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Vacation Rentals in Key West, FL

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All 485 Rentals in Key West
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From
$450
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
9 photos Details Reviews (4) Make Inquiry
From
$250
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
15 photos Details Reviews (1) Make Inquiry
From
$175
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
24 photos Details Reviews (3) Make Inquiry
Also consider
Luxury 2Bed/Bath condo on the beach. (Sleeps 6)
2 Bedrooms, sleeps 6
$220 - $400 / night
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
2 Bedrooms, sleeps 6
$210 - $285 / night
STEPS TO DUVAL!  LUXURY,  SLEEPS 2-4,
1 Bedroom, sleeps 4
$188 - $278 / night
OLD TOWN KEY WEST -  Historic & Charming - Cigar
1 Bedroom, sleeps 4
$285 / night
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
10 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed June 9, 2014
Very good price for a 2 bed 2 bath in Key West! It Was clean and just what we needed! It was also not right in downtown close to everything so we could get away hen we wanted.
4 of 5 stars Reviewed May 23, 2014
Condo was a great location. Near beaches and activities. Great place to relax. Owner was very courtious. Pool was a little small but the facilities were beautiful.
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From
$169
Per Night
1 Bedroom, 4 Bathrooms, Sleeps 2
Bookings
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
$149
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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
$233
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
12 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed October 17, 2014
My husband and I chose Key West to celebrate our 25th anniversary. Can't say enough about this gorgeous condo. In addition to the cleanliness, ease of reservation, security and...
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...
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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
$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, 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
$850
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
34 photos Details Reviews (15) Make Inquiry
5 of 5 stars Reviewed August 2, 2013
After reading great reviews about the Villa Tropicale, we rented this property for six nights last month. We were traveling with a group of eight and wanted a large home where we...
5 of 5 stars Reviewed January 27, 2013
This was not our first stay at Villa Tropicale and we certainly intend to come back. When we first opened the gate of the property a few years ago, we were delighted to discover...
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From
$230
Per Night
Studio, 1 Bathroom, Sleeps 1
14 photos Details Reviews (41) Make Inquiry
5 of 5 stars Reviewed March 13, 2013
This is the first time my husband and I have been to Key West and this was the perfect spot to stay. It was just the right size for a romantic getaway. Even though we were only a...
5 of 5 stars Reviewed November 1, 2012
Perfect for what we were asking for in a rental. Close to Duval and all the shopping and restuants. Rode Bikes and walked everywhere. Enough space for the two of us. Gardens were...
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From
$299
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed March 7, 2011
Really nice & spacious but a little to far from downtown.
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From
$300
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
43 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed May 1, 2014
We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the...
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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
$299
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details Reviews (13) Make Inquiry
4 of 5 stars Reviewed September 4, 2013
We had a nice experience @Sunrise Resort. The Villa was clean and in good conditions; as a recommendation, the king size matress in the Master Room should be replaced. Excellent...
4 of 5 stars Reviewed April 11, 2011
The grounds were beautiful and the pool was great. We had three rooms and all were very nice. I would stay there again with no hesitation!
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From
$350
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
11 photos Details Reviews (1) Make Inquiry
From
$350
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details Reviews (13) Make Inquiry
4 of 5 stars Reviewed February 27, 2014
This unit has recently been refreshed and is very comfortable. It has everything you need to have a perfect vacation. The kitchen is well stocked, if you are inclined to do some...
5 of 5 stars Reviewed March 8, 2013
We were very happy with our condo. Everything was neat and clean. Living room furniture was outdated but would not stop from returning.
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From
$275
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details Reviews (20) Make Inquiry
5 of 5 stars Reviewed May 18, 2014
Read the title. Would do it again. In a heartbeat. Clean, well-equipped, met ALL OF OUR NEEDS. Whether a family with children, or friend getaway, meets all needs.
5 of 5 stars Reviewed September 25, 2013
We had another couple with us, and we thoroughly enjoyed our stay. The rooms are large, airy, and bright...just like the photos. Nice fully equipped galley-style kitchen. The...
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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
$357
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
27 photos Details Reviews (11) Make Inquiry
5 of 5 stars Reviewed June 30, 2013
The house was very nice and well kept and within walking distance to just about anything. We did a lot of walking and actually ate in most of our meals.
5 of 5 stars Reviewed May 25, 2013
An absolutely fantastic holiday home away from home. The cleanliness of the house is an absolute joy, and there is every household amenity to make your stay comfortable. It is...
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From
$350
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
9 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed December 5, 2012
112 Beach Club is a large 2b/2b condo right on the atlantic! The complex is a secure property with very nice amenities. This condo itself is a bit dated, but was very clean and...
2 of 5 stars Reviewed February 2, 2012
It was a nice condo, accommodating my wife and I and another couple vacationing with us, but it was dirty. The refrig and appliances were not cleaned, the home was pretty much...
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From
$300
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
11 photos Details Reviews (12) Make Inquiry
4 of 5 stars Reviewed May 14, 2013
Overall the condo is very nice. Towels and sheets could use an update along with all of the kitchen amenities. Mainly pots, pans, silverware etc. overall the place worked out...
2 of 5 stars Reviewed April 4, 2013
First off, we are not the type of people looking for a 4star place on a beer budget, then trash the accommodations on trip advisor because a lamp was out or the water tasted...
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From
$595
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
10 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed February 20, 2011
Our stay at Townhomes on Windsor (808 Johnson Lane) was absolutely perfect. Even after reading all the glowing reviews and scrolling through the pictures of the property, this...
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From
$780
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 8
23 photos Details Reviews (27) Make Inquiry
5 of 5 stars Reviewed December 7, 2012
The Queen Conch property is a very well maintained property and provides the perfect setup for a small gathering of friends or family. The main common areas are large enough and...
5 of 5 stars Reviewed December 5, 2012
Had a large party (8 adults) and this was just the right kind of property for our group with 3 separate units in one. All amenities were great!! Loved it & highly recommended!
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From
$317
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 7
36 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed April 29, 2014
the service we received from Carlos the property manager from south street serenity was excellent. whenever we had a question he either answered the phone or called us back...
5 of 5 stars Reviewed June 7, 2014
Von der ersten Sekunde an haben wir uns sehr wohl in diesem tollen, gemütlichen und wunderbar eingerichteten Haus gefühlt. Das Haus bietet alles, was man braucht, nein, es bietet...
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From
$198
Per Night
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
$595
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
10 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 4, 2011
We stayed at 806 Johnson Lane in June 2007 when the unit was brand new and have spent our annual 10 day stay there every year since, watching the scratches, bumps and nicks grow...
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From
$255
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 5
25 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed September 17, 2014
The condo was spacious, well stocked, immaculate and close to everything that we could want. It was the best place we have ever stayed in Key West and we hope to book it again...
5 of 5 stars Reviewed March 18, 2014
The apartment is very comfortable and sunny. The beds are both great. Everything works perfectly. The washer/dryer, dishwasher, showers, air conditioner, coffee pot, toaster...
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From
$190
Per Night
1 Bedroom, 1 Bathroom, Sleeps 1
10 photos Details Reviews (44) Make Inquiry
4 of 5 stars Reviewed January 10, 2014
I stayed here with my mother from June 9-16 and again from 06/30-07/05. The price intrigued us the most with what the condo had to offer. The ocean views by far are some of the...
3 of 5 stars Reviewed December 4, 2013
My husband and I stayed in the one bedroom unit at Casa Atlanta for two weeks, in late November and early December of 2013. As other folks have mentioned, the ocean view upon...
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From
$1,000
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 10
24 photos Details Reviews (18) Make Inquiry
5 of 5 stars Reviewed August 19, 2014
This is a beautiful 5 bedroom house in a great location right on Duval Street which makes it very convenient . The layout of the house though keeps you in the back of the house...
5 of 5 stars Reviewed March 26, 2014
Absolutely loved this house. I came with my wife, 4yo and 1 yo along with my cousin and his wife and two 4yos. There is tons of space and the pictures really don't do the...
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From
$298
Per Night
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
$360
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details Reviews (26) Make Inquiry
5 of 5 stars Reviewed December 20, 2012
Very clean and great location right off Duval Street. Excellent Restaurants in the courtyard. "At Home in Key West" rental department was very helpful in secruing the perfect...
4 of 5 stars Reviewed September 12, 2012
The 3 bedroom condo I stayed in is nicely furnished and quiet, except for the roosters in the early morning! But even the roosters added to the charm of Duval Square. The 2...
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From
$490
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (38) Make Inquiry
5 of 5 stars Reviewed October 17, 2012
This amazing little house had everything you could need to make a Key West vacation even better. The whole house was clean, and with a tropical flair that told you the moment you...
5 of 5 stars Reviewed September 1, 2012
The house was spotless. Easy to live in. Close to everything. Comfortable. The small pool/grotto is where I hang out in my memories. Everyone was sweet, accommodating and...
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From
$325
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 9, 2010
The condo we stayed in had obviously been remodeled. It was gorgeous with plenty of space for 4 people! Also, the pool and jacuzzi were huge! We really enjoyed the accomodations...
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From
$400
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed September 23, 2014
This place was great for my spouse & me and grown daughter & friend to stay during our visit to Key West this summer. the two bedrooms are big, comfortable and have their own...
5 of 5 stars Reviewed April 9, 2014
This was our 11th visit to Key West and the past 10 years were spent in a hotel. So glad we made the change to a vacation home! Especially THIS vacation home. It was perfect...
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From
$245
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
7 photos Details Reviews (26) Make Inquiry
5 of 5 stars Reviewed July 23, 2014
This was a great place to stay with my husband and four teenage kids. We all had plenty of room as the rooms were huge...even the bathrooms! Everything we needed was there...even...
5 of 5 stars Reviewed March 12, 2014
This was our first trip to Key West and after staying at Henry's we will be back next year! Everything is perfectly laid out for you by Henry before you get there! The Condo is...
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From
$5,250
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed June 23, 2014
Very convenient to all the local sights and everything needed for a reasonably large group of people. Everyone had their space but also a large living/dining/kitchen for...
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From
$560
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details Reviews (39) Make Inquiry
4 of 5 stars Reviewed September 20, 2014
I would give this property 5 stars if only. If only the mattresses were comfortable. We all had soar backs from the experience. Some people complain about small things and the...
4 of 5 stars Reviewed March 31, 2014
Louisa House was in an excellent location with and amazing large pool for KW. We had room for 6 of us to be comfortable and room to spread out. The back yard is peaceful and...
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Book Online(225)

Suitability

  • Wheelchair access (22)
  • Elder access (109)
  • Suitable for children (73)
  • Pet friendly (133)
  • Smoking allowed (4)

Amenities

  • Air Conditioning (438)
  • Internet (392)
  • Other outdoor space (380)
  • All pools (322)
  • Grill (279)
  • 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.