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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Islamorada Paradise, Vacation Home on the Water
3BR/2BA
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Sleeps 6
– Islamorada #12753
From $1300 a wk/ $3,000 mo
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Cozy Keys Getaway- Great Dockage- Wifi-Clean & Open-Fishing Dream!
3BR/3BA
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Sleeps 6
– Islamorada #24330
Starts From $1000/wk (Fall) - $5600/mo
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Bayfront with Free Dockage and Outstanding View!
1BR+/2BA
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Sleeps 4
– #36559
$245/nt - $995- $1295/wk
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Luxurious Waterfront Condo - 2 Master Bedrooms - Contact for Specials
2BR+/2.5BA
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Sleeps 6
– Islamorada #50672
From $1400/wk
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Captain Shawn's Backyard on Deep Water Canal 'Bring Your Boat'
2BR+/2BA
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Sleeps 6
– #4563
$1575 per week 7 night min stay
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Paradise for Rent in the Florida Keys!! Designer Vacation Home on Deep Water
3BR/2BA
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Sleeps 7
– Islamorada #148809
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The Markeysa, the Ultimate Keys Experience - Private Beach
4BR+/4BA
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Sleeps 8-10
– Islamorada #40210
$1200 per night 4 night min stay
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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
1BR+/2BA
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Sleeps 4
– #72385
$1095- $1295/wk
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Islamorada - Private Oceanfront Estate - Heated Pool & Dockage
4BR+/4BA
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Sleeps 8
– Islamorada #43902
From $4300/wk
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Oceanfront End Unit, Internet, Pool, Tennis, Panoramic Ocean Views
2BR+/2BA
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Sleeps 4-5
– #77221
$775- $1,550/week
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Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
2BR+/2BA
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Sleeps 6-8
– #33938
$1095- $1295/wk
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Venetian Shores Finest Canal Front 'One Story' Vacation Home!!
4BR+/3BA
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Sleeps 8
– #319346
$1,975/wk --suite $750/wk
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Islamorada Waterfront-Great Dockage! Wonderful Views! Wifi & More!
3BR+/2BA
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Sleeps 8
– Islamorada #195489
$2000- $7500/mo
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(((( Dates Available from 4/30 Only $800 Weekly ))))
2BR/1.5BA
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Sleeps 4-6
– #29739
$600-$800/wk - $2200-$2800/mo
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Islamorada Oceanfront Vacation Rental Home
4BR/3BA
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Sleeps 8-10
– Islamorada #114644
From $3,800/wk - $14,400/mo
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'Debbie's Dream' Condo with Beach, Pool, Boat Slip
2BR/2BA
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Sleeps 4-6
– #461676
$1050 per week 7 night min stay
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Islamorada Oceanfront Estate 2 Lush Acres with Dockage Private
4BR+/4.5BA
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Sleeps 8-12
– Islamorada #73619
From $5800/wk - $17,400/mo
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Cocomo's
3BR+/2.5+BA
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Sleeps 14
– Islamorada #399647
6000 wkly
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Bay Front Home with Magnificent Views
3BR+/3BA
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Sleeps 8
– Plantation Key #452120
$3115 per week 3 night min stay
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Islamorada- Very Private Oceanfront Estate-White Sandy Beach
3BR+/3BA
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Sleeps 6
– Islamorada #390148
$12,000 mthly other charges apply
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Boaters Paradise! 2 Bed Luxury Townhouse W/Private Boat Slip-Sleeps 6
2BR/1.5BA
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Sleeps 4-6
– #422825
$1400/wk - $3,400/mo
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Ocean Front, Pool, Dock ***Oasis***
3BR/3BA
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Sleeps 8
– Islamorada #472391
$4000 per week 7 night min stay
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4 Lush Acres Ocean/Beach Front Estate Private Beach Deep Water Dock
3BR/3BA
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Sleeps 8
– Islamorada #469803
$335 per night 1 night min stay
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Invitation to Paradise
1BR+/1BA
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Sleeps 2-4
– #17144
$840 per week 6 night min stay
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Mitchell's Keys Villa - Private, Secluded House on the Bay
2BR+/1BA
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Sleeps 4
– #34491
$895- $1095/wk
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Heavenly Hideaway at Islamorada (Rental)
2BR+/2BA
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Sleeps 2-8
– #6759
$1,000 wk - $2400/mo
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Oceanfront Paradise W/ Large Screened Porch & Cable Internet
2BR+/2BA
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Sleeps 4-5
– #8612
$1400 per week 7 night min stay
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Island Paradise Best Fishing Area - Private Boat Slip
2BR+/1.5BA
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Sleeps 5-6
– Islamorada #7374
$1300/wk - $3400/mo
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Magnificent Ocean View from Private Roof Top Sundeck!
2BR+/2.5BA
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Sleeps 6
– #92694
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The Russell Estate, Beautiful 2 Acre Oceanfront Beach, DSL
3BR+/2BA
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Sleeps 6-8
– Islamorada #36742
$2800 per week 7 night min stay
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Ocean View Booking Spring & Summer Now- Free Kayak Use
1BR+/1BA
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Sleeps 4-5
– #9904
$635-$895/wk - $1750-$2900/mo
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Best Islamorada Vacation Rental
3BR/3BA
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Sleeps 6
– #117479
$2100 per week 7 night min stay
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Arte Paraiso Resort Canal3/3 Granit Kitch,Bk/Yrd,Tiki,W/Gas,Bq
3BR+/3BA
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Sleeps 6-8
– Plantation Key #298198
$3164 per month 28 night min stay
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Fabulous Bayharbour Condo! Deep Water Dock! Book Your Summer Vacation Now!
3BR+/2.5BA
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Sleeps 6-8
– Lower Matecumbe Key #113546
$2100 per week 7 night min stay
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Waterfront Paradise with Private Beach
3BR+/2BA
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Sleeps 6-10
– Lower Matecumbe Key #123633
$1490/wk
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Mitchell's Bayview Villa - Islamorada House on the Bay
2BR+/2BA
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Sleeps 6
– #286201
$1395 fall $1295
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White Marlin Beach House in Islamorada Florida Keys
2BR+/2BA
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Sleeps 5
– #29285
$1,300- $1,600/wk.
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Special Old Keys Apartment on Wooded Acre Estate
1BR/1BA
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Sleeps 2-3
– Islamorada #227906
$2900 monthly
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Beautiful Bay View Condo
1BR+/1BA
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Sleeps 2-4
– #177385
$750-$950/wk - $2400-$2800/mo
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'Chesa Mare' a Beautiful 3/2.5 on Open Water with Great Dockage!
3BR+/2.5BA
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Sleeps 6-8
– Lower Matecumbe Key #176138
$2000-$2450/wk - $5000/mo
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Where Canals Converge...Heated Pool... Openings Aug. 2013
4BR/2.5BA
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Sleeps 9-10
– Islamorada #26998
$5900- $7800/mo
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Beautiful New Bay Harbour Gated Condo Community on Matecumbe
3BR+/2.5BA
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Sleeps 6-8
– Lower Matecumbe Key #312619
$1,700-$2,000/wk - $5,000/mo
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Beautiful Water Front in Angler's Reef with View of Sand Bar
3BR+/2.5BA
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Sleeps 6-10
– #359378
$2800 per week 5 night min stay
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Luxury! Bayside - 3 BR - Paradise in the Keys with Boat Slip
3BR/2.5BA
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Sleeps 8
– Islamorada #108057
$2500- $4000/mo
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27 Steps to Paradise Bay
2BR+/1.5BA
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Sleeps 4-6
– Oceanside Isle #3488586ha
$168 per night 6 night min stay
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Luxury Oceanview Townhouse W/Private Beach & Free Dock
2BR/2.5BA
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Sleeps 6
– #219504
$1250-$1700/wk - $3750-$5550/mo
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A Beauty on Two Converging Crystal Clear Canals
4BR/3BA
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Sleeps 12
– Islamorada #223159
$1750-$2300/wk - $5250-$6500/mo
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Luxurious Home at Anglers Reef Oceanfront Resort with Boat Dock
2BR/2.5BA
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Sleeps 5
– #426200
$1900- $2400 per week
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Paradise - in Pristine Condition with Private Pool
5BR/4BA
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Sleeps 10
– #236597
$3250/wk - $8250/mo
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A Boating & Beachcombers Islamorada Dream & Deep Water Dock
3BR+/2BA
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Sleeps 6-8
– Lower Matecumbe Key #403822
$2500 per week
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Sunset Peninsula
4BR+/3BA
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Sleeps 8-12
– Islamorada #192685
$3000-$3500/wk - $6000/mo
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Happy Tarpon House on the Bay: Pool - Boat Dock - Fun!
3BR/3.5BA
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Sleeps 6
– Islamorada #370890
$5500- $11000/mo
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Ocean Front Heated Pool W/Stunning Ocean Views,Tiki Hut Bar, 90' of Dockage
3BR+/3BA
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Sleeps 8
– #423195
From $2500- $3,700/wk
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Waterfront Oasis, 85 Ft. New Dock & Fishing Station, 3 Bedroom,3,Bath
3BR+/3BA
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Sleeps 8-10
– Plantation Key #451523
$6300 per month 28 night min stay
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Islamorda Bayside.Great Get Away ! Fishing & Food
2BR+/1.5BA
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Sleeps 6-8
– #363291
$600- 800/wk In
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Perfect Location for Fishing, Fun and Friends!
3BR/2BA
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Sleeps 6
– #466083
$1700 per week 7 night min stay
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Venetian Waterfront Retreat Guaranteed Best Deal
5BR/3.5BA
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Sleeps 10
– #471048
$5500 - $6500 monthly
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Www.75240overseashwy.Com Bay Front Estate
3BR+/3BA
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Sleeps 3-8
– Lower Matecumbe Key #392561
$12,000/mo
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Venetian Shores, Totally Updated, Heated Pool, Two Boat Lifts.
3BR/3BA
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Sleeps 6-8
– #393120
$7,500 per month
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Beautiful Water Front Home on Plantation Key 4BR+/4BA – Sleeps 8-11 – Plantation Key #347281
Special offer Procrastinators save 15%! Summer weeks still left...!
Jun 8, 2013 to Aug 18, 2013
$2,400/wk -
Conch Bar South
4BR/3BA
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Sleeps 10-12
– Plantation Key #472077
$6000- 8500
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Your Own Piece of Paradise - Best Kept Secret in the Keys
Studio+/1BA
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Sleeps 4-5
– #379205
$560 per week 7 night min stay
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Canal Home with Quick Access to the Ocean
3BR/2BA
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Sleeps 4-6
– Plantation Key #453372
$3800- 4800/month
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Waterfront Cottage Conveniently Located Low Rate$
2BR/1BA
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Sleeps 4
– Islamorada #429859
$1000 weekly 2013, $1100 weekly 2014
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Beautiful 3/2 on 450’ of Waterfront W/ Tropical Pool and 4 Tiki Huts
3BR+/2BA
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Sleeps 6-8
– #423656
House Monthly rental $11,000-$13,000.00
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Ocean Front, Spectacular Home, Pool, Panoramic View, on Private Beach!
5BR+/4BA
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Sleeps 16
– Islamorada #425338
$6000 per week 7 night min stay
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Islamorada Tropical Escape! 2 Bedroom Clean and Affordable!
2BR/1.5BA
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Sleeps 6
– #16836
$750 per week 7 night min stay
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Water Front - Directly on Fl Bay
3BR+/2BA
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Sleeps 8
– Plantation Key #434755
$2205 per week 7 night min stay
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Beautiful Luxury Townhouse at Executive Bay Club, Florida Keys
2BR+/2.5BA
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Sleeps 6-8
– Islamorada #184901
$1260 per week 7 night min stay
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'Ocean Dream' ...Come Once and You Won't Go Anywhere Else!
2BR+/2BA
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Sleeps 4-6
– #74263
$900- $1300/wk
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Just Opened up July 6-20, Come to Paradise!!!!
2BR/3BA
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Sleeps 6
– #29679
$1050 per week 7 night min stay
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A Spectacular Rental Compound * Rent All or Rent Separately
10BR+/9.5BA
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Sleeps 20-28
– Islamorada #89412
$11000 per week 7 night min stay
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Private Historic Layton House with Pool & Spectacular Sunset & Waterfront
3BR+/5BA
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Sleeps 8
– Long Key #266547
$475 per night 3 night min stay
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Executive Bay Club - Islamorada- Private Beach 3bd/2.5 Baths
2BR+/2.5BA
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Sleeps 4-6
– Plantation Key #256175
$1000/wk $3000/mo
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Florida Keys Islamorada Deep Water Dockage Best Value in Keys
3BR+/2BA
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Sleeps 6-7
– Lower Matecumbe Key #210963
From $200/nt
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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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Family Fun Fishing House
3BR/2.5BA
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Sleeps 6-8
– Lower Matecumbe Key #301732
5000.00 month
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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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Keys Home in Anglers Reef - Ocean View, Dock, Cm Pool & Beach
2BR+/2.5BA
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Sleeps 4-6
– #322546
$2,000- $2400/wk
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A Fishermans Dream!
4BR+/3BA
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Sleeps 8-12
– Lower Matecumbe Key #70774
$6000/mo
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Ocean-View, Deluxe Condo with Boat Slip, Pool, Tennis and More
2BR+/2.5BA
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Sleeps 4-6
– Islamorada #136905
$1500-$2000/wk - $3200-$4200/mo
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Islamorada - Ocean Front House - Dazziling Sunsets.
5BR+/5BA
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Sleeps 12-14
– Islamorada #394116
$4200 per week 7 night min stay
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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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Sunset Serenity
3BR+/3BA
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Sleeps 6-8
– Islamorada #384431
$5500- 7500/month
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Discover the Charm of Island Living
2BR/2BA
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Sleeps 4-6
– #260818
$750 per week 7 night min stay
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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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Blue Water Retreat
3BR/3BA
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Sleeps 6-8
– Lower Matecumbe Key #254988
$5000- $6800/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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Keys Home in Anglers Reef with Ocean View, Dock, Comm. Pool & Beach
2BR+/2.5BA
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Sleeps 6
– Islamorada #431498
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Ocean Front Jewel, Private Pool,70 Ft Dock,Best Deal Around
4BR/3BA
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Sleeps 2-12
– Islamorada #360140
$300-$500 /nt- $2100-$3300/Week
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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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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 Oceanfront Condo
2BR/2BA
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Sleeps 4
– #461457
$2200- 3600 per month
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Canal Front Home Islamorada - Venetian Shores Tiki Hut Fun!
2BR+/2BA
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Sleeps 6-8
– #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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Beautiful Waterfront Home with Easy Gulf & Ocean Access
3BR/2BA
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Sleeps 6
– Islamorada #59813
$1500- $2000/wk
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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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Newly Renovated Luxury Townhome at Executive Bay Club
2BR+/3BA
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Sleeps 9-11
– #194989
$1100/wk - $3000/mo
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Executive Bay Club Townhome - Cottage Style
2BR/1.5BA
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Sleeps 4
– #307158
$1050 per week 7 night min stay
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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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Islamorada Paradise, Vacation Home on the Water
3BR/2BA
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Sleeps 6
– Islamorada #12753
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.