This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Islamorada Area Vacation Rentals Show this location only Back to top
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Blue Water Retreat
3BR/3BA
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Sleeps 6-8
– Lower Matecumbe Key #254988
$5000- $6800/mo
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Family Fun Fishing House
3BR/2BA
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Sleeps 6-8
– Lower Matecumbe Key #301732
5000.00 month
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My Paradise
3BR/2BA
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Sleeps 6
– Lower Matecumbe Key #299711
$6500- $8500/mo
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Island Get-a-Way Beautiful Canalfront Home
3BR+/3BA
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Sleeps 6-8
– Islamorada #97140
$1500 to $4500
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Limitless Bayfront View-Private Boat Basin-Blue, Blue Water!
5BR/4BA
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Sleeps 10
– Islamorada #108671
$11,400/mo
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Islamorada - Ocean Front House - Dazziling Sunsets.
5BR+/5BA
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Sleeps 12-14
– Islamorada #394116
$3500 - $4200 per week 7 night min stay
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The Perfect Vacation Home in Islamorada
2BR/2BA
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Sleeps 4-6
– Islamorada #120966
$1400.00/wk-$3200- $3500/mo
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New on the Market
1BR+/1BA
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Sleeps 4-5
– Lower Matecumbe Key #326043
$3500/mo
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Islamorada Beachfront Apartment - Spectacular Sunsets!
1BR/1BA
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Sleeps 1-2
– Lower Matecumbe Key #163451
$2250- $3000/mo
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Ocean Front Jewel, Private Pool,70 Ft Dock,Best Deal Around
4BR/2BA
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Sleeps 2-12
– Islamorada #360140
$300-$500 /nt- $2100-$3300/Week
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Discover the Charm of Island Living
2BR/2BA
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Sleeps 4-6
– Islamorada #260818
$750 - $1050 per week 7 night min stay
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Upscale "Nautica" - Private Boat Basin - Sunset in Backyard
4BR+/4BA
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Sleeps 8-10
– Islamorada #174286
$18,000/mo
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Keys Home in Anglers Reef with Ocean View, Dock, Comm. Pool & Beach
2BR+/2BA
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Sleeps 6
– Islamorada #431498
$1800 - $2100 per week
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Sunset Serenity
3BR+/3BA
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Sleeps 6-8
– Islamorada #384431
$5500- 7500/month
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Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier.
2BR+/2BA
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Sleeps 6-8
– Islamorada #299387
$500/nt
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Islamorada Pool Home Tropical Paradise
4BR+/2BA
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Sleeps 8-10
– Islamorada #279389
$2,700- $2,900/wk
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Simplicity
4BR/4BA
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Sleeps 8-12
– Plantation Key #455972
$3500 per week 7 night min stay
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Florida Keys Newly Renovated Townhouse in Gated Executive Bay Club
2BR/2BA
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Sleeps 8
– Plantation Key #3554611ha
$3080 - $3500 per month
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Fishermans Dream-Canal Home- Plantation Key - Islamorada
3BR/3BA
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Sleeps 5-10
– Plantation Key #350137
$2200- $3500 monthly
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2 Bedroom Condo in Oceanfront Complex
2BR/2BA
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Sleeps 4
– Islamorada #461457
$2200- 3600 per month
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Ocean Front Beach House
2BR/2BA
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Sleeps 6
– Islamorada #3581117ha
$3500 per week 7 night min stay
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Fishermans Paradise
3BR+/3BA
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Sleeps 6-10
– Islamorada #382421
1000.00 - 4000.00
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Paradise in the Florida Keys
White Sandy Beach as the Backyar
5BR+/3BA
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Sleeps 12-16
– Lower Matecumbe Key #401727
2000- 3000/wk
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Canal Front Home Islamorada - Venetian Shores Tiki Hut Fun!
2BR+/2BA
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Sleeps 6-8
– Islamorada #256458
$1000/wk - $2700/mo
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Completely Renovated Executive Bay Steps to Tennis Court/Poo
3BR+/2BA
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Sleeps 10
– Plantation Key #373291
$2,800/mo
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Newly Renovated Luxury Townhome at Executive Bay Club
2BR+/3BA
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Sleeps 9-11
– Islamorada #194989
$1100/wk - $3000/mo
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Cute & Clean Ground Level Bayside Canal Front Home
3BR+/3BA
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Sleeps 6-8
– Islamorada #140924
$2950- $3500/mo
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Vacation Home with Dock on Ocean Side!
2BR/1BA
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Sleeps 7
– Plantation Key #318710
From $1199/wk - $2299/mo
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Two Bedroom Ocean View Condo with Oceanside Pool & New Updates
2BR+/2BA
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Sleeps 5
– Islamorada #379281
Weekly $800- $1400/Monthly $2400-$3400
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Oceanfront Anglers Reef, Islamorada, Florida Keys, Video Tour
2BR/2BA
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Sleeps 6
– Islamorada #220235
$199 - $228 per night 5-7 night min stay
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Beautiful Captain's Cove
3BR/2BA
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Sleeps 8
– Islamorada #30773
$122 - $325 per night
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Fisherman's Paradise with 30 Foot Boat Slip and Pool
3BR+/2BA
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Sleeps 8
– Long Key #227285
$1750/wk
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Beautiful Waterfron/ Home with Easy Gulf & Ocean Access
3BR/2BA
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Sleeps 6
– Islamorada #59813
$1500- $2000/wk
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Luxury Townhome on a Private Beach, Great Views, Low Rates.
2BR+/1BA
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Sleeps 5
– Lower Matecumbe Key #283873
From $999.00 wk
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Islamorada – Simply Beautiful with Free Wifi & Many Extras
2BR+/2BA
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Sleeps 6
– Islamorada #397581
$180 - $250 per night 5 night min stay
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Futura Yacht Club- Penthouse Views - Get June and Fall Discounts Now
2BR/2BA
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Sleeps 4
– Islamorada #115485
$840 per week 7 night min stay
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Bay Front Beauty/ Summer Sea Must See!!!!
1BR+/1BA
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Sleeps 2-4
– Islamorada #197265
$700-$880/wk - $2100-$2950/mo
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Piece of Paradise in Islamorada
3BR+/3BA
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Sleeps 6-8
– Islamorada #158055
$1000- $1800/wk
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Venetian Dream Home
3BR+/4.5BA
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Sleeps 6-8
– Islamorada #163654
$4700- $6000/mo
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Islamorada Sandy Cove - Keys Paradise!
1BR+/1BA
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Sleeps 4
– Lower Matecumbe Key #283705
Contact Owner for Rates
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Secluded Stunning Oceanview Townhome
2BR+/2BA
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Sleeps 4-6
– Islamorada #274548
$1200-$1800/wk - $3500-$6000/mo
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Tropical Vacation Paradise Awaits You in Islamorada
4BR/2BA
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Sleeps 6-8
– Islamorada #44275
$1400-$1900/wk - $3000-$5000/mo
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Beautiful New Home in Island Paradise - Ideal for 2 Small Families
5BR/3BA
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Sleeps 10
– Islamorada #255007ha
$1283 - $4000 per week
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3BR/3BA Beautiful Waterfront Home Monthly Rental
3BR/3BA
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Sleeps 6
– Islamorada #152327
$6,000/mo
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Futura Yacht Club Bayside Condominium and Marina Dockage, Islamorada
3BR+/2BA
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Sleeps 6-8
– Islamorada #417149
$1000 - $1250 per week 7 night min stay
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Paradise - in Pristine Condition with Private Pool
5BR/4BA
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Sleeps 10
– Islamorada #236597
$3250/wk - $8250/mo
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Lobster Season Available! Lower Matecumbe Key, Islamorada
3BR+/2BA
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Sleeps 8-12
– Lower Matecumbe Key #67419
$1250- $2500/wk
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Pool/Spa Oceanside Home with 70' Seawall - Perfect Location
5BR+/4BA
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Sleeps 10
– Plantation Key #105279
$2500- $3750/wk
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Two Secluded Ocean Front Cottages with 235ft of Beachfront
3BR+/3BA
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Sleeps 6-8
– Islamorada #339953
$500 per night 5 night min stay
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Tarpon House at Bonefish Bay, Islamorada's Luxury Community
4BR/4.5BA
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Sleeps 8
– Lower Matecumbe Key #231149
$4000-$6000/wk - $12,500-$15,000/mo
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Oceanfront Islamorada Condo with Boat Slip
3BR+/2BA
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Sleeps 6-8
– Islamorada #147437
$4500 - $5000/month
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Keys Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip and Pool
2BR+/1BA
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Sleeps 4-6
– Islamorada #437741
$3200 per month 30 night min stay
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Ocean Front Views from Every Room
2BR+/2BA
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Sleeps 4-6
– Islamorada #384409
$2,850/mo
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Luxury Apartment - Sea View
1BR/1BA
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Sleeps 1-2
– Lower Matecumbe Key #132175
$3000/mo
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Immaculate Bay Harbour Condominium Ocean View and Boat Dock
3BR/2.5BA
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Sleeps 6-8
– Islamorada #248011
$2000-$3000/wk - $5000-$7500/mo
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Venetian Shores Saltwater Canal Front Pool Home
4BR/4BA
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Sleeps 10
– Islamorada #257828
$6000/mo
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Immaculate Spacious Ocean View Penthouse - Look at the Pictures
3BR/2BA
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Sleeps 6
– Lower Matecumbe Key #437229
$1700- $2300/week
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Premier Townhouse in Gated Community
2BR+/2.5BA
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Sleeps 4-6
– Islamorada #226011
$1200- $1500/wk
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Executive Bay Club Townhome - Cottage Style
2BR/1BA
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Sleeps 4
– Islamorada #307158
$1050 per week 7 night min stay
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Cute/Ocean Side/Great Fishing
2BR/1BA
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Sleeps 4
– Islamorada #407356
$800- $900/wk US
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Private and Secluded with Ocean View Special Rate for Fall
2BR+/2BA
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Sleeps 4-6
– Lower Matecumbe Key #275334
$1000-$1200/wk - $3800/mo
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100' Canal Front House W/ Sweeping Views Close to Point
3BR+/2BA
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Sleeps 6-9
– Islamorada #397831
$1500/wk $3500/mo US Dollas
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Affordable Oceanfront Luxury Rental in Florida Keys
3BR+/3.5BA
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Sleeps 6-8
– Long Key #249553
$3500- $5500/mo
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'Villa Vanessa' is Rigth for You!!!! Beautiful Canal Front Home
4BR/3BA
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Sleeps 6-11
– Plantation Key #438241
$1400- $1900/week, $3300-$3800/month
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Executive Bay Townhome
2BR/2BA
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Sleeps 6
– Islamorada #206153
$700/wk - $2750/mo
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Islamorada Getaway
2BR+/1BA
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Sleeps 4-6
– Islamorada #438303
$125 per night 6 night min stay
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Retreat in Florida Keys Oceanfront Paradise
2BR+/2BA
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Sleeps 4-6
– Islamorada #300388
From $2,275/wk - $5,000/mo
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Luxury Duplex with 70' Dock on Deep-Water Canal
2BR+/1BA
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Sleeps 4-6
– Lower Matecumbe Key #343579
$1100 per week 7 night min stay
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Ocean View Luxury Completely Renovated Home on the Water!
3BR+/3BA
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Sleeps 8
– Islamorada #423687
$2500-$3000/wk - $6000-$7500/mo
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A Perfect Getaway in the Beautiful Florida Keys
2BR/1BA
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Sleeps 4-6
– Plantation Key #452491
From $850 to $1200
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Waterfront Home. Huge Lot 120ft Seawall -20ft Boat Ramp
2BR+/2BA
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Sleeps 6
– Lower Matecumbe Key #378941
$1,600 - $1,900
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Perfect Location-Deep Water Canal W/Private Beach Access!
3BR/4BA
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Sleeps 6
– Lower Matecumbe Key #385271
$4,000.00 monthly
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Welcome to Paradise!
1BR+/1BA
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Sleeps 2-4
– Islamorada #365620
From $1000/mo off season
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Pool, Spa, Deep Water 17k Boat Lift, 3-4bedrooms, Fishing and Diving
4BR/4BA
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Sleeps 6-8
– Islamorada #452073
$10002 per month 28 night min stay
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Newly Remodeled Home in Great Location with Private Beach
3BR/2BA
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Sleeps 6-7
– Lower Matecumbe Key #369928
$250/nt
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Available Oct-Nov-Dec 2013 April-May-June 2014
2BR+/3BA
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Sleeps 4-9
– Lower Matecumbe Key #382032
$3500/mo
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Oceanfront Townhouses Free Dockage... Plantation Key
2BR+/2.5BA
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Sleeps 6
– Islamorada #3234
From $ 1000/wk
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Beautiful Futura Yacht Club - Islamorada Florida
2BR+/2BA
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Sleeps 2-5
– Islamorada #239069
$110 per night 5 night min stay
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Panoramic Ocean View, Sand Beach, Private Luxury Complex
2BR+/2BA
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Sleeps 6
– Islamorada #286399
$1300 - $1800 per week 7 night min stay
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Paradise Found - Oceanside with Pool
3BR/2BA
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Sleeps 8
– Islamorada #15808
$1,500- $2,000/wk
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Special Offers! Adorable 2BR Cottage with Pool & Ocean Access for Boat
2BR/1BA
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Sleeps 4
– Islamorada #98286
From $100/nt - From $750/wk
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Luxury,Elegant,Water Front Home,Heated Pool,Plantation Key,Islamorada
3BR/2BA
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Sleeps 8
– Plantation Key #119991
$1,800- $2,000/week
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Ocean Beach Retreat with Private Sandy Beach
3BR/3BA
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Sleeps 8
– Lower Matecumbe Key #47317
$2100-$2900/wk - $6200-$7500/mo
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Affordable Rates, Beautiful Home with Dockage, Optional Boat Charter
2BR+/2BA
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Sleeps 4-6
– Islamorada #133481
$1100/wk $4400/mo
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A Little Piece of Paradise!
Studio/1BA
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Sleeps 2
– Islamorada #6170
From $475. to $1500.
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Boat, Fish, Swim from Your Own Dock! Vr-003
3BR+/2BA
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Sleeps 6
– Islamorada #32885
$1400- $1815/wk
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Luxury Oceanfront Townhouse
4BR+/2BA
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Sleeps 8
– Long Key #9198
From $1750/wk
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Magnificent Sunrises Await You at This Oceanfront Condominium
2BR/2BA
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Sleeps 4-5
– Islamorada #18699
$900 - $1400 per week 7 night min stay
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Oceanfront-We Got it All- Gated Water 3 Sides 30' Dock - Private Pool
3BR/2BA
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Sleeps 6
– Lower Matecumbe Key #311382
$2975 - $3500 per week 7 night min stay
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Spectacular Top Floor Oceanfront View Condo
1BR+/1BA
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Sleeps 4
– Islamorada #259007
$750- $950/wk
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Atlantic Ocean Beachfront Duplex with Private Dock
2BR+/1BA
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Sleeps 4-6
– Layton #29457
From $250/nt - $1675/wk - $4500/mo
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Fabulous View, Split 2/2 up, 2/1 Down, Ideal for 2 Families
4BR+/3BA
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Sleeps 8
– Lower Matecumbe Key #80833
$5200/ $6200 or weekly $2200/2600
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Oceanside Resort Home for Elegant Get Away
2BR+/2BA
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Sleeps 6-8
– Islamorada #306819
$290 - $350 per night 2-7 night min stay
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Beautiful Bay Harbour with 30 Foot Deep Dockage
3BR/2BA
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Sleeps 3-6
– Islamorada #250672
$2500wk - $6500/mo summer season
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Just Another Day in Paradise. Canal Front Venetian Shores.
3BR/2BA
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Sleeps 8
– Islamorada #196037
$2900- $5900/mo
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Islamorada Waterfront Paradise Getaway
Studio/1BA
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Sleeps 2
– Islamorada #213752
$1400 per week 7 night min stay
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The Perfect Getaway with Brand-New, Heated, Swimming Pool
4BR/3BA
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Sleeps 8-10
– Islamorada #29889
$2000- $3500/wk
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Beautiful Pool Home Quick Ocean/Bay Access Heated Pool
4BR/3.5BA
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Sleeps 8-10
– Islamorada #113175
Inquire for rates
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Doug's Backwater Flat Islamorada on the Bay
1BR/1BA
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Sleeps 2
– Islamorada #72443
$4165 per week 7 night min stay
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Southern Diversion Estate Great Wedding Venue
5BR+/3BA
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Sleeps 13
– Islamorada #209276
6900
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Blue Water Retreat
3BR/3BA
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Sleeps 6-8
– Lower Matecumbe Key #254988
Overview of Islamorada Area Vacation Rentals
Islamorada House Rentals are the Ultimate Way to Experience the Florida Keys
For lovers of water activities, the Florida Keys can't be beaten as a vacation spot. The Islamorada area in the lower Keys has some of the best sport fishing in the world, as well as snorkeling, scuba diving, boating and parasailing, all in an environment that averages 75-80 degrees year-round.
The best way to experience the Florida Keys are through Islamorada house rentals. Sure, you could stay in a hotel room, but why do that when you could enjoy your morning coffee and breakfast on the front porch of your private beachfront home? And after an exhilarating but tiring day on the water, you can come "home" to grill your catch and relax in peace and comfort. With Islamorada vacation rentals you CAN have it all!
Incredible Beaches
From your Islamorada beach rentals home venture out to explore the plethora of great beaches; the beach at Plantation Yacht Harbor boasts a nice and deep swimming area. There's great snorkeling at Islamorada County Park, where the beach runs along a natural creek. But watch out for the strong currents here, especially if you're traveling with children. For a cozy beach with a boardwalk, go to Anne's Beach on Lower Matecumbe Key. There are plenty more. Just ask any local to point you in the direction of a great beach.
Enjoy a Night on the Town
Many local restaurants will cook your catch; just because you're staying in Islamorada house rentals, it doesn't mean you have to cook. You're on vacation. Use your Islamorada beach rentals property for the convenience it brings to brew a cup of morning coffee or do a load of laundry without searching for a laundromat, then get the best of both worlds by dining out and partaking of the area's rich nightlife.