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Islamorada Vacation Rentals

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165 rentals in Islamorada.
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Oceanfront Condo: Ocean Views, Pool, WIFI - June Special!, vacation rental in Islamorada
Oceanfront Condo: Ocean Views, Pool, WIFI - June Special!, vacation rental in Islamorada
Oceanfront Condo: Ocean Views, Pool, WIFI - June Special!, vacation rental in Islamorada

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, vacation rental in Islamorada
Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach, vacation rental in Islamorada
Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach, vacation rental in Islamorada

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, vacation rental in Islamorada
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach, vacation rental in Islamorada
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach, vacation rental in Islamorada

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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Luxurious Home at beautiful Anglers Reef with Boat Slip available, vacation rental in Islamorada
Luxurious Home at beautiful Anglers Reef with Boat Slip available, vacation rental in Islamorada
Luxurious Home at beautiful Anglers Reef with Boat Slip available, vacation rental in Islamorada

Luxurious Home at beautiful Anglers Reef with Boat Slip available

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip, vacation rental in Islamorada
Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip, vacation rental in Islamorada
Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip, vacation rental in Islamorada

Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach, vacation rental in Islamorada
Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach, vacation rental in Islamorada
Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach, vacation rental in Islamorada

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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Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach, vacation rental in Islamorada
Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach, vacation rental in Islamorada
Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach, vacation rental in Islamorada

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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Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef, vacation rental in Islamorada
Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef, vacation rental in Islamorada
Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef, vacation rental in Islamorada

Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 6, vacation rental in Islamorada
This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 6, vacation rental in Islamorada
This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 6, vacation rental in Islamorada

This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2 Sleeps 6

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tropical Paradise in Venetian Shores.  
100%...NOT ON CRAIGS LIST!!!, vacation rental in Islamorada
Tropical Paradise in Venetian Shores.  
100%...NOT ON CRAIGS LIST!!!, vacation rental in Islamorada
Tropical Paradise in Venetian Shores.  
100%...NOT ON CRAIGS LIST!!!, vacation rental in Islamorada

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, vacation rental in Islamorada
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool, vacation rental in Islamorada
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool, vacation rental in Islamorada

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., vacation rental in Islamorada
Brand New / Totally Renovated Luxurious Home New To Rental Market., vacation rental in Islamorada
Brand New / Totally Renovated Luxurious Home New To Rental Market., vacation rental in Islamorada

Brand New / Totally Renovated Luxurious Home New To Rental Market.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A little Piece of Heaven to wash your worries away, vacation rental in Islamorada
A little Piece of Heaven to wash your worries away, vacation rental in Islamorada
A little Piece of Heaven to wash your worries away, vacation rental in Islamorada

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, vacation rental in Islamorada
Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable, vacation rental in Islamorada
Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable, vacation rental in Islamorada

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, vacation rental in Islamorada
BROCK HAUS ON THE GULF, vacation rental in Islamorada
BROCK HAUS ON THE GULF, vacation rental in Islamorada

BROCK HAUS ON THE GULF

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SUNSHINE PLACE, vacation rental in Islamorada
SUNSHINE PLACE, vacation rental in Islamorada
SUNSHINE PLACE, vacation rental in Islamorada

SUNSHINE PLACE

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Mitchell's Bayview Villa - Islamorada House on the Bay, vacation rental in Islamorada
Mitchell's Bayview Villa - Islamorada House on the Bay, vacation rental in Islamorada
Mitchell's Bayview Villa - Islamorada House on the Bay, vacation rental in Islamorada

Mitchell's Bayview Villa - Islamorada House on the Bay

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef- Fall Discount, vacation rental in Islamorada
Anglers Reef- Fall Discount, vacation rental in Islamorada
Anglers Reef- Fall Discount, vacation rental in Islamorada

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 , vacation rental in Islamorada
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , vacation rental in Islamorada
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , vacation rental in Islamorada

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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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, vacation rental in Islamorada
Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, vacation rental in Islamorada
Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, vacation rental in Islamorada

Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views, vacation rental in Islamorada
Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views, vacation rental in Islamorada
Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views, vacation rental in Islamorada

Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK* available-Pool, vacation rental in Islamorada
Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK* available-Pool, vacation rental in Islamorada
Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK* available-Pool, vacation rental in Islamorada

Anglers Reef Islamorada*Bikes*Kayak*Paddle Boards*DOCK* available-Pool

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay, vacation rental in Islamorada
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay, vacation rental in Islamorada
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay, vacation rental in Islamorada

Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New Listing! Iconic Ted Williams Estate. Bayfront in the heart of Islamorada., vacation rental in Islamorada
New Listing! Iconic Ted Williams Estate. Bayfront in the heart of Islamorada., vacation rental in Islamorada
New Listing! Iconic Ted Williams Estate. Bayfront in the heart of Islamorada., vacation rental in Islamorada

New Listing! Iconic Ted Williams Estate. Bayfront in the heart of Islamorada.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Two acre oceanfront estate home in Islamorada - Southern Comfort, vacation rental in Islamorada
Two acre oceanfront estate home in Islamorada - Southern Comfort, vacation rental in Islamorada
Two acre oceanfront estate home in Islamorada - Southern Comfort, vacation rental in Islamorada

Two acre oceanfront estate home in Islamorada - Southern Comfort

Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Deep Dockage in the Center of Islamorada - Pool, vacation rental in Islamorada
Deep Dockage in the Center of Islamorada - Pool, vacation rental in Islamorada
Deep Dockage in the Center of Islamorada - Pool, vacation rental in Islamorada

Deep Dockage in the Center of Islamorada - Pool

Rental Home
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Bayside Condo, marina, pool and beach, vacation rental in Islamorada
Bayside Condo, marina, pool and beach, vacation rental in Islamorada
Bayside Condo, marina, pool and beach, vacation rental in Islamorada

Bayside Condo, marina, pool and beach

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate, vacation rental in Islamorada
Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate, vacation rental in Islamorada
Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate, vacation rental in Islamorada

Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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SANCTUARY IN PARADISE, vacation rental in Islamorada
SANCTUARY IN PARADISE, vacation rental in Islamorada
SANCTUARY IN PARADISE, vacation rental in Islamorada

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, vacation rental in Islamorada
Newly refinished  condo open water views very nice, vacation rental in Islamorada
Newly refinished  condo open water views very nice, vacation rental in Islamorada

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!!!, vacation rental in Islamorada
Oceanfront Oasis - Pinch me am I dreaming!!!, vacation rental in Islamorada
Oceanfront Oasis - Pinch me am I dreaming!!!, vacation rental in Islamorada

Oceanfront Oasis - Pinch me am I dreaming!!!

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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BEACON REEF 310, vacation rental in Islamorada
BEACON REEF 310, vacation rental in Islamorada
BEACON REEF 310, vacation rental in Islamorada

BEACON REEF 310

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Butterfly Haven - Beautiful Bayfront Home with Cottage, vacation rental in Islamorada
Butterfly Haven - Beautiful Bayfront Home with Cottage, vacation rental in Islamorada
Butterfly Haven - Beautiful Bayfront Home with Cottage, vacation rental in Islamorada

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, vacation rental in Islamorada
Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra, vacation rental in Islamorada
Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra, vacation rental in Islamorada

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, vacation rental in Islamorada
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B, vacation rental in Islamorada
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B, vacation rental in Islamorada

Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Anglers Reef # 136, vacation rental in Islamorada
Beautiful Anglers Reef # 136, vacation rental in Islamorada
Beautiful Anglers Reef # 136, vacation rental in Islamorada

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, vacation rental in Islamorada
Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage, vacation rental in Islamorada
Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage, vacation rental in Islamorada

Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy., vacation rental in Islamorada
Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy., vacation rental in Islamorada
Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy., vacation rental in Islamorada

Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury condo overlooking harbor with ocean view, vacation rental in Islamorada
Luxury condo overlooking harbor with ocean view, vacation rental in Islamorada
Luxury condo overlooking harbor with ocean view, vacation rental in Islamorada

Luxury condo overlooking harbor with ocean view

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The PERFECT Escape with pool & jacuzzi, vacation rental in Islamorada
The PERFECT Escape with pool & jacuzzi, vacation rental in Islamorada
The PERFECT Escape with pool & jacuzzi, vacation rental in Islamorada

The PERFECT Escape with pool & jacuzzi

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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132 Columbus - 2 Bedroom Oceanfront Home, vacation rental in Islamorada
132 Columbus - 2 Bedroom Oceanfront Home, vacation rental in Islamorada
132 Columbus - 2 Bedroom Oceanfront Home, vacation rental in Islamorada

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, vacation rental in Islamorada
Green Cottage - Beautiful 2 Bedroom Oceanfront Cottage with Pool, vacation rental in Islamorada
Green Cottage - Beautiful 2 Bedroom Oceanfront Cottage with Pool, vacation rental in Islamorada

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, vacation rental in Islamorada
Beautiful Maison #307, vacation rental in Islamorada
Beautiful Maison #307, vacation rental in Islamorada

Beautiful Maison #307

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bay Front Beauty/ Summer Sea Must See!!!! , vacation rental in Islamorada
Bay Front Beauty/ Summer Sea Must See!!!! , vacation rental in Islamorada
Bay Front Beauty/ Summer Sea Must See!!!! , vacation rental in Islamorada

Bay Front Beauty/ Summer Sea Must See!!!!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, vacation rental in Islamorada
Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, vacation rental in Islamorada
Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, vacation rental in Islamorada

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, vacation rental in Islamorada
A Good Stay ~ Islamorada Waterfront Residence, vacation rental in Islamorada
A Good Stay ~ Islamorada Waterfront Residence, vacation rental in Islamorada

A Good Stay ~ Islamorada Waterfront Residence

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708, vacation rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708, vacation rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708, vacation rental in Islamorada

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, vacation rental in Islamorada
PALMS 309, vacation rental in Islamorada
PALMS 309, vacation rental in Islamorada

PALMS 309

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Angler's Reef #118 - Charming 2 Bedroom House with Peekaboo Views, vacation rental in Islamorada
Angler's Reef #118 - Charming 2 Bedroom House with Peekaboo Views, vacation rental in Islamorada
Angler's Reef #118 - Charming 2 Bedroom House with Peekaboo Views, vacation rental in Islamorada

Angler's Reef #118 - Charming 2 Bedroom House with Peekaboo Views

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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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