom
1 Bathroom
5.0000
(@ct Reviews)
This Studio has everything you want and a location that can not be beat. Located on upper Duval St, you are walking distance to Southernmost Point, Mallory Square, shops, restaurants, beaches and bars. The tile floors and Dade Pine walls give this Studio a real Key West feel. Outfitted with a...

Cristobal Suite #411

2 Bedrooms
2 Bathrooms
4.6591
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Mary's Backyard Too

2 Bedrooms
1 Bathroom
4.8333
(@ct Reviews)
This 2 bedroom, 1 bathroom unit is right downtown and features everything you will need for your Key West getaway! Located next door to other vacation rentals such as Mary's Backyard and Banana's Foster Guesthouse and across the street from Seaport Suite.

The location itself could not be better!...

Andros Suite

1 Bedroom
1 Bathroom
4.8293
(@ct Reviews)
Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door!

Andros Suite is a bi-level suite with a very spacious bedroom upstairs with Caribbean colors and wood floors.

Key West Vacation Rentals...

Sweet Caroline

2 Bedrooms
2 Bathrooms
4.7027
(@ct Reviews)
Part of Banana's Foster Guest House

This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front...

Leeward Isle

2 Bedrooms
1 Bathroom
4.7600
(@ct Reviews)
One half of the group unit Tradewinds, opposite Windward Isle, the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and walls,...

Conch Casa

2 Bedrooms
1 Bathroom
4.7069
(@ct Reviews)
The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,...

Samana Cay Suite #405

2 Bedrooms
2 Bathrooms
4.6591
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Dominican Suite #110

2 Bedrooms
2 Bathrooms
4.4583
(@ct Reviews)
Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge...

Helen's Hideaway

2 Bedrooms
2 Bathrooms
4.8000
(@ct Reviews)
This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise...

Curry House Bed & Breakfast

9 Bedrooms
9 Bathrooms
5.0000
(1 Review)
The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as "Curry's Rooms" in the mid-1900's. Now the inn offers nine beautiful guestrooms and the commercial kitchen serves breakfast each morning by the pool. Eight of the rooms have doors onto verandas, four...

Four Flowers Guesthouse

4 Bedrooms
4 Bathrooms
4.8000
(@ct Reviews)
Four Flowers is the perfect island getaway spot for friends and family that want to be close together while maintaining privacy. Four Flowers is a combination of 4 condos located on Simonton St - Orchid Escape, Jasmine Suite, Hibiscus Hideaway, & Gardenia Getaway

Hibiscus Suite is a queen...

Papa's Hideaway #4 - Islands in the Stream

Studio
1 Bathroom
4.5682
(@ct Reviews)
Located at Papa's Hideaway an historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value.

Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds...

Papa's Hideaway #2 - Sun Also Rises

Studio
1 Bathroom
4.6087
(@ct Reviews)
Papa's Hideaway was an historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval Street. The perfect mix of location, atmosphere and value.

This studio is located on the second floor and offers a king-size bed, queen-size sleeper sofa,...

Poolside Suite

2 Bedrooms
1 Bathroom
4.6364
(@ct Reviews)
One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location.

Enjoy nearby bars, shops, and fine dining...

Gardenia Getaway

1 Bedroom
1 Bathroom
4.6000
(@ct Reviews)
Gardenia Getaway is part of the group unit "4 Flowers"- located on the corner of Simonton St and Freeschool Ln, just one block from world famous Duval St.

Welcome to the perfectly located and affordable apartment Gardenia Getaway. You will not find a better spot to spend your sunny days and...

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