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Key West Vacation Rentals

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157 rentals in Key West.
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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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Penthouse
#1 of 2 pools with waterfall
Penthouse
Living room
Penthouse
Porch off master bedroom overlooking Duval Street
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 16
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Ocean View Estate with Private Pool 15 minutes from Key West
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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Patio View
La Brisa Pool
Sunrise from our patio
Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Summer 2022 gaps Enchanting garden view on the Ocean- Fantastic Value
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Artist Cottage in Truman Annex
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Casa Del Sol, a Key West Vacation (Truman Annex)
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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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
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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
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My Condo by the Beach with Ocean View
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Attitude Key West (2 Bikes and Wireless Internet)
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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William Skelton House - Available Easter Weekend!
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 14
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Seaside Place Key West FL 5 Bedroom House 4 Baths
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Boli Townhouse - Luxury Rental in gated Truman Annex
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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
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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
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Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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The Mermaids House, Historic Old Town Key West
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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
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Duval Square Penthouse: A large, beautiful condo steps from the action
Condo/Apartment
4 bedrooms
5 bathrooms
Sleeps 10
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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Azure Morning- Oceanfront, near Marina, Pool & Jacuzzi
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Rose Lane Villas - Villa Vista - 2 bedrooms - Downtown Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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Harbour Place 115 in Truman Annex Key West
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Villa Paradiso: A unique mid-town paradise
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Conch Retreat in Beautiful Truman Annex with 2 Bikes
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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~$~1,500/wk - Best Deal in Key West - Plus 7 Bikes Included!
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Lazy River Pool, Enchanting Garden, Old Town Key West, Free WiFi, Bikes & Parkin
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Rose Lane Villas - Villa Grande - 3 bedrooms - Downtown Key West
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Beach House with Ocean View-No Contact Check-In
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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BARGAIN RATES! Pool, wifi, renovated 2/2 1/2 private courtyard.
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Henry's Piece Of Paradise On The Ocean In Key West
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Duval Square Retreat: A beautiful condo steps from the action
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
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Harbor Walk Hideaways
Private Room
4 bedrooms
3 bathrooms
Sleeps 8
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2022 IS THE FINAL YEAR. Giving it to a vacation rental company for 2023.
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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The Tree House Old Town 2 Bedroom MONTHLY Rental
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
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Colony Poolside: A charming bungalow near the historic cemetery
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
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Rent a Piece of Paradise!
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Simonton Studio, an Old Town get-away for 2
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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Sunrise at Seaside Condo 2 Bedroom
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Truman Annex Best Location in Town
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Enjoy gentle ocean breezes and gorgeous views at Sea Orchid (La Brisa #405E)
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
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Pete's East Cottage: Cypress east cottage steps from Duval
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Craig & Cindy Key West Truman Annex 212 Fleming House
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Truman Annex, two blocks from Duval
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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"TIDES ON SIMONTON" ~ Perfectly located just off Duval and all the fun!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
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Somewhere on the beach: 2 BR, 2 BA Condominium in Key West, Sleeps 6
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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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.
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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.