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101-150 of 176 Key West Rentals

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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 / 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 / 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 / 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
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

(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 / 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
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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 - 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 / 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
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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
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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 / 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 / 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 / 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 / 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 / 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 / 24

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 / 24

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 - Home
1 / 26

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 - 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 / 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
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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
1 / 29

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 - 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 / 27

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 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
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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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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 / 2 Bathrooms / Sleeps 4
Apartment / 2 Bedrooms / Sleeps 4

(34)“ Excellent ”34 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

LEEWARD ISLE KEY WEST RETREAT - - Dwell in the possibility! From the moment you park in the private parking lot you know you are some place special. A small gated and secured compound with only 13 properties, this townhome community is quiet and private while still being located...

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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 / 24

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 Florida Vacation Rentals - Home
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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
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 - Home
1 / 23

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

(27)“ Excellent ”27 Reviews

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

On a lovely tree- lined residential street in the heart of the historic Old Town district, this quiet, historic compound offers three separate vacation suites sharing a lush, large, sunny pool or combines for a wonderful four bedroom retreat. Downstairs enjoys a large, open floor...

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Key West Florida Vacation Rentals - Home
1 / 16

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

(47)“ Excellent ”47 Reviews

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

Beautiful four bedroom penthouse condo steps from the action has been recently upgraded. This four bedroom, 4. 5 bath condo is in the heart of the action at Duval Square just south of Truman. The residential units sit in a courtyard setting above a retail/office courtyard below with...

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Key West Florida Vacation Rentals - Home
1 / 18

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

(39)“ Excellent ”39 Reviews

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

Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home ...

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Key West Florida Vacation Rentals - Home
1 / 18

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

(34)“ Excellent ”34 Reviews

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

This mid- town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in...

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

(42)“ Excellent ”42 Reviews

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory...

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

(38)“ Excellent ”38 Reviews

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming...

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

(26)“ Excellent ”26 Reviews

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

In the heart of Old Town, convenient to everything, this condo is set above a brick and tree lined courtyard that includes shops and restaurants. This three bedroom two bath unit is in one of two standalone walkup buildings in the Duval Square complex. You enter a large open living,...

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

(3)“ Very Good ”3 Reviews

Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

30 DAY MINIMUM RENTALWalk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This...

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

(9)“ Excellent ”9 Reviews

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

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq...

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Key West Florida Vacation Rentals - Home
1 / 10

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

(2)“ Excellent ”2 Reviews

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

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq...

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Key West Florida Vacation Rentals - Home
1 / 10

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

(1)“ Excellent ”1 Review

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

Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq...

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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.