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Key West Florida Vacation Rentals - Home
1 / 24

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

(23)“ Excellent ”23 Reviews

from

$210

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$210 - $392
Per month:$6,300 - $11,760
Pets allowed:No
Internet:Yes

ISLAND PEARL: True island living in this 1 loft bedroom 1 bath cottage, complete with living room and kitchen. French doors open to a meandering deck surrounded by tropical foliage. This secluded hideaway is located behind a needlepoint store in historic Old Town Key West. Enter ...

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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 / 23

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

(23)“ Excellent ”23 Reviews

from

$625

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Home
Per night:$625 - $1,298
Per month:$18,750 - $38,940
Pets allowed:No
Internet:Yes

DUVAL PENTHOUSE - - A large luxury apartment located in downtown Key West. This property has it all, fabulous location, beautiful furnishings and plenty of space to accommodate your friends and family. Duval Penthouse is designed after a chic urban flat with an island twist, comfortable...

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Key West Florida Vacation Rentals - Home
1 / 23

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

(22)“ Excellent ”22 Reviews

from

$625

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$625 - $1,298
Per month:$18,750 - $38,940
Pets allowed:No
Internet:Yes

Bahama House - Location, Location, Location! Totally gorgeous, this spacious house is conveniently located on a quiet street in the heart ofOld Town Key West http://www. athomekeywest. com/bre/categories/OLD- TOWN/on ly one block from the fabulous shops, activities, restaurants...

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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
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 / 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

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 - 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 - Home
1 / 22

Key West Home
1 Bedroom / 1 Bathroom / Sleeps 4
Home / 1 Bedroom / Sleeps 4

(5)“ Very Good ”5 Reviews

from

$67

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$67 - $100
Per week:$467 - $700
Pets allowed:Yes
Internet:Yes

VARELA COTTAGE - A true Conch cutie snuggled in Old Town. Varela Cottage is a 1. 5 bedroom 1 bath cottage with loft including a 2nd sleeping area. As you walk up to your front porch sitting area the front door opens and you enter into a cozy hideaway with amazing space. Tile entry...

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Key West Florida Vacation Rentals - Home
1 / 22

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

(1)“ Excellent ”1 Review

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$97 - $160
Per week:$677 - $1,120
Pets allowed:Yes
Internet:No

TRES GATOS: Spend a month (or two) in one of Key West's most revered neighborhoods and live like a local in this sweet 2- bedroom Conch cottage. A few blocks from Higgs Beach, Sandy's Cafe and the infamous Fausto's Food Palace; a quick bike ride to Duval Street. Open floor plan ...

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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 / 33

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

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$70 - $110
Per week:$490 - $770
Pets allowed:No
Internet:Yes

AQUA: What comes to mind when you think of the color aqua? This home was lovingly designed to give you that sense of peace and serenity, balmy breezes and crystal clear waters. The front entrance opens to the kitchen - - neat, clean and fully stocked with all your culinary necessities....

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Key West Florida Vacation Rentals - Apartment
1 / 26

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

(32)“ Excellent ”32 Reviews

from

$265

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$265 - $472
Per month:$7,950 - $14,160
Pets allowed:No
Internet:Yes

CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, ...

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Key West Florida Vacation Rentals - Home
1 / 24

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

(2)“ Excellent ”2 Reviews

from

$60

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$60 - $119
Per week:$420 - $829
Pets allowed:Yes
Internet:Yes

IBIS - Located in The Colony compound, Ibis is a wonderful one bedroom one bath condo. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. Simple but comfortable, Ibis has kitchenette with granite countertop...

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Key West Florida Vacation Rentals - Home
1 / 20

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

from

$74

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$74 - $150
Per week:$514 - $1,050
Pets allowed:Yes
Internet:Yes

COCONUT COTTAGE - - Adorable, affordable, and near all the action.... You bet! Coconut Cottage is the perfect escape for a couple or singles looking to get away from it all in paradise… Located in a quiet neighborhood of Old Town Key West this one bedroom two bath cottage is...

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Key West Florida Vacation Rentals - Home
1 / 25

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

(2)“ Excellent ”2 Reviews

from

$67

/ night

Email Owner
Bedrooms:1
Bathrooms:2
Sleeps:2
Type:Home
Per night:$67 - $117
Per week:$467 - $817
Pets allowed:No
Internet:Yes

SUNNY VIEW - Adorable, affordable, and a great location! You bet! Sunny View is the perfect escape for a couple or singles looking to get away from it all in Paradise… Located in Old Town Key West this one bedroom two bath cottage is a gorgeous spot to rest and recuperate from...

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Key West Florida Vacation Rentals - Home
1 / 24

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

(2)“ Excellent ”2 Reviews

from

$786

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$786 - $1,625
Per week:$5,500 - $11,375
Pets allowed:No
Internet:Yes

BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private home that features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. Unique personal touches, beautiful furnishings and artwork can be found throughout to remind...

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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 - Apartment
1 / 27

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

(53)“ Excellent ”53 Reviews

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$225 - $457
Per month:$6,750 - $13,710
Pets allowed:No
Internet:No

DUVAL BREEZE: Enjoy the great location of this beautiful 2 bedroom 2. 5 bath townhome located in the gated rooftop community of Duval Square on Duval Street, in the middle of the action. Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval...

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Key West Florida Vacation Rentals - Apartment
1 / 25

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

(12)“ Excellent ”12 Reviews

from

$240

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$240 - $479
Per month:$7,200 - $14,370
Pets allowed:No
Internet:Yes

DUVAL STREET HIDEAWAY: This 2 story, 2 bedroom 2. 5 bath rooftop townhome is located above Duval Square, a perfect Old Town location to enjoy the sights and quiet retreat when relaxation is what is needed. Lots of upgrades in 2014 with new paint, new beds, new sofa. This property...

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Key West Florida Vacation Rentals - Home
1 / 29

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

(26)“ Excellent ”26 Reviews

from

$258

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Home
Per night:$258 - $529
Per week:$1,800 - $3,698
Pets allowed:No
Internet:Yes

ARTIST GARDEN - - Bright and breezy 2 bedroom 2. 5 bath private home located in the prestigious Admirals Lane neighborhood of Truman Annex. Ideal location, walking distance to allOld Town Key West http://www. athomekeywest. com/bre/categories/OLD- TOWN/ha s to offer including the...

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Key West Florida Vacation Rentals - Apartment
1 / 29

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

(21)“ Excellent ”21 Reviews

from

$222

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$222 - $492
Per week:$1,550 - $3,444
Pets allowed:No
Internet:No

A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2. 5 bath Conch- Style townhome in prestigous Truman Annex. On the main level this property features a fully equipped kitchen, dining area, half bath and living room with french...

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Key West Florida Vacation Rentals - Home
1 / 27

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

(1)“ Excellent ”1 Review

from

$117

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$117 - $227
Per week:$817 - $1,587
Pets allowed:Yes
Internet:Yes

ECCO DOMANI – Meaning "Here Tomorrow" this is a beautiful 3 story home with private pool, off street parking and attractive appointments - - a wonderful Key West escape. Centrally located just off Simonton Street, you are 1 block to Duval Street, walking distance to galleries,...

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Key West Florida Vacation Rentals - Apartment
1 / 27

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

(47)“ Excellent ”47 Reviews

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$225 - $457
Per month:$6,750 - $13,710
Pets allowed:No
Internet:Yes

DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around the...

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Key West Florida Vacation Rentals - Apartment
1 / 32

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

(30)“ Excellent ”30 Reviews

from

$236

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$236 - $508
Per week:$1,650 - $3,553
Pets allowed:No
Internet:Yes

KEY WEST FOUND – A striking 2 bedroom, 2. 5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first floor features...

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Key West Florida Vacation Rentals - Home
1 / 22

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

(4)“ Excellent ”4 Reviews

from

$87

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$87 - $150
Per week:$607 - $1,050
Pets allowed:Yes
Internet:Yes

SUNSET LAKE - - Discover paradise and empty yourself of worries & hurries. Set at the end of a quiet lane, amid tropical landscaping, this 3- bedroom 3- bath townhome exudes an ambiance of peace and tranquility. The spacious interior overlooks the 15th and 17th holes on the...

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Key West Florida Vacation Rentals - Apartment
1 / 25

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

(25)“ Excellent ”25 Reviews

from

$220

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$220 - $382
Per month:$6,600 - $11,460
Pets allowed:No
Internet:Yes

PAPAYA PLACE pops with color! This great 2 bedroom 2 bath condominium at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing you...

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Key West Florida Vacation Rentals - Apartment
1 / 19

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

(34)“ Excellent ”34 Reviews

from

$286

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$286 - $580
Per week:$2,000 - $4,060
Pets allowed:No
Internet:Yes

ISLAND SPICE - - A beautiful 2 bedroom, 2. 5 bath townhome, located in the historic Foundry building of the prestigious Truman Annex community. Plenty of space to relax and unwind, ocean breezes from the private patio and a great location where you can walk to all the Old Town...

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Key West Florida Vacation Rentals - Apartment
1 / 25

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

(34)“ Excellent ”34 Reviews

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$300 - $480
Per month:$9,000 - $14,400
Pets allowed:No
Internet:Yes

A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condominium for focusing on what is important in life. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated with your comfort and relaxation in mind. Located on the Atlantic...

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Key West Florida Vacation Rentals - Apartment
1 / 27

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

(6)“ Excellent ”6 Reviews

from

$345

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$345 - $532
Per month:$10,350 - $15,960
Pets allowed:No
Internet:Yes

KEY WEST CROWN JEWEL: We know you'll enjoy staying in our little bit of Paradise. This 2- bedroom, 2- bath, penthouse condominium with 1350 square feet of living space and vaulted ceilings offers breathtaking ocean views and the colors of the sunset from the 35- foot balcony, as...

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Key West Florida Vacation Rentals - Apartment
1 / 24

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

(33)“ Very Good ”33 Reviews

from

$222

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$222 - $441
Per week:$1,550 - $3,082
Pets allowed:No
Internet:Yes

CROWNER'S JEWEL: Experience the finest in Key West living when you stay in this delightful 2 bedroom 2. 5 bath Conch- style townhome. Lots of space for a family of 6. Master bedroom has bath ensuite and private balcony. Living room opens to your private deck for sipping cocktails,...

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Key West Florida Vacation Rentals - Home
1 / 24

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

(53)“ Excellent ”53 Reviews

from

$340

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Home
Per night:$340 - $682
Per month:$10,200 - $20,460
Pets allowed:Yes
Internet:Yes

AMELIA HOME - A 2 bedroom 2. 5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment - - this is the Key West vacation you have been seeking. An ideal location for walking and biking to...

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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

(16)“ Excellent ”16 Reviews

from

$193

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$193 - $435
Per week:$1,350 - $3,045
Pets allowed:No
Internet:Yes

BAHAMIAN REED: Bright and colorful 2 bedroom 1. 5 bathroom townhome located in the prestigious community of Truman Annex within the Old Town district of Key West. A great location and beautifully furnished accomodation make this property the home away from home you have been seeking....

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Key West Florida Vacation Rentals - Home
1 / 26

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

(8)“ Excellent ”8 Reviews

from

$84

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$84 - $150
Per week:$584 - $1,050
Pets allowed:Yes
Internet:No

ATLANTIC BLUES - A stylish example of a Conch cottage, renovated with gorgeous hardwood floors, beautiful glass tiles, shining granite countertops and décor that is playful and soothing. No detail has been overlooked in this home. Vaulted ceilings and an interesting collection...

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Key West Florida Vacation Rentals - Apartment
1 / 35

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

(2)“ Excellent ”2 Reviews

from

$70

/ night

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

LAKEVIEW - Come to Key West where the sun always shines! ! Stay in a beautiful 2 bedroom 1. 5 bath townhome in the gated Key West Golf Club community, located at the entrance to Key West within a mile of Smathers Beach and the airport, just minutes from some of our favorite local...

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Key West Florida Vacation Rentals - Apartment
1 / 26

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

(1)“ Excellent ”1 Review

from

$168

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$168 - $384
Per week:$1,175 - $2,683
Pets allowed:No
Internet:No

SIESTA BAY - - Beautiful two bedroom one bath upstairs condo in Truman Annex, just steps away from the shared pool and within walking distance of anything you'd want to do in Key West. Bright, airy and with plenty of Key West charm Siesta Bay will provide you with all the comforts...

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Key West Florida Vacation Rentals - Apartment
1 / 26

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

(8)“ Excellent ”8 Reviews

from

$265

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$265 - $472
Per month:$7,950 - $14,160
Pets allowed:No
Internet:Yes

ISLAND WIND: This charming 2 bedroom 2 bath Bahamian style townhome, with tin roof and white spindled decks reminiscent of old Key West, is located in award- winning Windward Park, a gated and secure compound consisting of 13 privately owned homes clustered around a 20' X 50' pool....

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Key West Florida Vacation Rentals - Apartment
1 / 25

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

(4)“ Excellent ”4 Reviews

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$74 - $107
Per week:$514 - $747
Pets allowed:No
Internet:Yes

EMMA'S ESCAPE - - Beautiful and spacious two bedroom one bath condo located in historic Old Town's Bahama Village neighborhood, Emma’s Escape is one of four condos within a restored historic home. The kitchen is well appointed with upgraded appliances, granite counters, and ...

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Key West Florida Vacation Rentals - Home
1 / 12

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

(11)“ Excellent ”11 Reviews

from

$94

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$94 - $197
Per week:$654 - $1,377
Pets allowed:No
Internet:Yes

VERANDAH - Tucked away on historic Frances Street lies your island escape… Verandah is a stunning two bedroom two bath home with a private pool and plenty of space for your family to stay and play! A gorgeous front porch surrounded by tropical foliage welcomes each guest and allows...

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Key West Florida Vacation Rentals - Home
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Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(8)“ Excellent ”8 Reviews

from

$74

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$74 - $140
Per week:$514 - $980
Pets allowed:No
Internet:Yes

SUNNY DAYS - Beautifully maintained while retaining its original style and structure. Dade County pine is throughout the property adding a feel of old Key West. The furnishings are tasteful and comfortable with a full kitchen and washe/dryer for your use. Sit in the sun room and ...

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Key West Florida Vacation Rentals - Apartment
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Key West Apartment
2 Bedrooms / 1 Bathroom / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

(25)“ Excellent ”25 Reviews

from

$168

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$168 - $384
Per week:$1,175 - $2,683
Pets allowed:No
Internet:Yes

KEY WEST CHARMING: This downstairs 2 bedroom 1 bath home has been lovingly cared for by the owners. They actually use the property themselves each spring so they know what will make their guests stay more comfortable. The living and dining area open out to the large back wooden deck...

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Key West Florida Vacation Rentals - Home
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Key West Home
2 Bedrooms / 1 Bathroom / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(8)“ Excellent ”8 Reviews

from

$94

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Home
Per night:$94 - $157
Per week:$654 - $1,097
Pets allowed:Yes
Internet:Yes

PERFECT PINEAPPLE - Long considered a sign of hospitality, the pineapple is now widely recognized as sign of Welcome and Friendship..... and so we welcome you to the Perfect Pineapple. On the corner of Southard and Margaret streets in the historic district of Old Key West, this...

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

(7)“ Very Good ”7 Reviews

from

$84

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$84 - $157
Per week:$584 - $1,097
Pets allowed:Yes
Internet:No

KEY LIME PIE - A little slice of Paradise located only one block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Key Lime Pie is located on a small narrow lane that is a secret from even many of the locals in Key West. This house has...

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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 Home
2 Bedrooms / 2 Bathrooms / Sleeps 4
Home / 2 Bedrooms / Sleeps 4

(4)“ Excellent ”4 Reviews

from

$84

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$84 - $167
Per week:$584 - $1,167
Pets allowed:No
Internet:Yes

NAUTICAL DREAMS: Here's the perfect spot for whatever you desire, parties or peace & quiet. This 2- bedroom 2- bath cottage is located in a small compound of 8 cottages behind its own privacy fence. French doors offer access from each bedroom, living room and kitchen onto a...

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Key West Florida Vacation Rentals - Apartment
1 / 32

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

(26)“ Excellent ”26 Reviews

from

$208

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$208 - $407
Per week:$1,450 - $2,843
Pets allowed:No
Internet:Yes

BEACH HOUSE CONDO: Beautiful 2 bedroom 2 bath ground level condo located in the gated Shipyard Condominium area of the prestigious Truman Annex community. Beach House Condo has the perfect back deck to sip a cafe con leche in the morning and grill your own fresh catch in the afternoon....

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Key West Florida Vacation Rentals - Apartment
1 / 28

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

(29)“ Excellent ”29 Reviews

from

$168

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$168 - $384
Per week:$1,175 - $2,683
Pets allowed:No
Internet:Yes

FINN KEY: A beautiful 2 bedroom 1 bath downstairs condominium located in the Shipyard section of Truman Annex. This pristine residential community is one of the most requested locations in the heart of historic Old Town Key West. A wonderful mix of a private gated community yet easy...

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Key West Florida Vacation Rentals - Apartment
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Key West Apartment
2 Bedrooms / 1 Bathroom / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

(50)“ Excellent ”50 Reviews

from

$200

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$200 - $430
Per week:$1,400 - $3,009
Pets allowed:No
Internet:No

SHIPYARD TREASURE - Great Key West location, this two bedroom one bath Shipyard condo has it all. You are centrally located to all the sites and attractions of Old Town Key West and the beach at Fort Zachary Taylor State Park. Located in the Truman Annex this property has a shared...

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

(24)“ Very Good ”24 Reviews

from

$193

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$193 - $435
Per week:$1,350 - $3,045
Pets allowed:No
Internet:No

THE HEMINGWAY - - A beautiful 2 bedroom 2 bath townhome located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street and the attractions of historic Old Town Key West. You can walk or bike to restaurants, nightlife, entertainment,...

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About Florida Keys

Florida Keys Travel Tips

The Florida Keys are a wonderful vacation spot for families in search of a little relaxation or adventure. Made up of Key Largo, Islamorada, Marathon, Key West, and Big Pine Key and the lower keys, these islands have plenty of family-friendly activities. The best way to visit this beautiful area is by choosing to stay in vacation rentals by owner. Florida Keys tourists can choose from a variety of different sized properties designed to make your time in the Keys comfortable and memorable. For families visiting the Florida Keys, vacation rentals by owner offer the maximum amount of space and privacy for the price. Your entire family will love exploring the islands and coming home to a private, spacious home or condo.

Beaches and Parks

While staying in one of the area's beautiful vacation rentals, Florida Keys tourists can enjoy a leisurely day at one of the best parks in the nation. These are just a few of the Keys most popular destinations:
  • John Pennekamp Coral Reef State Park is the oldest underwater park in the world. Located in Key Largo, families can explore the 47 campsites located on 67,845 acres, split between land and underwater areas. Nature trails, beaches, kayak and canoe rentals, and glass-bottom boat tours are available.
  • Everglades National Park has many fun activities for families. Kids can become Junior Rangers or go on a wildlife hike.
  • Bahia Honda State Park is known for its beautiful beaches and crystal clear water. Visitors can book a snorkeling tour online and enjoy over an hour of snorkeling in the Looe Key National Marine Sanctuary, where swimmers will explore the gorgeous Elkhorn and Star coral.

Things to Do

The Keys have plenty of fun things to do for every activity level. Families who enjoy the outdoors can take advantage of the wide availability of Florida Keys condo rentals and stay right on the beach!
  • Fishing enthusiasts visiting the Florida Keys will be very excited to hear that Islamorada is known as the sport fishing capital of the world, offering a variety of game fish.
  • Water sports are also very popular in the Keys. Hang gliding, parasailing, kayaking, and paddle boarding are great choices for adventurous families.
  • Swimming with dolphins is a unique experience that every tourist of the Florida Keys should try! Through Dolphins Plus in Key Largo, visitors can go on a structured or natural swim with the dolphins or visit the sea lions through the Sea ...

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