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Key West Rentals

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Sunrise Suites - Tortuga Suite 301

2 Bedrooms
2 Bathrooms
4.6250
(48 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Creme Brulee Getaway

Studio
1 Bathroom
4.6875
(64 Reviews)
Part of Banana's Foster Guest House

This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with...

Havana Daydream @ Key Cove

4 Bedrooms
4 Bathrooms
Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private waterfront pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down...

Caribbean Dreams

Studio
1 Bathroom
4.3000
(40 Reviews)
Caribbean Dreams is an inviting space, decorated in rich wood and cane furnishings, perfect for your Key West vacation!

Just a few steps up from the garden entry path, "Caribbean Dreams" offers a calm and cozy atmosphere. Enjoy the ultra comfy queen sized bed, free wifi, and daily housekeeping...

Sunrise Suites - Barbados Suite 204

2 Bedrooms
2 Bathrooms
4.5455
(66 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

Commodore's Compound

8 Bedrooms
7 Bathrooms
Commodore's Compound is comprised of 2 separate units - Seaport Suite and Commodore's Cove:

SEAPORT SUITE:

Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key West home in Old Town.. The location is as close to perfect as you can get, being one...

Osprey Suite

Studio
1 Bathroom
4.5135
(74 Reviews)
Part of Southernmost Sanctuary Suites

The Osprey Suite - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a Queen Bed as well as a sofa for...

Mary's Backyard Too

2 Bedrooms
1 Bathroom
4.8333
(60 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!...

Sunrise Suites - Saint Barts Suite 303

2 Bedrooms
2 Bathrooms
4.5581
(86 Reviews)

Sunrise Suites Resort is an island paradise.  Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our...

The Galleria - Carey's Corner

Studio
1 Bathroom
4.4167
(24 Reviews)
Affordable studio w/ private bathroom and kitchenette located in The Galleria condominium complex in the heart of "Old Town" Key West. Walking distance to Ft Zachary Taylor State Park & Beach, Blue Heaven, The Earnest Hemingway House, and much more! Free WiFi, cable TV, & daily housekeeping...

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...

The Galleria - Andy's Attic

Studio
1 Bathroom
4.4000
(20 Reviews)
Affordable studio w/ private bathroom and kitchenette located in The Galleria condominium complex in the heart of "Old Town" Key West. Walking distance to Ft Zachary Taylor State Park & Beach, Blue Heaven, The Earnest Hemingway House, and much more! Free WiFi, cable TV, & daily housekeeping...

Curry House Room 3

Studio
1 Bathroom
4.6750
(80 Reviews)
An excellent value, Room 3 is delightful and comfortable. This room is unique in the Curry House in that it is the only room with French doors that open up onto the second-floor porch. Room 3 shares a bathroom with Room 4. The bathroom is exclusive to these two rooms and has an island charm all it'...

Kate's Krawl Off Duval

1 Bedroom
1 Bathroom
4.7857
(28 Reviews)
This 1 bed 1 bath home is the perfect home for you to enjoy Key West and all it has to offer. Located just steps from the World-Famous Duval St. you will find yourself in one of the most desired locations in Key West. Downstairs in this home you will find a full kitchen and comfortable living...

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...

Curry House Room 2

Studio
1 Bathroom
4.8049
(82 Reviews)
Room 2's pale shade of colors will continually remind you that you're staying in a tropical paradise. Step out onto the semi-private veranda overlooking the pool. Sit and relax, surrounded by the tropical vegetation that abounds on this magnificent island. An oversized shower in the private...

Sunrise Suites - Bimini Suite 211

2 Bedrooms
2 Bathrooms
4.3636
(44 Reviews)
Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many...

Old Town Garden Villas

5 Bedrooms
6 Bathrooms
4.9231
(26 Reviews)
The location is set on Center Street, which is located ½ block off Duval Street. These Villas are a favorite of our guests who like to relax in the quiet, beautiful garden area. Your party can book 1 to 5 of these Villas for a relaxing vacation.

Old Town Garden Villas is comprised of the following...

Tropical Village - Tropical Cottage

2 Bedrooms
2 Bathrooms
4.6364
(66 Reviews)
Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free...

Paris Mango @ Key Cove

4 Bedrooms
4 Bathrooms
Enjoy the island life in your own oasis tucked away from the bustle of Old Town in a private waterfront retreat, with your own private heated pool. Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down,...

Nautical Wheeler @ Key Cove

4 Bedrooms
3 Bathrooms
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautiful outdoor spaces. Slow down, relax and prepare for life the way it should be at Nautical Wheeler. This home is located in the private community of Key Cove Landings, on an...

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