Search Vacation Homes in Key West

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Compare 645 Vacation Homes in Key West with updated reviews, rates, and availability.

Pool
Duval Square in Key West
10.0 out of 10, Exceptional, (12)
"Great location and nice accommodations. Very enjoyable trip. Located right by Duvall Loop free trolly so no reason to pay for the old Town Trolly. Only negative is I don’t like having to wash dishes and put away, having to strip beds and do their laundry. This is my vacation so I could do these things at home. Manager helped 2 old people with our luggage because we thought the elevator was out of order. He even took it up the stairs to our bedroom. So nice and helpful!"
Duval Square in Key West
Fridge, microwave, oven, stovetop
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
10.0 out of 10, Exceptional, (1)
"We had a great time at Pagitt House. The location is central to everything you’d want to do in Key West. The rooms are comfortable and well appointed. We didn’t use the kitchen much but it was well stocked with whatever you might need."
PAGITT HOUSE - 3/ 2 - OLD TOWN KEY WEST WITH POOL
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
Poolside Cottage #411
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Pool
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
10.0 out of 10, Exceptional, (72)
"This home was wonderful! House had all we needed and was very comfortable. Fully gated yard which was perfect for our dog. It was in such a quiet and peaceful part of town that we sat on the deck and enjoyed the small pool every day. We walked into town each day and we explored all of Old Town from the North end (great marina, restaurants and view) to the South end (great views, restaurants and shopping). Would absolutely recommend this home and would we definitely would rent here next time!"
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Pool
Great Family Vacation Rental.
10.0 out of 10, Exceptional, (3)
"The townhome was nice and is located in a quaint community. The pool area was beautiful. We found that we needed to Uber into Key West since parking is very limited and we were told the bus service is often not on time."
Great Family Vacation Rental.
Property grounds
Duval Street Suite in Key West
10.0 out of 10, Exceptional, (17)
"The house was spectacular!! The stairs were tough but when the hard work was done we had a great stay!!! Dave, Liz, Jeff and wendy"
Duval Street Suite in Key West
A heated pool
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
10.0 out of 10, Exceptional, (159)
"The property was perfect. We had everything we needed and the location is great. Would definitely stay there again."
Boli Townhouse - Luxury Rental in gated Truman Annex - Saturday to Saturday only
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (6)
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
Poolside Cottage #412
Fridge, microwave, oven, stovetop
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
10.0 out of 10, Exceptional, (31)
"We had an amazing time! The house is within walking distance of everything! Really cool layout, and we all had our own bedroom and bath. The pool is great as well!"
**QUEEN OF LOUISA @ DUVAL** Home in Old Town & Private Pool + LAST KEY SERVICES
A heated pool
**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…
10.0 out of 10, Exceptional, (1)
"The house is beautiful! Great set up and so well equipped and stocked! Highly recommend."
**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…
A heated pool
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
10.0 out of 10, Exceptional, (120)
"We enjoyed our stay at casa Victoria. Plenty of space for 7 adults. Unique and beautifully decorated. Close to downtown."
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
A heated pool
American Shoal Suite | 2 Bed, 1 Bath
10.0 out of 10, Exceptional, (2)
"Clean, decently appointed, attractive decor. Great host! Met our needs."
American Shoal Suite | 2 Bed, 1 Bath
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (189)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Beach
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
9.8 out of 10, Exceptional, (73)
"It was easy to slip into island time with this great location. Place was immaculate, PM Charity, was present shortly after we arrived to be sure we had everything and answer any questions. We quickly made our way to the lovely pool for a swim. We walked on the dock and ducked into Gumbo's right on the water on property. The bar tender was welcoming and encouraged my teens to play a round of pool.It was truly a flawless stay."
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Marina Villa + LAST KEY SERVICES…
Fridge, microwave, oven, stovetop
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
9.8 out of 10, Exceptional, (72)
"The whole process for a newbie was absolutely easy. The property was 5 star. The experience was perfect. Had two issues both were taken care of immediately. Will use again."
Nautical Wheeler: Waterfront Home with private Pool & lush landscaping
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (90)
"House was exactly as stated. We enjoyed it there. Close enough to downtown to enjoy it. Nice touch having the bikes there to use! Condo pool was great too. We enjoyed the amenities! Would stay again if we came back to the area!"
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Property grounds
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
9.6 out of 10, Exceptional, (46)
"This was a beautiful house in a great location. Very large, easily fit everyone comfortably. Awesome."
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
A heated pool
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
9.6 out of 10, Exceptional, (64)
"Enjoyed our stay…..Dan was very helpful with the smart tv issue…."
OFF CALL ~ Rustic, Nautical Decor With King Primary Suite & Heated Pool!
Interior
May 20-23 or 27-30 ngt. mid-wk..spec. beach kitchen & patio 142.ngt + ext
9.6 out of 10, Exceptional, (185)
"This was our third time staying at this location. It is as described and the location is fantastic."
May 20-23 or 27-30 ngt. mid-wk..spec. beach kitchen & patio 142.ngt + ext
Property grounds
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
9.4 out of 10, Exceptional, (44)
"Wonderful place. We rented 7 bikes and were able to store them in the garage and ride wherever we needed to go. Didn’t need to go much since the place was so great, between the pool and the spacious open kitchen and decks we were able to cook and make cocktails."
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
Don't see what you're looking for?
See all available properties in Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Key West

Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
Poolside Cottage #411
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is $99
$240 total
includes taxes & fees
20 May - 21 May
Steps from Duval, Pool & Bikes $129-$299 Night!
Outdoor pool
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very Good, (227)
"Perfect location - not to far of a walk from Duval Street and the action but tucked away just enough to be able to have some peace!"
The price is $273
$329 total
includes taxes & fees
29 May - 30 May
Hyatt Vacation Club at Sunset Harbor, Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Key West Vacation Homes information

Number of reviews
943
Accommodation
645 Vacation Homes
Lowest Price
Highest Price

Recent reviews of Key West hotels
Expedia 亿客行 verified reviews

Southernmost Beach Resort

Southernmost Beach Resort

5/5 Excellent
Best place to stay in Key West!!
"AMAZING time! We were greeted by Justin who offered a complimentary upgrade to a room in the Avalon House that came with daily breakfast and afternoon snacks at the Dewey House on the property. Thank you, Justin! Each morning at breakfast , Ophelia greeted us warmly and the woman making omelets always greeted us with a smile. We went in 3 of the 4 pools - all were great. The Pineapple pool had a DJ or other music. The Shores pool had music or a live guitar player. Both had full bar service with friendly staff. The beach right next to the Shores pool was never crowded with plenty of lounge chairs. Our room was beautiful and housekeeping was great. I’m usually one that winces at seeing resort fees, but the service and hospitality made it well worth it. Walking around Key West and seeing other options, we felt like we had the best location with the best amenities. We didn’t want to leave!"
A verified traveler stayed at Southernmost Beach Resort
Posted 8 hours ago
Southernmost Beach Resort