Key West: the End of the Road and the Beginning of Adventure!

The Southernmost City attracts those who love the year round warm Atlantic Ocean and all the exciting watersports – sailing, to sportfishing, snorkeling and SCUBA diving, kite surfing and stand up boarding, kayaking – as well as those who just love to relax on the beach or by the pool and save up their energy for the night’s Duval Crawl.

Key West nightlife and restaurants are just one more attraction to the Southernmost City. You don’t want to miss Key West best known watering hole, Sloppy Joe’s – famous for its toga parties, rocking music all day and night and its celebrated patron – Ernest “Papa” Hemingway. Hemingway cruised here from Europe with his new wife, expecting to pick up a car that was late in delivery. While the recently, married couple waited for the new car to show up, Hemingway discovered the incredible ocean and the opportunities for deep sea fishing that would become a lifelong pursuit of the famous author.

"Papa called" Key West the “poor man’s St. Tropez,” but today, most of the island’s beautiful historic homes have been renovated and restored to their 19th Century glory. In fact, Key West’s architecture and history is the attraction for many tourists. Visitors can tour the Oldest House, built circa 1829, Hemingway’s House and Gardens, the Audubon House built by wrecking captain John Geiger, and Truman’s Little White House.

Save on restaurants, attractions, golf, tours, recreation and more with FREE Florida Keys/Key West discount coupons from SavingsOnArrival.com.

Come and live like a local in a variety of Key West rentals. See sights and sounds, by bike or by foot that you wouldn’t be privy to in a stuffy overpriced hotel. Find beach homes, cottages, condos and more that are just right for families, couples and friends.

Key West is the island where anything goes and everyone who comes to play wants to stay.

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Key West Vacation Rental Accommodations - Page 1 of 8

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Key West Coral Hammock - Tropical Paradise Home (15)

  • 3 BR/3 BA Townhome (sleeps 6) Beach, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

Key West Brass Palm Villa, Private Luxury Home - ESCAPE TO PARADISE!!

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $2,500 - $5,000/wk
    $5,500 - $8,200/month
    per property, Near The Ocean, Town, Private Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Water views, step on your boat to Cuba!! minimum monthly rental

  • 3 BR/4 BA House (sleeps 10) accept credit card, Near The Ocean, Waterfront, Jacuzzi, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West Luxurious 4 bedroom/3 full bath home with private pool in Old Town Truman Annex

  • 4 BR/3 BA Townhome (sleeps 8)
    $2,900 - $3,500/wk
    per property, accept credit card, Downtown, Near The Ocean, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Canal-front home with ocean access in beautiful Key West, Florida

  • 4 BR House (sleeps 10)
    $2,800/wk
    $10,000/month
    per property, wheelchair accessible, Beach, Downtown, Near The Ocean, Town, Waterfront, Private Pool, Air Conditioning, Satellite / Cable, Television, DVD Player, barbecue

Key West Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West

  • 2 BR/2 BA House (sleeps 6)
    $975 - $1,600/wk
    per property, accept credit card, Resort, Communal Pool, Tennis Court, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Dock 80'Heated Pool Deep Channel Tennis 15 Min Key West

  • 2 BR/1 BA Bungalow (sleeps 6) Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West Paradise Manor with private pool available fall 2013

  • 4 BR/2 BA House (sleeps 9)
    $100 - $400/nt
    $1,790 - $1,990/wk
    $3,490 - $4,450/month
    per property, accept credit card, Beach, Near The Ocean, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean

  • 1 BR/1 BA Bungalow (sleeps 2) accept credit card, Tennis Court, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Private Luxury in Prestigious Casa Marina Neighborhood

  • 3 BR/3 BA, 1 half bath House (sleeps 7)
    $3,500 - $8,800/month
    per property, Downtown, Near The Ocean, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television
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Key West 'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...

  • 2 BR/2 BA, 1 half bath Condo (sleeps 5)
    $2,950 - $5,000/wk
    $9,000 - $18,000/month
    per property, accept credit card, Downtown, Near The Ocean, Waterfront, Communal Pool, Jacuzzi, terrace, Balcony, Air Conditioning, Internet

Key West 'SWEET CAROLINE'S SANCTUARY @ THE SEAPORT': Cozy 1BR/1BA Condo + Pool, Spa...

  • 1 BR/1 BA Condo (sleeps 4)
    $3,000 - $5,000/month
    per property, accept credit card, wheelchair accessible, Downtown, Near The Ocean, Communal Pool, Jacuzzi, Balcony, pets considered, Air Conditioning

Key West 'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $3,300 - $5,500/wk
    $9,900 - $19,000/month
    per property, accept credit card, Downtown, Near The Ocean, Town, Village, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Simonton Studio, an Old Town get-away for 2. New Pricing

  • 1 BA Studio (sleeps 2)
    $115 - $230/nt
    $750 - $1,500/wk
    per property, accept credit card, Near The Ocean, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Coral Hammock - Beautiful Poolside Home (28)

  • 3 BR/3 BA House (sleeps 6)
    $250 - $350/nt
    $1,400 - $2,000/wk
    $4,200 - $7,000/month
    per property, accept credit card, Communal Pool, Balcony, pets considered, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Ocean Retreat

  • 3 BR/2 BA, 1 half bath House (sleeps 5) accept credit card, Near The Ocean, Private Pool, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Ocean Paradise

  • 3 BR/4 BA House (sleeps 8) Beach, Near The Ocean, Private Pool, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Villa Soleil-Enjoy America's Caribbean with Style and Comfort

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $1,600/wk
    per property, accept credit card, Near The Ocean, Town, Lawn / Garden, terrace, Balcony, pets considered, Air Conditioning, Internet

Key West Walk to the beach!

  • 1 BR1 BA Studio (sleeps 2) Beach, Downtown, Near The Ocean, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West 'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...

  • 7 BR/7 BA House (sleeps 12)
    $9,500 - $12,900/wk
    $30,000 - $48,000/month
    per property, accept credit card, Downtown, Near The Ocean, Village, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television
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Key West 'SUZY'S PARROT PERCH @ SOUTHERNMOST': Cozy 2BR/1BA Suite Near Duval...

  • 2 BR/1 BA Apartment (sleeps 4)
    $230 - $425/nt
    $1,150 - $2,100/wk
    $3,900 - $8,000/month
    per property, accept credit card, Downtown, Near The Ocean, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...

  • 3 BR/3 BA House (sleeps 6)
    $5,500 - $14,000/month
    per property, accept credit card, Beach, Near The Ocean, Resort, Village, Private Pool, Lawn / Garden, terrace, Balcony, pets considered, Air Conditioning

Key West 'TOBA'S TREE HOUSE @ CASA EAST': Breezy 2BR/2BA Cottage & Pool near Beach...

  • 2 BR/2 BA House (sleeps 6)
    $4,000 - $7,700/month
    per property, Near The Ocean, Resort, Private Pool, terrace, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West New Potter's Cottage -Private Pool, Quiet, Yet Steps Off Duval

  • 2 BR House (sleeps 5)
    $375 - $400/nt
    $2,200 - $2,675/wk
    per property, Downtown, Near The Ocean, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Easy Livin'

  • 3 BR/4 BA House (sleeps 8)
    $4,000 - $9,200/wk
    per property, Private Pool, Air Conditioning, Television, DVD Player, Parking

Key West Osprey

  • 1 BR/1 BA Condo (sleeps 2)
    $130 - $321/nt
    $650 - $1,823/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player

Key West Artist Garden

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $1,700 - $3,425/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Tranquility

  • 1 BR/1 BA, 1 half bath House (sleeps 3)
    $210 - $413/nt
    $1,130 - $2,414/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player

Key West Island Pearl

  • 1 BR/1 BA House (sleeps 2)
    $210 - $391/nt
    $1,200 - $2,320/wk
    per property, Private Pool, Air Conditioning, Internet, DVD Player

Key West Crowner's Jewel

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,500 - $3,153/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking
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Key West A Zen Ocean Garden

  • 2 BR/2 BA Condo (sleeps 6)
    $300 - $487/nt
    $1,800 - $3,031/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Key West Charming

  • 2 BR/1 BA Condo (sleeps 4)
    $1,100 - $2,537/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Brisa del Mar

  • 2 BR/2 BA Condo (sleeps 6)
    $225 - $387/nt
    $1,300 - $2,381/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Papaya Place

  • 2 BR/2 BA Condo (sleeps 6)
    $220 - $381/nt
    $1,250 - $2,206/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West The Cristol Condo - Classic Key West Oceanfront Charm

  • 4 BR/4 BA Condo (sleeps 8)
    $4,989/wk
    per property, Waterfront, Communal Pool, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'LA DOLCE VITA' , Luxurious!, Steps To Duval! Sleeps 2-4

  • 1 BR/1 BA Condo (sleeps 4) accept credit card, Near The Ocean, Town, Balcony, Air Conditioning, Internet, Television, DVD Player

Key West Old Town location close to beach, shops & more

  • 2 BR/1 BA Condo (sleeps 5)
    $1,125 - $2,000/wk
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Luxury on Garrison Bight: 3 BR/3.5 BA Waterfront Home Sleeps 8

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $495 - $695/nt
    per property, accept credit card, Near The Ocean, Town, Waterfront, Private Pool, Balcony, pets considered, Internet, Satellite / Cable, Television

Key West Bargain Rates in Truman Annex - Heart of Old Town, Key West

  • 2 BR/1 BA Condo (sleeps 6)
    $225 - $350/nt
    $1,295 - $1,995/wk
    per property, accept credit card, Beach, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Oceanfront Condominium - Key West Oceanfront at the Coral Reef

  • 2 BR/2 BA Condo (sleeps 6)
    $265 - $495/nt
    $1,395 - $2,850/wk
    per property, accept credit card, wheelchair accessible, Beach, Near The Ocean, Resort, Waterfront, Private Pool, Jacuzzi, Sauna, Tennis Court, terrace
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Key West Exquisite 3BR Home on Shark Key - Enjoy the Best Tropical Sunsets of Your Life!

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $1,900 - $2,250/wk
    per property, Beach, Lawn / Garden, Balcony, Internet, Television

Key West Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes

  • 1 BR/1 BA Townhome (sleeps 4)
    $185 - $328/nt
    $1,295 - $2,295/wk
    per property, accept credit card, Resort, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Truman Annex Mike and Tevis Wernicoff

  • 2 BR/2 BA Condo (sleeps 6) accept credit card, Beach, Downtown, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

  • 2 BR/1 BA Condo (sleeps 4) accept credit card, Near The Ocean, Town, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Family-Friendly Luxury Home For The Discriminate Traveler

  • 5 BR/4 BA, 2 half baths Estate (sleeps 10) Near The Ocean, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!

  • 2 BR Condo (sleeps 4) accept credit card, Beach, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Sunshine Luxury Suite with 2 Free Bikes & Garage

  • 2 BR/2 BA Condo (sleeps 6)
    $1,300/wk
    per property, accept credit card, Near The Ocean, Resort, Communal Pool, Jacuzzi, Tennis Court, Balcony, pets considered, Fitness Room / Equipment

Key West Coral Hammock - Beautiful Home at the entrance to Key West (35)

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 4)
    $225 - $275/nt
    $1,000 - $1,500/wk
    $3,500/month
    per property, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

Key West Truman Annex: The Plantation SELF CATERING beautifully landscaped rear patio

  • 3 BR/3 BA Townhome (sleeps 6)
    $2,500 - $4,560/wk
    $7,500 - $10,500/month
    per property, Beach, Near The Ocean, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Key West vacation townhouse rental in the Truman Annex

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $1,400 - $2,750/wk
    $5,500 - $9,500/month
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television
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