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.

Destination: Search
Great Rentals is part of HomeAway.com, the world's leading vacation rentals marketplace. Search over 170,000 vacation rentals properties now! Click here to see more Key West Vacation Rentals

Key West Vacation Rental Accommodations - Page 1 of 8

Go to page 1 2 3 4 5 6 7 (1-50 of 368) Next Last
Sort by: Show rentals per page
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 '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

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
Back to Top

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 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
Back to Top

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

Key West 'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old Town...

  • 3 BR/2 BA House (sleeps 6)
    $5,500 - $14,000/month
    per property, accept credit card, Downtown, Town, Village, Private Pool, Lawn / Garden, terrace, Balcony, pets considered, Air Conditioning

Key West Contemporary Condo at Truman Annex-Walk to Beach/Duval St.

  • 2 BR/1 BA Condo (sleeps 5)
    $1,300 - $1,925/wk
    per property, accept credit card, Beach, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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
Back to Top

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 Island Pearl

  • 1 BR/1 BA House (sleeps 2)
    $210 - $391/nt
    $1,200 - $2,320/wk
    per property, Private Pool, Air Conditioning, Internet, DVD Player

Key West A Place in Paradise

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,500 - $2,900/wk
    per property, Communal Pool, Air Conditioning, Television, DVD Player, 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 Linger Longer

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

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 The Hemingway

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

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 Island Spice

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

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $225 - $435/nt
    $1,300 - $2,718/wk
    per property, Communal Pool, Air Conditioning, Television, DVD Player, Parking
Back to Top
Go to page 1 2 3 4 5 6 7 (1-50 of 368) Next Last

© 1996-Present HomeAway.com, Inc. All rights reserved.

Use of this Web site constitutes acceptance of the GreatRentals.com Terms and Conditions and Privacy Policy.