Key West Vacation Rentals

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May 6 - May 7
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May 7 - May 8
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May 10 - May 12
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May 17 - May 19

Vacation Rentals in Key West

Poolside Cottage #411
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (14)
"This place was so quiet and comfortable and was the perfect stay for us in Key West. The hosts are top notch."
The price is $216
$369 total
includes taxes & fees
May 14 - May 15
Poolside Cottage #411
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Duval Square in Key West
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
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Luxury 62' Yacht! In a Beautiful Resort
Outdoor pool, a heated pool
Luxury 62' Yacht! In a Beautiful Resort
10.0 out of 10, Exceptional, (6)
"Everything was great and we would love to visit again!"
Luxury 62' Yacht! In a Beautiful Resort
52' Power Catamaran Yacht at Luxury Resort Marina
Outdoor dining
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
Sailboat Getaway in Key West
Property grounds
Sailboat Getaway in Key West
10.0 out of 10, Exceptional, (2)
"From the moment i boarded it was so peaceful. I love that you are so close to everything, yet you feel your on an island. The host was amazing. I will be staying longer next time. Thanks again for everything."
The price is $129
$260 total
includes taxes & fees
May 8 - May 9
Sailboat Getaway in Key West
Bahama Village studio @ the Galleria!
Pool
Bahama Village studio @ the Galleria!
10.0 out of 10, Exceptional, (4)
"It was a good place to stay and reasonably proced"
Bahama Village studio @ the Galleria!
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
Pool
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
10.0 out of 10, Exceptional, (145)
"Like the location right and beach access"
**FOLLOW THE SUN @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
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
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pool | Outdoor pool, a heated pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (257)
"This property and host exceeded all of our expectations. It was spacious, comfortable, and welcoming with its amazing kitchen, breezy rooms, and friendly neighbors. The hosts were a pleasure to work with and easy to reach whenever we wished to communicate with them. 10/10 would return to this property. I highly recommend it!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Pool
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
9.8 out of 10, Exceptional, (147)
"Host was an outstanding communicator. Check-in process was fully remote and seamless! Thank you, Victor Redd! (Also the Key Lime pie was a hit!). The property itself was great and has its own little private oasis with the pool and private beach. Our place didn’t have the ocean view, but we didn’t need to pay all the extra money per night for that because we spent our time at 1800 Atlantic either at the pool, at Smithers Beach right next door, or Sleeping! The rest of the time we spent enjoying...
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
A heated pool
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
9.8 out of 10, Exceptional, (102)
"Excellent top drawer"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
CLARO ~ Adults Only, Poolview 1 BR, 1 Ba Suite in Azul Mansion!
Beach nearby
CLARO ~ Adults Only, Poolview 1 BR, 1 Ba Suite in Azul Mansion!
9.8 out of 10, Exceptional, (107)
"Perfect place for us. We had a quick getaway to Key West. The room was super clean and exactly as described. Would stay again for sure!"
The price is $139
$298 total
includes taxes & fees
May 8 - May 9
CLARO ~ Adults Only, Poolview 1 BR, 1 Ba Suite in Azul Mansion!
Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8
A heated pool
Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8
9.8 out of 10, Exceptional, (102)
"The front office team were very nice and accommodating. The home is perfect for a small group and located in the center of town and perfectly walkable. We will definitely be back!"
Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8
Steps from Duval, Pool & Bikes $129-$299 Night!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (328)
"First off the communication with Ken was amazing. Always got back to me right away. The property was very clean and just what was needed. Location. Was amazing and having the bikes was awesome. We rode them all over. Would definitely rent here again."
The price is $99
$240 total
includes taxes & fees
May 20 - May 21
Steps from Duval, Pool & Bikes $129-$299 Night!
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.6 out of 10, Exceptional, (89)
"Condo was clean and orderly and as-advertised. Host was easy to deal with. Would've hoped for more paper products for the price we paid! Overall enjoyed our stay. Pool was lovely."
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
May 20-23 or 27-30 ngt. mid-wk..spec. beach kitchen & patio 142.ngt + ext
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
Tranquility by Smathers and 10 minute bike downtown Key West value savings
A heated pool
Tranquility by Smathers and 10 minute bike downtown Key West value savings
9.4 out of 10, Exceptional, (93)
"Nice accommodations. Very clean and comfortable and secure."
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (196)
"The inside was as advertised. Great location and the front porch was nice. The inside of the unit was clean."
The price is $55
$289 total
includes taxes & fees
May 13 - May 14
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
34’ Catamaran Sailboat
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (22)
"So glad we stayed here! It is exactly what I was looking for. A unique way to visit Key West. It was nice to open the hatches and have a nice breeze and great view of the stars. He has a nice bathroom with shower in the car port. The host was great with communication and was really cool. Definitely recommend"
34’ Catamaran Sailboat
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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.

Key West Vacation Rental Travel Info

Number of vacation rentals
195
Popular accommodation
Key West private vacation homes
Known landmarks
Smathers Beach, South Beach and Fort Zachary Taylor Historic State Park
International airport
Key West, FL (EYW-Key West Intl.)

Price trends for vacation rentals in Key West

Less expensive
More expensive
This month
Next month
September
February
$403
$388
Month
Price
January
$457
February
$565
March
$451
April
$379
May
$403
June
$388
July
$415
August
$346
September
$289
October
$393
November
$357
December
$456
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Key West. Select dates and complete search for nightly totals inclusive of taxes and fees.

Other types of properties in Key West you may be interested in

Oceans Edge Key West Resort, Hotel & Marina
View from property
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1533)
"On the marina made for beautiful views. "
The price is $230
$318 total
includes taxes & fees
Jun 6 - Jun 7
Oceans Edge Key West Resort, Hotel & Marina
Havana Cabana at Key West
Outdoor pool, sun loungers
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1450)
"Has hard water. Needs a water softener system for the property."
The price is $259
$356 total
includes taxes & fees
May 7 - May 8
Havana Cabana at Key West
Margaritaville Beach House Key West
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1752)
"This was an incredible stay. We checked the bed when we arrived and it was a little suspicious, but they had no problem switching to another room. They explained that they regularly had someone come in to check all the rooms/beds with a multi spectrum UV light… We loved that the location was a distance from the hubbub of downtown. They offer a free cocktail at check in, popsicles and smoothies by the pool daily, and cookies from 3pm. Bottles of water in the room too. There is a shuttle into...
The price is $229
$321 total
includes taxes & fees
Jun 4 - Jun 5
Margaritaville Beach House 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.

Everything you need to know about Key West vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Key West vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Key West vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Key West vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Key West. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Key West in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $55 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Key West rentals

At Expedia, we put the best Key West vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Key West rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Key West vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Key West. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Key West?

Yes, there are vacation rentals in Key West close to Mel Fisher Maritime Museum, or you can select a more secluded option if you want a relaxing stay. Travelers who like culture and the arts give Key West high marks for its great live music and entertainment choices. While you're in the area, you can also enjoy the scenic seaside and lively festivals.

What are some of the best vacation rentals in Key West?

Poolside Cottage #411: This Key West vacation home rental offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a selection of games and a spa tub. Some other homes for rent in Key West include Duval Square in Key West and Pilar`s Secret - An oasis right off Duval Street - Sleeps up to 8.

How many vacation rentals will I find in Key West?

With 1062 Expedia vacation rentals, you're sure to find just the right place for your Key West stay.

What can I see and do in Key West?

Mel Fisher Maritime Museum and Florida Keys Eco - Discovery Center are a couple of family-friendly sights, whereas cultural attractions include Ernest Hemingway Home and Museum and Key West Lighthouse and Keeper's Quarters Museum. Duval Street and Harry S. Truman Little White House are other places to visit while you're in town.

What are vacation rentals like in Key West?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Key West. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for family gatherings.

Recent reviews of Key West properties
Expedia verified reviews

Southernmost Beach Resort

Southernmost Beach Resort

5/5 Excellent
"Highly recommend! Close to Duval and has all the amenities. "
A verified traveler stayed at Southernmost Beach Resort
Posted 1 day ago
Southernmost Beach Resort