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Key West Vacation Rentals

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265 rentals in Key West.
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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LOTUS BLOSSOM - Updated 3 BR Home With Tropical Courtyard & Hot Tub, Convenient

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Ocean Breezes, Morning Sunrises, Excellent nightly rental condo on the ocean.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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ATLANTIC PARADISE Condo 1800 Atlantic, shared pool, jacuzi, BBQ, family fun!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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KEY WEST CASA Large Condo, Truman Annex, Shared Pool, Downtown Key West

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Clean Apartment in Old Town Key West (Best Downtown Locations)

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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AMELIA HOME Spacious Private Home with Private Pool, BBQ Grill + Pet Friendly

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Casa Cay West ~ Beautiful Tropical House - 2 King Beds! Sleeps 8

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Artist Cottage in Truman Annex

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Casa Del Sol, a Key West Vacation (Truman Annex)

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Attitude Key West (2 Bikes and Wireless Internet)

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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'Oceanside Oasis' * Kings Pointe: Direct Ocean Views & 3 BR'S

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secret Villa I * Old Town with Private Pool, close to Duval!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Harbour Place 115 in Truman Annex Key West

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Seaside Place Key West FL 5 Bedroom House 4 Baths

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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My Condo by the Beach with Ocean View

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Mermaids House, Historic Old Town Key West

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Top Floor Ocean Views from every window Olympic Size Pool-Jacuzzi- Sauna-Tennis

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tom's 2000sf Direct Oceanfront Penthouse. Renovated, Heated Pool, Close To Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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William Skelton House - Available Easter Weekend!

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Catherine House: A charming Old Town Key West cottage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Attitude Key West at the Beach, 2 Bikes and Internet, Pool, Whirl Pool, Sauna

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sea Breeze Cottage- in Beautiful Truman Annex

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Boli Townhouse - Luxury Rental in gated Truman Annex

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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NEWLY RENOVATED ...LAST MINUTE SPECIALS...CHECK DATES

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Villa Paradiso: A unique mid-town paradise

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Henry's Piece Of Paradise On The Ocean In Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Enjoy More Privacy in a Truman Annex End Unit Townhome

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Beach House with Ocean View-No Contact Check-In

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Apple of Your Eye in Paradise (Truman Annex)!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Truman Annex Best Location in Town

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Ann Street Cottage: A bright and airy home near Duval Street

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Tropical Key West Get Away

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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BEST DEAL IN THE KEYS!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Key West





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.
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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.