Islamorada, Florida Vacation Rentals

Islamorada, FL vacation rentals, browse Islamorada, Florida vacation home rentals and plan your next Florida Keys vacation in Islamorada. Imagine relaxing in the Florida Keys Vacationing by yourself, vacationing with your family or vacationing with friends, make your next vacation a Florida Keys vacation.

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Beautifully Renovated 2BR Condo – Futura Yacht Club #205, Expansive Balcony w/Great Views Of The Florida Bay.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Beautiful Oceanfront
Property w/Pool — Alligator Reef, Conch & Lobster, Beautiful Views, Ocean Breezes, Private Balcony.

Sleeps: 14
Bedrooms: 5
Bathrooms: 5
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Paradise In Islamorada On The Water, Everything Brand New, Sit In Your Adirondack Chairs And Watch The Manatees.

Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Waterfront Cottage Great Rates! Pet Friendly! Kayak Rentals & Paddleboard Rentals Can Be Arranged, No Children Please.

Sleeps: 2
Bedrooms: 1
Bathrooms: 1
Pets Considered

Florida Keys Florida Vacation Rentals, Florida Keys Vacation Rentals, Florida Keys FL Vacation Homes, Key West FL Vacation Home Rentals, Key Largo FL Vacation Rentals

Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Vacation Condo At Futura Yacht Club, 2BR/2BA Second Floor,  Private, Gated Complex w/A Fabulous Marina & Pool, Breathtaking Sunsets.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Boat Slip, 2 Sand Beaches, Heated Pool, 5 Star Reviews, Oceanfront Anglers Reef,
Crib, High Chair & Pack-n-Play Available.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Single Family Home In Angler’s Reef Gated Community, Beautiful Ground, Lushly Landscaped Resort Pool.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Open – Endless Bay Views… Sues Promise Private Villas, Beach, Dock, Islamorada, Bikes, Kayaks Provided.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Secluded Stunning Oceanview Townhome, Chickee Hut, Small Sand Beach, Peacocks Are Commonly Seen On The Property.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
Pets Cpnsidered

Florida Keys Florida Vacation Rentals, Florida Keys Vacation Rentals, Florida Keys FL Vacation Homes, Key West FL Vacation Home Rentals, Key Largo FL Vacation Rentals

Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Anglers Reef, Ocean View, Boat Dock Available, Private Community, Private Balconies, Heated Swimming Pool, 2 Private Beaches.

Sleeps: 5
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

New Listing!! Incredible Luxury Townhouse, On The Water! (Boatslip Included), Million-Dollar Sunset Views, Balconies Overlooking The Bay.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Mitchell’s Bayview Villa – Islamorada House On The Bay, Private, Secluded Villa Facing Florida Bay, Gorgeous Sunsets.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Osprey Bay Villa On Fla. Bay-Has It All! Spectacular Sunsets, Pool, Spa & Dock!!
Sunning Decks Galore, Atrium Garden.

Sleeps: 10
Bedrooms: 5
Bathrooms: 3
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Beautiful Water Front In Angler’s Reef w/View Of Sand Bar w/Boat Slip, Luxury Villa, Tangerine Sunsets, Dolphin & Turtles Are Common.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Southern Diversion Estate Islamorada, Private Gated Estate Home, 200Ft Of Oceanfront, Tiki Hut On Private Beach, Heated Pool.

Sleeps: 16
Bedrooms: 5
Bathrooms: 3.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

5 Star Modern Oceanfront Islamorada Townhome On The Beach! Heated Pool, Chickee Hut, Ocean Front Sandy Beach, Beautiful Sunrise & Sunsets.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Wonderful 3BR/2BA Oceanfront Townhome w/Pool – Windy Cove #1, Overlooks The Sparkling Atlantic Ocean, Balcony Overlooking The Water.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Oceanfront 4BR Home, Pool, Dockage, Located In The Heart Of Islamorada Florida Keys, Beautiful Private Estate.

Sleeps: 8
Bedrooms: 4
Bathrooms: 4.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

#6 – Hidden Gem Islamorada Bay Side Condo – 2BD/2BA,  Amazing Sunsets & Gentle Bay Waters Await! Walking Distance To Shops & Restaurants.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

The “Nest” Villa – 2BR/2BA, Stunning Bay Views, Private Sun Deck, Boat Dock! Private & Secluded, Many Resident Fish, Lobster, An Octopus.

Sleeps: 4
Bedrooms: 1
Bathrooms: 2
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

3BR Beautiful Keys Home, Quick Walk To Private Beach,
Fishing, Boating, Diving & Snorkeling.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

The Perfect Getaway w/Heated Swimming Pool, Jacuzzi & Boat Slip, This Is Paradise!! Nice Location, Come & Spend A Perfect Vacation.

Sleeps: 10
Bedrooms: 4
Bathrooms: 3
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Islamorada Home In Anglers Reef w/Ocean Views From All 4 Balconies, Dock, Community Pool & 500Ft. Private Beach.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Truly Oceanfront Home 3BR/2.5BA, Panoramic Ocean Views, Lg Wraparound Decks, Lushly Landscaped Pool Area w/Lg Heated & Chilled Pool.

Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Mitchell’s Keys Villa – Private,
50Ft. From The Water, Secluded House On The Bay, 
Laid Back Atmosphere For Those Who Desire It.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Bayside: 1st Floor Apartment In Native Hammock On Florida Bay, Nature Lovers Dream w/Resident Fish, Lobster, An Octopus.

Sleeps: 4
Bedrooms: 1
Bathrooms: 2
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

4 Bedroom Private Oceanfront House – Bahia, Fire Pits, Private Outdoor Seating,
Chaise Lounges, Nestled In The Tropical Setting.

Sleeps: 8
Bedrooms: 4
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Stunning Beach Front Home w/Private Pool – Professionally Cleaned
& Sanitized, Amazing Ocean Views & Stunning Sunrises.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Little Basin Villas/Key Lime Villa 3/1, 2 or 3 Bedrooms Available, Swimming Pool, Dock & Beach Access, Tiki Hut w/BBQ.

Sleeps: 6
Bedrooms: 3
Bathrooms: 3.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

We’re Re-Open As Of June 1st! Book Quickly! You’ll Love it! Everyone Does! Huge Screened In Terrace, Beautiful Nearby Founders Park.

Sleeps: 5
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Ocean View Anglers Reef – Pool, Dock, Beach, Walk Or Bike To Local Food & Bars, Tree-Lined Yard w/A View Of The Ocean.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Coral Cove Resort – Fisherman’s Dream, Small Gated-Community Setting,
Heated Community Pool & Protected Cove.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

2 Large Bedrooms/2.5BA Oceanfront/Views – Dock Incl. Anglers Reef Islamorada, Private Balcony, 2 Open Porches w/Seating.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

Florida Keys Florida Vacation Rentals, Florida Keys Vacation Rentals, Florida Keys FL Vacation Homes, Key West FL Vacation Home Rentals, Key Largo FL Vacation Rentals

Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Beach Dream House, Most Panoramic Views, Wraparound Balcony,  Relax & Enjoy The Clear Waters Of Islamorada, FL

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered

Florida Keys Florida Vacation Rentals, Florida Keys Vacation Rentals, Florida Keys FL Vacation Homes, Key West FL Vacation Home Rentals, Key Largo FL Vacation Rentals

Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Tropical Paradise At Futura Yacht Club, 70 Unit Community, Spacious Pool Deck, Grand Sparkling Pool.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Comfortable Clean Fully Remodeled House Boat, Amazing Vacation “Baycation”, Picnic Area w/Sunshades & A Propane BBQ Grill.

Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Considered

Florida Keys Florida Vacation Rentals, Florida Keys Vacation Rentals, Florida Keys FL Vacation Homes, Key West FL Vacation Home Rentals, Key Largo FL Vacation Rentals

Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Oceanfront, Private Beach, Charming 2BR/2BA Beach Cottage – Kayaks Included, Surrounded By Palms, Pines & Lime Trees.

Sleeps: 5
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Oceanfront End Unit, Heated Pool, WiFi, Panoramic Ocean Views! Couple Fishing Rods & Bait Pails For Guest Use.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

Florida Keys Florida Vacation Rentals, Florida Keys Vacation Rentals, Florida Keys FL Vacation Homes, Key West FL Vacation Home Rentals, Key Largo FL Vacation Rentals

Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Anglers Reef Islamorada 2BR/2.5BA Bungalow w/Ocean Views. Boat Slip Available, Oceanfront Pool Is Serene.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Tropical Paradise in Venetian Shores. 100%…Not On Craigs List!! Luxury Heated Pool/Spa, Hobie Odyssey Kayak, 2 Cruiser Style Bicycles Incl.

Sleeps: 10
Bedrooms: 3
Bathrooms: 2
No Pets

Florida Keys Florida Vacation Rentals, Florida Keys Vacation Rentals, Florida Keys FL Vacation Homes, Key West FL Vacation Home Rentals, Key Largo FL Vacation Rentals

Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Direct Oceanfront Views In Anglers Reef, Islamorada.
Resort Pool, Dock, Beach, Kayaks Available, Lush, Tropical Landscape.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Oceanfront Condo In Quiet Setting 3BR/2BA, Pool Steps From Balcony, MM80 On Old Hwy, Gated Community Of Just 9 Condos.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Relax In Your Private Oceanfront Cottage! 4 Kayaks & 4 Bicycles For Your Use, Gorgeous Sunsets At The Tiki Hut.

Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

This Is Paradise! Beautiful 2 Acre Oceanfront Beach, A Must See. 3BR/2BA Sleeps 6,
Palm Shaded Hammocks, Tree Swings.

Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Anglers Reef Oceanfront Complex w/Pool & Beach-New Air Conditioning System 2019,
Resort Contains A Heated Pool, Tranquil Back Porch.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

4BR House In Angler’s Reef, Includes 31′ Boat Slip, Porch Offers Ocean Views, Master Suite Private Balcony w/Spectacular Views Of The Ocean.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

WWelcome To Paradise “Sandbar Bungalow Villa” @ Anglers Reef, Community Pool Overlooking The Atlantic Ocean & 500Ft Of Private Beach.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Luxurious Home Away From Home At Beautiful Anglers Reef w/Own Boat Slip
Available, Open Porches & Balconies, Kayaks (2).

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Islamorada Home In Paradise, Exclusive Oceanfront Gated Community, Heated Pool, Two Private Beaches, 2 Kayaks Incl.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

The World Famous Island Dog Villa Of Islamorada In The Florida Keys, Heated Pool, Tommy Bahama Furnishings.

Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

BLush Tropical Waterfront Oasis w/Heated Pool w/Pool Deck, Dock & WiFi, Balcony, Peaceful & Quiet Atmosphere.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

True Ocean Front & Pool Side Stunning 2BR/2.5BA, Optional Boat Slip #19,
Outdoor BBQ, Balconies w/Sweeping Ocean Views.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Beautiful Islamorada Home In Angler’s Reef. Amazing Views. Boatslip Included, Wrap Around Balconies, Gas Grill, Kayaks For Your Enjoyment.

Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Deep Dockage & Pool In Islamorada – 5BR – Perfect For 2+ Families, Manatees Visit The Dock Daily – They Are Sweet, Gentle Giants!

Sleeps: 10
Bedrooms: 5
Bathrooms: 4
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Islamorada Oceanfront Home In Anglers Reef, Ocean Views, Community Pool & Beach, Quiet Oceanfront Community.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Bayside Paradise In The Heart Of Islamorada, Patio, Lighted Plunge Pool w/A View Of The Sunset Over The Bay.

Sleeps: 6
Bedrooms: 4
Bathrooms: 3.5
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Keys Kottage; Remodeled Villa In Native Hammock On Florida Bay, 100Ft. From The Water, Swimming Area Right Off The Property.

Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Considered

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Super Penthouse – Futura Yacht Club #603, Balcony, Top Floor, Heated Pool w/Tiki Bar Area, Great Family Vacation Condo.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Islamorada Bungalow In The Heart Of The Florida Keys, Private Pool, Peaceful Neighborhood, Two Bikes Included, Great Place To Just Chill.

Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets

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Islamorada, FL

Islamorada, FL Area
Florida Keys Vacation Rentals

Breathtaking Ocean Views For Your Paradise Vacations, Private Dock & Ramp, Four Kayaks And Four Bicycles Provided.

Sleeps: 8
Bedrooms: 2
Bathrooms: 2
Pets Considered