Key West Vacation Rentals, Homes, & More

1-50 of 120 Key West Rentals

Sort:
1  2  3 
Living Room with 42" SONY LED, BOSE surround sound and screened deck
1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ 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....

See more

Close x

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

See all reviews

Close x

Living Room
1 / 1
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
No rental rates available - please contact the owner
 
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...

See more

Close x

1 / 25

Key West Home
5 Bedrooms / 5.5 Bathrooms / Sleeps 12

“ Excellent ”1 Review

from

$865

/ night

Email Owner
Bedrooms:5
Bathrooms:5.5
Sleeps:12
Type:Home
Per night:$865 - $1,225
Per month:$25,950 - $36,750
Pets allowed:No
Internet:Yes

THE VICTORIA HOUSE - This gracious historical property, dating from the early 20th century, was built by prominent cigar manufacturer, William Otis Johnson. It is located just three blocks from Duval Street, in the heart of Key West’s Old Town, within walking distance of restaurants,...

See more

Close x

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

See all reviews

Close x

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

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...

See more

Close x

1 / 55

Key West Villa
5 Bedrooms / 5.5 Bathrooms / 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...

See more

Close x

1 / 16

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4

from

$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

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 available) Bike & scooter...

See more

Close x

Private Heated Pool
1 / 15

Key West Home
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$386

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Home
Per night:$386 - $857
Per week:$2,699 - $5,999
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 ...

See more

Close x

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

See all reviews

Close x

1 / 21

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

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...

See more

Close x

Penthouse
#1 of 2 pools with waterfall
1 / 28

Key West Villa
6 Bedrooms / 7 Bathrooms / 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...

See more

Close x

Spectacular view of the Atlantic Ocean from your private balcony.
1 / 12

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”8 Reviews

from

$250

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$250 - $600
Per week:$2,100 - $3,475
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....

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

from

$134

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Home
Per night:$134 - $234
Per week:$934 - $1,634
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 ...

See more

Close x

1 / 36

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”37 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...

See more

Close x

Great Location

“ Excellent ”
January 20, 2015
This property was very clean and had everything we needed for our stay. The condo was 4 miles from the downtown area and duval street which was very convenient. The property was located in a nice area. I will definitely stay there again!!!
Alexandra Wilson, Stuart Florida

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”11 Reviews

from

$97

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Home
Per night:$97 - $229
Per week:$677 - $1,599
Pets allowed:No
Internet:Yes

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

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 24

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

from

$180

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$180 - $360
Per week:$1,260 - $2,520
Pets allowed:Yes
Internet:Yes

FAN- tastic GETAWAY: Formerly owned by actress and fan dancer, Sally Rand. 60" Smart TV and surround sound in living room; Dade County pine walls, wine cellar and every conceivable culinary tool in kitchen. 1st floor master suite with Smart TV, WIFI, and bathroom ensuite with...

See more

Close x

Key West Florida Vacation Rentals - Apartment
1 / 15

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6

from

$70

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$70 - $175
Per week:$490 - $1,225
Pets allowed:No
Internet:No

BOATER'S BEACH HAVEN: Located midtown on Florida Bay. Take advantage of the private boat dock; bring your own boat or rent one in Key West. Old Town is a quick bike ride away. 2- bedroom condo with fully- stocked kitchen. Master bedroom has bathroom ensuite with spa tub. Guest bedroom...

See more

Close x

Key West Florida Vacation Rentals - Townhouse
1 / 21

Key West Townhouse
2 Bedrooms / 2 Bathrooms / 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, ...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 27

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 6

“ 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...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 37

Key West Home
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ 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...

See more

Close x

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.

See all reviews

Close x

Twilight while moored
1 / 24

Key West Yacht
1 Bedroom / 1 Bathroom / 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' ...

See more

Close x

Pool, Spa and Sunshade Area
1 / 23

Key West Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”51 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...

See more

Close x

Pam's Condo at Key West

“ Excellent ”
January 5, 2015
This was, without a doubt, the best vacation we have had in a long, long time. My step-grandson passed away on September 8th of cancer at the young age of 23. It was absolutely devastating. My son and I treated his mother and grandmother to two nights in Key West at Pam's condo. It pleased me tremendously because of all the laughs and great times we all had. It was a much needed retreat and I am so appreciative of the wonderful accomodations Pam offered us. Best therapy ever. My thanks!!!!! :)
lorayne ives, Port Charlotte, Florida

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 25

Key West Home
1 Bedroom / 1 Bathroom / Sleeps 2

from

$100

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Home
Per night:$100 - $114
Per week:$700 - $794
Pets allowed:No
Internet:Yes

CONCH CABANA: Simple yet comfortable for just the two of you in this historic Conch studio cottage. Steps from Ernest Hemingway's Key West residence; easy walking or biking to all Key West has to offer. A lovely living room for reading, TV and planning your days. Kitchen is compact,...

See more

Close x

Key West Florida Vacation Rentals - Apartment
1 / 28

Key West Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”11 Reviews

from

$193

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Apartment
Per night:$193 - $425
Per week:$1,350 - $2,973
Pets allowed:No
Internet:Yes

CONCH CONDO - - 2- bedroom 2- bath upstairs condo features fully equipped kitchen, custom furniture, plasma TVs and home theatre in living room, plasma TVs in both bedrooms, and plenty of closet space. French doors in the living room open to a large balcony. Master bedroom has...

See more

Close x

Key West Florida Vacation Rentals - Townhouse
1 / 28

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ 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...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
3 Bedrooms / 4 Bathrooms / 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. ...

See more

Close x

community pool
1 / 17

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ 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...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Villa
1 / 10

Key West Villa
1 Bedroom / 1 Bathroom / 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...

See more

Close x

Key West Florida Vacation Rentals - Apartment
1 / 8

Key West Apartment
Studio / 1 Bathroom / Sleeps 2

“ Excellent ”5 Reviews

from

$295

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$295 - $385
Per week:$2,065 - $2,695
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! This property is on a lay of land tolerant, in keeping with the old Key West [to date] thru time within...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Cottage
1 / 8

Key West Cottage
4 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”8 Reviews

from

$540

/ night

Email Owner
Bedrooms:4
Bathrooms:3
Sleeps:8
Type:Cottage
Per night:$540 - $900
Per month:$16,200 - $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)...

See more

Close x

AWESOME PLACE!!!

“ Excellent ”
October 7, 2014
We rented the whole compound since there was 8 of us 4 couples. Everyone had their own space which was great. The patio area was amazing, we spent a lot of time there which was nice to save some extra cash. Every place was clean and well kept. Burt and Phillis where wonderful to work with on all levels. I would recommend to anyone. Especially a group!
Dawn Pullen, Clarinda, IA USA

See all reviews

Close x

1 / 22

Key West Condo
2 Bedrooms / 2.5 Bathrooms / 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...

See more

Close x

Key West Florida Vacation Rentals - Townhouse
1 / 11

Key West Townhouse
2 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ 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...

See more

Close x

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

See all reviews

Close x

View from Balcony
1 / 12

Key West Condo
2 Bedrooms / 2 Bathrooms / 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...

See more

Close x

The Conch Cottage
1 / 3

Key West Guesthouse
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ 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...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 12

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$415

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$415 - $858
Per week:$2,900 - $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...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 21

Key West Home
1 Bedroom / 1.5 Bathrooms / Sleeps 4

“ 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...

See more

Close x

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

See all reviews

Close x

Sunset at PirateHead Cove
1 / 29

Key West Home
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ 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...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Townhouse
1 / 26

Key West Townhouse
2 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ Excellent ”1 Review

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...

See more

Close x

Wonderful

“ Excellent ”
October 16, 2014
Perfect location...reasonable rent
Judy Kolbe, Okauchee,Wi usa

See all reviews

Close x

Island Wind
1 / 3

Key West Townhouse
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”9 Reviews

from

$205

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Townhouse
Per night:$205 - $300
Per month:$6,150 - $9,000
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...

See more

Close x

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

See all reviews

Close x

Key West Florida Vacation Rentals - Home
1 / 8

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

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

Tropical seclusion and privacy at its very best. Located just 15 miles from Key West. This luxury rental consists of 2 full suites. The first floor has a roomy living room, huge screen porch, queen sleeper sofa, bath and bedroom connected by an exterior staircase to the second ...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 24

Key West Home
5 Bedrooms / 6 Bathrooms / Sleeps 12

from

$785

/ night

Email Owner
Bedrooms:5
Bathrooms:6
Sleeps:12
Type:Home
Per night:$785 - $1,658
Per month:$23,550 - $49,740
Pets allowed:Yes
Internet:Yes

CASA GRANDE: Located on a quaint lane steps from Duval Street with room to park 2 vehicles off- street. Built for entertaining from the wide open floor plan that encompasses the spacious living room and gourmet kitchen to the magnificent pool. Master bedroom with bath ensuite shares...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 24

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”2 Reviews

from

$786

/ night

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

BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath in Truman Annex, a prestigious gated community in Old Town. Surrounded by tropical greenery in a beautiful quiet gated community 2 blocks from Duval Street...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 26

Key West Home
3 Bedrooms / 2 Bathrooms / Sleeps 8

“ Excellent ”78 Reviews

from

$465

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Home
Per night:$465 - $943
Per month:$13,950 - $28,290
Pets allowed:Yes
Internet:Yes

BAHAMA DREAMING: 3- bedroom Conch cottage with outdoor dining and private pool, fenced and landscaped, off- street parking, 1/2 block from Duval Street. Downstairs has 2 bedrooms (queen and 2 twins), living room with sleeper sofa and full bathroom, kitchen and covered back porch....

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
3 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”22 Reviews

from

$625

/ night

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

BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the ...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 23

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”23 Reviews

from

$625

/ night

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

DUVAL PENTHOUSE: Fabulous location, beautiful furnishings and plenty of space, suited to the casual lifestyle here in Key West. 2nd and 3rd story of the building; 3 bedrooms 2. 5 bathrooms and an open floor plan. Living room, kitchen and master suite on the 2nd floor; French ...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 29

Key West Home
3 Bedrooms / 4 Bathrooms / Sleeps 8

“ Excellent ”1 Review

from

$572

/ night

Email Owner
Bedrooms:3
Bathrooms:4
Sleeps:8
Type:Home
Per night:$572 - $1,315
Per week:$4,000 - $9,200
Pets allowed:No
Internet:No

EASY LIVIN' : Private home with pool in Truman Annex, a gated community in historic Old Town, in walking distance of anything you'll want to do during your visit. Bricked yard with outdoor living space and tranquil pool; custom built by the owners with family gatherings in mind....

See more

Close x

Key West Florida Vacation Rentals - Apartment
1 / 30

Key West Apartment
3 Bedrooms / 3 Bathrooms / Sleeps 8

“ Excellent ”10 Reviews

from

$220

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:8
Type:Apartment
Per night:$220 - $413
Per month:$6,600 - $12,390
Pets allowed:No
Internet:Yes

CORAL VILLA: A beautiful 3- bedroom townhome in the gated community of Coral Hammock. Just off U. S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport. Fully equipped kitchen, HDTVs, WIFI and...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 22

Key West Home
4 Bedrooms / 4 Bathrooms / Sleeps 8

“ 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...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 27

Key West Home
3 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”1 Review

from

$117

/ night

Email Owner
Bedrooms:3
Bathrooms:3
Sleeps:6
Type:Home
Per night:$117 - $247
Per week:$817 - $1,727
Pets allowed:Yes
Internet:Yes

ECCO DOMANI: A beautiful 3 story home with private pool and off street parking. Centrally located just off Simonton Street, you are 1 block to Duval Street, walking distance to galleries, shopping and restaurants. Living, dining and well- equipped kitchen, in an open floor plan...

See more

Close x

Key West Florida Vacation Rentals - Apartment
1 / 27

Key West Apartment
2 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”53 Reviews

from

$225

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$225 - $472
Per month:$6,750 - $14,160
Pets allowed:No
Internet:No

DUVAL BREEZE: 2 bedroom 2. 5 bath townhome in Duval Square. 1st floor offers an open floor plan with a well stocked kitchen, spacious living room, dining room, half bath and French doors to your own private balcony. 2nd floor has 2 bedrooms with bath ensuite. Master bedroom has...

See more

Close x

Key West Florida Vacation Rentals - Home
1 / 25

Key West Home
2 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”2 Reviews

from

$67

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Home
Per night:$67 - $210
Per week:$467 - $1,470
Pets allowed:Yes
Internet:Yes

DUVAL ON THE SQUARE: Located at the Duval Square on Duval but above all the hubbub, built on the 2nd and 3rd story of the complex. Nicely decorated with bedding for up to 6 guests. Sleeper sofa and loveseat in the living room are terrific for an afternoon of relaxing or to snuggle...

See more

Close x

Key West Florida Vacation Rentals - Apartment
1 / 25

Key West Apartment
2 Bedrooms / 3 Bathrooms / Sleeps 6

“ Excellent ”12 Reviews

from

$240

/ night

Email Owner
Bedrooms:2
Bathrooms:3
Sleeps:6
Type:Apartment
Per night:$240 - $486
Per month:$7,200 - $14,580
Pets allowed:No
Internet:Yes

DUVAL STREET HIDEAWAY: 2 story, 2 bedroom 2. 5 bath rooftop townhome above Duval Square. Lots of upgrades in 2014 with new paint, beds, sofa. New Jacuzzi in February 2015. Open floor plan on the 1st level with kitchen, dining room, living room with sleeper sofa and half bath....

See more

Close x

1  2  3 
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.
Loading...
Click for larger map
Loading...
Show Big Map
  • Price

  • Bedrooms

    Guests

  • Amenities

    • More