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Vacation Rentals in Key West, FL

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All 424 Rentals in Key West
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$250
Per Night
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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15 photos Details Reviews (1) Make Inquiry
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$233
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
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12 photos Details Reviews (3) Make Inquiry
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$199
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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10 photos Details Reviews (5) Make Inquiry
Also consider
KeyWestStay.com
2 Bedrooms, sleeps 4
$125 - $180 / night
The Victoria House - Fantastic 5 Bedroom Villa
5 Bedrooms, sleeps 12
$865 - $1,225 / night
A Touch of Bermuda in Key West
2 Bedrooms, sleeps 6
$275 - $300 / night
:: OCTOPUS'S GARDEN @ CORAL HAMMOCK :: Private Home / Gated +  Pool & Fitness....
3 Bedrooms, sleeps 6
$500 - $700 / night
From
$219
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 8
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12 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 25, 2014
Our place was beautiful. Beds were comfortable, beautifully appointed and more room than we ever imagined! Close to everything! Very clean and all the amenities you need. Check in...
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From
$199
Per Night
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2 Bedrooms, 1 Bathroom, Sleeps 6
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9 photos Details Reviews (10) Make Inquiry
5 of 5 stars Reviewed August 21, 2014
What an amazing location! Just half a block from Faustos market and one block from the Trolley stop. Could not have planned that any better. One of our group members had walking...
5 of 5 stars Reviewed August 4, 2014
Some close friends and I decided to go to key west for my 30th birthday. This place was amazing. You are so close to the action. I plan on going back every year. The location is...
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From
$195
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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14 photos Details Reviews (37) Make Inquiry
5 of 5 stars Reviewed August 17, 2014
For all going to Key west and need lodging. Tropical Escape is the place. It has the most perfect location in order to plan your trip around the island. It is also very safe and...
5 of 5 stars Reviewed June 29, 2014
This two bedroom condo met all of our needs and was perfectly located near the airport and within an easy drive of ALL of Key West activities. The condo was freshly painted and...
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From
$225
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
14 photos Details Reviews (10) Make Inquiry
5 of 5 stars Reviewed May 6, 2014
The location was great. Very Quiet. Exactly as described. Would definitely stay here again! I was also incredibly grateful the for the quick response times to my emails.
4 of 5 stars Reviewed November 6, 2013
Very nice, clean, and quiet. Was just as advertised. Very roomy, kitchen was great. Pool & spa were very nice for the end of the day enjoyment. Coouldn't have asked for anything...
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From
$239
Per Night
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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9 photos Details Reviews (7) Make Inquiry
5 of 5 stars Reviewed August 18, 2014
This place was everything we could've hoped and MORE! The house was beautiful and had such am authentic key west charm. The historic nature of the building really made it warm and...
2 of 5 stars Reviewed July 15, 2014
We had a family of five stay in the Grand Bahama Suite July 6-9. Three days before our vacation we received an email that there would be construction going on and there was a...
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From
$169
Per Night
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1 Bedroom, 4 Bathrooms, Sleeps 2
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21 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 2, 2014
This was such a rare find. We will be back and refer our friends. Loved that we had access to the pool. Absolutely the perfect spot!
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From
$290
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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26 photos Details Reviews (12) Make Inquiry
5 of 5 stars Reviewed June 23, 2014
We had a wonderful stay at the Atlantic Sunrise condo. The condo was tastefully decorated and well appointed. It was roomy and very comfortable for the four of us. The fine...
5 of 5 stars Reviewed June 21, 2014
We have just returned from holiday in this wonderful Condo. The pictures really do match the high quality accommodation. We spent many hours relaxing on the veranda with the...
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From
$198
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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23 photos Details Reviews (29) Make Inquiry
5 of 5 stars Reviewed October 20, 2014
Our Key West trip was amazing, and this apartment was a big part of it. Very clean and has everything you need on a trip as well as the amenities like the kitchen and other...
5 of 5 stars Reviewed September 30, 2014
Excellent facilities within the apartment and in the grounds of the condo. The owner is friendly and very helpfull. You are only a short taxi drive from the main entertainment...
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From
$257
Per Night
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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26 photos Details Reviews (19) Make Inquiry
5 of 5 stars Reviewed July 31, 2014
Great rental, right in the middle of everything. We arrived and everything was as described. Wifi was a great bonus for teenage son. House clean and tidy with plenty of linen...
4 of 5 stars Reviewed June 14, 2014
Everything about our vacation at Casa del Sol was perfect. The apartment is a perfect size and the rooms were decorated to match the Key West atmosphere, which we loved! The...
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From
$245
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 photos Details Reviews (1) Make Inquiry
3 of 5 stars Reviewed September 3, 2013
Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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From
$110
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
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54 photos Details Reviews (1) Make Inquiry
From
$500
Per Night
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Studio, 1 Bathroom, Sleeps 2
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11 photos Details Make Inquiry
From
$285
Per Night
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3 Bedrooms, 2 Bathrooms, Sleeps 8
18 photos Details Make Inquiry
From
$249
Per Night
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Studio, 1 Bathroom, Sleeps 2
19 photos Details Make Inquiry
From
$150
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Make Inquiry
From
$215
Per Night
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1 Bedroom, 2 Bathrooms, Sleeps 4
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6 photos Details Make Inquiry
From
$215
Per Night
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2 Bedrooms, 1 Bathroom, Sleeps 6
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6 photos Details Make Inquiry
From
$2,650
Per Week
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2 Bedrooms, 3 Bathrooms, Sleeps 6
12 photos Details Make Inquiry
From
$215
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
4 photos Details Make Inquiry
From
$183
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
20 photos Details Make Inquiry
From
$395
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
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8 photos Details Make Inquiry
From
$138
Per Night
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Studio, 1 Bathroom, Sleeps 4
14 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 5, 2014
The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or a...
4 of 5 stars Reviewed July 25, 2014
The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we were...
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From
$225
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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19 photos Details Reviews (4) Make Inquiry
2 of 5 stars Reviewed April 15, 2014
We certainly did not get what we thought we were paying for. WiFi was virtually non-existent. The "fully-equipped" kitchen had no serving spoons, only two dish towels, and ants...
5 of 5 stars Reviewed February 10, 2014
I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
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From
$149
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
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25 photos Details Reviews (10) Make Inquiry
5 of 5 stars Reviewed October 14, 2014
My wife and I stayed here from Oct 4th thru the 11th. The Condo is situated minutes away from the airport so it was a quick taxi ride. The grounds of the complex are well taken...
5 of 5 stars Reviewed August 11, 2014
My wife, 2 adult daughters, and I, stayed at Pam's La Brisa "Jungle Breeze" condo from August 2 - 9, 2014. The condo is located in a very safe and friendly gated community. Pam...
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From
$178
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed October 8, 2014
Everything was great! The location was perfect - and the private hot tub was the best! Only down side (which wasn't a big deal) was there were ants on the kitchen counter! Very...
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From
$278
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
13 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed July 9, 2014
Nice little cottage with private patio, located adjacent to the pool. Cottage was clean and well maintained, and had a full kitchen with all the amenities. It was walking...
5 of 5 stars Reviewed December 22, 2012
Kevin, Shelby, and all the folks at KW Hideaways, I wanted to take a moment to thank you all for a wonderful experience! You and your team worked hard to ensure everything...
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From
$298
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
9 photos Details Reviews (13) Make Inquiry
4 of 5 stars Reviewed September 11, 2014
Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
5 of 5 stars Reviewed May 22, 2014
Great location 2 blocks off Duval. Bright, airy, tropical decor. Clean, lots of amenities. Pool was great. Onsite parking. Perfect size for our group of 5 women. Would...
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From
$495
Per Night
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3 Bedrooms, 4 Bathrooms, Sleeps 6
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25 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed April 17, 2014
This house was gorgeous. Clean, updated and simply beautiful. It also had everything we needed...hair dryers, ironing board, laundry room, etc. If you are looking for something...
5 of 5 stars Reviewed October 9, 2013
Six women stayed in this beautiful townhome for three nights for a girls getaway. We would normally have booked hotel rooms, but staying here far exceeded our expectations and we...
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From
$250
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
5 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed March 22, 2014
A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
5 of 5 stars Reviewed January 23, 2014
The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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From
$178
Per Night
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1 Bedroom, 1 Bathroom, Sleeps 4
15 photos Details Reviews (20) Make Inquiry
5 of 5 stars Reviewed June 26, 2014
Our stay at the Abaco Suite through Key West Vacation Rentals was near perfect. The rental company was very professional and helpful. The check-in and out was seamless. We...
4 of 5 stars Reviewed April 7, 2014
TThis is a lovely 1-bedroom townhome situated in an ideal location among 8-9 units on around a truly beautiful courtyard. First off, you really get the bang from your buck at this...
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From
$138
Per Night
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Studio, 1 Bathroom, Sleeps 4
14 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed October 17, 2014
We had an excellent experience staying in this studio for our honeymoon. Only drawback was the lack of kitchen equipment which made it difficult to cook a full meal for...
4 of 5 stars Reviewed September 24, 2014
It was a great location out of the way but by everything. Also the room was very secluded to the back of the property for a nice romantic time.
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From
$138
Per Night
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Studio, 1 Bathroom, Sleeps 4
11 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 28, 2014
This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin to...
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From
$118
Per Night
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Studio, 1 Bathroom, Sleeps 2
7 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 17, 2014
This unit was perfect for our needs. It's just a small studio cottage, but has a nice porch and access to the large "shared" (and I put it in quotations because we had the pool...
4 of 5 stars Reviewed July 28, 2014
This rental was almost exactly how I imagined it to be when I booked it. It was small, yet quiet with an adjacent pool that was large enough for my float and warm enough for me...
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From
$198
Per Night
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Studio, 1 Bathroom, Sleeps 4
Booking
10 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed August 12, 2014
We rented three units for 5 nites. We had a great week. The staff was very friendy. Everything was clean, Couldn't have ask for a better place to spend our vacation. Cant wait to...
5 of 5 stars Reviewed July 29, 2014
From the minute we stepped off the plane, we were extremely impressed by Key West Vacation Rentals. We flew in on a Saturday morning, and they do not typically do airport pick-ups...
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From
$408
Per Night
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3 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 29, 2014
This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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From
$1,575
Per Night
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2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed June 6, 2014
This is our 7th or 8th vacation in Key West. It was our 3rd time going through Key West Vacation Rentals. This company is top notch and we have loved each property we've stayed...
4 of 5 stars Reviewed January 11, 2014
Southern Winds is a stand alone 2 story, 2 BR, 2 bath ( only 1 bathroom on 2nd floor), condo in a private, gated 14 unit complex. Nicely decorated and offered all supplies and...
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From
$408
Per Night
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3 Bedrooms, 4 Bathrooms, Sleeps 8
21 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed March 25, 2014
Lovely house, tastefully decorated with bright colors - very Key West! House is conveniently located just off Duval Street, but with that convenience comes some associated noise...
4 of 5 stars Reviewed February 5, 2014
This was a nice place to stay and I would recommend it to anyone looking to have a good time in Key West. It's just off of Duval Street but out of the way of the local foot...
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Book Online(224)

Suitability

  • Wheelchair access (22)
  • Elder access (108)
  • Suitable for children (73)
  • Pet friendly (122)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (378)
  • Other outdoor space (343)
  • Internet (336)
  • All pools (265)
  • Grill (234)
  • View all amenities
Key West Vacation Rentals

Great deals on vacation rentals make Key West a favorite beach getaway spot for all types of travelers. It’s a laid-back beach town with a twist of eccentricity—along with a diverse dining scene and, of course, famous (one might even say infamous) nightlife. From luxury beach houses to budget cottages, you’ll find it in Key West… and our Key West vacation rental reviews will help you book with confidence.

Where to rent in Key West, Florida

Vacation rentals in Key West can be found all over town. Renting in Old Town (the historic district) will put you in the center of the action—steps from restaurants, bars, boutiques, souvenir shops and major attractions. Live like a local and catch an ocean breeze on your verandah (a typical feature of “conch” architecture). Or how about a modern apartment rental near Duval Square? If you’re craving privacy and relaxation, though, consider a Key West vacation rental away from the center of town—enjoy oceanfront views away from the hustle and bustle. No matter where you make your home base, if you rent a moped or scooter in Key West, you’ll find it easy to get around without a rental car.

Key West Bars and Restaurants

Forget paying a premium for mediocre room service in a hotel—book a vacation rental home in Key West and put that money toward excellent meals in restaurants. (Or, if you’re patterning your vacation after Ernest Hemingway, your bar tab.) Be sure to try the conch fritters. And we recommend trying as many different versions of key lime pie as possible—after all, you do want to find the best key lime pie in Key West, right? Parrotheads (you know who you are) should make a beeline to Jimmy Buffet’s Margaritaville Café, where you can order up your very own Cheeseburger in Paradise.

Sightseeing and Activities in Key West

Now that you’ve found a great vacation house in Key West, what are you going to do with yourself during your vacation? Beach bums will naturally gravitate toward, well, the beach (try Smathers Beach or Fort Taylor Beach)… but there are plenty of other options if you want a more cerebral or active vacation. Hemingway’s house (complete with seven-toed cats descended from his own beloved pets) is a must-see for any literature buff, and you’ll find plenty of secondhand bookstores in town too. Historians will want to explore Henry Truman’s Little White House (located right on Front Street), as well as Fort Zachary Taylor Historic State Park. And definitely don’t leave town without taking in at least one sunset in Mallory Square. Not surprisingly, many of the best things to do in Key West take place out on the water. If you’re new to saltwater fishing, try a fishing charter excursion. A local captain can take you to the best spots for tarpon, marlon, tuna and grouper. Rent a Jet Ski and tour the coastline, or take a charter sunset cruise. Feel like a bit of gambling? You’ll find plenty of casino cruises in Key West as well. They’ll take you out to international waters, where you’re free to hit the slot machines.