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Florida Keys Rentals

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SPECIAL OFFER! 4 bed 5 bath waterfront pool & dock home April 26 - May 31

Marathon Marathon Pool Home, 135 Ft. Dock, Waterfront, Balcony Sleeps 10

  • 4 BR/5 BA House (sleeps 10)
    $2,100 - $5,259/wk
    per property, accept credit card, Near The Ocean, Waterfront, Private Pool, Tennis Court, terrace, Balcony, Air Conditioning, Internet
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
SPECIAL OFFER! April and May reduced rate weeks April 12 - June 7

Marathon PEACE AND HAPPINESS...Luxury Oceanfront ..Heated oceanside pool

  • 3 BR/3 BA House (sleeps 8)
    $371 - $543/nt
    $2,600 - $3,800/wk
    per property, wheelchair accessible, Beach, Near The Ocean, Town, Waterfront, Private Pool, Lawn / Garden, terrace, Air Conditioning, Internet, Satellite / Cable
SPECIAL OFFER! Special Rate for April, 2014 April 12 - May 3

Marathon Rent Your Own Private Island- Seabird Key, Marathon, Florida

  • 3 BR/3 BA House (sleeps 8)
    $6,295 - $7,995/wk
    per property, accept credit card, Beach, Lawn / Garden, terrace, Balcony, Internet, Satellite / Cable, Television

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 ‘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 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

Marathon *$1395 wk 3/2.5 Lg Gulfside House with Dock & Cabana Club

  • 3 BR/2 BA, 1 half bath House (sleeps 8)
    $1,395 - $2,095/wk
    per property, pets considered, limited accessibility, Near The Ocean, Waterfront, Private Pool, Communal Pool, Air Conditioning, Internet, Satellite / Cable

Big Pine Key Spectacular Oceanfront Views Directly On The Water! Minimum 28 days!

  • 2 BR/2 BA House (sleeps 6)
    $3,136/month
    per property, pets considered, Lawn / Garden, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

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 Largo Brand New 3 Bedroom 3 Bathroom Townhome in Luxurious Resort

  • 3 BR/3 BA Condo (sleeps 7)
    $275 - $375/nt
    $1,750 - $2,450/wk
    $7,500 - $9,750/month
    per property, Hot Tub, Resort, Communal Pool, Lawn / Garden, Balcony, Fitness Room / Equipment, Air Conditioning, Internet

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

Cudjoe Key Water Front, Private Boat Dockage, Heated Private Pool, Minutes From Key West.

  • 4 BR/2 BA House (sleeps 8)
    $2,400 - $3,100/wk
    per property, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

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

Big Pine Key On a Deep Water Canal with Open Water Views! - A Gift From the Sea

  • 2 BR/2 BA House (sleeps 6)
    $1,300 - $1,500/wk
    $3,800 - $4,000/month
    per property, accept credit card, Waterfront, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player, Parking

Big Pine Key Explore the Keys! Canal Front Property - Beautiful Sunsets

  • 2 BR/1 BA, 1 half bath House (sleeps 8)
    $2,700/month
    per property, accept credit card, Beach, Waterfront, Balcony, Air Conditioning, Internet, Satellite / Cable, DVD Player

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 Largo Waterfront Key Largo luxury home with Bay access!!

  • 3 BR/2 BA, 1 half bath House (sleeps 6)
    $210 - $315/nt
    $1,300 - $1,550/wk
    $4,000 - $4,500/month
    per property, accept credit card, pets considered, Near The Ocean, Waterfront, terrace, Balcony, Air Conditioning, Internet, Satellite / Cable

Marathon Florida Keys Beach Home Heated pool Docks

  • 2 BR/2 BA Condo (sleeps 6)
    $125 - $350/nt
    per property, accept credit card, Hot Tub, Beach, Waterfront, Communal Pool, Jacuzzi, Tennis Court, Balcony, Air Conditioning

Marathon Oceanfront (Gulf) Condo, Fabulous Views, Heated Pool & Dock

  • 2 BR/2 BA, 1 half bath Condo (sleeps 6)
    $1,086 - $1,686/wk
    per property, Near The Ocean, Waterfront, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television, DVD Player

Key Largo Luxury Bayfront Estate

  • 6 BR/4 BA, 2 half baths Estate (sleeps 12)
    $6,000/wk
    $22,000/month
    per property, Waterfront, Private Pool, Lawn / Garden, terrace, Balcony, Fitness Room / Equipment, Air Conditioning, Internet

Key West Luxury 2 Bedroom 2.5 Bath Condo On Duval Street. Great Location 'NEW LISTING'

  • 2 BR/2 BA, 1 half bath Condo (sleeps 4)
    $365 - $495/nt
    $2,236 - $3,150/wk
    $8,944 - $12,150/month
    per property, wheelchair accessible, Downtown, Communal Pool, Balcony, Air Conditioning, Internet, Satellite / Cable, Television

Marathon Manatee Bay - 5 bdr-Sleeps 12+ Special Lower Fall Rates

  • 5 BR/4 BA House (sleeps 14)
    $3,300 - $7,800/wk
    $13,200 - $13,600/month
    per property, accept credit card, wheelchair accessible, Near The Ocean, Waterfront, Private Pool, Balcony, Air Conditioning, Internet, Satellite / Cable
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