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Vacation Rentals in Key West, FL

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All 422 Rentals in Key West
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From
$250
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
15 photos Details Reviews (1) Make Inquiry
From
$198
Per Night
Studio, 1 Bathroom, Sleeps 4
Booking
10 photos Details Reviews (2) Make Inquiry
From
$175
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
24 photos Details Reviews (3) Make Inquiry
Also consider
Tropical Escape
2 Bedrooms, sleeps 6
$195 - $385 / night
Conch Haven Built 1883 Beautiful ! MONTHLY Rental
1 Bedroom, sleeps 4
$93 - $140 / night
Artist cottage with hot tub
1 Bedroom, sleeps 4
$100 - $110 / night
KEY WEST LIVIN'  BEAUTIFUL 50' Yacht 3 Bed , 2 bath, WIFI, Flatscreen,Sleeps 6
3 Bedrooms, sleeps 6
$300 - $400 / night
From
$178
Per Night
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
$233
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
12 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 12, 2014
Checking in was a fast no hassle process. Condo was clean and decorations were wonderful with all the comforts if home . Although we did not use the bikes they are a nice touch...
5 of 5 stars Reviewed May 24, 2014
I hesitate not giving this rental a fifth star, because it was such a wonderful retreat. There was nothing second class about the beautiful decor or the comfortable spaces. The...
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From
$199
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
10 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed October 9, 2014
Our small group of 3 were impressed with the great location as well as the property itself. The landlord was pleasant and accommodating. Was able to walk everywhere. Will return...
5 of 5 stars Reviewed September 8, 2014
Stayed in this suite over the weekend (sept 5th- 7th) and I do not have one bad thing to say about this place! Easy to get to, perfect location! I felt very at home here! Also we...
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From
$219
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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
$275
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
25 photos Details Reviews (25) Make Inquiry
5 of 5 stars Reviewed July 31, 2014
We had a great time in Key West and would strongly recommend this apartment. Very comfortable, good sized pool, ideal location. Would definitely go again.
5 of 5 stars Reviewed July 11, 2014
Two couples stayed July 6 through July 11. Loved the condo. Great location, great pool. Very quiet and peaceful location that is close to all the great Key West attractions...
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From
$225
Per Night
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
$138
Per Night
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
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
$138
Per Night
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
$348
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed October 13, 2014
The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
5 of 5 stars Reviewed July 25, 2014
I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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From
$408
Per Night
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
$198
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
23 photos Details Reviews (29) Make Inquiry
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...
5 of 5 stars Reviewed September 20, 2014
The condo was beautifully appointed and thoroughly clean. I am OCD and had absolutely no anxiety in the space. The owner was very helpful in that she furnished a basket of helpful...
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From
$248
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
16 photos Details Reviews (8) Make Inquiry
5 of 5 stars Reviewed July 4, 2009
My husband and I stayed here with my parents and had a really wonderful time. The house was adorable, clean and had everything we needed. It was close to all the action on Duval...
5 of 5 stars Reviewed July 2, 2009
Great location off the upper section of Duval. Close enough to walk to everything but far enough to be quiet. Perfect size for 2 or 4 people. Clean and comfortable. Would...
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From
$378
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
21 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed July 25, 2014
This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a great...
5 of 5 stars Reviewed June 6, 2014
Very clean, looks recently redone. Great set up, plenty of room for the six of us. Most comfortable bed ever. Literally steps from Duval St. I would definitely stay here again.
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From
$178
Per Night
Studio, 1 Bathroom, Sleeps 2
12 photos Details Reviews (35) Make Inquiry
5 of 5 stars Reviewed May 16, 2014
Heaven in the middle of Key West. Beautifully decorated, clean, perfect pool & hot tub, Amazing! Staff is very attentive and replenishes towels, changes garbage, maintains the...
5 of 5 stars Reviewed March 31, 2014
We stayed with our yorkie, love love it. Very clean (although the bed was a bit uncomfortable) very clean staff was very friendly and helpful.five stars in our book we will stay...
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From
$188
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details Reviews (18) Make Inquiry
5 of 5 stars Reviewed June 25, 2014
I can't say enough about this rental! Excellent location, very clean and the courtyard is amazingly beautiful.. You feel like you are in a private paradise on the island.. The...
5 of 5 stars Reviewed June 14, 2014
We stayed here the first week of June 2014. We were welcomed by management at the rental office, offered a cold beverage, and given an umbrella for our use. We were picked up at...
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From
$258
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
20 photos Details Reviews (34) Make Inquiry
4 of 5 stars Reviewed June 5, 2014
This house is the perfect little hideaway. Close enough to Duval and all the action but far enough away that you can shut out the world and just relax. The hot tub is very...
5 of 5 stars Reviewed March 27, 2014
Leeward Isle is a great place to stay for a trip to Key West. It is within walking distance to all the hot spots and to the beautiful sunsets at Mallory Square, yet far enough...
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From
$188
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details Reviews (20) Make Inquiry
4 of 5 stars Reviewed January 7, 2014
The listing was completely accurate and the property maintenance was good. The furniture and utensils (knives, peeler, grater) were tired and due for replacement. We had very...
3 of 5 stars Reviewed November 17, 2013
The audubon House is perfect if you're just looking for a place to stay in walking distance to everything. The pictures were a bit deceiving regarding the pool. There is no pool...
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From
$198
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
20 photos Details Reviews (25) Make Inquiry
5 of 5 stars Reviewed October 8, 2014
Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
5 of 5 stars Reviewed August 19, 2014
My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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From
$268
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
18 photos Details Reviews (32) Make Inquiry
4 of 5 stars Reviewed July 2, 2014
Condo was in a great location, the staff was very helpful and friendly. Had one maintenance problem which was the garbage disposal and was fixed with in 24 hours. There is no...
3 of 5 stars Reviewed December 20, 2013
The service and location were great. We could walk everywhere. Our car never left the free parking garage throughout our stay. The apartment was clean but tired-looking. The...
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From
$5,000
Per Month
3 Bedrooms, 3 Bathrooms, Sleeps 6
22 photos Details Reviews (4) Make Inquiry
4 of 5 stars Reviewed March 12, 2014
We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
5 of 5 stars Reviewed January 23, 2014
Tobago House is very nice, close to Duval - quiet street. Nice amenities, pool, hot tub, great outdoor area. Would recommend to anyone. Close walk to everything. Wonderful!
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From
$188
Per Night
Studio, 1 Bathroom, Sleeps 2
12 photos Details Reviews (14) Make Inquiry
4 of 5 stars Reviewed September 1, 2014
We found the room to be charming, and a great location for Duval St roming around. Parking can be an issue, but we were happy with our stay. When in Key West one needs to be out...
5 of 5 stars Reviewed November 16, 2013
This little cottage is adorable. I do not have one complaint! Clean, Updated, We maintained. Perfect, perfect, perfect!
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From
$1,195
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
14 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed January 15, 2014
Love Key West and staying at the Shipyard condominiums put us right with in walking distance to every thing we love to do. We have been to Key West four times in four years and...
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From
$239
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
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
$208
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
12 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed October 13, 2014
The location of our rental was fabulous. We were in walking distance of everything Key West had to offer. Having the front porch open would have made the stay even better.
4 of 5 stars Reviewed September 29, 2014
Great place to stay! Located right on Duval Street. Two rooms with double beds and a pull out bed-couch. A/C nice and cold when you need to get out of the summer heat in the...
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From
$408
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
22 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 1, 2014
We took our family of 6 to Toon Hall and were greeted by 2 Cadillac SUV's at the airport to check us in and take us to our home. Toon Hall was very spacious and comfortable...
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From
$1,575
Per Night
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
$208
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
15 photos Details Reviews (21) Make Inquiry
3 of 5 stars Reviewed September 30, 2014
If you don't mind the Anchors away people hanging out around your bedroom porch all hours of the night, or the people up stairs playing basketball at 430 in the morning, you...
2 of 5 stars Reviewed September 19, 2014
The rental office is well organized and accommodating, and that is the only good thing I can say. The unit itself was clean, though sparsely furnished, especially the bathroom...
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From
$268
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Booking
23 photos Details Reviews (14) Make Inquiry
5 of 5 stars Reviewed August 21, 2014
I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
5 of 5 stars Reviewed August 18, 2014
Positioned right with ammeneties, beaches, and bars close by. Short stroll to any need. Place was very clean and with 2 bedrooms, 2.5 baths , pull out beds was very...
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From
$257
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
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
$198
Per Night
Studio, 1 Bathroom, Sleeps 2
11 photos Details Reviews (19) Make Inquiry
5 of 5 stars Reviewed September 2, 2014
Really enjoyed this place. Pics are accurate as this place looks in great condition. Loved the patio/hot tub area, also the use of the pool just across the street and grill...
5 of 5 stars Reviewed March 12, 2014
We absolutely loved Harrison's Hideaway. It was in the perfect location - 1/2 block off of Duval, a very short bike ride to the beach. It was immaculate, too - must have been...
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From
$7,000
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed January 23, 2014
B+ no Choices in cable channels no prkg On site , parrot sanctuary adjacent Property's remote pool. Access. K
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From
$2,500
Per Month
1 Bedroom, 2 Bathrooms, Sleeps 4
11 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed January 8, 2014
Super-cute house, adorably decorated, with nice bathrooms & a great Viking range for when you're eating in. Great location in Bahama Village.
5 of 5 stars Reviewed December 19, 2013
Fishtail was the nicest rental I ever had. The home was comfortable and very well appointed. The location was awesome because you could walk or bike everywhere beach, town...
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From
$2,500
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
20 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed January 10, 2014
Great lodging! Beautifully decorated and maintained, amenities way beyond what is expected! Would highly recommend staying here!
5 of 5 stars Reviewed December 5, 2011
First let me say that management was very accomodating. The location of the apartment is excellent and within a short walking distance of nearly everything. The apartment is very...
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From
$6,500
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
20 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed February 3, 2011
We spent the month of March at Villa azul in 2008. It was amazing. We discovered Key West in a way I never thought possible...some of our best moments were spent in the oasis...
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From
$638
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 16
Bookings
42 photos Details Reviews (10) Make Inquiry
5 of 5 stars Reviewed September 3, 2014
I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
5 of 5 stars Reviewed January 30, 2014
This is a great place for large families to stay. Wonderful courtyard with the pool and the hot tub and lots of areas to entertain. Remodeled kitchen has everything you need...
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Book Online(224)

Suitability

  • Wheelchair access (22)
  • Elder access (108)
  • Suitable for children (75)
  • Pet friendly (122)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (375)
  • Other outdoor space (340)
  • Internet (333)
  • All pools (273)
  • Grill (233)
  • 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.