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Holiday Villas Florida Keys, FL

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From
$2,210
/ Month
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1 / 15
5 of 5 stars (1) Excellent
Islamorada
1 Bedroom / 2 Bathrooms / Sleeps 4
Overview Reviews (1) Make Enquiry
From
$169
/ Night
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1 / 30
4 of 5 stars (1) Very good
Key West
Studio / 1 Bathroom / Sleeps 4
traveller have booked this property
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From
$367
/ Night
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1 / 28
4.5 of 5 stars (8) Very good
Key Largo
4 Bedrooms / 4 Bathrooms / Sleeps 10
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From
$366
/ Night
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1 / 9
4.5 of 5 stars (14) Very good
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 6
travellers have booked this property
Overview Reviews (14) Make Enquiry
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  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you... View all property information
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From
$252
/ Night
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1 / 16
Tavernier
2 Bedrooms / 2 Bathrooms / Sleeps 6
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Amenities & Details
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Shared Outdoor Pool...
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: Dec 22 - Dec 25 : Monday check-in required, Tuesday, Wednesday and Thursday check-out required.; Jan 10 - Jan 11 : Saturday and Sunday check-out required.; Jan 15 - Jan 16 : Thursday and Friday check-out required.; Jan 20 - Jan 22 :... View all property information
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From
$368
/ Night
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1 / 8
4 of 5 stars (3) Very good
Key West
2 Bedrooms / 1 Bathroom / Sleeps 5
Overview Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage is made completely private... View all property information
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From
$1,872
/ Night
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1 / 31
4.5 of 5 stars (6) Very good
Key West
7 Bedrooms / 7 Bathrooms / Sleeps 16
Overview Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and... View all property information
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From
$252
/ Night
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1 / 12
4.5 of 5 stars (11) Very good
Key West
1 Bedroom / 1 Bathroom / Sleeps 4
Overview Reviews (11) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
• Wireless Internet • Full Kitchen Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs tiled... View all property information
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From
$1,473
/ Night
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1 / 36
5 of 5 stars (1) Excellent
Key West
6 Bedrooms / 5 Bathrooms / Sleeps 12
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Island Rendezvous vacation rental offers the perfect solution for a gathering of family or friends who desire to be in the heart of Old Town Key West. Here you will enjoy a completely private retreat with an atmosphere of wonderfully unchanged Caribbean charm. By combining Pavilion Villa and Down... View all property information
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From
$258
/ Night
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1 / 28
Key Largo
3 Bedrooms / 3 Bathrooms / Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy your own private paradise and have fun in the Keys! This beautiful, clean, spacious and airy vacation rental home has three wonderfully decorated, clean and cozy bedrooms. Two and 1/2 comfortable and clean bathrooms. Full kitchen is stocked with all necessary cookware, china and silverware... View all property information
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From
$430
/ Night
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1 / 9
5 of 5 stars (1) Excellent
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Key West cottage architecture has been thoroughly 'time-tested' in 'island life and culture' in this somewhat infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.' Since its original construction in the early 1900's this note-worthy Cockadoodle... View all property information
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From
$264
/ Night
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1 / 22
5 of 5 stars (1) Excellent
Key West
1 Bedroom / 1 Bathroom / Sleeps 4
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on... View all property information
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From
$368
/ Night
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1 / 7
5 of 5 stars (1) Excellent
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during... View all property information
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From
$2,210
/ Week
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1 / 8
4.5 of 5 stars (2) Very good
Key West
2 Bedrooms / 3 Bathrooms / Sleeps 6
Overview Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern luxury condominium constructed within an important piece of historic American architecture. Situated along the gateway... View all property information
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From
$246
/ Night
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1 / 13
Marathon
2 Bedrooms / 1 Bathroom / Sleeps 6
Overview Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Ask About our Specials! Seaside Escape! Boater’s Paradise! In the heart of the Florida Keys, 'La Casita' is on MM 52. 'La Casita' is a quaint 1/2 duplex canal home with 2 bedrooms and 1 bathroom that can comfortably accommodate 4-6 guests. This lovely home sits on the Atlantic Ocean side, just 2... View all property information
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From
$6,445
/ Week
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1 / 18
4 of 5 stars (1) Very good
Key West
4 Bedrooms / 3 Bathrooms / Sleeps 8
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
If you've been searching for a private home overlooking the tropical turquoise sea, you've probably found that nearly all water-view vacation rental properties on Key West are hotels, condominiums, or time-shares, and that it's nearly impossible to find a private Key West house that offers both an... View all property information
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From
$246
/ Night
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1 / 5
5 of 5 stars (2) Excellent
Key West
2 Bedrooms / 1 Bathroom / Sleeps 4
Overview Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our home across the pond. We know you will enjoy your time in Key West as much as we do and Our... View all property information
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From
$368
/ Night
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1 / 16
4.5 of 5 stars (24) Very good
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Reviews (24) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront condos have a range of room types to suite your... View all property information
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From
$491
/ Night
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1 / 13
4.5 of 5 stars (4) Very good
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
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From
$6,690
/ Week
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1 / 34
Marathon
4 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Endless vistas of Vaca Cut, the Gulf of Mexico and Atlantic Ocean, all from your rooftop Pool! Over 400 feet of deep water dockage adjacent to Vaca Cut which runs between the Atlantic and Gulf. 4 Br, 2 Ba, tastefully furnished, with 2 kings, 1 queen and 2 twins. Huge open concept, kitchen, and... View all property information
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From
$264
/ Night
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1 / 25
4.5 of 5 stars (10) Very good
Key West
1 Bedroom / 1 Bathroom / Sleeps 2
Overview Reviews (10) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Having spent a long weekend in this one bedroom, one and a half bath apartment, one previous guest described it as a 'cozy condo hideaway in the heart of historic Key West.' The historic significance is close to home. It starts with the white stucco building that houses this suite and other... View all property information
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From
$491
/ Night
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1 / 10
5 of 5 stars (2) Excellent
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Open the front door of the hand crafted Havana Moon Key West cottage, step from the porch, and look south toward Havana Cuba and... Mmmm... You'll catch a view of the ocean where the full moon rises with a soft salt southern breeze. Originally built in the late 1800's as a cigar makers' cottage the... View all property information
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From
$169
/ Night
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1 / 35
4.5 of 5 stars (3) Very good
Key West
Studio / 1 Bathroom / Sleeps 4
travellers have booked this property
Overview Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back... View all property information
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From
$304
/ Night
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1 / 26
4.5 of 5 stars (11) Very good
Key West
2 Bedrooms / 1 Bathroom / Sleeps 6
travellers have booked this property
Overview Reviews (11) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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,... View all property information
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From
$1,228
/ Night
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1 / 26
Marathon
3 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Private Outdoor...
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Close Your Eyes And Imagine...Your Own Private Island In The Crystal Clear Blue Waters Of the Atlantic Ocean, Off The Shores Of Marathon, In The Florida Keys. Home of North America's Only Living Coral Barrier Reef, and the Third Largest Coral Barrier Reef in the World! With Your Own Boat You... View all property information
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From
$522
/ Night
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1 / 33
5 of 5 stars (18) Excellent
Key Largo
4 Bedrooms / 3 Bathrooms / Sleeps 10
Overview Reviews (18) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Spacious and gracious, 4 bedroom, 3 bath, top floor, corner villa with a jaw-dropping view of the resort`s harbor and the Atlantic. Thoughtful floor plan with open living concept, a wide, private balcony that beckons for those who enjoy dining alfresco. Master has a king bed with en-suite bath... View all property information
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From
$169
/ Night
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1 / 24
5 of 5 stars (1) Excellent
Key West
Studio / 1 Bathroom / Sleeps 4
travellers have booked this property
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of Southernmost Sanctuary Suites The Osprey Suite (Formerly 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... View all property information
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From
$338
/ Night
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1 / 28
5 of 5 stars (4) Excellent
Key Largo
3 Bedrooms / 3 Bathrooms / Sleeps 8
Overview Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Tri-level, 3/3 pool and oceanview townhouse ~ accommodates 8 Wake up to this idyllic view over the oasis pool out to the Atlantic Ocean...close your eyes and just breathe.... whether searching for a peaceful romantic getaway or an adventure vacation for the whole family, this 3-bedroom, 3-bath,... View all property information
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From
$427
/ Night
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1 / 22
4.5 of 5 stars (3) Very good
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 6
travellers have booked this property
Overview Reviews (3) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
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1 / 10
Key Colony Beach
3 Bedrooms / 3 Bathrooms / Sleeps 7
Overview Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
An updated 3 bedroom, 3 bath ground level half duplex. Large bedroom with 1 king, 1 queen, and 2 full size beds. Three full bathrooms. Four TV's - 3 flat screens and 2 DVD players, high speed wireless internet. You can watch the kids from living room, dining room, kitchen as they play in 8x14... View all property information
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From
$737
/ Night
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1 / 24
5 of 5 stars (9) Excellent
Key West
3 Bedrooms / 3 Bathrooms / Sleeps 6
Overview Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort... View all property information
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From
$304
/ Night
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1 / 29
4.5 of 5 stars (8) Very good
Key West
2 Bedrooms / 1 Bathroom / Sleeps 6
travellers have booked this property
Overview Reviews (8) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Part of POOLSIDE PARADISE 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,... View all property information
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From
$706
/ Night
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1 / 28
5 of 5 stars (2) Excellent
Key West
4 Bedrooms / 4 Bathrooms / Sleeps 8
Overview Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically... View all property information
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From
$145
/ Night
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1 / 20
4.5 of 5 stars (2) Very good
Key West
Studio / 1 Bathroom / Sleeps 2
traveller have booked this property
Overview Reviews (2) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of TROPICAL VILLAGE Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning... View all property information
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From
$6,138
/ Month
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1 / 17
Long Key
3 Bedrooms / 3 Bathrooms / Sleeps 8
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
From the minute you step foot in this luxurious condo, the water dominates your view and your activities. Oceanfront views from living room and master bedroom, 3 balconies... lush gardens, pool, palm trees, the finest sandy beach in the keys and the magnificent Atlantic Ocean are your constant... View all property information
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From
$859
/ Night
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1 / 25
4.5 of 5 stars (9) Very good
Key West
4 Bedrooms / 3 Bathrooms / Sleeps 10
Overview Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located... View all property information
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From
$307
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1 / 22
4.5 of 5 stars (67) Very good
Key West
1 Bedroom / 1 Bathroom / Sleeps 2
Overview Reviews (67) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Old Key West style defines this charming Bahamian Colonial studio hidden away on Rose Lane, which runs only one block from Simonton to Duval. The building right next door on Simonton, Casa Antigua, was Hemingway's first island residence, where in 1928 he wrote Farewell to Arms. Going the other way,... View all property information
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From
$76
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1 / 19
4.5 of 5 stars (3) Very good
Key Largo
2 Bedrooms / 1 Bathroom / Sleeps 4
Overview Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Enjoy your Own Private Secluded Retreat, RUMRUNNER'S DEN is a One (1) Bedroom Unit, Queen Size Bed in the Master Bedroom, with a Queen Size Adjustable Air Mattress, Standard Bed Height in the Den, 40 FT. Park Trailer, w/ Three Pullouts, and One Full Bath. Water Views from the Living Areas. Both,... View all property information
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From
$255
/ Night
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1 / 25
4.5 of 5 stars (3) Very good
Key West
2 Bedrooms / 1 Bathroom / Sleeps 4
travellers have booked this property
Overview Reviews (3) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people... View all property information
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From
$171
/ Night
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1 / 12
Long Key
3 Bedrooms / 3 Bathrooms / Sleeps 8
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located in the prestigious Port Antigua neighborhood and situated in Islamorada, FL, the Sportfishing capital of the world, this canalfront home offers 60 feet of dockage and immediate bay and ocean access. Spend your days fishing, diving or snorkeling the beautiful Florida Keys' waters or... View all property information
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From
$399
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1 / 9
5 of 5 stars (1) Excellent
Key West
1 Bedroom / 1 Bathroom / Sleeps 4
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate... View all property information
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From
$368
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1 / 15
4.5 of 5 stars (26) Very good
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Reviews (26) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront condos have a range of room types to suite your... View all property information
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From
$368
/ Night
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1 / 17
4.5 of 5 stars (12) Very good
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront condos have a range of room types to suite your... View all property information
Make Enquiry
From
$399
/ Night
View Details
1 / 18
5 of 5 stars (1) Excellent
Key Largo
3 Bedrooms / 3 Bathrooms / Sleeps 8
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This spectacular 2600 square foot villa boasts a blissful atmosphere and breathtaking view of the harbor and Atlantic Ocean. Three bedroom, three bath plus den, top floor, corner villa with private entrance...comfortably accommodates 8. Master bedroom has a king bed and sumptuous spa tub in the... View all property information
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From
$74
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1 / 13
Key Largo
3 Bedrooms / 1 Bathroom / Sleeps 5
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our home is available for the months of December, April and May ONLY. Weekly rental minimum . Thanks! Sit back and relax under a coconut tree while watching a great sunset on our sandy private community beach. Come and enjoy the Florida Keys and everything it has to offer. Stay at our newly... View all property information
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From
$356
/ Night
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1 / 26
5 of 5 stars (14) Excellent
Key West
2 Bedrooms / 2 Bathrooms / Sleeps 6
travellers have booked this property
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Wake up to the sun rising over the sparkling Atlantic Ocean. Watch heron fish for breakfast in the flats below as you drink your coffee. Stretch out on the balcony while flocks of pelicans soar above you and the rocks disappear and reappear with the tide below you. Sip a cocktail and watch the... View all property information
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From
$982
/ Night
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1 / 18
4.5 of 5 stars (5) Very good
Key West
4 Bedrooms / 4 Bathrooms / Sleeps 10
Overview Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Have you ever outgrown a favorite small space, and dreamed about transforming it into something larger and even better?  Wishing you could somehow magically gain enough room to expand it so it offered twice the space, while keeping all its original charm?  Well … that’s exactly what happened right... View all property information
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From
$231
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1 / 31
4.5 of 5 stars (37) Very good
Key West
1 Bedroom / 2 Bathrooms / Sleeps 4
Overview Reviews (37) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located inside the Villas known as Old Town Garden Villas Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly... View all property information
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From
$501
/ Night
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1 / 33
5 of 5 stars (1) Excellent
Key West
3 Bedrooms / 2 Bathrooms / Sleeps 6
traveller have booked this property
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been... View all property information
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From
$982
/ Night
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1 / 29
Key West
4 Bedrooms / 4 Bathrooms / Sleeps 10
Overview Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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