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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SPECIAL OFFER! Summer Special - $1,000.00/Week July 1 - October 18

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
SPECIAL OFFER! June 2013 - Month at 20% SAVINGS June 3 - August 29

Key West Namaste Key West - Tropical Retreat in a Key West Conch Cottage

  • 2 BR/1 BA Cottage (sleeps 4)
    $3,000 - $5,000/month
    per property, accept credit card, Beach, Downtown, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television
SPECIAL OFFER! **SAVE** $350.00 OFF WEEKLY RATES June 15 - June 22

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

Key West Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West

  • 3 BR/2 BA House (sleeps 10)
    $1,800 - $2,950/wk
    per property, accept credit card, Beach, Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!

  • 2 BR/1 BA Townhome (sleeps 6) wheelchair accessible, Beach, Downtown, Near The Ocean, Communal Pool, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Paradise Manor with private pool available June 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 Full Month Discounts Now Available in Truman Annex, Key West

  • 2 BR/2 BA, 1 half bath Condo (sleeps 5) accept credit card, Beach, Downtown, Near The Ocean, Town, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Spa On Duval

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $240 - $456/nt
    $1,400 - $2,900/wk
    per property, Communal Pool, Air Conditioning, DVD Player, Parking

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 Conch Wind

  • 2 BR/2 BA Condo (sleeps 4)
    $230 - $471/nt
    $1,375 - $2,755/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking
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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 Finn Key

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

  • 1 BR/1 BA House (sleeps 4)
    $190 - $384/nt
    $1,050 - $2,247/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player

Key West Bahamian Reed

  • 2 BR/1 BA, 1 half bath Condo (sleeps 5)
    $1,300 - $2,863/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

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 Parrot Perch

  • 2 BR/2 BA Condo (sleeps 5)
    $1,100 - $2,537/wk
    per property, Communal Pool, Air Conditioning, 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 Lavender Jungle

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

Key West Large private home just 2 blocks to Duval St

  • 4 BR/4 BA House (sleeps 10)
    $4,400 - $6,500/wk
    per property, accept credit card, Downtown, Town, Private Pool, Fitness Room / Equipment, Air Conditioning, Internet, Television, Parking
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Key West Casa Mara Is An Adorable Cottage on A Small Quiet Lane In Old Town

  • 2 BR/2 BA Cottage (sleeps 4) Near The Ocean, Town, Internet, Satellite / Cable, Television

Key West Walking to everything, Close to Beach, Old town

  • 3 BR/3 BA, 1 half bath House (sleeps 6) Downtown, Near The Ocean, Private Pool, Balcony, Air Conditioning, Television, Parking

Key West 'Mango Gardens' Charming, Walking Distance to Duval, and Historic Seaport Area

  • 4 BR House (sleeps 8) accept credit card, Downtown, Near The Ocean, Private Pool, Air Conditioning, Satellite / Cable, DVD Player

Key West Villa Soleil

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,600 - $3,407/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Tropical Dreaming

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $340 - $681/nt
    $2,100 - $4,350/wk
    per property, Private Pool, pets considered, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Southern Wind

  • 2 BR/2 BA House (sleeps 4)
    $265 - $471/nt
    $1,575 - $2,900/wk
    per property, Communal Pool, Air Conditioning, Television, DVD Player, Parking

Key West Leeward Isle Key West Retreat

  • 2 BR/2 BA Condo (sleeps 4)
    $265 - $471/nt
    $1,575 - $2,900/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Surf Side

  • 3 BR/2 BA Condo (sleeps 6)
    $375 - $662/nt
    $2,350 - $4,343/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Conch Condo

  • 2 BR/2 BA Condo (sleeps 4)
    $1,300 - $2,791/wk
    per property, Communal Pool, Air Conditioning, Parking

Key West The Hemingway

  • 2 BR/2 BA Condo (sleeps 6)
    $1,300 - $2,863/wk
    per property, Private Pool, Communal Pool, Air Conditioning
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Key West Key West Casa

  • 3 BR/2 BA Condo (sleeps 6)
    $2,000 - $5,075/wk
    per property, Communal Pool, pets considered, Air Conditioning, Television, DVD Player, Parking

Key West Coral Suite

  • 2 BR/3 BA Condo (sleeps 6)
    $150 - $306/nt
    $900 - $1,906/wk
    per property, Communal Pool, pets considered, Air Conditioning, Television, Parking

Key West Shipyard Treasure

  • 2 BR/1 BA Condo (sleeps 4)
    $1,300 - $2,791/wk
    per property, Communal Pool, Air Conditioning, Television, DVD Player, 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 Beach House Condo

  • 2 BR/2 BA Condo (sleeps 4)
    $1,300 - $2,791/wk
    per property, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Coral Garden

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $150 - $306/nt
    $900 - $1,906/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, 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 Caribbean Duval

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $225 - $435/nt
    $1,300 - $2,718/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Luxury Waterfront at the Galleon Resort in Old Town

  • 2 BR/2 BA Condo (sleeps 8)
    $400 - $600/nt
    $2,400 - $3,600/wk
    per property, accept credit card, limited accessibility, Resort, Waterfront, Communal Pool, Sauna, Balcony, Fitness Room / Equipment, Air Conditioning

Key West Island Escape Condo in Beautiful Truman Annex

  • 1 BR/1 BA Condo (sleeps 3)
    $1,200/wk
    per property, accept credit card, Beach, Downtown, Near The Ocean, Town, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable
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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 'AZURE MORNING @ OCEANSIDE MARINA': Lavish 3BR/2BA Oceanfront Condo + Pool....

  • 3 BR/2 BA Condo (sleeps 6)
    $1,850 - $2,950/wk
    $6,600 - $10,500/month
    per property, accept credit card, Near The Ocean, Waterfront, Communal Pool, Jacuzzi, terrace, Balcony, Fitness Room / Equipment, Air Conditioning

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 'PROMENADE TO PARADISE @ THE ANNEX': Spacious 2BR/2BA Waterfront Condo...

  • 2 BR/2 BA Condo (sleeps 6)
    $2,100 - $3,800/wk
    $8,500 - $15,000/month
    per property, accept credit card, Communal Pool, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

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 'CARIBBEAN FLING @ SOUTHARD': Delightful 2BR/1.5BA Island Cottage + Private Pool

  • 2 BR/1 BA, 1 half bath House (sleeps 6)
    $4,000 - $7,000/month
    per property, Downtown, Village, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

Key West Spacious Ocean Front Resort - 3 Bedroom Condo

  • 3 BR/3 BA Condo (sleeps 8) accept credit card, wheelchair accessible, Beach, Communal Pool, Jacuzzi, Sauna, Tennis Court, Lawn / Garden

Key West 2 Bed / 2 Bath Luxury Condo on the Ocean - Sleeps 6 (next to Smather's Beach)

  • 2 BR/2 BA Condo (sleeps 6) accept credit card, wheelchair accessible, Beach, Near The Ocean, Resort, Communal Pool, Jacuzzi, Sauna, Tennis Court, Lawn / Garden

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

  • 1 BR/1 BA Condo (sleeps 4)
    $208/nt
    $1,350/wk
    per property, accept credit card, Near The Ocean, Town, Balcony, Air Conditioning, Internet, Television, DVD Player
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