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Our Islamorada Vacation Rentals section features the following homes, villas, cabins, cottages or condos listed below. Please click on the description to view any of the Islamorada rentals you see listed for more information. Vacation rentals in Islamorada, Florida are added and updated every week, so please bookmark us and visit again. Be sure to check out Tavernier (9 miles), Long Key (13 miles), Key Largo (17 miles), Duck Key (20 miles), Grassy Key (22 miles), and Key Colony Beach (28 miles) for additional vacation rental choices. Notice a problem with our distances? Report it here.

Photo's available Pets? please inquire Swimming pool Jacuzzi Availability Calendar
Min Rate Max Rate Per Property Type Beds Baths Pets Pool Jacuzzi
          Type Bed  Bath  Sleeps Rates or Community Sort By
 Condo 1 1 2-4 $500-$600 USD/wk Islamorada studio condominium
 Condo 1 1 1-4 $700-$950 USD/wk Seagulls oceanfront condos on Atlantic Ocean
 Condo 1 1 1-2 $600-$700 USD/wk Doug's Backwater Flat on Florida Bay w/marina
 Condo 1 1 1-3 $700-$900 USD/wk Sea Gulls Condos on The Atlantic Ocean
 Condo 1 1 3 $500-$650 USD/wk Summer Sea Condominium
 Condo 1 1 1-4 $750-$950 USD/wk Spectacular Oceanfront condo with breathtaking views
 Condo 1 1 2-4 $1800-$2500 USD/mth Incredible Bay Views!!! ••• Summer Sea Condo ••• Heated Pool
 House 1 1 2 $700-$900 USD/wk Serenity Waterfront w/Dock, View, Jacuzzi, Tiki Hut
 Cottage 1 1 2 $1000-$1200 USD/wk Quiet Open Water Overlooking Nature Refuge
 Cottage 1 1 1-4 $900-$1200 USD/wk The Perfect Location for The Perfect Vacation Quiet Clean
 Condo 1 1 4 $700-$800 USD/wk Summer Sea Majestic Beauty
 Condo 1 2 2-4 $1200-$1300 USD/wk Holzman's Bayside; condo on Florida Bay
 Apartment 2 1 1-2 $1500-$1500 USD/mth 2 bed,1bath furnished Apt-canal front-private beach
 House 2 1 1-4 $1200-$1400 USD/wk Keys Villa. Private Secluded House on the Bay.
 Duplex 2 1 1-5 $600-$1000 USD/wk Plantation Key Paradise
 House 2 1 4-6 $900-$1200 USD/wk Deep Water Paradise
 Cottage 2 1 4-5 $1350-$1550 USD/wk Oceanfront Cottage
 House 2 1 4-6 $950-$1200 USD/wk Cocktail Cottage in Paradise
 House 2 1 4 $2000-$2500 USD/yr +++Comfortable, Relaxing Islamorada 2/1 Home++
 House 2 1 5-6 $600-$1200 USD/wk bay front cottage
 House 2 1 4-6 $700-$750 USD/wk Paradise Retreat
 Villa 2 1 2-4 $1200-$1400 USD/wk Quiet Open Water Wild Life Sanctuary
 Condo 2 4-6 $600-$850 USD/wk * * * Awesome Islamorada Getaway * * * Paradise Awaits * * *
 Townhome 2 8 $2600-$2800 USD/mth Executive Bay Club - Islamorada Vacation in the Florida Keys
 Townhome 2 8 $2100-$2500 USD/mth Executive Bay Club Townhome
 House 2 2 6 $1500-$1800 USD/wk By The Sea / Weekly Rental
 Condo 2 2 2-6 $600-$950 USD/wk Tropical Paradise at Futura Yacht Club
 Condo 2 2 6 $700-$950 USD/wk Florida Keys Vacation Rental an Ocean Front Paradise
 House 2 2 2-6 $1300-$1500 USD/wk Deep Water Canalfront Home W/ Boat Ramp
 Villa 2 2 4-8 $1100-$1300 USD/wk Keys Kottage A villa in secluded hammock on Florida Bay
 Condo 2 2 2-6 $800-$1400 USD/wk Futura Yacht Club - Penthouse - Marina & Deeded Boat Slip
 Condo 2 2 4-6 $700-$1350 USD/wk Islamorada Paradise on the Bay
 Townhome 2 2 2-6 $2500-$2700 USD/mth Executive Bay Club at Islamorada, Florida Keys. 2/2 Townho
 Townhome 2 2 6-8 $2100-$2600 USD/yr Gated - 2/2 w/ Pool & Private Beach-Fall Special Available!
 Condo 2 2 6 $850-$1200 USD/wk Lovely Futura condo, Bay views, pool, dockage
 Townhome 2 2 8 $1900-$3500 USD/mth "Tommy Bahama " Bayside Beauty Townhouse - sleeps 8
 Townhome 2 2 2-8 $1800-$2500 USD/mth Executive Bay Club / Islamorada Vacation Paradise
 House 2 2 4-9 $2000-$4500 USD/mth Florida Keys Waterfront Home
 House 2 2 5 $1500-$1800 USD/wk " The White Marlin Beach House "
 Condo 2 2 6 $900-$1300 USD/wk Oceanfront 2BR/2BA Condo in Paradise
 Condo 2 2 6 $800-$1100 USD/wk Tropical Getaway at Futura Yacht Club
 House 2 2 6 $2600-$2600 USD/wk Lo-Key Estates Guest House Three
 Condo 2 2 4-6 $850-$1500 USD/wk Oceanfront condo Plantation Key screened porch and internet
 House 2 2 6-8 $5000-$5000 USD/mth Matecumbe Paradise
 House 2 2 5-7 $950-$1700 USD/mth Plantation Key Colony Dream Home!
 Townhome 2 2 4-8 $2800-$2800 USD/mth Executive Bay Club
 House 2 2 3-8 $3000-$3500 USD/mth Ocean side Lower Matecumbe
 Condo 2 2 4 $3500-$4500 USD/mth Beacon Reef Condo - Available Winter 2008!! Oceanview!
 Townhome 2 3-6 $1200-$1950 USD/wk Port of Call Townhomes
 Townhome 2 6-8 $1200-$1600 USD/wk Futura Townhouse- Pool! Dockage!
 House 2 3 4-6 $950-$1250 USD/wk Canal front home in paradise, Islamorada/Get away & relax!
 House 3 2 6-8 $1900-$2200 USD/wk Villa Marlin, private sandy beach
 House 3 2 7 $1500-$1800 USD/wk Tejas Chickee / Weekly Rental
 House 3 2 6-8 $1500-$2000 USD/wk Paradise Found - Oceanside with Pool
 House 3 2 6 $1500-$1650 USD/wk Casa Linda Vacation Home Rental
 House 3 2 6-10 $1250-$1500 USD/wk Ocean View House, Protected Dockage, Private Island Retreat!
 Villa 3 2 6-8 $1650-$1850 USD/wk Beautiful Captain's Cove
 House 3 2 6-8 $2000-$3300 USD/wk The Russell Estate, Beautiful 2 acre oceanfrnt w/ beach, DSL
 House 3 2 6-8 $2000-$3300 USD/wk Private Resort-Like, Oceanfront Estate, DSL
 House 3 2 6-7 $1650-$1800 USD/wk Venetian Shores 3 bd 2 ba Deep Water Tropical Paradise
 House 3 2 8 $4200-$4200 USD/wk Lo-Key Estates Guest House One
 House 3 2 12 $3650-$3650 USD/wk Lo-Key Estates Guest House Two
 Condo 3 2 6-8 $1200-$1500 USD/wk 3/2 bayview condo Futura Yacht Club
 House 3 2 6 $1500-$2500 USD/wk Islamorada Canalfront 3/2 with Dockage
 House 3 2 6-8 $3750-$3750 USD/mth Beautiful Beach House
 House 3 2 6 $5000-$6000 USD/mth Madeira Bay Beauty
 Condo 3 2 6-8 $800-$1600 USD/wk Futura Yacht Club Condominium - Boat Slip - 3BR
 House 3 2 10 $1000-$1600 USD/wk Islamorada Ocean View Home
 House 3 2 8-10 $1500-$7500 USD/mth Boater's Delight/Fishing Paradise
 House 3 2 5-6 $1600-$2500 USD/wk Florida Keys Dream Home
 Condo 3 2 8-10 $2400-$2600 USD/mth Executive Bay Club
 House 3 2 5-6 $2500-$2750 USD/wk Port Anigua Paradise MM74
 House 3 2 2-6 $5500-$5500 USD/mth Oceanfront Private Home On Sandy Beach
 House 3 2 6-8 $4900-$4800 USD/mth Morada Bay Paradise on the Bay
 House 3 2 6-8 $5000-$6500 USD/mth Key Lime Treat
 Condo 3 6-8 $1900-$2500 USD/wk Beautiful Bay Harbour Condo w/a 30' Dock for your Boat!
 House 3 4-6 $1300-$1600 USD/wk Islamorada Tropical Escape
 Townhome 3 8 $2500-$4000 USD/mth Luxury! Bayside 3 BR - Keys Paradise with Boat Slip!
 House 3 2-6 $1650-$2500 USD/wk Oceanfront Luxury on Bonefish Flat with 63' of Dockage
 House 3 6-8 $2200-$3000 USD/wk New Waterfront Pool Oasis in Islamorada
 House 3 3 6-8 $1100-$1400 USD/wk This is Paradise,waterfront home, with large dock.l
 House 3 3 2-6 $1500-$1800 USD/wk Honey Azalea / Weekly Rental
 House 3 3 2-6 $2000-$2000 USD/wk Kingfisher / Weekly Rental
 House 3 3 2-8 $1700-$2600 USD/wk Sea House/ Weekly Rental/POOL
 House 3 3 6-8 $5000-$5000 USD/mth Exquisite Port Antigua Waterfront Home with Sandy Beach
 House 3 3 6-8 $10000-$12000 USD/mth West Indies Bayfront
 Duplex 3 3 4-6 $1800-$2850 USD/wk Florida Keys Vacation Rental -Beachfront in Paradise
 House 3 3 8-10 $1350-$1800 USD/wk Piece of Paradise in Islamorada
 House 3 3 6-10 $1500-$2000 USD/wk My Father's House
 House 3 3 2-8 $900-$1500 USD/wk Waterfront Jewels/Private beach/ With Dock & Boat Ramp
 House 3 3 7-10 $2800-$3200 USD/wk Islamorada-Getaway Cedar Chalet
 House 3 3 6-7 $2650-$3250 USD/wk NEW! House, 3-story Luxury home 100' Dock
 House 3 3 2-10 $1200-$1800 USD/wk Ocean Side Island Getaway...
 Townhome 3 3 8-10 $3000-$4300 USD/mth Sunset View at Executive Bay Club
 House 3 3 8-10 $1200-$1500 USD/wk Tropical Waterfront Paradise
 House 3 3 5-7 $1000-$3500 USD/wk Secluded Luxury Estate
 House 3 3 6 $1600-$2000 USD/wk Tarpon Cove
 House 3 3 6-8 $3800-$4500 USD/wk Unique Oceanfront with Pool & Deepwater Dockage
 House 3 3 6-8 $1200-$1600 USD/wk Oceanside Canal Home - Tropical Paradise
 House 3 3 8 $4000-$4700 USD/wk Ocean Front, Pool, Beach, 5 Acres..."Peaceful Palms"
 Condo 3 2-6 $1500-$2500 USD/wk Beautiful Ocean & Bay at Sandy Cove w/ up to 30" Boat Slip
 House 3 6-8 $5000-$7000 USD/mth Venetian Dream
 House 4 2 4-8 $1750-$2500 USD/wk Tropical Oasis! LAKEFRONT Retreat Near BEACH!
 House 4 2 4-10 $1200-$1800 USD/wk Islamorada Jewel- 2 Homes in 1!!
 House 4 3 8-10 $3000-$3500 USD/wk The PERFECT getaway with brand new HEATED swimming pool
 House 4 3 2-8 $4000-$5000 USD/wk Islamorada Oceanfront Executive rental
 House 4 3 6-8 $2200-$3000 USD/wk Bayfront Paradise Pool Home on the Bay
 House 4 3 6-8 $2750-$3250 USD/wk Sunset Paradise
 House 4 3 8-10 $1900-$2400 USD/wk Fabulous View, Split 2/2up,2/1 Down Ideal for 2 families
 House 4 3 12 $4700-$4700 USD/wk Lo-Key Estates Main House
 House 4 3 8 $4000-$5500 USD/wk Islamorada Oceanfront Vacation Rental Home
 House 4 3 8-10 $2300-$3000 USD/wk Summer Special Weekly Rate $2300.00
 House 4 3 6-8 $3500-$4500 USD/wk Executive and Immaculate Pool Home - April and May Specials
 House 4 3 10 $1500-$3000 USD/wk Ocean Front, Beach "The Beach House"
 House 4 3 8 $1600-$2200 USD/wk Gardenia Bay
 House 4 8-10 $3200-$3500 USD/wk Islamorada Waterfront Pool Home
 House 4 2-8 $1650-$2200 USD/wk Island Oasis! HTD POOL/Walk to BEACH!
 House 4 8 $2000-$3000 USD/wk Beautiful home with Great Dockage - April and May Specials
 House 4 4 10 $2800-$6500 USD/wk Islamorada, Canal Front, Beautiful 4BR 4BA Pool Home
 House 4 4 10 $4000-$6000 USD/wk Bay Front, Pool, Dockage... "Nautica"
 House 4 10 $4000-$6000 USD/wk Ocean Front, Pool, Sandy Beach "Turtle Nest Estate"
 House 5 3 8-12 $3000-$3500 USD/wk Dream home in the keys With Heated Pool
 House 5 3 12-14 $15000-$18000 USD/mth Marchettiville
 House 5 13 $8000-$8000 USD/wk Southern Diversion Estate
 House 5 4 10 $2000-$3500 USD/wk Sailfish / Weekly Rental
 House 5 4 13-14 $4900-$6000 USD/wk Oceanfront compound in the heart of Islamorada
 House 5 4 16 $4000-$6500 USD/wk Oceanfront Oasis. 5 bed, 4 bath beachfront retreat
 House 5 3-8 $3500-$5500 USD/wk BRAND NEW & Beautiful Waterfront Home in Venetian Shores
 House 5 5 10-14 $5000-$6800 USD/wk May Specials! Bayfront Sanctuary 5 bdr 5 bth Pool Hot Tub
 House 6 4 10-13 $3000-$4900 USD/wk Bayview Place
 House 6 4-10 $3600-$3600 USD/wk Bayfront Islamorada
 House 6 6-12 $7000-$8500 USD/wk La Casa Grande with Dirct ocean veiw & acess
 House 8 5 8-24 $850-$6500 USD/wk SuCasa Vacation Rentals
 House 10 18-20 $10000-$20000 USD/wk Keys Oceanfront Mansion - Keys Largest Vacation Rental Home
 House 10 8 25-29 $4900-$11000 USD/wk Alligator Reef: Luxury Compound