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Key West Holiday Vacation with Pools

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212 rentals in Key West.
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Verandah
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Perfect Pineapple
2 bedrooms
1 bathroom
Sleeps 4
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Emma's Secret
2 bedrooms
1 bathroom
Sleeps 4
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Emma's Escape
2 bedrooms
1 bathroom
Sleeps 4
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Tropical Dreaming
2 bedrooms
2 bathrooms
Sleeps 6
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Crowner's Jewel
2 bedrooms
2 bathrooms
Sleeps 6
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Amelia Home
2 bedrooms
2 bathrooms
Sleeps 6
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A Place In Paradise
2 bedrooms
2 bathrooms
Sleeps 6
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Linger Longer
2 bedrooms
1 bathroom
Sleeps 5
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Conch Condo
2 bedrooms
2 bathrooms
Sleeps 5
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A Siesta Bay
2 bedrooms
1 bathroom
Sleeps 4
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Parrot Perch
2 bedrooms
2 bathrooms
Sleeps 5
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Shipyard Treasure
2 bedrooms
1 bathroom
Sleeps 4
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Key West Charming
2 bedrooms
1 bathroom
Sleeps 4
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Key West Casa
3 bedrooms
2 bathrooms
Sleeps 6
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Finn Key
2 bedrooms
1 bathroom
Sleeps 4
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Brisa Del Mar
2 bedrooms
2 bathrooms
Sleeps 6
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Beach House Condo
2 bedrooms
2 bathrooms
Sleeps 5
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Papaya Place
2 bedrooms
2 bathrooms
Sleeps 6
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Nautical Dreams
2 bedrooms
2 bathrooms
Sleeps 4
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Artist Garden
2 bedrooms
2 bathrooms
Sleeps 4
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Key West Found
2 bedrooms
2 bathrooms
Sleeps 6
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Lavender Jungle
2 bedrooms
1 bathroom
Sleeps 4
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Duval Sea Turtle
2 bedrooms
2 bathrooms
Sleeps 6
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Duval Breeze
2 bedrooms
2 bathrooms
Sleeps 6
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Ecco Domani
3 bedrooms
2 bathrooms
Sleeps 6
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Key Lime Pie
2 bedrooms
2 bathrooms
Sleeps 4
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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
Match: Sleeps, All pools
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7 other travellers have booked this property
HISTORIC KEY WEST - Main House - Sleeps 8
4 bedrooms
2 bathrooms
Sleeps 8
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2 other travellers have booked this property
HISTORIC KEY WEST - Turtle House - Sleeps 6
2 bedrooms
1 bathroom
Sleeps 6
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1 other traveller has booked this property
HISTORIC KEY WEST - Conch House - Sleeps 5
2 bedrooms
1 bathroom
Sleeps 5
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1 other traveller has booked this property
Alluring Porches
3 bedrooms
3 bathrooms
Sleeps 6
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HISTORIC KEY WEST - Cigar House - Sleeps 4
1 bedroom
1 bathroom
Sleeps 4
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Paradise Place
1 bedroom
1 bathroom
Sleeps 4
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Conch Wind
2 bedrooms
2 bathrooms
Sleeps 4
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Osprey
0 bedrooms
1 bathroom
Sleeps 2
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Ibis
1 bedroom
1 bathroom
Sleeps 2
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Seaside Place Key West FL 5 Bedroom House 4 Baths
5 bedrooms
4 bathrooms
Sleeps 12
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2 bedrooms
2 bathrooms
Sleeps 6
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** Totally Renovated Ocean View Condo Great Prices **
2 bedrooms
2 bathrooms
Sleeps 6
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3 other travellers have booked this property
* Book today Anchor drop key west short bike ride from old Town*
2 bedrooms
2 bathrooms
Sleeps 6
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5 other travellers have booked this property
Real World MTV House Key West
10 bedrooms
6 bathrooms
Sleeps 22
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11 other travellers have booked this property
** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **
1 bedroom
1 bathroom
Sleeps 4
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2 other travellers have booked this property
Artist Cottage in Truman Annex
2 bedrooms
1 bathroom
Sleeps 4
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Tropical Escape
2 bedrooms
2 bathrooms
Sleeps 5
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112 other travellers have booked this property
** Fantastic Spring& Summer Stay Downtown walk everywhere **
2 bedrooms
1 bathroom
Sleeps 4
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Easy Livin'
3 bedrooms
4 bathrooms
Sleeps 8
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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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Oceanfront 2 Bedroom 2 Bath Condo Key West Florida
2 bedrooms
2 bathrooms
Sleeps 6
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29 other travellers have booked this property
Tranquility
1 bedroom
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.