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 9

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

  • 2 BR/2 BA Condo (sleeps 6)
    $250 - $485/nt
    $1,395 - $3,395/wk
    per property, accept credit card, wheelchair accessible, Beach, Near The Ocean, Resort, Waterfront, Private Pool, Jacuzzi, Sauna, Tennis Court, terrace

Key West Beautiful Duval St. Condo, Location, Location!!!!

  • 2 BR/1 BA Condo (sleeps 4)
    $250 - $300/nt
    $1,200 - $1,600/wk
    $4,500 - $6,000/month
    per property, accept credit card, pets considered, Downtown, Near The Ocean, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Coral Hammock - Tropical Paradise Home (15)

  • 3 BR/3 BA Townhome (sleeps 6)
    $275 - $350/nt
    $1,500 - $2,000/wk
    $5,500 - $7,000/month
    per property, Beach, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

Key West Beautiful Waterfront Single Family Home - 5 miles from Key West

  • 3 BR/3 BA House (sleeps 6)
    $250 - $300/nt
    $1,705 - $1,840/wk
    $7,830/month
    per property, Near The Ocean, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

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

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $5,500 - $20,000/month
    per property, pets considered, Near The Ocean, Town, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West La Dolce Vita - Luxury Monthly Rental Private heated pool

  • 3 BR/4 BA House (sleeps 8)
    $8,633 - $10,967/month
    per property, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Quaint Houseboat with wet bar and awesome views - Key West Fishing Vacation

  • 2 BR/2 BA House Boat (sleeps 5)
    $240/nt
    $1,680/wk
    $7,200/month
    per property, accept credit card, Beach, Waterfront, Balcony, Air Conditioning, Satellite / Cable, Television, Parking

Key West Coral Cove - Freshly renovated

  • Studio/1 BA Condo (sleeps 2)
    $128 - $248/nt
    $1,736/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Southernmost Retreat

  • 2 BR/1 BA House (sleeps 6)
    $248 - $438/nt
    $3,066/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Island Oasis

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $358 - $568/nt
    $3,976/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Casa Margarita

  • 3 BR/3 BA House (sleeps 8)
    $408 - $768/nt
    $5,376/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Casa Key West

  • 3 BR/2 BA Condo (sleeps 8)
    $338 - $598/nt
    $4,186/wk
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Key West Hideaway

  • 4 BR/4 BA House (sleeps 10)
    $538 - $948/nt
    $6,636/wk
    per property, pets considered, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

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

  • 1 BR/1 BA Condo (sleeps 4)
    $188 - $278/nt
    per property, accept credit card, Near The Ocean, Town, Balcony, Air Conditioning, Internet, Television, DVD Player

Key West Spacious Ocean Front Resort - 3 Bedroom Condo

  • 3 BR/3 BA Condo (sleeps 8)
    $350 - $500/nt
    $2,275 - $3,150/wk
    per property, accept credit card, Hot Tub, wheelchair accessible, Beach, Communal Pool, Jacuzzi, Sauna, Tennis Court

Key West Casa Serendipity

  • 3 BR/2 BA House (sleeps 6)
    $408 - $768/nt
    $5,376/wk
    per property, pets considered, Private Pool, Air Conditioning, Internet, Satellite / Cable

Key West Helen`s Hideaway Private Heated Pool

  • 2 BR/2 BA House (sleeps 6)
    $388 - $588/nt
    $4,116/wk
    per property, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West Key West Charming: 2 BR / 1.0 BA condo in Key West, Sleeps 4

  • 2 BR/1 BA Condo (sleeps 4)
    $1,175 - $2,682/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Beach House Condo: 2 BR / 2.0 BA condo in Key West, Sleeps 4

  • 2 BR/2 BA Condo (sleeps 4)
    $1,350 - $2,972/wk
    per property, Hot Tub, Communal Pool, Air Conditioning, Internet, DVD Player, Parking

Key West Conch Retreat in Key West Truman Annex with 2 Bikes

  • 2 BR/1 BA Condo (sleeps 4)
    $1,300 - $1,950/wk
    $4,420 - $6,630/month
    per property, accept credit card, Beach, Downtown, Near The Ocean, Town, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Amelia House

  • 3 BR/2 BA House (sleeps 8)
    $318 - $578/nt
    $4,046/wk
    per property, pets considered, Hot Tub, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Tiki Beach Too, Charming Townhome, OldTown, Pool Access, Budget, Hideaway Porch!

  • 2 BR/1 BA Townhome (sleeps 6)
    $1,346 - $1,946/wk
    $2,995 - $4,865/month
    per property, pets considered, wheelchair accessible, Beach, Downtown, Near The Ocean, Communal Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Key West Location, Location, Location! Ocean View, Lagoon Beach Front

  • 3 BR/2 BA House Boat (sleeps 10)
    $395 - $745/nt
    $3,661 - $7,117/wk
    accept credit card, Hot Tub, Beach, Downtown, Near The Ocean, Resort, Waterfront, Communal Pool, Jacuzzi, Sauna, Balcony, Air Conditioning

Key West 'The Bungalow Too'

  • 1 BR/1 BA House (sleeps 2)
    $125 - $199/nt
    $795 - $1,295/wk
    $3,392/month
    per property, Hot Tub, Resort, Communal Pool, Lawn / Garden, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West (New) Gorgeous 2 Bedroom Two Bathroom In Old Town Key West. Newly Renovated!

  • 2 BR/3 BA House (sleeps 4)
    $4,200 - $7,000/month
    per property, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Family House - Stunning 2-Br 1.5-Ba w/PVT Hot Tub! Walking distance to Duval

  • 2 BR/1 BA, 1 half bath Cottage (sleeps 6)
    $268 - $448/nt
    $3,136/wk
    per property, pets considered, Hot Tub, Communal Pool, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Casa Grande

  • 5 BR/5 BA, 1 half bath House (sleeps 14)
    $768 - $1,398/nt
    $9,786/wk
    per property, pets considered, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Hemingway's View

  • 3 BR/2 BA House (sleeps 8)
    $338 - $608/nt
    $4,256/wk
    per property, pets considered, Hot Tub, Communal Pool, Air Conditioning, Internet, Satellite / Cable

Key West IMMACULATE KEY WEST VACATION RENTAL - 'ALEXANDRIA'S SECRET' - PRIVATE POOL

  • 3 BR/3 BA, 1 half bath Townhome (sleeps 8)
    $408 - $768/nt
    $5,376/wk
    per property, pets considered, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

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

  • 2 BR/2 BA House (sleeps 6)
    $995 - $1,600/wk
    per property, accept credit card, Resort, Communal Pool, Tennis Court, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Old Town Key West by Southernmost Beach and Duval Main Street.

  • 5 BR/4 BA House (sleeps 12)
    $800 - $1,100/nt
    $5,600 - $7,700/wk
    per property, accept credit card, Beach, Downtown, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West Galleon Resort Efficiency Historic District

  • 1 BR/1 BA Condo (sleeps 2)
    $219 - $299/nt
    $1,573 - $2,093/wk
    $6,730 - $7,770/month
    per property, accept credit card, Hot Tub, Near The Ocean, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach

  • 2 BR/2 BA House (sleeps 6)
    $9,147/month
    per property, Beach, Near The Ocean, Town, Waterfront, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Poolside Paradise

  • 3 BR/2 BA House (sleeps 10)
    $408 - $768/nt
    $5,376/wk
    per property, pets considered, Balcony, Air Conditioning, Internet, Satellite / Cable

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)
    $595 - $795/nt
    per property, accept credit card, pets considered, Near The Ocean, Town, Waterfront, Private Pool, Balcony, Internet, Satellite / Cable, Television

Key West The Cristol Condo - Classic Key West Oceanfront Charm

  • 4 BR/4 BA Condo (sleeps 8)
    $849/nt
    per property, pets considered, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West KEY WEST HOT SPOT! 'ALMOST SOUTHERNMOST' CLOSE TO SOUTHERNMOST POINT - SLEEP

  • 2 BR/1 BA House (sleeps 6)
    $258 - $448/nt
    $3,136/wk
    per property, pets considered, Hot Tub, Air Conditioning, Internet, Satellite / Cable, DVD Player

Key West Egret Cottage: 1 BR / 1.0 BA house in Key West, Sleeps 4

  • 1 BR/1 BA House (sleeps 4)
    $190 - $384/nt
    $1,050 - $2,320/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player

Key West Tropical Dreaming: 2 BR / 2.5 BA house in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath House (sleeps 6)
    $340 - $681/nt
    $2,100 - $4,350/wk
    per property, pets considered, Private Pool, Air Conditioning, Internet, 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 Linger Longer: 2 BR / 1.5 BA condo in Key West, Sleeps 5

  • 2 BR/1 BA, 1 half bath Condo (sleeps 5)
    $1,350 - $3,045/wk
    per property, Communal Pool, Air Conditioning, DVD Player, Parking

Key West Key West Casa: 3 BR / 2.0 BA condo in Key West, Sleeps 6

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

Key West Coral Suite: 2 BR / 3.0 BA condo in Key West, Sleeps 6

  • 2 BR/3 BA Condo (sleeps 6)
    $150 - $337/nt
    $900 - $2,093/wk
    per property, pets considered, Communal Pool, Air Conditioning, Television, Parking

Key West Key West Found: 2 BR / 2.5 BA condo in KEY WEST, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,650 - $3,552/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Coral Garden: 2 BR / 2.5 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $150 - $337/nt
    $900 - $2,093/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Lavender Jungle: 2 BR / 1.0 BA condo in Key West, Sleeps 4

  • 2 BR/1 BA Condo (sleeps 4)
    $1,175 - $2,682/wk
    per property, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West Luxurious Garden Home Paradise with Pool in Midtown Key West

  • 2 BR/1 BA House (sleeps 6)
    $127 - $173/nt
    $3,547 - $4,853/month
    per property, accept credit card, pets considered, Beach, Near The Ocean, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable

Key West WATERFRONT Penthouse, Key West between MM 10 just 5 min to KW

  • 2 BR/1 BA Condo (sleeps 4)
    $150/nt
    $850/wk
    $3,294/month
    per property, accept credit card, Near The Ocean, Waterfront, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Casa Bonita - Beautiful 2/2.5 Condo w/ Pool on Duval Street! Sleeps up to 7!

  • 2 BR/2 BA, 1 half bath Condo (sleeps 7)
    $258 - $458/nt
    $3,206/wk
    per property, pets considered, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Luxury Waterfront at the Galleon Resort in Old Town

  • 2 BR/2 BA Condo (sleeps 8)
    $450 - $625/nt
    $2,750 - $3,750/wk
    per property, accept credit card, Hot Tub, limited accessibility, Resort, Waterfront, Communal Pool, Sauna, Balcony, Fitness Room / Equipment
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