Vacation Rentals & House Rentals in Key West

Updating...

age 0-16
334 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

334 house rentals

Steps to Duval, Old Town Charm -Grand Bahama Suite

Key West apartment

3 bedrooms / 2 bathrooms / sleeps 8

“Can't wait to return” We loved staying at the Grand Bahama suite. It was spacious, clean and centrally located just a street from all the action. We loved the courtyard and pool. I was a little concerned about parking but it worked out fine for us. We just coordinated with the other tenants. We will definitely be staying here again.

Responds fast! avg. 3 hours 22 minutes

Match: Clothes dryer

All filters match

Price per night from

$377

Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach

Key West townhouse

2 bedrooms / 3 bathrooms / sleeps 6

Match: Clothes dryer

All filters match

Price per night from

$572

Center of It All - Paradise Island Suite

Key West apartment

2 bedrooms / 1 bathroom / sleeps 6

“Great location in the heart of Old Town Key West, just a block off Duval..” We stayed in the Paradise Suite. Great front porch to hang out on, pool in back with pergola for lounging. Place was set up perfect, pool towels hanging by the door, bathroom had necessary items, kitchen well set up with needed items as well. Very well maintained and cleaned, bedding all set. Wi-Fi and other amenities available. Perfect for two couples, with room for even an extra guest. Driveway accommodates three cars, unmetered parking around the corner. Local market just 1/2 block away, and the highly recommended Thirsty Mermaid restaurant on the corner. Owner and managers very available and responsive. Will certainly stay again.

Responds fast! avg. 3 hours 22 minutes

Match: Clothes dryer

All filters match

Price per night from

$285

Best Location, 1/2 Block to Duval, Bimini Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Perfect!” This was the perfect size suite for 4 adults, with a little pool oasis right off our doorstep, in the center of it all without the noise of Duval. Loved every second of my stay!

Responds fast! avg. 3 hours 22 minutes

Match: Clothes dryer

All filters match

Price per night from

$297

1/2 Block to Duval, World of its own -Nassau Suite

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Our wedding family stayed here awesome” Fabulous. Clean roomy pool fantastic. Short walk to schooners Wharf Both inside and outside area were excellent

Responds fast! avg. 3 hours 22 minutes

Match: Clothes dryer

All filters match

Price per night from

$320

Spectacular Atlantic Ocean View Condo (MONTHLY)

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranquil. The patio faces south so you don't get blasted with the morning or evening sun making it very comfortable having your morning coffee or evening cocktail while enjoying the view. The owners have put a lot of thought into furnishing and accessorizing the unit. Tess and Mimi were wonderful to work with (Mimi met us at the condo and had great advice on where to eat, what to do...)I have stayed in several condos and this was by far my favorite, if your thinking of staying here you will not be disappointed. I will definitely be back the next time I visit the keys.

Match: Clothes dryer

All filters match

Price per night from

$330

Conch Haven Old Town 1/1 MONTHLY Rental

Key West apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 56 minutes

Match: Clothes dryer

All filters match

Price per night from

$105

Casa Del Sol, a Key West Vacation (Truman Annex)

Key West house

2 bedrooms / 3 bathrooms / sleeps 6

“awesome” the condo was beautiful. very good location. 2 suggestions. the grill did not have gas . the bed that opens up to king. not so much, mattress is 2 different heights and slides if you try to sleep on it. very very uncomfortable.

Responds fast! avg. 1 hour 19 minutes

Match: Clothes dryer

All filters match

Price per night from

$229

Southard Square Hideaway

Key West condo

1 bedroom / 1 bathroom / sleeps 4

Match: Clothes dryer

All filters match

Price per night from

$147

Key West Florida Beachfront Condo

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

“Better than the photos” Condo is perfectly located at the beach. Well designed for easy living both inside and out. Great advise on where to visit and eat thanks

Match: Clothes dryer

All filters match

Price per night from

$401

Key West Island Vacation

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Clothes dryer

All filters match

Price per night from

$480

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Responds fast! avg. 2 hours 36 minutes

Match: Clothes dryer

All filters match

Price per night from

$430

The Water's Edge

Key West house

3 bedrooms / 4 bathrooms / sleeps 8

“Perfect for a Memorable Key West Experience!” My family and I absolutely loved staying in this beautiful Key West home. Located in Truman Annex (a quiet, private community in Old Town Key West), the location is perfect for whatever you wish to do during your Key West experience. Ocean Paradise has gorgeous views from the 3rd level balcony, a wonderful screened-in porch on the main level (perfect for al fresco dining), and an incredible pool area with a larger than expected private pool and stunning landscaping that provides both shade and privacy. The home's interior is both spacious and functional, including lovely furnishings and everything you need for a memorable vacation in beautiful Key West. Just as important to us was the ease in managing our visit to Ocean Paradise. The owner and his staff were absolutely incredible to work with throughout the entire rental process. We had originally scheduled our visit for the 2014 Thanksgiving holiday week. However, a need arose which required us to cancel that planned stay. The property owner was gracious enough to work with us in our desire to reschedule our visit for May 2015, demonstrating a focus on and respect for his guests throughout the entire process. Our Key West vacation, and specifically our week-long stay in Ocean Paradise, was undoubtedly a memorable experience for me, my husband and our two adult children (as well as the little "furry" member of our family who also joined us for our Key West adventure). We will be returning to Key West, and when we do, Ocean Paradise will be our chosen "home away from home" during our stay!

Match: Clothes dryer

All filters match

Price per night from

$842

Tropical Escape

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Very comfortable and all around great place to stay.” It was very clean, comfortable and homey. The pool was great and it's very close to Key West and a beach. We really enjoyed our stay. Provided plenty of towels, pool accessories, kitchenware, etc.... No complaints.

Match: Clothes dryer

All filters match

Price per night from

$246

Admiral's Lane

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

“Fabulous family rental” We have stayed in Key West for four years now. This was the best rental property so far. The location is perfect for beach days and walking both ends of Duval at night. The property itself had all the amenities we needed and was run well by the property managers. The major reason we didn’t give five stars is that all of the tv’s were from the 90’s. They offered cable but on screens that are archaic. Not great for unwinding or catching up with March Madness. For this level of home/rental, the owners could spring for even just ONE flat screen.

Match: Clothes dryer

All filters match

Price per night from

$625

The Mermaid's Garden

Key West house

4 bedrooms / 5 bathrooms / sleeps 8

Match: Clothes dryer

All filters match

Price per night from

$625

Campbell Suite

Key West apartment

1 bedroom / 2 bathrooms / sleeps 2

“Comfortably furnished and decorated with a very convenient locat” We really enjoyed staying at the Campbell Suite. It served our requirements nicely. The amenities and location were excellent. Potential visitors do need to note that the entrance to the unit is on the 2nd floor, and there is also a circular metal staircase to get from the living area of the unit up to the bedroom. So occupants do need to be reasonably fit to do the stairs and get their luggage up there. We had no problems with this, but others need to be aware depending on their individual circumstances. As far as improvements, we did notice that there was some water that leaked into the closet on the 2nd floor and accumulated a bit in the center of the closet floor after the heavy rain the morning of Tue. 3/25. Didn't cause any problems for us but just wanted to bring it to someone's attention to check into before it gets worse.

Match: Clothes dryer

All filters match

Price per night from

$200

A Touch Of Havana In Key West

Key West condo

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 2 minutes

Match: Clothes dryer

All filters match

Price per night from

$352

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 33 minutes

Match: Clothes dryer

All filters match

Price per night from

$1,797

Big house

Key West house

5 bedrooms / 5 bathrooms / sleeps 12

“Bachelorette in Key West” I rented this house for my sister-in-law's bachelorette weekend in Key West. The house was spacious, clean, and overall the best place I've ever stayed! It was worth every penny!

Match: Clothes dryer

All filters match

Price per night from

$750

Island Style

Key West house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Clothes dryer

All filters match

Price per night from

$770

Shipyard-1/2 Block Duval Street

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

Match: Clothes dryer

All filters match

Price per night from

$245

Seaside Place Key West FL 5 Bedroom House 4 Baths

Key West house

5 bedrooms / 4 bathrooms / sleeps 12

“Paradise in Paradise” Just returned from a marvelous vacation in Key West. While the tan is already starting to fade, the memories of our stay at Seaside Place remain vivid. We absolutely loved this house. It is very charming and offers all the amenities you'll ever need and then some, from a kitchen that Julia Child would not have found wanting, gorgeous, large rooms each with its very own character, spacious communal dining areas and a beautiful large pool with romantic lighting, a soothing waterfall feature and total privacy. The owners' love for providing the best experience is evident in every detail, from the painstaking labeling of all switches and outlets to the folders of carefully compiled information about where to go, and what to do and see. The house is just a block from the quiet end of Duval Street (there is such a thing), yet far enough removed from the Key West bar scene responsible for the prevailing serious shortage of liver donors. We thoroughly enjoyed every minute of our stay and can't wait to return soon. And we can't help but think that if Hemingway had stayed here he might still be alive today

Responds fast! avg. 3 hours 15 minutes

Match: Clothes dryer

All filters match

Price per night from

$1,260

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

Responds fast! avg. 1 hour 47 minutes

Match: Clothes dryer

All filters match

Price per night from

$319

Duval Breeze

Key West house

2 bedrooms / 2 bathrooms / sleeps 6

“Warm and inviting condo” The condo is very cozy and inviting. I would definitely go back. Everything you need is right there (even a starter kit) in the condo. Duval street is heaven and parking is safe. We walked to everywhere (restaurant, groceries, shopping). What a great place to stay..

Match: Clothes dryer

All filters match

Price per night from

$240

Belle Marie

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Clothes dryer

All filters match

Price per night from

$303

** Fantastic Spring& Summer Stay Downtown walk everywhere **

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

Match: Clothes dryer

All filters match

Price per night from

$367

Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes

Key West townhouse

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 52 minutes

Match: Clothes dryer

All filters match

Price per night from

$359

Havana Hideaway

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 5

“Wonderful Experience!” I had a great experience with Historic Hideways during my 5 week stay in Havana Hideway. Everything exceeded my expectations. A great place and exteremely friendly service with Historic Hideways. I would recommend to anyone.

Match: Clothes dryer

All filters match

Price per night from

$310

>

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 4

Match: Clothes dryer

All filters match

Price per night from

$515

City Cay

Key West apartment

1 bedroom / 1 bathroom / sleeps 2

Match: Clothes dryer

All filters match

Price per night from

$160

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms / 2 bathrooms / sleeps 7

Match: Clothes dryer

All filters match

Price per night from

$1,259

Poinciana House

Key West house

1 bedroom / 2 bathrooms / sleeps 4

“Awesome” The house was just as Historic Hideaways pictured and described...beautiful. The house was very clean, a pool service came twice a week to clean the pool and Tim, (agent) was very informative and helpful. Everything was supplied from towels to suntan lotion. There was nothing we needed to bring except our clothes & food. I would definitely stay here again.

Match: Clothes dryer

All filters match

Price per night from

$385

Shipyard

Key West apartment

2 bedrooms / 1 bathroom / sleeps 4

“Wish I could live here all year.” Check-in was very quick and Tim did an excellent job at explaining the area and providing us with useful information regarding restaurants and activities. I really felt that he did an above-and-beyond job at making sure we had a great vacation. The house was clean and anything that we needed (cleaning supplies, detergent, etc) as well as information regarding the house was available to us. The location was nice. Most everything was within walking distance or was a $5 cab ride. The only thing we found a bit annoying was that the community pool hours were not followed by the community staff. Often we found the pool locked during the middle of the day. Of course I understand that Historic Hideaways has no control over this as they simply own one of the lots on the site. After a long day of swimming, charters, and walking around town, we were always looking forward to relaxing at the house. My fiance and I really enjoyed our stay. We're already planning to return next year!

Match: Clothes dryer

All filters match

Price per night from

$185

Banana Key

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 5

“Key West in December.” We chose Banana Key just a few days before we actually got there due to a last minute vacation opportunity. I worked with Tim at Historic Hideways and couldn't have been happier with him and the staff in this office. He assured me that we would love it there and he was right. The home was beautiful, the bed was extremely comfortable and the kitchen well stocked with everything we needed for our time there. We were on a working vacation and found the living room to have plenty of electrical outlets which helped us in being able to accomplish our work efficiently and comfortably in order for us to get out and enjoy the sunshine. We had a couple of maintenance issues such as a hot water heater problem and a smoke detector activation, but when I called H.H they took care of those issues promptly. Last but not least, location location location!! You could not ask for better access to all of the great shops, bars and restaurants just a few blocks off of Duval. We had bicycle delivered to us and we rode bikes nearly every day. We would totally recommend this rental and were very pleased with the staff at Historic Hideways.

Match: Clothes dryer

All filters match

Price per night from

$310

Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families

Key West house

2 bedrooms / 2 bathrooms / sleeps 4

“Fabulous luxury home in Fabulous Key West” Beautiful, private, historic 2 BR/2 bath home, lovely heated pool, outdoor dining & living areas in addition to most attractive indoor spaces. Wonderful Old Town neighborhood. Can walk, cycle, & Lyft everywhere (including great restaurants)--no car needed. 2nd BR is in the guest house beyond the pool--fabulous outdoor shower completes the "only-in-Key West" ambiance. The owner, Kim, is super responsive.

Responds fast! avg. 2 hours 49 minutes

Match: Clothes dryer

All filters match

Price per night from

$557

** Totally Renovated Ocean View Condo Great Prices **

Key West apartment

2 bedrooms / 2 bathrooms / sleeps 6

Match: Clothes dryer

All filters match

Price per night from

$602

Royal Palm

Key West house

2 bedrooms / 3 bathrooms / sleeps 5

“Key west is always fun” 3 of us rented a condo in the foundry located in the Truman annex. I have stayed here before and knew what to expect. Any unit in Truman annex is an easy walk to everything there is to do downtown. Since it is a gated community a person feels very safe there. These units have fully equipped kitchens plus a washer & dryer. My first stay in the foundry was several years ago and these units are starting to show their age. The steps up to the porch had become unattached from the porch which made it a slight inconvenience. Also we flipped some light switches and nothing came on. Don't know if bulbs were burned out or if the switches didn't work. I reported all of this to the rental agency and hopefully these things have been taken care of. Would I go back to the foundry? You bet I would. Probably next year.

Match: Clothes dryer

All filters match

Price per night from

$270

Viewing 38 of 334
rentals in Key West

×

Also consider