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1-50 of 114 Key West Rentals

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The Lion's Paw is a Catalina Morgan 440 with two cabins, two heads.
1 / 13

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

from

$325

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Yacht
Per night:$325
Per week:$2,275
Pets allowed:No
Internet:No

Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half day, full day, and overnight sails. The yacht club has it's own...

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Key West Florida Vacation Rentals - Condo
1 / 5

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

from

$188

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$188 - $298
Per month:$5,640 - $8,940
Pets allowed:Yes
Internet:Yes

The Bella Vita has been totally renovated. It is a one bedroom, one bathroom condo on the first floor. This condo is steps to Duval Street! The large bedroom has a king size bed with a memory foam mattress. The living room has a Natuzzi sleeper sofa which sleeps 2. There is a galley...

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Pool, Spa and Sunshade Area
1 / 23

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

(54)“ Excellent ”54 Reviews

from

$210

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$210 - $325
Per month:$6,300 - $9,750
Pets allowed:No
Internet:Yes

This is a non- smoking condo (you may smoke on the balcony only) with that "home away from home" comfortable appeal. My condo is reasonably priced and includes 2 bedrooms (1 king in the master suite/1 queen in the guest suite) and a sofabed. All bed linens are provided. Wait, there...

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The Stacey & Adey Family Key West Vacation

“ Excellent ”
April 29, 2015
We spent 3 wonderful days at this property. It was very well appointed with all the necessities. All appliances and electronics worked really well. For a rental property it was a very pleasant surprise. We wouldn't hesitate to rent it again. Thank you Pam.
Charles Stacey, Newfoundland Canada

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The Conch Cottage
1 / 3

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

(1)“ Excellent ”1 Review

from

$393

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Guesthouse
Per night:$393 - $472
Per week:$2,750 - $3,300
Pets allowed:No
Internet:Yes

Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully...

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Great Get-a-Way

“ Excellent ”
February 8, 2010
We rented this cottage on the beautiful property of Sea Vista Estate for our 4oth wedding anniversary. We wanted a place to feel relaxed and renewed from the everyday complications of life. This was the perfect place for us. The property is beautiful, the cottage clean and neat with wonderful sunrise vistas and cool ocean breezes. The property owners were gracious and provided delicious key lime pie, daily newspapers and were ready to help with any needs we might have. The beach is quiet and private only shared with the three other houses' renters. The pool area is also very special in a lush tropical setting. We would love to come again and would highly recommend this place which is a quiet oasis to come back to after a fun trip to Key West and all the fun things to do in the area. Don't miss the restaurants, Blue Heaven in Key West and Square Grouper at Mile Marker 22!
Connie Simpson, Oak Ridge, Tennessee

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Key West Florida Vacation Rentals - Apartment
1 / 24

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

(43)“ Excellent ”43 Reviews

from

$145

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$145 - $341
Per month:$4,350 - $10,230
Pets allowed:No
Internet:Yes

OSPREY: Studio cottage located in The Colony Suites, a compound nestled in Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room. Sunny and bright, sitting area, queen size bed, full bathroom and kitchenette. French doors open to ...

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Pool
1 / 8

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

(10)“ Excellent ”10 Reviews

from

$580

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Cottage
Per night:$580 - $967
Per month:$17,400 - $29,010
Pets allowed:No
Internet:Yes

Daily price varies by season, and length of stay. Range of prices shown above. Private compound right in the heart of old town. 1 minute or less from Schooner Wharf with all the water activities imaginable; Sloppy Joe's and Conch Republic (with some of the best music on the rock)...

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perfect location, relaxing space

“ Excellent ”
June 28, 2015
This place has it all. Lounging on the private deck in the mornings drinking coffee in front of the pool. So everyone had privacy and then our central spot was at the pool. Plenty of seating and space to dip your legs in and watch the water fall from the conchs and coral. The pool is much bigger than the photos show! Its a perfect little pool actually. There is a huge grill with a sideburner in addition to the kitchenette in Pilar. The space is very large and accomodating. Plenty of linens and towels. The rooms are super cold (actually my husband said if i could come up with anything to complain about it would be the rooms are cold lol...not really just turn the a/c up if you are cold) Literally you walk outside and are two minutes from Schooner Wharf, Alonsos, AB Lobster House, White Tarpon. ...all our favorites. And if you take a left out of the gate two blocks and you are at Sloppy Joes on Duval. There is a perfect little antique store next door and plenty of corner markets within walking distance. The price is competitive and reasonable. I spent weeks comparing and searching vacation rentals for our trip and i was quite pleased. We will stay again and again. Everyone in my family loved my choice and even people who walk by kept stopping and tried to peak in to see whats back there in our private little oasis. Dont worry they cant see anything bc of the landscaping and layout and anyway the cute little picket fence is locked :)
Cori Moss, miami beach, fl

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Key West Florida Vacation Rentals - Condo
1 / 12

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

(2)“ Excellent ”2 Reviews

from

$100

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$100
Per week:$700
Pets allowed:No
Internet:Yes

Discover paradise of Key West in a distinctive setting. Luxury, two- bedroom, two- bath, (sleeps 4- 6) condominium set in a tropical garden with sweeping balconies with views of the Gulf. Your vacation hideaway is decorated in authentic island tradition with fully- equipped modern...

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Awesome!

“ Excellent ”
June 22, 2015
This place couldn't have been better. Our jaws literally dropped when we walked in. This is a beautiful place. Would not stay anywhere else. 2 miles to Duval St., close enough to the action but if you just want a quiet evening watching the ocean this is it. The best pool ever and situated where you can sit by the pool and enjoy the ocean. Awesome!
Mary Clower Tuggle, Sumter, SC USA

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1 / 21

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

(1)“ Excellent ”1 Review

from

$513

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$513
Per week:$3,590
Pets allowed:No
Internet:Yes

PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN CASA ROSA is a classic four bedroom, four bath "eyebrow" style home located in historic Old Town Key West that is just 1 block of Duval Street and a short walk to Harbor Walk & Mallory Square. This home has...

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Great time, great house

“ Excellent ”
April 1, 2015
We came for a family vacation, 9 of us in all, we rented the lower and upper house. There was plenty of room for everyone, good size kitchen with all the necessities, large dining room, tvs in all the bedrooms, small but comfy backyard with very chlorinated small pool. We walked to almost everything, great location. We are planning to return and have another fabulous vacation soon.the only complaint was the noise from the street at all hours and being that it's an old house the windows aren't great. Other than that we Highly recommend!!
Kim Sevigny, Debary florida

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1 / 55

Key West Villa
5 Bedrooms / 5.5 Bathrooms / Sleeps 12
Villa / 5 Bedrooms / Sleeps 12

from

$785

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Villa
Per night:$785 - $1,780
Per month:$23,550 - $53,400
Pets allowed:Yes
Internet:Yes

CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off- street - - a bonus in Old Town where parking is worth its weight in...

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Living Room with 42" SONY LED, BOSE surround sound and screened deck
1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$250

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$250 - $500
Per month:$7,500 - $15,000
Pets allowed:No
Internet:Yes

"TEE BY THE SEA" vacation rental (we include 7 bikes free for our guests! ! ! ) If you love... GOLF, SPORT FISHING/BOATING, ART/THEATER AND FANTASTIC LIVE ENTERTAINMENT... than you'll love "Tee by the Sea". We're less then 1/2 mile outside of Key West, located in Stock Island....

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Key West Paradise

“ Excellent ”
April 26, 2015
Our condo was AMAZING! So clean and had all the comforts of home! Their was a detailed binder of places to eat and what to do in the area! Our vacation was perfect because of all the extra touches and information we were provided!
Winnie Lucht, Wisconsin

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Penthouse
#1 of 2 pools with waterfall
1 / 28

Key West Villa
6 Bedrooms / 7 Bathrooms / Sleeps 16
Villa / 6 Bedrooms / Sleeps 16

Bedrooms:6
Bathrooms:7
Sleeps:16
Type:Villa
Per night:$1,143 - $2,000
Per week:$7,995 - $13,995
Pets allowed:No
Internet:Yes

Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless...

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Private Heated Pool
1 / 15

Key West Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6
Home / 3 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$400 - $858
Per week:$2,800 - $6,000
Pets allowed:Yes
Internet:Yes

Private Luxury Home surrounded by lush tropical landscaping. The fusion of a mid- century Florida home with dramatic Caribbean design, has created an ideal contemporary “Floribbean” style villa in the Casa Marina district of Key West. Walking distance to all Old Town has ...

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Amazing Experience Each and Every Time!!!

“ Excellent ”
October 10, 2010
I have stayed at the Brass Palm Villa several times and I would never stay anywhere else on the island. It is decorated beautifully and exceptionally well maintained. There are many places to relax inside and outside the home. I especially enjoy the outside dining area. If you are looking to rent I would highly recomend the Brass Palm Villa!
Lynne Martino, New Jersey

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1 / 24

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

(1)“ Excellent ”1 Review

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$300 - $395
Per month:$9,000 - $11,850
Pets allowed:No
Internet:Yes

A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View Florida Keys condo 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...

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Amazing location for fun filled girls getaway!

“ Excellent ”
September 12, 2013
I was very impressed with the house. It was perfectly located so that we didn't have to rent bikes or move the car often. We absolutely loved lounging at the pool and couldn't have asked for a better lay out for our 7 girls retreat weekend. We will absolutely stay here again. I am missing it already and we all can't stop talking about it. Thank you for the perfect long weekend away!
Katie Skiff, Washington, DC

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Key West Florida Vacation Rentals - Townhouse
1 / 11

Key West Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 6
Townhouse / 2 Bedrooms / Sleeps 6

(14)“ Excellent ”14 Reviews

from

$258

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Townhouse
Per night:$258
Per week:$1,800
Pets allowed:No
Internet:Yes

This 2 bedroom, 1 and ½ bath end unit town home is located on President's walk ( Ivory Coast) in the prettiest section of the Truman Annex. The home is decorated in exceptional taste; including a King size bed in the master bedroom with ample closet space and its own private covered...

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Beautiful Escape in Truman Annex!

“ Excellent ”
January 17, 2015
This is a beautiful place in the heart of Truman Annex. Just 2 blocks from Duval so your close to everything, but far enough away if you prefer some quiet time. Very Relaxing Pool is a definite plus! The place does look like it the pictures if anything nicer. We loved our stay! We will stay there again! The Owners are just wonderful. This was our first time visiting Key West and We couldn't have picked a better place to stay. Thru the Week My Husband kept saying "Good Job finding this place its Great"! I can honestly say you wont be disappointed! Great Place to Vacation!
deb strieter, Unionville, Mi USA

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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

(1)“ Excellent ”1 Review

from

$665

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$665 - $1,513
Per week:$4,650 - $10,585
Pets allowed:No
Internet:Yes

THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of...

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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

(25)“ Excellent ”25 Reviews

from

$180

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$180 - $350
Per month:$5,400 - $10,500
Pets allowed:No
Internet:Yes

CORAL GARDEN: 2- bedroom 2. 5 bath townhome in the private gated community of Coral Hammock. Fully- equipped kitchen, comfortable dining area, and living room sports a gigantic 52" HDTV for your viewing pleasure. Master bedroom with bath ensuite offers a comfy queen bed; 2nd bedroom...

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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

$87

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$87 - $193
Per week:$607 - $1,348
Pets allowed:Yes
Internet:Yes

KEY LIME PIE: One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom....

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Back of Home on the water
1 / 23

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

(1)“ Excellent ”1 Review

from

$134

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$134 - $334
Per week:$934 - $2,334
Pets allowed:No
Internet:Yes

OVERVIEW: Right in Key West - - NOT the upper keys. MONTHLY RENTAL ONLY. Swimming pool, Right on the water. Salt water fishing on location. Sea Kayaks on premises. Salt pond tours on premises. Swim with manatees on premises. Ping pong table. 7 doors down from Jimmy Buffett's old...

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Incredible house!

“ Excellent ”
March 10, 2015
This house is immaculately kept and one of the few houses on a canal in KW. Beautiful interior and plenty of room in the bedrooms. The pool overlooks the canal and has an absolutely beautiful view! If you want a house that makes you feel like you're on a tropical island (and you are) then this is the house for you! Close to everything and we're going to be staying there again every year we go.
Travis Haddock, Memphis

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Key West Florida Vacation Rentals - Apartment
1 / 26

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 - $469
Per week:$1,550 - $3,278
Pets allowed:No
Internet:Yes

CROWNER'S JEWEL: Delightful 2 bedroom 2. 5 bath Conch- style townhome in the quiet gated community of Truman Annex, surrounded by historic buildings and tropical flora; only a short walk to Duval Street. Master bedroom has small bath ensuite and private balcony (note: both bathrooms...

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Key West Florida Vacation Rentals - Home
1 / 37

Key West Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Home / 2 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$340

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$340 - $470
Per month:$10,200 - $14,100
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 is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods...

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Amelia House

“ Excellent ”
May 20, 2015
This home was more than expected. It was close enough to all the night life of Duval Street, yet are enough to enjoy peace and quiet when needed. I would recommend this home to anyone looking for a great vacation getaway.
Francine Sheehan, Florida

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Key West Florida Vacation Rentals - Townhouse
1 / 21

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

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Townhouse
Per night:$225 - $343
Per week:$1,575 - $2,400
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 - Condo
1 / 36

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

(41)“ Excellent ”41 Reviews

from

$199

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$199 - $269
Per week:$1,393 - $1,883
Pets allowed:Yes
Internet:Yes

Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun- filled days pampered by our warm and friendly...

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Very nice condo

“ Excellent ”
July 8, 2015
Clean, nicely decorated. Had a great time here and would love to go back again.
Cheryl Griffith, Punta Gorda , FL

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Key West Florida Vacation Rentals - Home
1 / 27

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

(1)“ Excellent ”1 Review

from

$100

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$100 - $275
Per week:$700 - $1,925
Pets allowed:Yes
Internet:Yes

Welcome to the Duncan House - your home away from home in beautiful Key West. The Duncan house is a recently renovated private home with three bedrooms and two baths located in a quiet, Old Town, Key West neighborhood only 10 minutes to Duval Street and only 5- 10 minutes to...

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Amazing Place to Stay...

“ Excellent ”
January 5, 2014
Nice Place. Super Location. Everything is very near by... Sea is also close by... Downtown area... All food and restaurants are also close by...We as a family full enjoy our stay and love the place... Its bit small place but still not bad personally we all fully enjoy and and we had lot fun....
Nikhil Thakkar, KeyWest, Florida USA

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Key West Florida Vacation Rentals - Yacht
1 / 24

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

from

$175

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Yacht
Per night:$175 - $300
Per week:$1,100 - $2,000
Pets allowed:No
Internet:Yes

Ever watch Captain Ron? Remember the classic sailboat? Want a unique Keys experience? Romantic, private and relaxing? Rent a sailboat, sleep on water. It's dockside at Key West Harbour, 5 miles from Old Town Key West, and offers amenities. The sailboat is a 1979 41' ...

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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

(13)“ Very Good ”13 Reviews

from

$180

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$180 - $350
Per month:$5,400 - $10,500
Pets allowed:Yes
Internet:No

CORAL SUITE: 2 bedroom 3 bath townhome for 6 people, and your pet! Both bedrooms (ensuite) are on the 2nd floor of this stilt home. Master bedroom has a private balcony. Guest bedroom is roomy and private. The Murphy bed in the living room is sturdy and comfortable. Kitchen is equipped...

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Key West Florida Vacation Rentals - Townhouse
1 / 28

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Townhouse / 2 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Townhouse
Per night:$225 - $360
Per month:$6,750 - $10,800
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...

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Key West Vacation

“ Excellent ”
May 9, 2015
Great time in Key West. We were close to all activities. A very relaxing vacation.
Daniel N Charlotte Snider, Ohio

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Key West Florida Vacation Rentals - Villa
1 / 10

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

(1)“ Excellent ”1 Review

from

$142

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Villa
Per night:$142
Per week:$990
Pets allowed:No
Internet:Yes

PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like...

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Good Times

“ Excellent ”
June 18, 2015
Great location, great people to work witk.Can walk or ride bike anywhere on the island. Beach 3 blocks away. Will be back.
Gerald Jack, Marin County California

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community pool
1 / 17

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Townhouse / 2 Bedrooms / Sleeps 6

(13)“ Excellent ”13 Reviews

from

$172

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Townhouse
Per night:$172 - $329
Per week:$1,200 - $2,300
Pets allowed:No
Internet:Yes

Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker...

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Excellent place to stay

“ Excellent ”
July 2, 2015
This place was fabulous! Clean linen, plenty of towels, all the amentities that you could ever need. Just bring yourself and bathing suits! Everything was clean and the location was perfect! The only thing I wish a little different was the pool is a little small and grill is a small electric one. Butterflies, birds and landscaping beautiful. Cant wait to go back again soon!
Michelle Harding, Franklinville, NJ

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Key West Florida Vacation Rentals - Apartment
1 / 8

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

(5)“ Excellent ”5 Reviews

from

$249

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$249
Per week:$1,743
Pets allowed:No
Internet:No

ATTENTION RATES ARE HERE IN NEXT PARAGRAPH not correct in rate section - this site has a glitch Scuze for this inconvenience. at least include your number for service- Want to have a piece of Paradise to call your own? Even tho it for a short stay?… Come have breakfast lunch ...

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Rooms with a View

“ Excellent ”
April 15, 2012
When we first entered the 2nd floor apartment ( via a spiral staircase- heavy luggage is a little tricky.) we were blown away by the view out of every window! ( And so many windows!) It is everything that it claimed to be and more!! We never tired of looking at the ocean, the pier and the activity all around. Holly was so helpful, even offering to pick up a few things for us at the grocery store, as she was going herself. The location was great for us, on the quieter side of the island. But nothing is too far away. We did a lot of walking, as we chose not to rent a car. We took cabs when we didn't want to walk and that worked out just great. We visited Duval Street frequently. We ate out most of the time, but there is an oven, microwave and full size refrigerator. We ordered in pizza one night and our "around the back" location was no problem for our deliveryman. The only unusual thing is arrangement of the bathroom. The toilet area and shower are seperate and there is no bathroom sink, you need to use the kitchen sink. But we were fine with that, and Holly mentioned it ahead of time so it wasn't a surprise to us. Our last day (we spent a week.) we decided to just stay at "home" and enjoy the ocean and pool next door. It was wonderful and relaxing. Holly had a list of things to do and see and restaurants that she recommended. They were outstanding. "Louie's Backyard" restaurant (a stone's tthrow away) was pricey but awesome. We were very happy with our selection of a place to stay in Key West. So much nicer than a hotel, in our opinion. Thanks for sharing your paradise with us Holly and Javier!
Molly Barth, Fort Thomas, KY USA

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Key West Florida Vacation Rentals - Home
1 / 21

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

from

$572

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$572 - $1,029
Per week:$4,000 - $7,200
Pets allowed:No
Internet:Yes

EASY LIVIN' - - The name says it all! This lovely private home with pool is located in a secluded cul- de- sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. ...

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Key West Florida Vacation Rentals - Apartment
1 / 16

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

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$215

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$215 - $400
Per week:$1,500 - $2,800
Pets allowed:No
Internet:Yes

7 day minimum please This fully furnished newly updated getaway is so close to all the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... A car is really not necessary in Key west (though parking space for one auto is ...

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You are home at the signpost, on the corner of the property.
1 / 14

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

from

$60

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$60 - $150
Per week:$420 - $1,050
Pets allowed:No
Internet:Yes

You are home at the Signpost, at the property edge. Tropical apartment: 1 Bedroom, 1 bath, large and roomy spaces; private deck, washer/dryer enclosed on deck. Walking distance to all the attractions, neighborhood restaurants and pubs. You don't need a car; bikes are easy to...

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Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
1 Bedroom / 1.5 Bathrooms / Sleeps 4
Home / 1 Bedroom / Sleeps 4

(2)“ Excellent ”2 Reviews

from

$210

/ night

Email Owner
Bedrooms:1
Bathrooms:1.5
Sleeps:4
Type:Home
Per night:$210 - $342
Per month:$6,300 - $10,260
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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A heart-warming and tranquil oasis

“ Excellent ”
August 1, 2013
We truly enjoyed our stay at Tranquility on Olivia Street. The neighbourhood is charming and very peaceful. There are many interesting restaurants to discover in the surroundings and many other services easily accessible at walking and biking distance. We enjoyed relaxing in the swimming pool at the end of the day and meeting many of the interesting folks renting other cottages at the Colony. I highly recommend Tranquility for its location, the peaceful neighbourhood, the physical setting at the Colony, and the charming interior decoration of the cottage. The colors are fresh, bright and full of joy. Our only recommendation would be to provide vacationers with a binder presenting essential information on things to do, to see and, especially, a list of surrounding service providers such as: grocery store, fish market, pharmacy, bike rental, local restaurants, and hospital in case of emergency. The sofa-bed mattress would need to be changed. It’s really not comfortable. And finally, the master bedroom air conditioner is quite noisy. Should we plan to visit the Keys in the near future, Tranquility would be our place to stay. What a great place to call home for a week on vacation. Thanks!
Paul Turpin, Key West, FL, USA

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Living Room
1 / 1

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

(1)“ Excellent ”1 Review

from

$259

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$259
Per week:$1,813
Pets allowed:No
Internet:Yes

Decorator furnished two bedroom, two full bath condo in Key West, Florida. Only a five minute drive to Key West's largest beach - Smather's Beach. Full kitchen, three flat screen TV's, outside porch overlooking the beautiful pool and jacuzzi area on property, and one covered...

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Key West Condo

“ Excellent ”
March 2, 2015
The owner published an excellent letter with the directions, key code, parking space, and internet code there was. We arrived approximately an hour early and call her and she had no problem with us going in early. The condo was exactly as described. I would recommend to everybody to use this condo.
charlie besch, Overland Park, KS

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Key West Florida Vacation Rentals - Townhouse
1 / 3

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

(9)“ Excellent ”9 Reviews

from

$215

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Townhouse
Per night:$215 - $272
Per week:$1,500 - $1,900
Pets allowed:No
Internet:Yes

"Island Wind" welcomes you to a sun drenched oasis in the heart of Old Town. Charming Bahamian style townhome with tin roof and white spindled porches reminiscent of Old Key West Just a block off Duval Street at the corner of Truman & Simonton in Windward Park a gated community consisting...

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Amazing place

“ Excellent ”
July 28, 2014
Amazing place just like we thought. Close to everything and beautiful. We will deffinatly be staying here again!!!!
James Edwards, Charlotte NC

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Key West Florida Vacation Rentals - Townhouse
1 / 26

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Townhouse / 2 Bedrooms / Sleeps 6

(2)“ Excellent ”2 Reviews

from

$236

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Townhouse
Per night:$236 - $420
Per week:$1,650 - $2,940
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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Stairs

“ Excellent ”
April 10, 2015
Nice facilities. Two flights of stairs tough with bags. Great location
Alexa Canady-Davis, Pensacola fl

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Key West Florida Vacation Rentals - Home
1 / 29

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

(9)“ Excellent ”9 Reviews

from

$249

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$249 - $349
Per week:$1,743
Pets allowed:No
Internet:Yes

Ahoy! PirateHead Cove, your affordable vacation dream- come- true is now taking bookings for 2015/16! Please check the calendar on this site for availability. We do not take partial weeks or bookings of less than 7 nights unless it is between 2 already booked weeks, and ONLY...

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Great place for a Key West vacation

“ Excellent ”
May 12, 2015
We have taken several vacations in Key West, but this was the first time we stayed at this property. The location provides easy access to all the Key West sites, the property is spacious with great indoor and outdoor space. Fantastic deck out back on the channel where you can grill your dinner, sun bathe, enjoy the hot tub or keep an eye on the sea life all around you. The indoor space has 2 lovely bedrooms, well stocked kitchen and a comfortable living room. The owners provided wonderful directions and advice on restaurants, shops and sites to enjoy. Will definitely look into renting this unit again, when we have the opportunity to return to Key West.
Pat Dubberke, Minneapolis, Minnesota

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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

(1)“ Excellent ”1 Review

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$400 - $858
Per week:$2,800 - $6,000
Pets allowed:No
Internet:Yes

This elegant two- story island home is a quiet retreat in the heart of Old Town Key West. Margaux's Hideaway is stylishly decorated, perfectly highlighting the classic nature of a Key West home while integrating modern amenities. This home is designed to bring the beauty of the outdoors...

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Perfect Vacation Home for Family Trips

“ Excellent ”
May 11, 2014
My cousins and I get together the first weekend of May every year, this year we picked Key West. In our hunt for the perfect house to vacation in we came across Margaux's Hideaway. After a quick phone call with Lynda, property manager, I knew it was perfect. The photos DO NOT do it justice. The house is absolutely beautiful, located on a very quiet street, about 4 blocks from Duval. There was bike rental place right next door so we quickly rented bikes and explored for 5 days. Even though there is SO much to do in Key West, we found our self enjoying the outdoor living room and pool, after dealing with Chicago winters, it was so relaxing to hang with the family and enjoy a cold beverage. The house has EVERYTHING you would need once you do a quick trip to the grocery store – all you need to bring is your clothes. Once we arrived, we were welcomed by the caretaker, a very nice man who showed us everything and quickly left. He came back by the day we left to ensure everything was in order. It truly felt like it was our vacation house and not a rental. My cousins and I had the BEST time and are making plans to go back, this will be the place we’ll stay!
Chris Junkerman, Chicago, IL

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Key West Florida Vacation Rentals - Apartment
1 / 6

Key West Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$170

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$170
Per week:$1,190
Pets allowed:No
Internet:No

Key West, where a friendly staff member is waiting to welcome you with a freshly baked chocolate chip cookie. Everything you need is available in the hotel, from a 24- hour business center to three meals a day served in the full- service Palm Haven Restaurant. Relax in luxury...

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1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

from

$180

/ night

Email Owner
Bedrooms:2
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$180 - $324
Per month:$5,400 - $9,720
Pets allowed:Yes
Internet:Yes

CORAL GARDEN: A 2- bedroom 2. 5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start...

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Guest bedroom
1 / 15

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

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$134
Per week:$934
Pets allowed:No
Internet:Yes

Beautiful ocean front condo. Great view, beautiful pool and hot tub. Area for BBQ. Close to to Duval st. Call or email for more details and picture....

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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: 2- bedroom, 2- bath, penthouse condominium with 1350 square feet of living space. WIFI, flat- screen plasma television with Bose surround sound system in the living room, as well as TV/VCR/DVD/CD players in each bedroom. Large, fully- equipped modern kitchen...

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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 - $486
Per month:$7,950 - $14,580
Pets allowed:No
Internet:Yes

LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2- bedroom 2- bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique property. Flatscreen...

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Key West Florida Vacation Rentals - Apartment
1 / 24

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

(1)“ Excellent ”1 Review

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$77 - $147
Per week:$537 - $1,027
Pets allowed:No
Internet:Yes

EMMA'S SECRET: 2 bedroom 1 bath condo in a historic Old Town neighborhood in walking distance to Duval Street. Upgraded appliances, granite countertops, beautiful wood cabinets, flatscreen TV and WIFI. Master bedroom features a queen bed; 2nd bedroom has bunk beds with full- size...

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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

(35)“ Excellent ”35 Reviews

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$300 - $494
Per month:$9,000 - $14,820
Pets allowed:No
Internet:Yes

A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condo. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated for your comfort and relaxation. Located on the Atlantic Ocean with views from the living room and both bedroom; ...

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Key West Florida Vacation Rentals - Home
1 / 24

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

(12)“ Excellent ”12 Reviews

from

$60

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Home
Per night:$60 - $154
Per week:$420 - $1,074
Pets allowed:Yes
Internet:Yes

CASITA de CATHERINE - This classic rental cottage with hot tub in Key West is a one bedroom home with gorgeous decor yet still plenty of space to entertain friends. Enjoy the private home of a local author; come stay on an island where every day writers write, roosters crow and...

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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

(54)“ Excellent ”54 Reviews

from

$340

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Home
Per night:$340 - $704
Per month:$10,200 - $21,120
Pets allowed:Yes
Internet:Yes

AMELIA HOME - 2 bedroom 2. 5 bath home with sparkling private pool only four blocks from the Atlantic Ocean and one block from Duval Street entertainment. Kitchen complete with everything to create a gourmet meal. Large open dining and living area. Lush garden with private pool that...

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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

(9)“ Excellent ”9 Reviews

from

$265

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$265 - $486
Per month:$7,950 - $14,580
Pets allowed:No
Internet:Yes

ISLAND WIND: 2 bedroom, 2 bath Bahamian- style townhome, with tin roof and white spindled decks. Snuggle into an oh- so- comfy king bed in the Master bedroom upstairs; bathroom is ensuite. Guest bedroom downstairs with 2 twin beds; bathroom ensuite with entrance from the kitchen....

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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 - $180
Per week:$584 - $1,260
Pets allowed:Yes
Internet:Yes

ATLANTIC BLUES - Stylish Conch cottage with hardwood floors, glass tiles, granite countertops and décor that is playful and soothing. Kitchen opens to the living and dining areas allowing the cook to remain part of the party. Step outside to the pool deck and splash in the heated...

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Key West Florida Vacation Rentals - Apartment
1 / 26

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

(22)“ Excellent ”22 Reviews

from

$180

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$180 - $404
Per week:$1,255 - $2,828
Pets allowed:No
Internet:No

PARROT PERCH: Great location and great value for a great vacation. Parrot Perch is an upstairs 2 bedroom 2 bath condo with a balcony from the living room offering a view of the neighborhood and BBQ grill. The best priced 2 bedroom 2 bath condo in Truman Annex with a queen bed and ...

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About Key West

A laid-back city in the Florida Keys, Key West should be on every traveler's vacation list. With equal parts nature, history, and nightlife, this Florida destination has a little something for everyone.


A Short History of Key West

At the very end of the Florida Keys, this four-square-mile island was first settled by Spanish explorers led by Ponce de León. The remote location was sparsely populated until it was claimed by the United States in the early 19th century. By the turn of the 20th century, Key West was actually the largest and most moneyed city in Florida, thanks to its quick development, naval base, and cigar industry. The locale began to develop its reputation as a tourist hotspot around that time, and this southernmost U.S. city still holds that identity today.


What Key West Does Best

This small island is packed with attractions and activities. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches. History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street, the center of Key West’s nightlife scene.


Natural Beauty

Key West isn’t known for its beaches, but Fort Zachary Taylor Historic State Park is a great place to swim, snorkel, and catch the sunset. Explore the waters around Key West by sailboat, kayak, or sunset cruise to get a closer look at the sparkling gulf. For a unique adventure, head 70 miles offshore to Dry Tortugas National Park. Explore Fort Jefferson, the coral reefs, and the island’s impressive variety of wildlife and tropical plants.
 

Historical Markers

To get a quick look at everything Key West has to offer, hop on the Conch Tour Train. You’ll get an earful of the area’s past, along with a little local trivia. When you’re ready to dig in, make the Ernest Hemingway Home & Museum your first stop. Here you can learn more about the famous writer’s life and see where he penned some of his best selling novels.

Don't miss a tour of the Harry S. Truman Little White House, a command center during World War I and II as well as the winter home of President Harry S. Truman. Today the house is both a museum and a political retreat, and it’s well worth a visit.
 

Vibrant Nightlife

No trip to Key West is complete without a night out on the town, and options range from family-friendly to wildly ...

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