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Key West

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Vacation Rentals in Key West, Florida Keys

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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.

 
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$1,100 - $1,950 / week
2 Bedrooms, sleeps 4
1 Bathroom
$210 - $285 / night
2 Bedrooms, sleeps 8
2 Bathrooms
$2,800 / week
2 Bedrooms, sleeps 4
2 Bathrooms
$2,900 - $7,500 / week
3 Bedrooms, sleeps 6
3 Bathrooms
$225 - $495 / night
2 Bedrooms, sleeps 6
2 Bathrooms

Traveler Rating | Price / nt | Price / wk | Bedrooms | # of photos | # of reviews
Florida, Florida Keys, Key West Vacation Rentals
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$325 - $400
Week:
$1,850 - $2,550
Minimum rental - 3 nights
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Week:
$1,250 - $1,750
Month:
$5,357 - $6,429
Minimum rental - 1 week
Check availability
  • Condo/Apartment
  • 3 Bedrooms, sleeps 10
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$350 - $400
Week:
$2,450 - $3,150
Month:
$10,500 - $12,000
Minimum rental - 1 night
Check availability
Also consider
$1,100 - $1,950 / week
2 Bedrooms, sleeps 4
1 Bathroom
$210 - $285 / night
2 Bedrooms, sleeps 8
2 Bathrooms
$2,800 / week
2 Bedrooms, sleeps 4
2 Bathrooms
$2,900 - $7,500 / week
3 Bedrooms, sleeps 6
3 Bathrooms
$225 - $495 / night
2 Bedrooms, sleeps 6
2 Bathrooms
Florida, Florida Keys, Key West Vacation Rentals
  • Rental Home
  • 3 Bedrooms, sleeps 8
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$300 - $425
Week:
$1,600 - $2,500
Minimum rental - 3 nights
Check availability
Map unavailable
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$200 - $290
Week:
$1,330 - $1,960
Minimum rental - 6 nights
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$250 - $471
Week:
$1,500 - $2,755
Minimum rental - 5 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Month:
$5,000
Minimum rental - 4 weeks, 2 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$250 - $471
Week:
$1,500 - $2,755
Minimum rental - 5 nights
Check availability
  • Condo/Apartment
  • 2 Bedrooms, sleeps 8
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$250 - $300
Week:
$1,750 - $2,450
Month:
$7,500 - $9,000
Minimum rental - 1 night
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Rental Home
  • 2 Bedrooms, sleeps 4
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$350 - $500
Minimum rental - 4 nights
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 6
  • 3 Bathrooms
  • Professional
EMAIL MANAGER
Week:
$1,600 - $3,190
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Condo/Apartment
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$225 - $400
Minimum rental - 1 week
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Condo/Apartment
  • 3 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Night:
$310 - $823
Week:
$2,030 - $3,959
Minimum rental - 3 nights
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Rental Home
  • 2 Bedrooms, sleeps 4
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Month:
$6,500
Minimum rental - 8 weeks, 4 nights
Check availability
Florida, Florida Keys, Key West Vacation Rentals
  • Condo/Apartment
  • 1 Bedroom, sleeps 4
  • 1 Bathroom
  • Professional
EMAIL MANAGER
Night:
$170 - $348
Week:
$900 - $2,030
Minimum rental - 3 nights
Check availability
Map unavailable
  • Rental Home
  • 2 Bedrooms, sleeps 6
  • 2 Bathrooms
  • Professional
EMAIL MANAGER
Special offer details »
Month:
$3,750 - $7,000
Minimum rental - 4 weeks, 2 nights
Check availability

Key West Vacation Rental Advice

Posted by 3and8fan, May 21, 2011
... gets priority. Facility Name MWR Vacation Rentals at ... ... West's Trumbo Point MWR Vacation Rentals The MWR townhouses have been completely renovated and are open for rentals. MWR mobile homes, 2 bedroom/1 bath, are available and can house up to four people. The mobile homes are fully furnished with ... more
Posted by Orion_240, Jan 12, 2012
I just saw this in today's e-mail, under "Top Vacation Rentals": Valhalla http://www.tripadvisor.com/VacationRentalReview-g34345-d1282993-Valhalla-Key_West_Florida_Keys_Florida.html ... more
Posted by flattop, Mar 16, 2011
... islands: Increasingly, those who book vacation rentals listed ... ... Realty who specializes in the vacation-rental-heavy Truman Annex neighborhood of Key West, said he started to notice problems in October. Since then, he said, things have gotten significantly worse. "It started off with maybe one a month," Smith said, "and ... more
Posted by CaptBonez, Oct 3, 2011
... It would be great if the city had available on-line a list of licensed vacation rentals. It would be a fast and easy way to see if a property was at least legal to rent. (as I suspect most advertised on Craig's list and other places are not ... more
Posted by Tim T, Dec 9, 2011
... in response to Craigs list vacation rental listing these were very sketchy. The website bounces back and forth from making it appear they have one property to multiple properties. Many of the wording on their website is not in proper English and their contract on there quite frankly looks like ... more
Posted by Gypsabelle, Jan 11, 2012
... and Cindy's Key West Vacation Rentals (rentmyparadise.com). We stayed in one of their Fleming Street town homes with my two kids (7&8) this past summer. They feel very private, are an easy 3 minute walk to the comminuty pool (although it was a little tricky to find ... more
Posted by dmilbury, Dec 21, 2011
... very good job of screening vacation rentals, unlike Craigslist where there is no screening. I took a look, and almost all the units for bid or buy now on E-Bay in Key West were time shares, which is usually the case on ebay. That is the reason for the ... more
Posted by LynnDetroit, Dec 14, 2011
... for the information. I had already tried KW Vacation Rentals, but they have a 5-night minimum, and we're only planning to stay 3 nights in KW. I will look into the options you mention, SDT as we will first be in Miami and will have a car. Thanks ... more
Posted by Sirabi, Nov 20, 2011
... For our 25th anniversary dinner at Cafe Marquesa, we arrived to find the table strewn with ribbons and sparkles! Key West Vacation Rentals made our reservation for the Yankee Freedom this year, using the CC we had our cottage rented with. When we checked out, they asked about our experience ... more
Posted by bluewater, Nov 8, 2011
It's the busiest week of the year in South FL. Look at the rental/real estate companines for vacation rentals. lastkeyrealty.com has several. ... more
Featured Events
Each year thousands descend on Key West for the annual Lobster Fest with live music and delicious lobster!
21-Oct - 30-Oct
FantasyFest 2011
Only an event that rivals Mardi Gras in New Orleans could boast this many themed parties, elaborate costumes, contests, vendors and more. Culminating in a wild parade, this week-long Halloween event attracts thousands of visitors each year and provides an opportunity for tourists and locals alike to show off their creativity.
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