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! June 2013 Month ONLY - at 25% SAVINGS June 3 - July 2

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! 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

Key West Sea Breeze Cottage-Gulf View in Truman Annex

  • 3 BR/2 BA Condo (sleeps 6)
    $2,500/wk
    per property, Beach, Downtown, Near The Ocean, Town, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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

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

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 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

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
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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 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 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 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
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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 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 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 'Amberjack' A Little Slice of Key West Heaven

  • 2 BR/2 BA Townhome (sleeps 6)
    $1,500 - $2,750/wk
    $5,250 - $8,250/month
    per property, Downtown, Near The Ocean, Communal Pool, Balcony, pets considered, 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 'PARADISE @ GARRISON BIGHT': Large 5BR/4BA Waterfront Home + Private Dock...

  • 5 BR/4 BA Townhome (sleeps 14)
    $1,200 - $1,800/nt
    $5,000 - $9,000/wk
    $18,000 - $33,000/month
    per property, accept credit card, wheelchair accessible, Downtown, Near The Ocean, Town, Village, Waterfront, Private Pool, terrace, Balcony, Air Conditioning, Internet

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 'NATALIE'S BAHAMA CONCH' @ THE SANCTUARY': Lush 3BR/2.5BA Home, Pool...

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $5,000 - $9,500/month
    per property, accept credit card, Near The Ocean, Resort, Village, Private Pool, Communal Pool, Lawn / Garden, terrace, Balcony, pets considered

Key West Waterfront Luxury in Old Town Key West

  • 1 BR/1 BA Condo (sleeps 5)
    $335 - $460/nt
    $2,000 - $2,750/wk
    per property, accept credit card, Resort, Waterfront, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Turquoise Mermaid ~ Old Town Key West

  • 2 BR/2 BA Condo (sleeps 4)
    $4,000 - $6,000/month
    per property, Downtown, Communal Pool, Air Conditioning, Internet, Television, Parking
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Key West The Kaleidoscope - an elegantly colorful Key West home.

  • 4 BR/4 BA, 1 half bath House (sleeps 8)
    $5,500 - $8,500/month
    per property, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

Key West Southernmost Belle a Grand home in Historic Old Town Key West

  • 5 BR/3 BA House (sleeps 10) accept credit card, Downtown, Near The Ocean, Town, Private Pool, Air Conditioning, Internet

Key West Seaport Villa

  • 3 BR/2 BA House (sleeps 6)
    $4,500 - $9,500/month
    per property, Downtown, Near The Ocean, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West Perfect Old Town Getaway

  • 3 BR/3 BA (sleeps 6)
    $4,500 - $9,000/month
    per property, Downtown, Near The Ocean, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, Parking

Key West Oceanside Condo

  • 2 BR/2 BA Condo (sleeps 4) Beach, Waterfront

Key West Dreamcatcher- A Tropical Conch Cottage In Old Town Key West

  • 2 BR/1 BA House (sleeps 4)
    $3,000 - $5,000/month
    per property, Beach, Downtown, Near The Ocean, Town, Lawn / Garden, Balcony, pets considered, Air Conditioning, Satellite / Cable, Television

Key West Cheerful Truman Annex Home

  • 2 BR/2 BA Townhome (sleeps 4)
    $1,800 - $2,600/wk
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Amazing Town home with Pool and Tiki Bar

  • 3 BR/3 BA Townhome (sleeps 8)
    $230 - $370/nt
    $1,395 - $2,500/wk
    per property, accept credit card, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West 616 Caroline #6

  • 1 BR/1 BA Condo (sleeps 2)
    $4,500/month
    per property, Near The Ocean, Waterfront, Communal Pool, Sauna, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West 516 Louisa Street

  • 2 BR/1 BA, 1 half bath House (sleeps 4)
    $350 - $650/nt
    $2,250 - $4,550/wk
    per property, accept credit card, Downtown, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television
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Key West Historic Home near the Seaport

  • 4 BR/2 BA, 1 half bath House (sleeps 10)
    $6,000 - $9,500/month
    per property, accept credit card, Downtown, Private Pool, Air Conditioning, Internet

Key West Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon

  • 2 BR/2 BA Yacht (sleeps 4) accept credit card, Downtown, Waterfront, Communal Pool, Air Conditioning

Key West 'LA CASA AZUL @ SOLARES HILL': Elegantly Renovated 3BR/3BA Home + Heated Pool...

  • 3 BR/3 BA House (sleeps 6)
    $5,500 - $15,000/month
    per property, accept credit card, Downtown, Resort, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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

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

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 Modern Luxury and Privacy Just Steps from Duval

  • 2 BR/2 BA House (sleeps 6)
    $425 - $2,800/nt
    per property, accept credit card, Beach, Downtown, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

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

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $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 Margaux's Hideaway - Spacious Private Tropical Home with Pool - KEY WEST LIVING!

  • 3 BR/3 BA House (sleeps 6)
    $2,500 - $4,000/wk
    $5,300 - $8,200/month
    per property, Near The Ocean, Town, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'POOLSIDE RETREAT @ THE POOL': Poolside 2BR/2.5BA Villa with 2 Master Suites...

  • 3 BR/2 BA, 1 half bath Villa (sleeps 6)
    $3,000 - $5,750/month
    per property, accept credit card, Near The Ocean, Resort, Communal Pool, Jacuzzi, Lawn / Garden, Balcony, pets considered, Fitness Room / Equipment
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