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Holiday Homes in Islamorada

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166 rentals in Islamorada.
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Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach, holiday rental in Islamorada
Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach, holiday rental in Islamorada
Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach, holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
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Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach, holiday rental in Islamorada
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach, holiday rental in Islamorada
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach, holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious Home at beautiful Anglers Reef with Boat Slip available, holiday rental in Islamorada
Luxurious Home at beautiful Anglers Reef with Boat Slip available, holiday rental in Islamorada
Luxurious Home at beautiful Anglers Reef with Boat Slip available, holiday rental in Islamorada

Luxurious Home at beautiful Anglers Reef with Boat Slip available

Holiday Rental House
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, holiday rental in Islamorada
Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip, holiday rental in Islamorada
Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip, holiday rental in Islamorada

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach, holiday rental in Islamorada
Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach, holiday rental in Islamorada
Direct Oceanfront Views In Anglers Reef, Islamorada.  Resort Pool, Dock, Beach, holiday rental in Islamorada

Direct Oceanfront Views In Anglers Reef, Islamorada. Resort Pool, Dock, Beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach, holiday rental in Islamorada
Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach, holiday rental in Islamorada
Islamorada Oceanfront Home In Anglers Reef Ocean Views, Dock, Comm Pool & Beach, holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef

Holiday Rental House
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, holiday rental in Islamorada
This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 6, holiday rental in Islamorada
This is Paradise! Beautiful 2 Acre Oceanfront Beach, A MUST SEE. 3/2  Sleeps 6, holiday rental in Islamorada

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Tropical Paradise in Venetian Shores.  
100%...NOT ON CRAIGS LIST!!!, holiday rental in Islamorada
Tropical Paradise in Venetian Shores.  
100%...NOT ON CRAIGS LIST!!!, holiday rental in Islamorada
Tropical Paradise in Venetian Shores.  
100%...NOT ON CRAIGS LIST!!!, holiday rental in Islamorada

Tropical Paradise in Venetian Shores. 100%...NOT ON CRAIGS LIST!!!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool, holiday rental in Islamorada
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool, holiday rental in Islamorada
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool, holiday rental in Islamorada

Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Brand New / Totally Renovated Luxurious Home New To Rental Market., holiday rental in Islamorada
Brand New / Totally Renovated Luxurious Home New To Rental Market., holiday rental in Islamorada
Brand New / Totally Renovated Luxurious Home New To Rental Market., holiday rental in Islamorada

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Mitchell's Keys Villa - Private, Secluded House on the Bay

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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A little Piece of Heaven to wash your worries away, holiday rental in Islamorada
A little Piece of Heaven to wash your worries away, holiday rental in Islamorada
A little Piece of Heaven to wash your worries away, holiday rental in Islamorada

A little Piece of Heaven to wash your worries away

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable, holiday rental in Islamorada
Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable, holiday rental in Islamorada
Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable, holiday rental in Islamorada

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BROCK HAUS ON THE GULF, holiday rental in Islamorada
BROCK HAUS ON THE GULF, holiday rental in Islamorada
BROCK HAUS ON THE GULF, holiday rental in Islamorada

BROCK HAUS ON THE GULF

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

SUNSHINE PLACE

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Anglers Reef- Fall Discount, holiday rental in Islamorada
Anglers Reef- Fall Discount, holiday rental in Islamorada
Anglers Reef- Fall Discount, holiday rental in Islamorada

Anglers Reef- Fall Discount

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , holiday rental in Islamorada
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , holiday rental in Islamorada
Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental , holiday rental in Islamorada

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mitchell's Bayview Villa - Islamorada House on the Bay, holiday rental in Islamorada
Mitchell's Bayview Villa - Islamorada House on the Bay, holiday rental in Islamorada
Mitchell's Bayview Villa - Islamorada House on the Bay, holiday rental in Islamorada

Mitchell's Bayview Villa - Islamorada House on the Bay

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, holiday rental in Islamorada
Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, holiday rental in Islamorada
Anglers Reef Islamorada 2/2.5 dock available Bikes, Kayak available, Pool, holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views, holiday rental in Islamorada
Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views, holiday rental in Islamorada
Amazing Oceanfront: Pool, Paddleboards & Kayaks - 180 degree ocean views, holiday rental in Islamorada

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

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

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay, holiday rental in Islamorada
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay, holiday rental in Islamorada
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay, holiday rental in Islamorada

Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

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

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

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

Two acre oceanfront estate home in Islamorada - Southern Comfort

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

Deep Dockage in the Center of Islamorada - Pool

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Bayside Condo, marina, pool and beach, holiday rental in Islamorada
Bayside Condo, marina, pool and beach, holiday rental in Islamorada
Bayside Condo, marina, pool and beach, holiday 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, holiday rental in Islamorada
Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate, holiday rental in Islamorada
Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate, holiday rental in Islamorada

Exquisite Oceanfront - Gorgeous 5 Bedroom Oceanfront Estate

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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SANCTUARY IN PARADISE, holiday rental in Islamorada
SANCTUARY IN PARADISE, holiday rental in Islamorada
SANCTUARY IN PARADISE, holiday rental in Islamorada

SANCTUARY IN PARADISE

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Oceanfront Condo: Ocean Views, Pool, WIFI - June Special!, holiday rental in Islamorada
Oceanfront Condo: Ocean Views, Pool, WIFI - June Special!, holiday rental in Islamorada
Oceanfront Condo: Ocean Views, Pool, WIFI - June Special!, holiday 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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Newly refinished  condo open water views very nice, holiday rental in Islamorada
Newly refinished  condo open water views very nice, holiday rental in Islamorada
Newly refinished  condo open water views very nice, holiday 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!!!, holiday rental in Islamorada
Oceanfront Oasis - Pinch me am I dreaming!!!, holiday rental in Islamorada
Oceanfront Oasis - Pinch me am I dreaming!!!, holiday rental in Islamorada

Oceanfront Oasis - Pinch me am I dreaming!!!

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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BEACON REEF 310, holiday rental in Islamorada
BEACON REEF 310, holiday rental in Islamorada
BEACON REEF 310, holiday rental in Islamorada

BEACON REEF 310

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

Butterfly Haven - Beautiful Bayfront Home with Cottage

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra, holiday rental in Islamorada
Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra, holiday rental in Islamorada
Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra, holiday rental in Islamorada

Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra

Holiday Rental House
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, holiday rental in Islamorada
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B, holiday rental in Islamorada
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe - B, holiday 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
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Beautiful Anglers Reef # 136, holiday rental in Islamorada
Beautiful Anglers Reef # 136, holiday rental in Islamorada
Beautiful Anglers Reef # 136, holiday rental in Islamorada

Beautiful Anglers Reef # 136

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage, holiday rental in Islamorada
Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage, holiday rental in Islamorada
Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage, holiday rental in Islamorada

Leatherback Cottage - Charming 2 Bedroom Oceanfront Cottage

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Luxury condo overlooking harbor with ocean view, holiday rental in Islamorada
Luxury condo overlooking harbor with ocean view, holiday rental in Islamorada
Luxury condo overlooking harbor with ocean view, holiday rental in Islamorada

Luxury condo overlooking harbor with ocean view

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy., holiday rental in Islamorada
Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy., holiday rental in Islamorada
Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy., holiday rental in Islamorada

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The PERFECT Escape with pool & jacuzzi, holiday rental in Islamorada
The PERFECT Escape with pool & jacuzzi, holiday rental in Islamorada
The PERFECT Escape with pool & jacuzzi, holiday rental in Islamorada

The PERFECT Escape with pool & jacuzzi

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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132 Columbus - 2 Bedroom Oceanfront Home, holiday rental in Islamorada
132 Columbus - 2 Bedroom Oceanfront Home, holiday rental in Islamorada
132 Columbus - 2 Bedroom Oceanfront Home, holiday rental in Islamorada

132 Columbus - 2 Bedroom Oceanfront Home

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Green Cottage - Beautiful 2 Bedroom Oceanfront Cottage with Pool, holiday rental in Islamorada
Green Cottage - Beautiful 2 Bedroom Oceanfront Cottage with Pool, holiday rental in Islamorada
Green Cottage - Beautiful 2 Bedroom Oceanfront Cottage with Pool, holiday rental in Islamorada

Green Cottage - Beautiful 2 Bedroom Oceanfront Cottage with Pool

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful Maison #307, holiday rental in Islamorada
Beautiful Maison #307, holiday rental in Islamorada
Beautiful Maison #307, holiday rental in Islamorada

Beautiful Maison #307

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

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, holiday rental in Islamorada
Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, holiday rental in Islamorada
Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool, holiday rental in Islamorada

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

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, holiday rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708, holiday rental in Islamorada
Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708, holiday rental in Islamorada

Bay Views from this Charming 2 Bedroom Condo - Futura Townhome 708

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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PALMS 309, holiday rental in Islamorada
PALMS 309, holiday rental in Islamorada
PALMS 309, holiday rental in Islamorada

PALMS 309

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

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Islamorada

Yes, here are some popular holiday rentals in Islamorada that have a pool:\n\nSee all holiday rentals with a pool in Islamorada on Tripadvisor

Yes, here are some popular holiday rentals in Islamorada that have internet access:\n\nSee all holiday rentals in Islamorada on Tripadvisor