Key West Vacation Rentals

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Vacation Rentals in Key West

Hyatt Residence Club Key West, Sunset Harbor
3.5 out of 5
200 Sunset Lane, Key West, FL, 33040
The price is $329 per night from Jun 1 to Jun 2
Stay at this 3.5-star business-friendly condo in Key West. Enjoy free WiFi, onsite parking, and an in-room DVD player. Our guests praise the pool and the helpful ...
4.1/5 Very Good! (206 reviews)
"Super location. Very nice property. Only criticism we would have is no balcony in this studio unit."

Reviewed on Feb 28, 2022

Hyatt Residence Club Key West, Sunset Harbor
Carey's Corner #10 // Second Floor Small Studio at The Galleria
The price is $135 per night from May 30 to May 31
Stay at this apartment in Key West. Enjoy free WiFi, a patio, and a TV. Popular attractions Southernmost Point and Duval Street are located nearby. Discover ...
4.6/5 Wonderful! (7 reviews)
"Small and perfect place to rest and sleep during our stay in Key West."

Reviewed on Apr 25, 2022

Carey's Corner #10 // Second Floor Small Studio at The Galleria
Coconut Mallory Resort And Marina By Kees Vacations
3 out of 5
1445 S Roosevelt Blvd, Key West, FL, 33040
Stay at this 3-star condo in Key West. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the spacious rooms in our reviews. ...
4/5 Very Good! (700 reviews)
"Our apartment was great, Marina great, employs great!! Fantastic stay! A bit disappointed with hot tub, pools ok. Over all a great place!! Thank you!!"

Reviewed on May 12, 2022

Coconut Mallory Resort And Marina By Kees Vacations
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Happy’s Houseboat Key West
Stay at this houseboat in Key West. Enjoy a kitchen, 1 bedroom, and an oven. Popular attractions Smathers Beach and Duval Street are located nearby. Discover ...
4.7/5 Exceptional! (16 reviews)
Perfect relaxing getaway
"I can’t say enough about this great vacation experience! So relaxing under the stars but only 5 min to key West’. We loved watching the fish and even saw a dolphin swimming around the boat in the morning while we watched the Sunrise! We are repeat guests, just can’t say enough about this great vacation ..."

Reviewed on Apr 18, 2022

Happy’s Houseboat Key West
ATLANTIC PARADISE Condo at 1800 Atlantic, shared pool, gated community
Stay at this condo in Key West. Enjoy free WiFi, a spa tub, and a fitness center. Our guests praise the pool in our reviews. Popular attractions Smathers Beach ...
4.7/5 Exceptional! (53 reviews)
Unit 108
"The condo was nice and clean. The pool area was great. The condo needed to be updated. It felt old. The biggest disappointment was not being able use the nice looking outdoor balcony. The bugs would absolutely eat you alive. Overall we had a good experience."

Reviewed on Apr 19, 2022

ATLANTIC PARADISE Condo at 1800 Atlantic, shared pool, gated community
The Hollinsed House
3 out of 5
609 Southard Street, Key West, FL, 33040
Stay at this 3-star apartment in Key West. Enjoy free WiFi, a free beach shuttle, and billiards or a pool table. Popular attractions Duval Street and Mallory ...
4.5/5 Wonderful! (32 reviews)
"Great location. Very nice property"

Reviewed on Jan 8, 2022

The Hollinsed House
Sunset Key Cottages
3.5 out of 5
245 Front Street, Key West, FL, 33040
Stay at this 3.5-star beach aparthotel in Key West. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the pool and the helpful staff in ...
4.5/5 Wonderful! (57 reviews)
"Lovely place will come back next year! Everything and everyone excelente"

Reviewed on Jul 10, 2021

Sunset Key Cottages
Mesa House Dos // Updated 2BR Home In Perfect Location
The price is $359 per night from Jun 6 to Jun 7
Stay at this apartment in Key West. Enjoy free WiFi, a porch, and a patio. Popular attractions Mallory Square and Duval Street are located nearby. Discover genuine ...
4.8/5 Exceptional! (10 reviews)
The location was excellent! Just a couple block to everything. The neighborhood was very safe,
"The property was nice, close walking to everything. Safe neighborhood. Only downside is that the property is right next door to a city parking lot and it was a bit noisy in the morning. Overall, I would recommend this property."

Reviewed on Jan 3, 2022

Mesa House Dos // Updated 2BR Home In Perfect Location
VRBO SPECIAL OFFER! 48' Sailing Yacht & nightly 2 hour Sunset Sails included!
Stay at this houseboat in Key West. Enjoy a fitness center, onsite parking, and barbecue grills. Popular attractions Smathers Beach and Duval Street are located ...
VRBO SPECIAL OFFER! 48' Sailing Yacht & nightly 2 hour Sunset Sails included!
Galleon Resort Waterfront Luxury in Old Town Key West
Stay at this condo in Key West. Enjoy free WiFi, an outdoor pool, and private spa tubs. Our guests praise the WiFi in our reviews. Popular attractions Mallory ...
4.8/5 Exceptional! (56 reviews)
Spring Vacation
"Unbelievable! This place was perfect.. the amenities, the location, the room and that rooftop deck! Everything was just as advertised. Our host Ed, answered any questions we had and was very easy to work with. Great time! Can't wait for our next Key West trip!"

Reviewed on Apr 28, 2022

Galleon Resort Waterfront Luxury in Old Town Key West
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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.

Price trends for vacation rentals in Key West

Less expensive
More expensive
Next month
September
November
$512
Month
Price
January
$492
February
$539
March
$532
April
$428
May
$436
June
$512
July
$520
August
$450
September
$340
October
$501
November
$557
December
$544
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard, Key West, FL, 33040
Fully refundableReserve now, pay when you stay
The price is $299 per night from Jun 2 to Jun 3
Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd, Key West, FL, 33040
Fully refundableReserve now, pay when you stay
The price is $199 per night from May 26 to May 27
Havana Cabana at 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.

Unlock your dream Key West Vacation Rental

Live like a Conch (local) with a Key West vacation rental getaway

Head to a place of pastel houses and thick palm trees swaying in the salty air and put your bags down in your very own Key West vacation rental. Stroll down Duvall Street after a slice of Key Lime pie, find your new favorite rum bar, then join the flocks lining up to watch the sunset in Mallory Square. You can get busy doing nothing or take it easy doing plenty, before unwinding at your own slice of paradise—whether it’s a modern motel with ocean views, a cute townhouse in historic Old Town Key West, or a private vacation home hideaway on the waterfront.

Prices start at just $135 and go up to $359 a night for deluxe Key West vacation rentals—so there’s a property for every budget. Remember prices and availability are subject to change, and additional terms may apply.

Uncover your perfect vacation rental in Key West Florida

Our filters and map make it easy to narrow your Key West vacation rental search by price, location, and amenities. If you’re bringing along your four-legged pal, use the pet-friendly filter to find a getaway that welcomes your furry buddy. Check out this dog-friendly 2-bedroom condo with a west-facing private deck for snuggles at sunset. If you crave a cool dip after a day exploring, the pool filter shows you all the vacation rentals with pools. This studio apartment in Old Town Key West has a heated pool and includes bikes for getting around like a Conch. If the idea of waking up to the sound of lapping waves is pure heaven, use our map to find places to stay on the waterfront. This 3 bedroom, 4 bathroom waterfront vacation home comes with its own private dock so you can rent a boat and explore the local islands, too.

How to find Key West vacation rental deals

For some terrific vacation rental deals in Key West, enter your travel dates and hit search to discover some of the best vacation rentals in Key West, FL. You can then filter by price, rating, or location to find your ideal vacation spot. If you have flexible travel dates, try adjusting those to see different prices, or book your stay during , when it’s usually easier to find great cheap Key West vacation rentals compared to when bookings are popular, and prices can be higher.

Why choose a vacation rental in Key West FL with Expedia?

At Expedia, you can easily compare top vacation rentals in Key West all in one place, then simply click to book the best one for you. We’ve locked in low prices on a vast number of properties, many with buy now, pay later options. You also save money when you bundle your flight and rental car bookings. If you book a vacation rental in Key West with free cancellation, you can rest easy knowing if your plans change you won’t be out of pocket. So, let Expedia help you get away to your dream vacation rental in the USA’s southernmost city and feel a world away.

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