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Islamorada Rentals with Pools

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132 rentals in Islamorada.
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100' Private Beach Front Ocean Front Estate, vacation rental in Islamorada

100' Private Beach Front Ocean Front Estate

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Mitchell's Keys Villa - Private, Secluded House on the Bay, vacation rental in Islamorada

Mitchell's Keys Villa - Private, Secluded House on the Bay

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SUNSHINE PLACE, vacation rental in Islamorada

SUNSHINE PLACE

1 bedroom
1 bathroom
Sleeps 3
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

2 bedrooms
3 bathrooms
Sleeps 4
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

3 bedrooms
3 bathrooms
Sleeps 8
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

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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January 10% OFF! Boat Slip included, 2 Beaches, Pool, Oceanfront Anglers Reef, vacation rental in Islamorada

January 10% OFF! Boat Slip included, 2 Beaches, Pool, Oceanfront Anglers Reef

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Waterfront Paradise Getaway!, vacation rental in Islamorada

Islamorada Waterfront Paradise Getaway!

1 bedroom
1 bathroom
Sleeps 2
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

2 bedrooms
3 bathrooms
Sleeps 6
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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxurious Anglers Reef with Boat Slip, Pool, Ocean, vacation rental in Islamorada

Luxurious Anglers Reef with Boat Slip, Pool, Ocean

2 bedrooms
3 bathrooms
Sleeps 5
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

3 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

2 bedrooms
2 bathrooms
Sleeps 6
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

3 bedrooms
3 bathrooms
Sleeps 8
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

3 bedrooms
2 bathrooms
Sleeps 6
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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bayside Condo, marina, pool and beach, vacation rental in Islamorada

Bayside Condo, marina, pool and beach

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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75731 Overseas Highway, vacation rental in Islamorada

75731 Overseas Highway

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Completely Remodeled 2 Bedroom, 2 Bath Florida Keys Condo On the Atlantic Ocean, vacation rental in Islamorada

Completely Remodeled 2 Bedroom, 2 Bath Florida Keys Condo On the Atlantic Ocean

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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SANCTUARY IN PARADISE, vacation rental in Islamorada

SANCTUARY IN PARADISE

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Oceanfront Oasis - Pinch me am I dreaming!!!, vacation rental in Islamorada

Oceanfront Oasis - Pinch me am I dreaming!!!

5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Luxury condo overlooking harbor with ocean view, vacation rental in Islamorada

Luxury condo overlooking harbor with ocean view

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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BEACON REEF 310, vacation rental in Islamorada

BEACON REEF 310

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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140 Atlantic Lane, vacation rental in Islamorada

140 Atlantic Lane

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!, vacation rental in Islamorada

NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Paradise Beach Sandy Oceanfront, vacation rental in Islamorada

Paradise Beach Sandy Oceanfront

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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132 Columbus Drive, vacation rental in Islamorada

132 Columbus Drive

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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THE PERFECT GETAWAY, vacation rental in Islamorada

THE PERFECT GETAWAY

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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82754 Overseas Highway, vacation rental in Islamorada

82754 Overseas Highway

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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76004 Overseas Highway, vacation rental in Islamorada

76004 Overseas Highway

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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$2500 A MONTH FOR OCTOBER AND NOVEMBER.  OCEANFRONT 2 BEDROOM/2 BATH CONDO, vacation rental in Islamorada

$2500 A MONTH FOR OCTOBER AND NOVEMBER. OCEANFRONT 2 BEDROOM/2 BATH CONDO

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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137 LeSerra Lane, vacation rental in Islamorada

137 LeSerra Lane

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

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

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, vacation rental in Islamorada

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Come relax in Islamorada, the tropical jewel of the Florida Keys!!, vacation rental in Islamorada

Come relax in Islamorada, the tropical jewel of the Florida Keys!!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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LITTLE BAY - Upper Duplex, vacation rental in Islamorada

LITTLE BAY - Upper Duplex

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys., vacation rental in Islamorada

3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LITTLE BAY - Lower Duplex, vacation rental in Islamorada

LITTLE BAY - Lower Duplex

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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VILLA RIOLO, vacation rental in Islamorada

VILLA RIOLO

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean-Front Caribbean Home., vacation rental in Islamorada

Ocean-Front Caribbean Home.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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LITTLE BAY - Cottage, vacation rental in Islamorada

LITTLE BAY - Cottage

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada - PARADISE FOUND 3 bedroom/2 bath, vacation rental in Islamorada

Islamorada - PARADISE FOUND 3 bedroom/2 bath

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Islamorada Waterfront Paradise 2, vacation rental in Islamorada

Islamorada Waterfront Paradise 2

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BEACON REEF 222, vacation rental in Islamorada

BEACON REEF 222

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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PALMS 309, vacation rental in Islamorada

PALMS 309

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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MANATEE MANOR, vacation rental in Islamorada

MANATEE MANOR

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Little Bay Compound, vacation rental in Islamorada

Little Bay Compound

5 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Mile Marker 87 - Mina Bay - Oceanfront 'Million Dollar View', vacation rental in Islamorada

Mile Marker 87 - Mina Bay - Oceanfront 'Million Dollar View'

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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107 San Remo Drive, vacation rental in Islamorada

107 San Remo Drive

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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