Islamorada Vacation Rentals
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165 rentals in Islamorada.
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Oceanfront Condo: Ocean Views, Pool, WIFI - June Special!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
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 4
Match: Sleeps
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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
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Luxurious Home at beautiful Anglers Reef with Boat Slip available
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
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Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Direct Oceanfront Views In Anglers Reef, Islamorada. Resort Pool, Dock, Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
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Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
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Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2 Sleeps 6
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Tropical Paradise in Venetian Shores. 100%...NOT ON CRAIGS LIST!!!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Mitchell's Keys Villa - Private, Secluded House on the Bay
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Brand New / Totally Renovated Luxurious Home New To Rental Market.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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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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Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable
Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BROCK HAUS ON THE GULF
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
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SUNSHINE PLACE
Rental Home
1 bedroom
1 bathroom
Sleeps 3
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Mitchell's Bayview Villa - Islamorada House on the Bay
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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Anglers Reef- Fall Discount
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
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
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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
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Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
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Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK* available-Pool
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
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New Listing! Iconic Ted Williams Estate. Bayfront in the heart of Islamorada.
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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Two acre oceanfront estate home in Islamorada - Southern Comfort
Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
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Deep Dockage in the Center of Islamorada - Pool
Rental Home
7 bedrooms
5 bathrooms
Sleeps 14
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Bayside Condo, marina, pool and beach
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
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SANCTUARY IN PARADISE
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Newly refinished condo open water views very nice
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Oasis - Pinch me am I dreaming!!!
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
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BEACON REEF 310
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Butterfly Haven - Beautiful Bayfront Home with Cottage
Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Anglers Reef # 136
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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Luxury condo overlooking harbor with ocean view
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The PERFECT Escape with pool & jacuzzi
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
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132 Columbus - 2 Bedroom Oceanfront Home
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Green Cottage - Beautiful 2 Bedroom Oceanfront Cottage with Pool
Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Maison #307
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bay Front Beauty/ Summer Sea Must See!!!!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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A Good Stay ~ Islamorada Waterfront Residence
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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PALMS 309
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Angler's Reef #118 - Charming 2 Bedroom House with Peekaboo Views
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
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Frequently Asked Questions about Islamorada
- Yes, here are some popular vacation rentals in Islamorada that have a pool:\n\nSee all vacation rentals with a pool in Islamorada on Tripadvisor
- Yes, here are some popular vacation rentals in Islamorada that have internet access:\n\nSee all vacation rentals in Islamorada on Tripadvisor
- The best pet friendly rentals in Islamorada are:\n
- \n
- Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental \n
- LITTLE BAY - Upper Duplex \n
- LITTLE BAY - Lower Duplex \n
- Some of the most popular kid friendly rentals in Islamorada are:\n
- \n
- Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental \n
- Bayside Condo, marina, pool and beach \n
- SANCTUARY IN PARADISE \n