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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SPECIAL OFFER! LAST MINUTE SPECIALS...SAVE HUNDREDS May 10 - August 29

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 Unique Vacation Rental on Water! Available Fantasy Fest Week Starting Oct. 27th!

  • 3 BR/2 BA Yacht (sleeps 8)
    $250 - $500/nt
    per property, accept credit card, pets considered, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Satellite / Cable, Television

Key West UNBELIEVEABLE 3 Bedroom Houseboat Rental in First Class Marina w/ pool and more!

  • 4 BR/2 BA House Boat (sleeps 8)
    $350 - $500/nt
    per property, accept credit card, pets considered, Resort, Communal Pool, Sauna, Balcony, Fitness Room / Equipment, Air Conditioning

Key West Garden of Eden - Papas Hideaway Historic Inn's 2br/2ba cottage

  • 2 BR/2 BA House (sleeps 6)
    $268 - $468/nt
    per property, Communal Pool, Air Conditioning, Internet, Satellite / Cable

Key West A Zen Ocean Garden

  • 2 BR/2 BA Condo (sleeps 6)
    $300 - $487/nt
    $1,800 - $3,250/wk
    per property, Hot Tub, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West 4 Palms: 2 BR / 2.0 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA Condo (sleeps 6)
    $220 - $381/nt
    $1,250 - $2,406/wk
    per property, Hot Tub, Near The Ocean, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West 'THE COMMODORE'S MANOR @ PARADISE HARBOR ': Grand 5BR/4BA Waterfront Home + Dock

  • 5 BR/4 BA Townhome (sleeps 14)
    $1,250 - $1,800/nt
    $6,900 - $10,000/wk
    $20,000 - $33,000/month
    per property, accept credit card, pets considered, wheelchair accessible, Downtown, Near The Ocean, Town, Village, Waterfront, Private Pool, terrace, Balcony, Air Conditioning

Key West Truman Annex: Paradise Lost Self Catering Unique ground floor condominium

  • 2 BR/2 BA Condo (sleeps 6)
    $214 - $400/nt
    $1,500 - $2,800/wk
    $4,500/month
    per property, Near The Ocean, Communal Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West 'OCTOPUS'S GARDEN @ CORAL HAMMOCK': 3BR/3BA Spacious Home w Pool & Gym

  • 3 BR/3 BA House (sleeps 7)
    $2,100 - $3,200/wk
    $7,500 - $11,750/month
    per property, Beach, Near The Ocean, Town, Communal Pool, Lawn / Garden, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Tom's Chicken Coop: Ocean View, Heated Pool, Close to Beach

  • 2 BR/2 BA Condo (sleeps 6)
    $226 - $290/nt
    $1,500 - $1,820/wk
    $4,000 - $6,300/month
    per property, accept credit card, Hot Tub, Waterfront, Communal Pool, Sauna, Tennis Court, Lawn / Garden, Balcony

Key West ‘THE SMILING IBIS @ OLD TOWN’: Immaculate 3BR/3.5BA Old Town Home + Private Pool

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $700 - $1,050/nt
    $3,850 - $5,950/wk
    $13,000 - $20,500/month
    per property, pets considered, Downtown, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'CASA BLANCA 1888 @ WHITE': Historic 4BR/3BA Old Town Home + Very Large Pool....

  • 4 BR/3 BA House (sleeps 10)
    $7,467 - $16,333/month
    per property, accept credit card, pets considered, Downtown, Near The Ocean, Resort, Private Pool, Lawn / Garden, terrace, Balcony, Air Conditioning

Key West Tom's Parrot Perch: Gut Renovation, Ocean View, Heated Pool, Close to Beach

  • 2 BR/2 BA Condo (sleeps 6)
    $216 - $270/nt
    $1,680/wk
    $5,800/month
    per property, accept credit card, Downtown, Waterfront, Communal Pool, Sauna, Tennis Court, Balcony, Air Conditioning, Internet

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

  • 2 BR/1 BA Condo (sleeps 4)
    $1,400 - $2,050/wk
    $4,800 - $7,000/month
    per property, accept credit card, Beach, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Excellent Price for an Amazing Townhome with Pool and Tiki Bar

  • 3 BR/3 BA Townhome (sleeps 8)
    $230 - $400/nt
    $1,360 - $2,500/wk
    per property, accept credit card, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Sweet Cottage and Guest House with Large Private Pool!

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $550 - $750/nt
    $3,550 - $4,950/wk
    per property, accept credit card, Downtown, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Excellent Value - Coral Cabana - Beautiful Townhome overlooking Pool and Tiki

  • 3 BR/3 BA Townhome (sleeps 8)
    $230 - $400/nt
    $1,360 - $2,500/wk
    per property, accept credit card, Resort, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Relax on the Spacious Porch with Ocean Views for a Great Value!

  • 2 BR/2 BA Condo (sleeps 4)
    $245 - $375/nt
    $1,470 - $2,250/wk
    per property, Beach, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Amelia Home: 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 Villa Soleil: 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, DVD Player, Parking

Key West Papaya Place: 2 BR / 2.0 BA condo in Key West, Sleeps 6

  • 2 BR/2 BA Condo (sleeps 6)
    $220 - $381/nt
    $1,250 - $2,406/wk
    per property, Hot Tub, Communal Pool, Air Conditioning, Internet, Television, Parking

Key West Duval Street Hideaway

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $240 - $478/nt
    $1,450 - $3,275/wk
    per property, Hot Tub, Communal Pool, Air Conditioning, Internet, Television, DVD Player, Parking

Key West 'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...

  • 2 BR/2 BA, 1 half bath Villa (sleeps 6)
    $2,000 - $3,750/wk
    $6,600 - $13,500/month
    per property, accept credit card, Downtown, Near The Ocean, Resort, Town, Village, Communal Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West 'SOUTHERNMOST BLISS @ LOVE LANE': Stunning 3.5BR/3BA Old Town Home On Quiet Lane

  • 3 BR/3 BA House (sleeps 8)
    $7,187 - $17,267/month
    per property, pets considered, Downtown, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $3,500 - $5,750/wk
    $9,900 - $19,500/month
    per property, accept credit card, Downtown, Near The Ocean, Waterfront, Communal Pool, Jacuzzi, terrace, Balcony, Air Conditioning, Internet

Key West “THE CAPTAIN'S ANNEX @ PARADISE HARBOR”: Ample 4BR Home + Pool & Boat Slip...

  • 4 BR/3 BA, 1 half bath House (sleeps 12)
    $650 - $1,000/nt
    $4,000 - $6,000/wk
    $14,000 - $21,000/month
    per property, pets considered, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'AVALYNN HOUSE @ THE ANNEX': The Ideal 5BR Key West Home + Large Pool..

  • 5 BR/3 BA, 1 half bath House (sleeps 8)
    $8,800 - $12,000/wk
    $30,000 - $44,500/month
    per property, pets considered, Downtown, Near The Ocean, Private Pool, Jacuzzi, Tennis Court, terrace, Fitness Room / Equipment, Air Conditioning

Key West “THE MELLOW MACAW @ SOUTHERNMOST”: Cheerful 2BR/1BA + Spa Off Duval…

  • 2 BR/1 BA Condo (sleeps 6)
    $290 - $450/nt
    $1,450 - $2,350/wk
    $4,900 - $8,250/month
    per property, Hot Tub, Downtown, Village, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, Parking

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)
    $3,250 - $5,500/wk
    $9,000 - $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 'EDEN @ THE ANNEX': 2BR/1.5BA Old Town Villa near Beach & Sunset Pier...

  • 2 BR/1 BA, 1 half bath Villa (sleeps 6)
    $1,850 - $3,100/wk
    $6,000 - $10,800/month
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

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

  • 3 BR/2 BA Cottage (sleeps 8)
    $425 - $825/nt
    $2,550 - $4,500/wk
    $8,000 - $16,000/month
    per property, accept credit card, pets considered, Town, Village, Private Pool, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage + Private Pool...

  • 2 BR/3 BA House (sleeps 6)
    $390 - $750/nt
    $2,150 - $3,950/wk
    $6,600 - $14,000/month
    per property, accept credit card, pets considered, Downtown, Town, Village, Private Pool, terrace, Balcony, Air Conditioning, Internet

Key West “SOUTHERNMOST HOSPITALITY @ UPPER DUVAL”: Superlative 5BR/5.5BA Estate + Pool..

  • 5 BR/5 BA Estate (sleeps 12)
    $1,200 - $2,100/nt
    $7,000 - $12,000/wk
    $25,500 - $41,000/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West “THE IBIS & THE CRANE @ OLD TOWN”: Spacious 6BR/6+BA Compound + 2 Private Pools

  • 6 BR/6 BA, 2 half baths Townhome (sleeps 16)
    $1,400 - $2,100/nt
    $7,700 - $11,900/wk
    $26,000 - $41,000/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'THE CONTENTED CRANE @ OLD TOWN': Pristine 3BR/3.5BA Home + Private Pool...

  • 3 BR/3 BA, 1 half bath Townhome (sleeps 8)
    $700 - $1,050/nt
    $3,850 - $5,950/wk
    $13,000 - $20,500/month
    per property, pets considered, wheelchair accessible, Downtown, Village, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'COOL BREEZE @ THE ANNEX': Meticulously Furnished 2BR/2.5BA Old Town Villa...

  • 2 BR/2 BA, 1 half bath Villa (sleeps 6)
    $2,000 - $3,750/wk
    $6,600 - $13,500/month
    per property, accept credit card, Downtown, Near The Ocean, Resort, Town, Village, Waterfront, Communal Pool, Lawn / Garden, terrace, Balcony, Air Conditioning, Internet

Key West 'NANCY'S SEASIDE RETREAT @ THE FLORIDA BAY': Waterfront 4BR/4BA Home + Pool..

  • 4 BR/4 BA House (sleeps 10)
    $5,600 - $11,667/month
    per property, pets considered, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'BRISA FRESCA @ THE ANNEX': Bright & Airy 3BR/3BA Private Home + Pool...

  • 3 BR/3 BA House (sleeps 8)
    $4,800 - $6,975/wk
    $18,000 - $27,000/month
    per property, Downtown, Resort, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'THE SEAFARER'S REFUGE @ PARADISE HARBOR': Old Town Home By Water + Pool & Dock.

  • 4 BR/3 BA, 1 half bath House (sleeps 12)
    $7,000 - $13,067/month
    per property, pets considered, Downtown, Village, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Ocean Paradise

  • 3 BR/4 BA House (sleeps 8)
    $5,200 - $12,500/wk
    per property, pets considered, Beach, Near The Ocean, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Ocean Retreat

  • 3 BR/2 BA, 1 half bath House (sleeps 5)
    $3,200 - $7,500/wk
    per property, accept credit card, Near The Ocean, Private Pool, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West Waterfront Luxury in Old Town Key West

  • 1 BR/1 BA Condo (sleeps 5)
    $350 - $480/nt
    $2,125 - $2,900/wk
    per property, accept credit card, Hot Tub, Resort, Waterfront, Communal Pool, Sauna, Fitness Room / Equipment, Air Conditioning, Internet

Key West Rare Penthouse 2 bed/2bath additional King in loft

  • 2 BR/2 BA Condo (sleeps 8)
    $495 - $750/nt
    $3,465 - $5,250/wk
    $14,850 - $19,350/month
    per property, accept credit card, Downtown, Waterfront, Communal Pool, Jacuzzi, Sauna, Balcony, Fitness Room / Equipment, Air Conditioning

Key West Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10

  • 3 BR/3 BA Condo (sleeps 10)
    $695 - $875/nt
    $4,865 - $6,125/wk
    $20,850 - $25,500/month
    per property, accept credit card, Hot Tub, wheelchair accessible, Beach, Downtown, Waterfront, Communal Pool, Sauna, Balcony, Fitness Room / Equipment

Key West Island Escape Condo in Beautiful Truman Annex

  • 1 BR/1 BA Condo (sleeps 3)
    $1,200 - $1,750/wk
    $4,080 - $5,950/month
    per property, accept credit card, Beach, Downtown, Near The Ocean, Town, Waterfront, Communal Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

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

  • 4 BR/3 BA Townhome (sleeps 8)
    $414 - $786/nt
    $2,900 - $4,900/wk
    per property, accept credit card, Downtown, Near The Ocean, Private Pool, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / 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)
    $1,400 - $2,050/wk
    $4,800 - $7,000/month
    per property, accept credit card, Near The Ocean, Town, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Spacious Two Bedroom In Casa Marina Resort

  • 2 BR/2 BA Villa (sleeps 8)
    $400/nt
    $2,800/wk
    $11,000/month
    per property, Hot Tub, Communal Pool, Sauna, Internet, Satellite / Cable, Television, DVD Player, Parking

Key West Real World MTV House---Not Just a House Your Own Private Resort

  • 10 BR/5 BA, 1 half bath House (sleeps 20)
    $1,500 - $2,500/nt
    $10,000 - $12,500/wk
    $40,000 - $50,000/month
    per property, accept credit card, pets considered, Hot Tub, Resort, Waterfront, Jacuzzi, Tennis Court, Lawn / Garden, Balcony

Key West The Victoria House: 5 BR / 5.5 BA house in Key West, Sleeps 12

  • 5 BR/5 BA, 1 half bath House (sleeps 12)
    $865 - $1,776/nt
    $5,800 - $12,035/wk
    per property, Hot Tub, Private Pool, Air Conditioning, Internet, Television, DVD Player, Parking
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