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.

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 Tom's Parrot Perch: GUT RENOVATION COMPLETED 9/16/11!!

  • 2 BR/2 BA Condo (sleeps 6)
    $270 - $380/nt
    $1,620 - $2,280/wk
    per property, accept credit card, waterfront, pool, tennis court, garden, balcony, air-conditioning, satellite or cable

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)
    $1,300 - $1,950/wk
    per property, accept credit card, near the ocean, town, pool, balcony, air-conditioning, internet access, satellite or cable, TV

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)
    $265/nt
    $1,590/wk
    $3,500/month
    per property, accept credit card, beach, resort, pool, jacuzzi, sauna, tennis court, garden, terrace

Key West See & Hear Atlantic Ocean from Studio & King bed! ! Sunny! Beachy! See Horizons!

  • 1 BA Studio (sleeps 2)
    $1,500/wk
    per property, accept credit card, beach, downtown, air-conditioning, internet access, TV, DVD, barbecue

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

  • 3 BR/3 BA Townhome (sleeps 6)
    $2,500 - $3,500/wk
    $7,500 - $10,500/month
    per property, beach, near the ocean, pool, garden, balcony, air-conditioning, internet access, satellite or cable, TV

Key West Oceanfront Condominium - Direct Oceanfront at the Coral Reef

  • 2 BR/2 BA Condo (sleeps 6)
    $250 - $450/nt
    $1,295 - $2,795/wk
    per property, accept credit card, resort, waterfront, jacuzzi, sauna, tennis court, terrace, balcony, air-conditioning

Key West Southernmost Escape

  • 3 BR/3 BA, 1 half bath House (sleeps 6)
    $3,500 - $5,000/wk
    per house, downtown, near the ocean, private pool, balcony, pets considered, air-conditioning, internet access, TV

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

  • 2 BR House (sleeps 5)
    $320 - $395/nt
    $2,000 - $2,500/wk
    per property, downtown, near the ocean, pool, pets considered, air-conditioning, internet access, satellite or cable, DVD

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

  • 3 BR/3 BA House (sleeps 6)
    $1,470/wk
    $6,300/month
    per property, near the ocean, waterfront, balcony, air-conditioning, internet access, satellite or cable, TV, DVD, parking

Key West 'CASA DE ROSALIE @ BAYVIEW PARK': Freshly Renovated 3BR/2BA Home In Town...

  • 4 BR/2 BA House (sleeps 8)
    $4,400 - $11,000/month
    per property, town, village, pool, pets considered, air-conditioning, internet access, TV, DVD
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Key West La Brisa #405E Sea Orchid

  • 2 BR/2 BA Condo (sleeps 4)
    $200 - $370/nt
    $1,330 - $2,590/wk
    per condo, beach, communal pool, balcony, satellite or cable

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

  • 2 BR/1 BA Condo (sleeps 4)
    $225 - $275/nt
    $1,100 - $1,500/wk
    $4,000 - $5,500/month
    per property, accept credit card, downtown, near the ocean, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV

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

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $1,600 - $2,350/wk
    per property, accept credit card, near the ocean, town, garden, terrace, balcony, pets considered, air-conditioning, internet access

Key West Charming Yacht Located in Exclusive, Beautiful Key West Harbour Yacht Club

  • 2 BR/1 BA Yacht (sleeps 4)
    $150 - $200/nt
    $1,050 - $1,400/wk
    per property, accept credit card, beach, waterfront, pool, sauna, fitness room, air-conditioning, satellite or cable, TV

Key West 2012 Special Pricing Hemingway Style Cottage/Tropical Pool

  • 3 BR/2 BA Cottage (sleeps 8)
    $8,820 - $12,500/month
    per property, accept credit card, beach, town, pool, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West Louisa's Private Courtyard

  • 3 BR/3 BA House (sleeps 6)
    $450 - $720/nt
    $2,940 - $5,040/wk
    per house, beach, near the ocean

Key West Modern home with great location - room for whole family - including pets

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $2,500 - $4,500/month
    per property, accept credit card, beach, town, garden, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West William Skelton -- Location, location, location -- in Old Town Key West!

  • 6 BR/3 BA House (sleeps 16)
    $600 - $1,200/nt
    per property, accept credit card, downtown, near the ocean, garden, balcony, air-conditioning, satellite or cable, TV

Key West Amelia's Great Escape

  • 4 BR/3 BA House (sleeps 10)
    $470 - $800/nt
    $3,150 - $5,600/wk
    per house, beach, air-conditioning, TV, DVD

Key West Beach Club #303

  • 2 BR/2 BA Condo (sleeps 4)
    $270 - $480/nt
    $1,820 - $3,360/wk
    per condo, beach, communal pool, satellite or cable, parking
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Key West Pristine Condo with Pool & Ocean Peek, 2 Bikes in Key West's Truman Annex

  • 1 BR/1 BA Condo (sleeps 2)
    $1,200 - $1,850/wk
    per property, accept credit card, near the ocean, town, pool, garden, terrace, balcony, air-conditioning, internet access

Key West Modern Luxury and Privacy Just Steps from Duval

  • 2 BR/2 BA House (sleeps 6)
    $400/nt
    $2,700/wk
    per property, accept credit card, beach, downtown, pool, garden, balcony, air-conditioning, internet access, satellite or cable

Key West My Condo by the Beach with Ocean View

  • 1 BR/1 BA Condo (sleeps 4)
    $950 - $1,550/wk
    per property, accept credit card, beach, town, pool, balcony, air-conditioning, internet access, satellite or cable, TV

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

  • 2 BR/1 BA Condo (sleeps 5)
    $1,100 - $2,000/wk
    per property, accept credit card, downtown, near the ocean, pool, air-conditioning, internet access, satellite or cable, TV, DVD

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

  • 1 BA Studio (sleeps 2)
    $112 - $228/nt
    $700 - $1,500/wk
    per property, accept credit card, near the ocean, air-conditioning, internet access, satellite or cable, TV, DVD

Key West A Zen Ocean Garden

  • 2 BR/2 BA Condo (sleeps 6)
    $300 - $488/nt
    $1,800 - $3,031/wk
    per condo

Key West A Place in Paradise

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,500 - $2,900/wk
    per condo

Key West Easy Livin'

  • 3 BR/4 BA House (sleeps 8)
    $4,000 - $9,200/wk
    per house

Key West Olivia Cottage

  • 2 BR/2 BA, 1 half bath House (sleeps 4)
    $5,000 - $7,500/month
    per house, beach, near the ocean, air-conditioning, TV, parking

Key West Surf Side

  • 3 BR/2 BA Condo (sleeps 6)
    $375 - $662/nt
    $2,350 - $4,344/wk
    per condo
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Key West Key West, 'Bella Vita', Luxurious, Sleeps 2-4, Steps from Duval Street!

  • 1 BR/1 BA Condo (sleeps 4)
    $188 - $258/nt
    per property, accept credit card, beach, near the ocean, pets considered, air-conditioning, satellite or cable, TV, DVD

Key West 'SOUTHERN STAR' @ WILLIAM STREET' Historic 3BR/3BA Home with Pool...

  • 3 BR/3 BA House (sleeps 6)
    $6,000 - $15,000/month
    per property, downtown, near the ocean, village, waterfront, pool, balcony, air-conditioning, internet access, satellite or cable, TV, DVD

Key West 'SUNSET DREAMS @ FLORIDA BAY': Luxury 3BR/2BA Waterfront Condo by Marina...

  • 3 BR/2 BA Condo (sleeps 8)
    $3,300 - $7,700/month
    per property, accept credit card, near the ocean, waterfront, pool, jacuzzi, terrace, balcony, pets considered, air-conditioning

Key West 'THE LILAC COTTAGE @ SOLARES HILL': 2.5BR/2BA Old Town Cottage, Quiet Street...

  • 2 BR/2 BA House (sleeps 7)
    $4,400 - $9,900/month
    per property, accept credit card, downtown, near the ocean, town, village, pool, garden, terrace, pets considered, air-conditioning, internet access

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

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $2,500 - $5,000/wk
    $9,000 - $15,000/month
    per property, accept credit card, downtown, near the ocean, town, village, waterfront, pool, balcony, air-conditioning, internet access, satellite or cable, TV

Key West 'COLORFUL CONCH @ THE SANCTUARY': Immaculate 4BR/3BA Private Home, Pool...

  • 4 BR/3 BA House (sleeps 8)
    $4,500 - $11,000/month
    per property, beach, near the ocean, resort, pool, pool, terrace, balcony, pets considered, fitness room, air-conditioning

Key West 'OLD TOWN OASIS @ TRUMAN ANNEX': Spacious 2BR/2BA Oceanfront Condo + Pool...

  • 2 BR/2 BA Condo (sleeps 7)
    $1,950 - $3,600/wk
    $7,000 - $13,000/month
    per property, accept credit card, downtown, waterfront, pool, balcony, air-conditioning, internet access, satellite or cable, TV

Key West Best Deal in Truman Annex - Cead Mile Failte

  • 2 BR/1 BA Condo (sleeps 4)
    $200 - $275/nt
    $1,400 - $1,950/wk
    $3,500 - $5,400/month
    per property, accept credit card, beach, downtown, pool, air-conditioning, internet access, DVD, barbecue

Key West “AZURE AFTERNOON @ OCEANSIDE MARINA': 3BR/2BA Oceanfront Condo + Pool & Spa...

  • 3 BR/2 BA House (sleeps 6)
    $1,775 - $2,900/wk
    $6,000 - $9,900/month
    per property, accept credit card, near the ocean, waterfront, pool, jacuzzi, garden, terrace, balcony, pets considered

Key West 'CONCH CASA GRANDE @ TRUMAN ANNEX': Grand 7BR/7BA Home, 6 Master Suites...

  • 7 BR/7 BA House (sleeps 12)
    $9,000 - $16,000/wk
    $30,000 - $44,000/month
    per property, accept credit card, downtown, near the ocean, village, balcony, pets considered, air-conditioning, internet access, satellite or cable, TV
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Key West “THE AVIARY NEST @ ARONOVITZ LANE': 2BR/2BA Cottage in Old Town, Pool...

  • 2 BR/2 BA House (sleeps 6)
    $4,400 - $8,800/month
    per property, accept credit card, downtown, near the ocean, town, village, pool, garden, pets considered, air-conditioning, internet access, satellite or cable

Key West 'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..

  • 3 BR/2 BA Cottage (sleeps 8)
    $400 - $700/nt
    $2,300 - $5,000/wk
    $8,000 - $14,750/month
    per property, accept credit card, town, village, pool, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West Vista Verde

  • 2 BR/2 BA Condo (sleeps 4)
    $190 - $380/nt
    $1,260 - $2,660/wk
    per condo, beach, communal pool, balcony, air-conditioning, satellite or cable, parking

Key West Beach Club #108

  • 3 BR/2 BA Condo (sleeps 6)
    $350 - $530/nt
    $2,390 - $3,710/wk
    per condo, beach, communal pool

Key West Quiet, elegant, Key West Condo close to the Ocean

  • 2 BR/2 BA Condo (sleeps 6)
    $165 - $195/nt
    $1,155 - $1,365/wk
    per property, accept credit card, beach, near the ocean, pool, tennis court, balcony, pets considered, fitness room, air-conditioning

Key West Carpe Diem- a tropical Conch Cottage in old town Key West -

  • 2 BR/1 BA Cottage (sleeps 4)
    $2,200 - $4,500/month
    per property, accept credit card, beach, near the ocean, town, garden, pets considered, air-conditioning, internet access, satellite or cable, TV

Key West Campbell Courtyard Townhouse 'In the Sky'

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $3,500 - $4,500/month
    per property, accept credit card, downtown, terrace, balcony, air-conditioning, internet access, TV, DVD

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, beach, sauna, tennis court, garden, terrace, balcony, air-conditioning

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 - $4,900/wk
    $17,500/month
    per property, accept credit card, downtown, near the ocean, pool, garden, balcony, air-conditioning, internet access, satellite or cable

Key West Coral Hammock - Beautiful Poolside Home

  • 3 BR/3 BA House (sleeps 6)
    $225 - $350/nt
    $1,250 - $1,800/wk
    $3,750 - $5,400/month
    per property, accept credit card, pool, balcony, pets considered, fitness room, air-conditioning, internet access, satellite or cable
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