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Holiday Rentals with Pools in Islamorada

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74 rentals in Islamorada.
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This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2 Sleeps 6
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Islamorada Keys Home In Anglers Reef With Ocean View, Dock, Pool & Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Luxurious Home at beautiful Anglers Reef with Boat Slip available
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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A little Piece of Heaven to wash your worries away
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Direct Oceanfront Views In Anglers Reef, Islamorada. Resort Pool, Dock, Beach
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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BROCK HAUS ON THE GULF
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Save time - get the best Islamorada rentals sent straight to your email!
Tropical Paradise in Venetian Shores. 100%...NOT ON CRAIGS LIST!!!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Mitchell's Bayview Villa - Islamorada House on the Bay
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Anglers Reef- Fall Discount
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Brand New / Totally Renovated Luxurious Home New To Rental Market.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK* available-Pool
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Bayside Condo, marina, pool and beach
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Deep Dockage in the Center of Islamorada - Pool
Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Newly refinished condo open water views very nice
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Oceanfront Condo: Ocean Views, Pool, WIFI - Discounted Rate August
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Oceanfront Oasis - Pinch me am I dreaming!!!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps, All pools
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BEACON REEF 310
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Luxury condo overlooking harbor with ocean view
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Bay Front Beauty/ Summer Sea Must See!!!!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps, All pools
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A Good Stay ~ Islamorada Waterfront Residence
Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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PALMS 309
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Come relax in Islamorada, the tropical jewel of the Florida Keys!!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
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*Searenity Beach House* - Ocean Front Home with Views of the Atlantic Ocean
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
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MANATEE MANOR
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
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PARADISE AWAITS YOU IN ISLAMORADA, FLORIDA!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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BEACON REEF 222
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Oceanfront Anglers Reef Islamorada Florida Keys
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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San Roc - Private 150 Ft Oceanfront 2.5 Acre Millionaire Row Estate, Pool, Spa,
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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PALMS 314
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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BEACON REEF 501
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
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Florida Keys Peaceful Paradise in Executive Bay Club, Islamorada
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
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Lazy Daze Beach House 5 Star Modern Oceanfront Islamorada Townhome on the Beach!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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LYONS LANDING
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
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LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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PALMS 417
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, All pools
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PALMS 301
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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New Listing! Luxury Oceanfront Estate in Islamorada - Booking now for 2023
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Islamorada trop paradise pool, fishing, 2fls luxury with a filet stationn
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Majestic estate, 200' of private oceanfront beach & pool, ideal wedding venue
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
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