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Key West Holiday Vacation with Pools

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215 rentals in Key West.
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Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage
2 bedrooms
2 bathrooms
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Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
2 bedrooms
2 bathrooms
Sleeps 6
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6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
6 bedrooms
7 bathrooms
Sleeps 16
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Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE
2 bedrooms
3 bathrooms
Sleeps 6
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Artist Cottage in Truman Annex
2 bedrooms
1 bathroom
Sleeps 4
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Secret Villa I * Old Town with Private Pool, close to Duval!
3 bedrooms
3 bathrooms
Sleeps 6
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'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool
3 bedrooms
2 bathrooms
Sleeps 8
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LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!! SLEEPS 2-4, 3 BLKS TO BEACH
1 bedroom
1 bathroom
Sleeps 4
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Sunrise At Seaside Condo 2 bedroom 2 bath
2 bedrooms
2 bathrooms
Sleeps 5
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'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval
3 bedrooms
3 bathrooms
Sleeps 8
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Island Hideaway
2 bedrooms
2 bathrooms
Sleeps 6
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Sunrise at Seaside Condo 2 Bedroom
2 bedrooms
2 bathrooms
Sleeps 5
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BEST DEAL IN THE KEYS!
2 bedrooms
1 bathroom
Sleeps 6
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CONCH ADVENTURE Cozy, Relaxing Patio, Walk to Duval Street, Shared Pool
2 bedrooms
1 bathroom
Sleeps 4
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Casa Del Sol, a Key West Vacation (Truman Annex)
2 bedrooms
3 bathrooms
Sleeps 6
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Henry's Piece Of Paradise On The Ocean In Key West
2 bedrooms
2 bathrooms
Sleeps 5
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TRANQUILITY - Quaint Cottage in Gated Compound with Shared Pool + Private BBQ
1 bedroom
1 bathroom
Sleeps 4
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Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -
2 bedrooms
3 bathrooms
Sleeps 4
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Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
1 bedroom
1 bathroom
Sleeps 2
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Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
2 bedrooms
1 bathroom
Sleeps 4
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Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio
3 bedrooms
3 bathrooms
Sleeps 6
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Conch Get Enough! - Key West's Old Town Truman Annex
2 bedrooms
3 bathrooms
Sleeps 4
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Seaside Place Key West FL 5 Bedroom House 4 Baths
5 bedrooms
4 bathrooms
Sleeps 12
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Tom's Chicken Coop: Nice Ocean View, Pool, Renovated, Close to Beach
2 bedrooms
2 bathrooms
Sleeps 6
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The Tree House Old Town 2 Bedroom MONTHLY Rental
2 bedrooms
1 bathroom
Sleeps 7
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Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!
3 bedrooms
3 bathrooms
Sleeps 6
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Attitude Key West (2 Bikes and Wireless Internet)
2 bedrooms
1 bathroom
Sleeps 2
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'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!
3 bedrooms
3 bathrooms
Sleeps 8
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Harbour Place 115 in Truman Annex Key West
2 bedrooms
3 bathrooms
Sleeps 6
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A Castle on An Island Your Santuary Retreat Key West Sleeps up to 20
8 bedrooms
8 bathrooms
Sleeps 20
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The Mermaids House, Historic Old Town Key West
2 bedrooms
1 bathroom
Sleeps 4
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Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool
2 bedrooms
2 bathrooms
Sleeps 6
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Majestic Escape near Duval! Pool, wifi, renovated 2/2 1/2, private courtyard.
2 bedrooms
3 bathrooms
Sleeps 6
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'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!
3 bedrooms
3 bathrooms
Sleeps 8
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Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo
3 bedrooms
3 bathrooms
Sleeps 8
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Conch Haven Old Town 1/1 MONTHLY Rental
1 bedroom
1 bathroom
Sleeps 4
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'SOUTHERNMOST BELLE'~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!
5 bedrooms
4 bathrooms
Sleeps 10
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Tropical Key West Get Away
3 bedrooms
3 bathrooms
Sleeps 8
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Harbor Walk Hideaways
4 bedrooms
3 bathrooms
Sleeps 8
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Truman Annex Best Location in Town
2 bedrooms
1 bathroom
Sleeps 5
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'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!
2 bedrooms
3 bathrooms
Sleeps 6
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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
2 bedrooms
2 bathrooms
Sleeps 6
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Craig & Cindy Key West Truman Annex 212 Fleming House
2 bedrooms
3 bathrooms
Sleeps 6
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KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI
2 bedrooms
1 bathroom
Sleeps 4
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Truman Annex, two blocks from Duval
2 bedrooms
3 bathrooms
Sleeps 4
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'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!
1 bedroom
1 bathroom
Sleeps 4
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Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families
2 bedrooms
2 bathrooms
Sleeps 4
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Ocean View Estate with Private Pool 15 minutes from Key West
4 bedrooms
2 bathrooms
Sleeps 10
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'THE QUARTERDECK' ~ Colorful & Comfortable 2Ba/ 1Ba Unit in The Shipyard!
2 bedrooms
1 bathroom
Sleeps 4
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Real World MTV House Key West
10 bedrooms
6 bathrooms
Sleeps 20
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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.