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Key West Rentals for Fishing Vacations

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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
SPECIAL OFFER! June 2013 - Month at 20% SAVINGS June 3 - August 29

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! **SAVE** $350.00 OFF WEEKLY RATES June 15 - June 22

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

  • 2 BR/2 BA Condo (sleeps 6)
    $265 - $495/nt
    $1,395 - $2,850/wk
    per property, accept credit card, wheelchair accessible, Beach, Near The Ocean, Resort, Waterfront, Private Pool, Jacuzzi, Sauna, Tennis Court, terrace

Key West Paradise Manor with private pool available June 2013

  • 4 BR/2 BA House (sleeps 9)
    $100 - $400/nt
    $1,790 - $1,990/wk
    $3,490 - $4,450/month
    per property, accept credit card, Beach, Near The Ocean, Private Pool, Lawn / Garden, Air Conditioning, Internet, Satellite / Cable, Television

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 Large private home just 2 blocks to Duval St

  • 4 BR/4 BA House (sleeps 10)
    $4,400 - $6,500/wk
    per property, accept credit card, Downtown, Town, Private Pool, Fitness Room / Equipment, Air Conditioning, Internet, Television, Parking

Key West Casa Mara Is An Adorable Cottage on A Small Quiet Lane In Old Town

  • 2 BR/2 BA Cottage (sleeps 4) Near The Ocean, Town, Internet, Satellite / Cable, Television

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 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

Key West Island Escape Condo in Beautiful Truman Annex

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

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)
    $3,300 - $5,500/wk
    $9,900 - $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 '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 'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...

  • 2 BR/2 BA, 1 half bath Condo (sleeps 5)
    $2,950 - $5,000/wk
    $9,000 - $18,000/month
    per property, accept credit card, Downtown, Near The Ocean, Waterfront, Communal Pool, Jacuzzi, terrace, Balcony, Air Conditioning, Internet

Key West 'PROMENADE TO PARADISE @ THE ANNEX': Spacious 2BR/2BA Waterfront Condo...

  • 2 BR/2 BA Condo (sleeps 6)
    $2,100 - $3,800/wk
    $8,500 - $15,000/month
    per property, accept credit card, Communal Pool, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'TOBA'S TREE HOUSE @ CASA EAST': Breezy 2BR/2BA Cottage & Pool near Beach...

  • 2 BR/2 BA House (sleeps 6)
    $4,000 - $7,700/month
    per property, Near The Ocean, Resort, Private Pool, terrace, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable

Key West 'CARIBBEAN FLING @ SOUTHARD': Delightful 2BR/1.5BA Island Cottage + Private Pool

  • 2 BR/1 BA, 1 half bath House (sleeps 6)
    $4,000 - $7,000/month
    per property, Downtown, Village, Private Pool, pets considered, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West 'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...

  • 7 BR/7 BA House (sleeps 12)
    $9,500 - $12,900/wk
    $30,000 - $48,000/month
    per property, accept credit card, Downtown, Near The Ocean, Village, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Spacious Ocean Front Resort - 3 Bedroom Condo

  • 3 BR/3 BA Condo (sleeps 8) accept credit card, wheelchair accessible, Beach, Communal Pool, Jacuzzi, Sauna, Tennis Court, Lawn / Garden

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 '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

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 Exquisite 3BR Home on Shark Key - Enjoy the Best Tropical Sunsets of Your Life!

  • 3 BR/3 BA, 1 half bath House (sleeps 8)
    $2,250/wk
    per property, Beach, Lawn / Garden, Balcony, Internet, Television

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 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 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 Bargain Rates in Truman Annex - Heart of Old Town, Key West

  • 2 BR/1 BA Condo (sleeps 6)
    $225 - $350/nt
    $1,295 - $1,995/wk
    per property, accept credit card, Beach, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key West Luxury Living in Key West Aboard Your Own Private 58ft Hatteras Yach

  • 3 BR/2 BA, 1 half bath Yacht (sleeps 6)
    $275 - $325/nt
    $1,800/wk
    per property, Waterfront, Communal Pool, Balcony, pets considered, Satellite / Cable, Television, Parking

Key West Stunning Brand New SleepAfloat HOUSEBOAT in Paradise!

  • 4 BR/2 BA House Boat (sleeps 8) Resort, Communal Pool, Sauna, Balcony, pets considered, Fitness Room / Equipment, Air Conditioning, Internet

Key West LOOK! Vacation on a Yacht in First-Class Marina!

  • 2 BR/2 BA Boat (sleeps 4)
    $300 - $350/nt
    $2,000/wk
    per property, accept credit card, Communal Pool, Jacuzzi, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Television

Key West 5 bedroom property in the heart of Old Town!

  • 5 BR/3 BA House (sleeps 10)
    $7,000 - $8,000/month
    per property, Downtown, Near The Ocean, Air Conditioning, Internet, Satellite / Cable, Television

Key West Boli Townhouse - a Key West Luxury Rental close to everything ! ! !

  • 2 BR/2 BA Townhome (sleeps 6)
    $1,600/wk
    $5,500/month
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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 - $3,500/wk
    per property, accept credit card, Downtown, Near The Ocean, Private Pool, Lawn / Garden, 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) Beach, Near The Ocean, Town, Waterfront, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, 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 Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean

  • 1 BR/1 BA Bungalow (sleeps 2) accept credit card, Tennis Court, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West 'MAISON SUR LA MER' / Private Enclave With Pool

  • 4 BR/3 BA Villa (sleeps 10)
    $15,000 - $20,000/month
    per property, Near The Ocean, Private Pool, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, DVD Player, Parking

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

  • 2 BR/1 BA Condo (sleeps 4)
    $1,200/wk
    per property, accept credit card, Beach, Downtown, Near The Ocean, Town, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Key West Ocean Paradise

  • 3 BR/4 BA House (sleeps 8) Beach, Near The Ocean, Private Pool, Balcony, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Coral Hammock - Tropical Paradise Home (15)

  • 3 BR/3 BA Townhome (sleeps 6) Beach, Near The Ocean, Communal Pool, Balcony, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable, Television

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

  • 3 BR/1 BA, 1 half bath House (sleeps 6)
    $2,500 - $4,000/month
    per property, accept credit card, Beach, Town, Lawn / Garden, pets considered, Air Conditioning, Internet, Satellite / Cable, Television

Key West Attitude Key West At the Beach

  • 1 BR Condo (sleeps 4) accept credit card, wheelchair accessible, Beach, Downtown, Near The Ocean, Resort, Town, Waterfront, Communal Pool, Sauna, Lawn / Garden, Balcony, Air Conditioning

Key West Sunshine Luxury Suite with 2 Free Bikes & Garage

  • 2 BR/2 BA Condo (sleeps 6)
    $1,300/wk
    per property, accept credit card, Near The Ocean, Resort, Communal Pool, Jacuzzi, Tennis Court, Balcony, pets considered, Fitness Room / Equipment

Key West Coral Hammock - Beautiful Poolside Home (28)

  • 3 BR/3 BA House (sleeps 6)
    $250 - $350/nt
    $1,400 - $2,000/wk
    $4,200 - $7,000/month
    per property, accept credit card, Communal Pool, Balcony, pets considered, Fitness Room / Equipment, Air Conditioning, Internet, Satellite / Cable

Key West Bahama Gardens - Private Historic Old Town

  • 4 BR/1 BA, 1 half bath House (sleeps 8)
    $3,000 - $4,000/wk
    $8,000 - $9,000/month
    per property, accept credit card, Near The Ocean, Town, Jacuzzi, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable

Key West 'NOONA'S MANSION-by-the-SEA @ THE ANNEX' Sumptuous 7BR/5.5BA Home with Pool...

  • 7 BR/5 BA, 1 half bath House (sleeps 14)
    $11,000 - $14,900/wk
    $39,000 - $55,000/month
    per property, accept credit card, Downtown, Near The Ocean, Private Pool, Jacuzzi, Balcony, 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) accept credit card, Near The Ocean, Waterfront, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

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

  • 1 BA Studio (sleeps 2)
    $115 - $230/nt
    $750 - $1,500/wk
    per property, accept credit card, Near The Ocean, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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

  • 2 BR/2 BA, 1 half bath Townhome (sleeps 6)
    $1,600 - $1,800/wk
    per property, accept credit card, Near The Ocean, Town, Lawn / Garden, terrace, Balcony, pets considered, Air Conditioning, Internet

Key West Villa Nomade, Elegant Truman Annex condo in Old Town

  • 2 BR/1 BA Condo (sleeps 4)
    $1,200 - $1,500/wk
    per property, accept credit card, Near The Ocean, Town, Communal Pool, Lawn / Garden, Air Conditioning, Satellite / Cable, Television, DVD Player

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

  • 2 BR/1 BA Condo (sleeps 5)
    $1,125 - $2,000/wk
    per property, accept credit card, Downtown, Near The Ocean, Communal Pool, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player
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