We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Key West, FL

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 485 Rentals in Key West
loading...
Sort by
From
$250
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
15 photos Details Reviews (1) Make Inquiry
From
$169
Per Night
1 Bedroom, 4 Bathrooms, Sleeps 2
Bookings
21 photos Details Reviews (1) Make Inquiry
From
$138
Per Night
Studio, 1 Bathroom, Sleeps 4
14 photos Details Reviews (2) Make Inquiry
Also consider
Key West Beachfront Luxury 2/2 Condo  A212
2 Bedrooms, sleeps 6
$275 - $400 / night
Key West Beach Front vacation is HERE! Ocean view!
Sleeps 2
$257 - $414 / night
:: FOLLOW THE SUN @ THE BEACH :: Ocean View / Pool & Jacuzzi...
2 Bedrooms, sleeps 6
$332 - $567 / night
Stay in the nicest part of Truman Annex
2 Bedrooms, sleeps 6
$257 / night
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...
See all reviews
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...
See all reviews
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...
See all reviews
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...
See all reviews
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...
See all reviews
Get the List
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.
See all reviews
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...
See all reviews
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...
See all reviews
From
$188
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
19 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...
See all reviews
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!
See all reviews
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...
See all reviews
From
$118
Per Night
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...
See all reviews
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...
See all reviews
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...
See all reviews
From
$178
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
9 photos Details Reviews (28) Make Inquiry
5 of 5 stars Reviewed August 5, 2014
I stand by my first review in June of 09. Recent updates to the unit are looking good altho there is a bit more work needed - e.g., recover sofa, paint here and there, and the...
2 of 5 stars Reviewed May 8, 2014
Foe as much as they charge, the place was in bad shape. A lot of cracked tiles throughout, worn furniture, a stove that didn't work (they had a hot plate), no oven, The Wi-Fi...
See all reviews
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...
See all reviews
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...
See all reviews
From
$268
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
20 photos Details Reviews (20) Make Inquiry
5 of 5 stars Reviewed May 16, 2014
We loved the Duval Square Penthouse. It was very clean and spacious. We received fresh linens everyday and the staff was delightful. The pool was nice and had a nice shaded area...
5 of 5 stars Reviewed January 7, 2014
This condominium was on Duval - the main drag - but quiet once we were in it. It had a pool, hot tub and everything we needed. The beds were comfortable. Would stay there again.
See all reviews
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...
See all reviews
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...
See all reviews
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...
See all reviews
From
$248
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
28 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed June 7, 2014
This property was a beautiful way to do Key West. Private beach, big salt water pool and Jacuzzi and grills. The view was the best part of the condo! It was also very clean...
See all reviews
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...
See all reviews
From
$178
Per Night
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...
See all reviews
From
$378
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (12) Make Inquiry
3 of 5 stars Reviewed August 12, 2014
Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
5 of 5 stars Reviewed July 27, 2014
Stayed at Passover Cottage for my wife's 50th birthday with friends and family. The property was well-maintained and clean. Location was perfect, close enough to the activities...
See all reviews
From
$408
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
21 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed September 4, 2014
This was our first time doing a vacation rental home and it was well worth it. Prices for hotel rooms in key west are extremely pricey and this was such a better way to go. The...
5 of 5 stars Reviewed January 8, 2014
Casa Margarita is located blocks from the Marina and all that you would want to do in Key West, yet is on a very quiet and relatively untrafficked street. The house is small, but...
See all reviews
From
$468
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 12
36 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed July 29, 2014
Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
See all reviews
From
$290
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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...
See all reviews
From
$258
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
22 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed August 5, 2014
Nice condo right on duval st. Good location for a more quiet stay.Cvs right around the corner Rooms where nice. Hot tub on patio is a plus. Only negative comment is I wish we...
See all reviews
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.
See all reviews
From
$408
Per Night
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...
See all reviews
From
$258
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
18 photos Details Reviews (7) Make Inquiry
4 of 5 stars Reviewed July 21, 2014
Very nice place, beds were super comfy. Close to Duval but quiet. This place does have a parking spot, but we were not told about it until I called.
5 of 5 stars Reviewed March 24, 2014
Excellent accommodations! Slept five adults comfortably, but the one bathroom was a little rough at times. We're all friends so no big deal! Especially enjoyed the hot tub and...
See all reviews
From
$158
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
21 photos Details Reviews (20) Make Inquiry
5 of 5 stars Reviewed August 19, 2014
Definitely an ideal location for all things Key West. Never had to walk very far to get to most every place we wanted to go. The place was clean and always comfortable...
4 of 5 stars Reviewed July 28, 2014
To start the manager was very pleasant. The drive from the rental office to the rental property was just a couple of seconds away. Nice to see personal parking onsite. Inside...
See all reviews
From
$138
Per Night
Studio, 1 Bathroom, Sleeps 2
Booking
12 photos Details Reviews (29) Make Inquiry
4 of 5 stars Reviewed May 5, 2014
Great location - walking distance to everything! It was clean and friendly great for the price! Would rent Monroe Efficiency again
2 of 5 stars Reviewed March 31, 2014
We arrived at 11pm and the email directions given were not helpful. The address was not what was on the sheet and we were lost and frustrated after 15 hrs of traveling. We had to...
See all reviews
From
$208
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
9 photos Details Reviews (35) Make Inquiry
3 of 5 stars Reviewed March 29, 2014
First the pros. The location is great if you want to be close to Duval Street and an easy walk to many restaurants and other attractions. The pool area is very nice and well...
4 of 5 stars Reviewed November 21, 2013
Perfect location and nice unit. Wife loved the privacy of the hot tub. We had a great time.
See all reviews
From
$368
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
21 photos Details Reviews (8) Make Inquiry
5 of 5 stars Reviewed March 10, 2013
2br 2 bath with sleeper sofa in main room. Pictures are accurate. Private pool and location make this an ideal stay for more than 3 nights. VERY close to the action on Duvall...
4 of 5 stars Reviewed October 8, 2011
DuPont House was a great place to stay in a great location. You are close enough to walk to everything but just far enough off on a side street so you don't hear any noise from...
See all reviews
From
$228
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
14 photos Details Reviews (20) Make Inquiry
5 of 5 stars Reviewed April 24, 2014
Place was spacious and accomodated our 5 guests great. Great amenities and management staff was great. Housekeeping realized on the last night that the a/C was not working and...
3 of 5 stars Reviewed February 27, 2014
Very busy location but surprisingly quite. Pool is over two blocks away across a busy street, disappointing. Clean except for the ants and other big bugs, had to keep all food...
See all reviews
Go to map view
Book Online(225)
Use filters to find the best results!

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
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List

More Beach destinations:

More Family destinations:

Filter search results by:
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.