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Vacation rental houses in Key West

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Top-rated houses in Key West

Guests agree: these stays are highly rated for location, cleanliness, and more.

Old Town - Room Opens to Pool and Garden
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Old Town - Room Opens to Pool and GardenLocated in the heart of Old Town, we are three blocks from Duval Street, a 10-minute walk to Higgs Beach, and around the corner from the best, least-expensive meal in town--El Siboney Cuban Restaurant. We suggest bicycling around Key West. Rentals from We-Cycle Bike Shop can be delivered to our door. Two blocks away, The Duval Loop offers free air-conditioned bus service 7 a.m. until midnight. We also offer a link with recommendations for excursions, tours, & restaurants.

Waterfront Gem! With Boating access!
SUPERHOST
Entire residential home · 4 guests · 2 beds · 2 baths

Waterfront Gem! With Boating access!7 day rental now available! Enjoy new comfortable waterfront living in a 2 bedroom, 2 bath open floor plan home. Central A/c, full kitchen with microwave, coffee maker, washer/dryer, dinning table sits (6), lots of closet space, master bedroom with private bathroom with walk-in shower. The Waterfront home has a large dock with BBQ Grill, outdoor seating. Spend the day and evening fishing from your dock or enjoy kayaking or paddle boarding activities from your private backyard.

A Little Place in Key West
SUPERHOST
Private room · 1 guest · 1 bed · 1 private bath

A Little Place in Key WestJust one bedroom for a single traveler with a private entry and private bathroom. Luxury finishings, linens, claw foot tub; cable internet, easy parking out-front. Walking distance to beach, cafes and Duval Street life. Max 1 person no exceptions. Cozy private and comfortable.

Vacation rentals for every style

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Popular house amenities in Key West

  • Pool
  • Air conditioning
  • Kitchen
  • Wifi
  • Pets allowed

Apartments in Key West

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Dog-friendly studio in historic building w/ shared pool - beach nearby!
$264 per night
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Duval Retreat- Contemporary Duval Street Condo
$457 per night
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Key West - Sunrise ❀ The Green House
$192 per night
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Duval Balcony - Street Suite
$190 per night
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Key West Suites #202
$281 per night
SUPERHOST
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Bella Vita - 1B/1B Condo Just Steps from Duval
$250 per night
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Duval Balcony Spanky's Retreat
$193 per night
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Luxurious upstairs apartment with pool #3
$150 per night
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Mile Zero Suite
$202 per night
SUPERHOST
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Key west in town studio with free bikes
$154 per night
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The Green House ❀ Garden
$192 per night
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Key West Suites #201
$281 per night

Pet-friendly houses

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Mango Tree Cottage
$99 per night
SUPERHOST
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WYLAND PENTHOUSE- Luxury 2BDR Penthouse in prime Downtown location
$450 per night
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Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!
$561 per night
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Vacasa | Family and dog-friendly island condo w/ full kitchen and a great location!
$849 per night
SUPERHOST
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Family House, 2 K BR's, Private Spa/Deck, 2 pools.
$598 per night
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Peaceful home w/ yard, hot tub, off street-parking
$175 per night
SUPERHOST
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Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
$468 per night
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Clean and Bright Key West Inspired Home/ Oct 8
$179 per night
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Vacasa | Charming house w/ private patio - great central location, dogs OK
$478 per night
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Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok
$1,108 per night
SUPERHOST
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Casa Cristol - Family Friendly Classic KW Charm
$556 per night
SUPERHOST
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**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
$490 per night

Houses with pools

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Key West, Home, Pool and Electric Car!
$131 per night
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Vacasa | Renovated home w/ shared pool & furnished patio - near Duval Street, dogs ok
$399 per night
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Coral Hammock Poolside House
$395 per night
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Royal Poinciana Cottage-
$217 per night
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Vacasa | Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok
$301 per night
SUPERHOST
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LOOK!! Bargain reduced Sept. private pool, wifi.
$495 per night
SUPERHOST
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Spacious Waterfront Condo, 2/2 Pool, Dock, Pet OK
$400 per night
SUPERHOST
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Historic Key West - Turtle House - Sleeps 6
$799 per night
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Papa's Hideaway - Garden of Eden
$567 per night
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Elegant home w/ patio & shared pool - walk to beaches, Duval St., and much more!
$666 per night
SUPERHOST
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McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
$468 per night
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Restored historic home w/ private pool & reserved off-street parking - Dogs OK!
$1,178 per night

Top-rated things to do in Key West

Unique activities hosted by local experts vetted for quality

  • Reef Snorkel & Sunset Sail
    We will snorkel the reef and enjoy the sunset while sailing on a spacious and fun sailing catamaran. You will also get to enjoy fresh organic fruit, veggies and hummus from our favorite local organic cafe, Date and Thyme. Florida’s Barrier Reef is right off the coast of Key West. We only provide this trip during a limited time, June through September, because we want to snorkel the reef when the weather is just right. Explore the wondrous wildlife of the reef with one of our biologists. It truly is one of the most beautiful places you need to see while in the keys. Sailing, the original form of renewable energy transportation! I am on a mission to spread the value of conservation and I think amazing nature experiences with a knowledgeable biologist is the best way to do that! But sometimes all you need to do to appreciate nature is go sailing and watch a sunset! Other things to note Meet at the boat 15 minutes before departure. Call or text my wife Jen with any questions. 305-294-6306.
    From Price:$99 / person
  • Biologist Guided Dolphin Watch & Snorkel
    You will meet me at my electric catamaran, Squid, under our HONEST ECO sign. If you do not see a time or date that works for you let me know! I can probably figure something out. We will depart from the dock located at the Historic Seaport. We will then head out on the water to an area that I know which provides a year round home for about 200 wild Bottlenose Dolphins. This is my moment to share the wonders of these marine mammals with you, while always operating my vessel in a manner that is safe and respectful of the dolphins and their need for space. With the right know-how I can usually find dolphins in under an hour and in calm waters. After observing the dolphins many different behaviors from the boat we will head to one of my favorite spots to snorkel with sponges, coral heads or a patch reef. I will take you to the best place with the best visibility that day. I'll be your guide, leading you around a calm snorkeling spot and point out animals that make our ecosystem unique and answer any questions that you have. Other things to note Check in at the HONEST ECO boat Squid. The maximum number of guests I have on board is usually around 15 guests. I can take up to 24 guests on a private charter.
    From Price:$109 / person
  • Ultimate Party Boat Cruise In Key West
    If you’re looking for the ultimate way to enjoy Key West, you’re in the right place. This is the party boat everyone is talking about! Head to the water with your friends on one of our pedal-powered party boats. We launch from Garrison Bight Marina, located in Key West. From there we will check you in and head out to the ocean for a 2.5 hour party cruise. While on the water, pop open your favorite included beverages, take in the fresh ocean views, and enjoy the party! We adjust the resistance to make pedaling as easy as you want, and we have a gas engine that we can turn on at any time. Pedaling is optional! We include everything but the drinks (bring your own beer, wine, hard seltzer, and liquor!), we will supply the coolers, ice, music, party lights and a bathroom on board! During the cruise, you are welcome to pedal, hang out with your friends, chill on the bench seats and just have a plain old good time! Be sure to select our sunset cruise to get one of the best views of the sunset in Key West. This is guaranteed to be a party to remember. We look forward to meeting you and having you aboard! Other things to note Get ready for a great time! If you have questions just let us know!
    From Price:$45 / person
  • Mangrove Maze Tour
    Welcome to Blue Moon Kayak Key West! Once you are checked in each person will get instruction on how to kayak and we will go over the layout of our route for the experience. Once we are ready we will launch from Floating docks. Our Kayaks are very stable with nice back rests to support you through out the trip. We cross Cow Key Channel and go West into the Center of Key West where we will show you how to navigate the Mangrove Mazes into the Salt ponds. All the while you will get to see Iguanas, Parrot Fish, Barracuda, Small Sharks, Night Crown Herons, Great Blue Herons, White Herons, Green Herons and more! Learn about the history and culture of Key West while we take in all the nature. We will end at our starting location. Other things to note: If there are high winds or Lightning the trip may be delayed or rescheduled. Your guide will determine safety for the trip. We will still go if there is just rain. We also provide alternate routes along the North side of Stock Island if necessary to avoid the elements.
    From Price:$75 / person
  • Bar Hop like a Local - Off Duval Street
    We'll veer vacationing drinkers off the infamous Duval Street into some of the city’s best, most locally loved bars to sample fresh spins on old classics. Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era, each of it’s 5 stops revealing a new secret. This bar hop is is about getting off touristy Duval Street and into local watering holes! What To Expect: -5 stops with preselected drinks featuring: a craft draft cocktail, a Hemingway Daiquiri, a locally made beer, a tiki drink, and a signature margarita. -Tantalizing food tastings and historical tidbits to accompany your cocktails. -Relax as an expert local guide takes you on an escape through the hustle and bustle of Key West’s Old Town. -The ultimate 3 hr happy hour experience in Key West. -Complimentary Food Tour booklet packed with coupons and recommended eateries included! Other things to note -Drinks are preselected. No substitutions. Any drink options not included must be purchased. -No dietary preferences or restrictions can be accommodated. -Operates rain or shine! Ponchos provided. COVID Safety Precautions: Guaranteed groups of 10 or less. We will wear masks according to local mandates. Spreading out: We will help you stretch out & most of our tour is outdoors, but we may be required to sit indoors
    From Price:$81 / person

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