Islamorada Vacation Rentals
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532 rentals in Islamorada.
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Islamorada Waterfront Paradise Getaway!
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lovely Islamorada Studio in the Heart of the Keys
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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BROCK HAUS ON THE GULF
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 2
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Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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�AQUAMARINE OCEANVIEW�FLASH SALE⚡️JAN 3-17+100+⭐️⭐️⭐️⭐️⭐️DOCK+1,700 SQ FEET+++
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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SUNSHINE PLACE
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Truly OceanFRONT Home 3BR 2.5BA, Panoramic Ocean Views, Two 350+ sqft Decks
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
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Luxurious Home at beautiful Anglers Reef, with private Boat Slip available
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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OCEANFRONT ANGLERS REEF LUXURY HOME - Pool, Slip, Beach, Kayaks, Paddle Boards
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Direct Oceanfront Views In Anglers Reef, Islamorada. Resort Pool, Dock, Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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5 bedroom - Deep Dockage & Heated Pool in Islamorada.
Rental Home
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Renovated - Boat slip, pool, beach - Anglers Reef oceanside gated community
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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GREAT LOCATION !!! White Marlin Beach House, Islamorada
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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WATERFRONT COTTAGE GREAT RATES !
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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4 Bedroom House In Angler's Reef, Includes 31' Boat Slip
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
Rental Home
5 bedrooms
5 bathrooms
Sleeps 5
Match: Sleeps
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PVT Beachfront Villa | Heated Pool+Ocean Views
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Single Family Home In Angler's Reef Gated Community,Beautiful Ground,Resort Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gated Oceanfront 1.8 acre Estate on Millionaire's Row, Private Saltwater Pool
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 2
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Beach Dream House, relax and enjoy the clear waters of Islamorada FL
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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☀️Luxury 3 Bedroom all Remodeled! Ocean View, Pool/Spa, Marina, Kayak/Bikes�
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock
Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Heated Pool, Kayaks, SUP’s, Bikes, Boat Ramp, BBQ, Fire Pit, beach chairs, more
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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WALK TO RESTAURANTS | POOL | WATERFRONT | PERSONAL BALCONY | Conch Villa 6
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to Paradise "Sandbar Bungalow Villa" * Anglers Reef
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful 'Keysey' Condo in Gated Community (VR-196)
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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A little Piece of Heaven to wash your worries away
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Southern Diversion Estate Islamorada
Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BAYSIDE PARADISE ~ Heart of Islamorada *Private Boat Dockage Upon Request*
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Location. Location. Location.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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WALK TO RESTAURANTS | POOL | SUNSETS | Little Basin Villas | Key Lime Villa 3
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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5 Star Modern Oceanfront Islamorada Townhome on the Beach!
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef- Fall Discount
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Brand New / Totally Renovated Luxurious Home New To Rental Market.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Anglers Reef Islamorada home with ocean views, private marina, beach & pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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