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151-173 of 173 Key West Rentals

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Key West Florida Vacation Rentals - Home
1 / 26

Key West Home
2 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$107

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Home
Per night:$107 - $217
Per week:$747 - $1,517
Pets allowed:No
Internet:Yes

CAYO HUESO SUNSHINE: Awaken your senses with tropical breezes, tourquoise waters and Key West Sunshine in this brand new 2- bedroom, den, 3- bath home. A secluded location yet the best of both worlds allows you an easy stroll over to the sandy shores of Smather's Beach or just ...

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Key West Florida Vacation Rentals - Home
1 / 28

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$70 - $110
Per week:$490 - $770
Pets allowed:No
Internet:Yes

BOGEY'S RETREAT: Welcome to Bogey's Retreat, your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy all that Key West has to offer while staying in a relaxing environment. If you're a golfer, this house...

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Key West Florida Vacation Rentals - Apartment
1 / 25

Key West Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

from

$150

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$150 - $353
Per week:$1,050 - $2,465
Pets allowed:No
Internet:Yes

CITY CAY: Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This is the place! City Cay is our 1- bedroom 1- bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style of the most hip ...

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Key West Florida Vacation Rentals - Home
1 / 17

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$107

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$107 - $184
Per week:$747 - $1,284
Pets allowed:No
Internet:Yes

ISLAND BREEZE - - Located in the exclusive Sanctuary within the Key West Golf Club, this spacious home allows for lots of visitors with 3 bedrooms and a sleeper sofa. Enter an open floor plan of kitchen, dining room, half- bath and living room, with French doors leading outside...

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Key West Florida Vacation Rentals - Home
1 / 32

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Home
Per night:$70 - $110
Per week:$490 - $770
Pets allowed:Yes
Internet:Yes

A LITTLE SLICE OF PARADISE (monthly rental): Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, airport and some of the local's favorite restaurants. Spend a month (or two) in A Slice of Paradise and you may never return home. Two...

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Key West Florida Vacation Rentals - Apartment
1 / 24

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

(9)“ Excellent ”9 Reviews

from

$272

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$272 - $539
Per week:$1,900 - $3,770
Pets allowed:No
Internet:Yes

SUNDOWN REFUGE: Balmy breezes, brilliant sunshine and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex in Truman Annex. You'll spend most of your time overlooking Florida Bay in one direction and Truman's Little White House...

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Key West Florida Vacation Rentals - Apartment
1 / 24

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

(9)“ Excellent ”9 Reviews

from

$272

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$272 - $539
Per week:$1,900 - $3,770
Pets allowed:No
Internet:Yes

TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. This lovely condo in the exclusive Harbour Place condominium complex in Truman Annex offers all the comforts of home and...

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Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
1 Bedroom / 2 Bathrooms / Sleeps 2
Home / 1 Bedroom / Sleeps 2

from

$82

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$82 - $100
Per week:$572 - $700
Pets allowed:Yes
Internet:Yes

ROBIN'S ROOST (monthly rental): Tucked away in a quiet local neighborhood, Robin's Roost sits pretty in its own little world. Step through the front entry into an open living space that leads to your private backyard with jacuzzi to soothe your mind and soul. Bright, tropical colors...

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Key West Florida Vacation Rentals - Home
1 / 27

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 7
Home / 2 Bedrooms / Sleeps 7

(1)“ Excellent ”1 Review

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:7
Type:Home
Per night:$100 - $217
Per week:$700 - $1,517
Pets allowed:Yes
Internet:Yes

REJUVENATE! ! ! : This is a Key West experience you don't often find. This spacious 2- bedroom 2- bath cottage is part of a small compound with shared pool, but has its own jacuzzi within a private lanai. RECREATE: Master bedroom with king bed, brand new extra firm mattress, and...

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Key West Florida Vacation Rentals - Home
1 / 32

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

from

$100

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$100 - $204
Per week:$700 - $1,424
Pets allowed:Yes
Internet:Yes

FIRST BREATH: Lovely 3- bedroom 2- bath Conch home with pool located right in the middle of the action in Old Town Key West. Fenced in and lushly landscaped for the ultimate in privacy. Back gate opens onto Elgin Lane. Two bedrooms upstairs, one with king and one with queen bed, ...

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Key West Florida Vacation Rentals - Home
1 / 25

Key West Home
1 Bedroom / 2 Bathrooms / Sleeps 4
Home / 1 Bedroom / Sleeps 4

(25)“ Excellent ”25 Reviews

from

$210

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:4
Type:Home
Per night:$210 - $414
Per month:$6,300 - $12,420
Pets allowed:No
Internet:Yes

TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked. Fabulous artwork, fun collectables, beautiful stained glass all give this cottage the unique feel that keeps bringing visitors back...

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Key West Florida Vacation Rentals - Apartment
1 / 30

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

from

$84

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$84 - $160
Per week:$584 - $1,120
Pets allowed:No
Internet:Yes

SEASIDE ESCAPE (monthly rental): The name says it all. Stay for a month at Seaside Escape and enjoy the ocean views, balmy breezes and casual lifestyle that is the essence of Key West living. Open living space includes the living room, dining area and kitchen. Kitchen is stocked...

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Key West Florida Vacation Rentals - Home
1 / 19

Key West Home
4 Bedrooms / 3 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking...

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Key West Florida Vacation Rentals - Home
1 / 10

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Completely surrounded by luscious tropical greenery in beautiful quiet gated community of Truman Annex yet only one block away from Duval and Mallory Square. Covered porches overlooking private swimming pool. Beautiful hardwood and tiled floors with high ceilings and lots of ceiling...

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Key West Florida Vacation Rentals - Home
1 / 1

Key West Home
4 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 4 Bedrooms / Sleeps 8

Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi- private deck and lounge area with steps into a large kidney ...

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Key West Florida Vacation Rentals - Home
1 / 20

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(3)“ Excellent ”3 Reviews

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

30 DAY MINIMUM RENTALWelcome to Casa Alegria! An extended vacation at this Bahamian style conch house is sure to bring you happiness and joy! As you approach the front of the house you'll notice ample off- street parking on either side (a rarity in Old Town! ) as well as an easy...

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Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
2 Bedrooms / 3 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:3
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

30 DAY MINIMUM RENTALCasa de Mundo is found on a quiet street in the Heart of Old Town. Set amid plumerias and palm trees, the property is conveniently located near favorite restaurants like Mangia Mangia, Michael's, Azur, 5 Brothers and Help Yourself. The modern interior adds...

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Key West Florida Vacation Rentals - Home
1 / 7

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

30 DAY MINIMUM RENTAL .... NO PETS ACCEPTEDBreak away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the...

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Key West Florida Vacation Rentals - Home
1 / 1

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi- private deck and lounge area with steps into a large kidney ...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 1

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(1)“ Excellent ”1 Review

Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi- private deck and lounge area with steps into a large kidney ...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 9

Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

President†™ s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minutes from Fort Zachary Taylor State Park and its beach, this gated community offers lush gardens and a beautiful community pool at your doorstep. For Key West history...

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Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Tucked away near the upper end of Duval Street you'll find this stylish, newly renovated three bedroom, three bath home. Thoughtful details are luxuriously appointed to suit the vacation guest looking for privacy and high design. Walk up the brick drive and enter the gate to the...

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About Key West

Amenity-rich Key West vacation rentals are a superb way to enhance a visit to the southernmost city in the US. A wonderland of open-air bistros and bars, Euro-style cafes, hip boutiques, trendy art galleries, dynamic festivals, and seemingly every water sport imaginable, this island is a one-of-a-kind tropical city paradise.

One of the most prized experiences in the city is watching a sunset, which is possible from the balcony or patio of the many Key West condo rentals available in the area.

For the ultimate sunset celebration, of course, head to Mallory Square Dock, where a nightly arts festival attended by flocks of tourists from around the world features jugglers and fire eaters, art and jewelry exhibitors, local delicacies like Conch Fritters and Key Lime Tea, and Tarot card readers, hypnotists, and astrologers.

Beyond the glorious colors of a stunning Key West, FL sunset, there is much to see and do in the city. To immerse yourself in the laid-back, party lifestyle made famous by singer Jimmy Buffett, head to his restaurant, Jimmy Buffett's Margaritaville, where you'll find frosty margaritas and courtyard dining. Atop your sightseeing hit list should be the Ernest Hemingway Home and Museum, Harry S. Truman Little White House, the Aquarium, and the Shipwreck Historeum Museum.

When it's time to enjoy the blue-green waters encircling the city, your options range from snorkel and Scuba dive tours, parasailing, and jet skiing to deep sea fishing charters, dolphin cruises, and sailboat rentals.

If you're seeking Key West condo rentals on the beach, you'll find a selection of options with features like large porches with spectacular views, outdoor entertainment areas, and spacious dining areas. Vacation home rentals include everything from small, two-bedroom, pastel colored cottages to expansive homes that can accommodate more than a dozen people.

Many Key West rentals by owner come equipped with luxury amenities such as private pools and expansive outdoor veranda dining areas, multiple DVD players, flat-screen televisions, game rooms, and high-speed Internet access. Increasing the appeal is a fully equipped kitchen, which allows you to prepare money-saving meals and snacks.

The convenience and home-like comfort of Key West vacation rentals will make your visit to this special tropical town one to thoroughly enjoy and fondly remember.