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1-50 of 176 Key West Rentals

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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

$386

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$386 - $858
Per week:$2,700 - $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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Island Wind
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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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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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

(3)“ Excellent ”3 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

“ Excellent ”
May 6, 2013
The unit was very comfortable and well equipped. The pool area was terrific and location to Key West couldn't be better. The only thing we found negative at all was the close proximity to the road but that being said it did not ruin our visit. We would stay here again.
Veronica Laliberte, Oakville, Ontario Canada

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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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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

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 a large living room and dining room with a kitchen that overlooks your own...

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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 / 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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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 - 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

Want to have a piece of Paradise to call your own? Even tho it for a short stay?…Come have breakfast lunch or dinner in your hidden GEM of a suite overlooking the beach! We are So glad you found us! The Best Stay In Key West! {{{ 5nt Here! $1550 includes tax & cleaning! ...

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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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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

Monthly rental. Key West private home right on the water - family owned for three generations (former home to WWII war hero Admiral Edward McCarthy, the former mayor of Key West (Mayor Alan Cleare), and the former District Attorney (Alan B. Cleare)). Just a few doors down from ...

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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 - Home
1 / 24

Key West Home
5 Bedrooms / 4 Bathrooms / Sleeps 10
Home / 5 Bedrooms / Sleeps 10

(18)“ Excellent ”18 Reviews

Bedrooms:5
Bathrooms:4
Sleeps:10
Type:Home
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything ...

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Key West Florida Vacation Rentals - Home
1 / 18

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 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 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 - 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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1 / 36

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

(40)“ Excellent ”40 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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Great place to stay in Key West

“ Excellent ”
April 21, 2015
Our first time in Key West and I am so happy that I found this Condo for our stay. It was clean, roomy and had everything we needed. We had easy access to all the activities we planned and we are alreadylooking forward to our next visit.
Christopher Capets, Pittsburgh,PA

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Key West Florida Vacation Rentals - Condo
1 / 23

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

(53)“ Excellent ”53 Reviews

from

$200

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$200 - $275
Per month:$6,000 - $8,250
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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We're Back!!!

“ Excellent ”
April 17, 2015
This was our 3rd time staying at pam's condo and it was like coming home. We LOVE this place. It provides us with everything we need. It is very clean and comfortable. Having the kitchen is amazing - we were able to take the fish we caught, bring them back and cook them for dinner and have a wonderful meal on the balcony on a warm Key West Night. You are able to bike around to everything, which we did all week long. Pam is very accommodating and helpful. We already can't wait to come back!
Tammy, Manasquan, NJ

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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

(1)“ Excellent ”1 Review

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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Emerson Enamroado Pejuan

“ Excellent ”
April 22, 2014
the house is fine , but must change the furniture of living room , are very old ., dont have iron and iron board .Opción of payed pictures
Emerson Enamorado, Honduras C.A.

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Key West Florida Vacation Rentals - Home
1 / 12

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

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

In the fabulous Truman Annex enclave in downtown Key West, this nicely decorated home features a thirty foot pool with waterfall, expansive decks and extensive tropical landscaping for privacy and outdoor enjoyment. Inside, an enormous living/dining area is surrounded by French...

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Key West Florida Vacation Rentals - Home
1 / 34

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

(15)“ Excellent ”15 Reviews

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

Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various...

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community pool
1 / 17

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

(12)“ Excellent ”12 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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Anns street

“ Excellent ”
October 9, 2014
We loved staying in this small but very cute place. The location is perfect, close to all the fun, but quiet. We loved how the place was decorated. Very cozy, and very comfortable. We will recommend it to our friends, and we hope to return our selves someday.
Rhandy Scrivner, Denver, Colorado

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Pool
1 / 8

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

(9)“ Excellent ”9 Reviews

from

$580

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Cottage
Per night:$580 - $900
Per month:$17,400 - $27,000
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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If you don't like sleep great stay

“ Average ”
February 26, 2015
The beds are uncomfortable, no extra blanks, had extra pillows but no pillow cases, no free parking had to pay 30 a day to park, the futton had a spring broke in it, but the worst was the cigar store in front of cottage it played real loud music on a Sundaynight until 2:00 am and then on Monday night again played the same. Would not stay again until the cigar store is evicted. The court yard was a great place to hang out and get together with friends.
P Scott Purdin, Jensen Beach fl

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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 - Townhouse
1 / 28

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

(3)“ Excellent ”3 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 Get Away

“ Excellent ”
October 20, 2014
We could not have picked a better place to stay. Within walking distance to the beach and all locations down on Duval. Very clan location great for two couples. Look forward to booking this location again for next years trip.
Mike Moore, Germantown 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

from

$170

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Villa
Per night:$170
Per week:$1,190
Pets allowed:No
Internet:Yes

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 the Southernmost Point, Hemingway House, Mallory Square, and the Historic...

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Sunset at PirateHead Cove
1 / 29

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

(8)“ Excellent ”8 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! Please check the calendar on this site for availability. We do not take rentals of less than 7 nights unless it is between 2 already booked weeks, and ONLY if it shows as available...

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Water front Key West

“ Excellent ”
December 18, 2014
Cozy home, well supplied, welcoming and engaging owners with lots of sunshine. Tucked in a quiet neighborhood on Stock Island. Great vacation.
Patricia Dubberke, Minnesota

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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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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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View from Balcony
1 / 12

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

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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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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Private Large L-Shape Heated Pool
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 - 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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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 - Apartment
1 / 16

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

Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
No rental rates available - please contact the owner
 
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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Key West Florida Vacation Rentals - Condo
1 / 12

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

(8)“ Excellent ”8 Reviews

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

TAKE 25% OFF: - - Stay April 4- 6 (2 nights) and pay a reduced rate of $765 for both nights instead of $1, 025. - - Stay April 11- 14 (3 nights) and pay a reduced rate of $1, 125 for all three nights instead of $1, 500. - - Note, taxes and fees will be added to all rates....

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Better than ice cream!

“ Excellent ”
May 16, 2014
I spend a week in Key west this time every year with my cousins, in celebration of one's birthday. We have a goal to always find a place to stay that allows us the most time all together. We have found some nice places on VRBO but this welcoming home captured our hearts the moment we entered. The attention to detail was impeccable. The view was gorgeous. The beds were cozy. Linens comparable to a four star hotel. Peaceful and serene. All the wants taken care of. We fell in love, so will everyone.
April Rubenstrunk, New York

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Key West Florida Vacation Rentals - Apartment
1 / 21

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

from

$77

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$77 - $110
Per week:$537 - $770
Pets allowed:No
Internet:Yes

HIDDEN TREASURE (monthly rental): You could easily pass by this jewel of a home without ever knowing it was there. Located down Wong Song Alley behind a private fence, just a few steps from the pool and you've reached your sanctuary. Comfortable open floor space includes living, ...

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Key West Florida Vacation Rentals - Home
1 / 16

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 8
Home / 3 Bedrooms / Sleeps 8

(1)“ Excellent ”1 Review

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$400 - $791
Per month:$12,000 - $23,730
Pets allowed:Yes
Internet:No

SOUTHARD CHARM (formerly Garden House): A lovely jewel, Southard Charm is a quaint Conch house nestled in the center of historic Old Town Key West. Sit on the front porch and while away the hours with a good book. Duval Street is a short block away, so close to all the activity ...

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Key West Florida Vacation Rentals - Home
1 / 22

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

(1)“ Excellent ”1 Review

from

$643

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:8
Type:Home
Per night:$643 - $1,418
Per week:$4,500 - $9,925
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 / 25

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

(13)“ Very Good ”13 Reviews

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$175 - $338
Per month:$5,250 - $10,140
Pets allowed:Yes
Internet:No

CORAL SUITE: If you're looking for a home away from home that will leave you with money in your pocket, Coral Suite is the place for you. This 2 bedroom 3 bath townhome accommodates up to 6 people, and your pet! Both bedrooms (ensuite) are on the 2nd floor of this stilt home. Master...

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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

from

$180

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$180 - $275
Per week:$1,260 - $1,925
Pets allowed:No
Internet:Yes

HELICONIA HOUSE (monthly rental): Beautiful and exotic as the plant itself, Heliconia House is an exceptional example of luxurious living in its simplest form. This pristine 3 bedroom private home has been lovingly restored with meticulous attention to detail bringing it to its stunning...

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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

(41)“ Excellent ”41 Reviews

from

$140

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$140 - $327
Per month:$4,200 - $9,810
Pets allowed:No
Internet:Yes

OSPREY - This bright and colorful studio cottage is located in the same small community once known as The Colony Suites, a charming and secluded Key West style compound nestled in the heart of historic Old Town Key West. This is absolutely the ideal location just three blocks from...

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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 - Apartment
1 / 23

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

(4)“ Excellent ”4 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:No

SPA ON DUVAL - Is a tropical two story, 2 bedroom 2. 5 bath townhome located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, speciality shops and the action of Duval Street. Spa On Duval is truly a Key West experience to enjoy!...

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Key West Florida Vacation Rentals - Home
1 / 26

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

(1)“ Excellent ”1 Review

from

$107

/ night

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

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

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Key West Florida Vacation Rentals - Home
1 / 28

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

from

$70

/ night

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

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

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Key West Florida Vacation Rentals - 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 - Apartment
1 / 24

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

(9)“ Excellent ”9 Reviews

from

$272

/ night

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

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

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Key West Florida Vacation Rentals - Apartment
1 / 24

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

(9)“ Excellent ”9 Reviews

from

$272

/ night

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

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

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Key West Florida Vacation Rentals - Home
1 / 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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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.