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Islamorada Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
746 rentals in Islamorada.
Wonderful 2 Bedroom Condo with Ocean Views, vacation rental in Islamorada
Wonderful 2 Bedroom Condo with Ocean Views, vacation rental in Islamorada
Wonderful 2 Bedroom Condo with Ocean Views, vacation rental in Islamorada

Wonderful 2 Bedroom Condo with Ocean Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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ULTIMATE outdoor living area at this 4/4 canal home with pool!, vacation rental in Islamorada
ULTIMATE outdoor living area at this 4/4 canal home with pool!, vacation rental in Islamorada
ULTIMATE outdoor living area at this 4/4 canal home with pool!, vacation rental in Islamorada

ULTIMATE outdoor living area at this 4/4 canal home with pool!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Modern Oceanview Paradise at Islamorada, vacation rental in Islamorada
Modern Oceanview Paradise at Islamorada, vacation rental in Islamorada
Modern Oceanview Paradise at Islamorada, vacation rental in Islamorada

Modern Oceanview Paradise at Islamorada

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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You will love my "Fl Keys Luxury Home", vacation rental in Islamorada
You will love my "Fl Keys Luxury Home", vacation rental in Islamorada
You will love my "Fl Keys Luxury Home", vacation rental in Islamorada

You will love my "Fl Keys Luxury Home"

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!, vacation rental in Islamorada
4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!, vacation rental in Islamorada
4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!, vacation rental in Islamorada

4BR waterfront home with POOL, boat slip with straight shot to Alligator Reef!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast, vacation rental in Islamorada
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast, vacation rental in Islamorada
Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast, vacation rental in Islamorada

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169, vacation rental in Islamorada
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169, vacation rental in Islamorada
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169, vacation rental in Islamorada

Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip, vacation rental in Islamorada
The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip, vacation rental in Islamorada
The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip, vacation rental in Islamorada

The Perfect Getaway with Swimming Pool, Jacuzzi and Boatslip

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tropical Paradise, vacation rental in Islamorada
Tropical Paradise, vacation rental in Islamorada
Tropical Paradise, vacation rental in Islamorada

Tropical Paradise

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront, Private Pool Oasis!, vacation rental in Islamorada
Oceanfront, Private Pool Oasis!, vacation rental in Islamorada
Oceanfront, Private Pool Oasis!, vacation rental in Islamorada

Oceanfront, Private Pool Oasis!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Incredible Bayside Home in the Florida Keys!, vacation rental in Islamorada
Incredible Bayside Home in the Florida Keys!, vacation rental in Islamorada
Incredible Bayside Home in the Florida Keys!, vacation rental in Islamorada

Incredible Bayside Home in the Florida Keys!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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ISLAMORADA BEACH HOUSE, vacation rental in Islamorada
ISLAMORADA BEACH HOUSE, vacation rental in Islamorada
ISLAMORADA BEACH HOUSE, vacation rental in Islamorada

ISLAMORADA BEACH HOUSE

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking, vacation rental in Islamorada
4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking, vacation rental in Islamorada
4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking, vacation rental in Islamorada

4 Family-friendly Rooms w/ Balcony | Refreshing Outdoor Pool & Free Parking

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed, vacation rental in Islamorada
Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed, vacation rental in Islamorada
Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed, vacation rental in Islamorada

Indulge in Home Like Comfort! Courtyard View, Free Parking, Pool, Pets Allowed

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private 2 Acre Bayside Waterfront  Estate 
2/2 All To Yourself  ~ New Listing!, vacation rental in Islamorada
Private 2 Acre Bayside Waterfront  Estate 
2/2 All To Yourself  ~ New Listing!, vacation rental in Islamorada
Private 2 Acre Bayside Waterfront  Estate 
2/2 All To Yourself  ~ New Listing!, vacation rental in Islamorada

Private 2 Acre Bayside Waterfront Estate 2/2 All To Yourself ~ New Listing!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream, vacation rental in Islamorada
Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream, vacation rental in Islamorada
Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream, vacation rental in Islamorada

Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream

Rental Home
4 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more, vacation rental in Islamorada
Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more, vacation rental in Islamorada
Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more, vacation rental in Islamorada

Exec Bay 3 Bedroom townhouse w/heated pool, marina, tennis & more

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront Estate in the Heart of Islamorada, vacation rental in Islamorada
Oceanfront Estate in the Heart of Islamorada, vacation rental in Islamorada
Oceanfront Estate in the Heart of Islamorada, vacation rental in Islamorada

Oceanfront Estate in the Heart of Islamorada

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Bayside: 1st Floor Apartment in Native Hammock on Florida Bay, vacation rental in Islamorada
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay, vacation rental in Islamorada
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay, vacation rental in Islamorada

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast, vacation rental in Islamorada
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast, vacation rental in Islamorada
Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast, vacation rental in Islamorada

Relax and Unwind! Pet-Friendly Property, Onsite Pool, Free Breakfast

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Tropical Oasis, vacation rental in Islamorada
Private Tropical Oasis, vacation rental in Islamorada
Private Tropical Oasis, vacation rental in Islamorada

Private Tropical Oasis

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relax in this updated townhome while overlooking the sparkling Atlantic Ocean, vacation rental in Islamorada
Relax in this updated townhome while overlooking the sparkling Atlantic Ocean, vacation rental in Islamorada
Relax in this updated townhome while overlooking the sparkling Atlantic Ocean, vacation rental in Islamorada

Relax in this updated townhome while overlooking the sparkling Atlantic Ocean

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Studio Apartment - Summer Sea Condo #230, vacation rental in Islamorada
Beautiful Studio Apartment - Summer Sea Condo #230, vacation rental in Islamorada
Beautiful Studio Apartment - Summer Sea Condo #230, vacation rental in Islamorada

Beautiful Studio Apartment - Summer Sea Condo #230

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!, vacation rental in Islamorada
3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!, vacation rental in Islamorada
3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!, vacation rental in Islamorada

3 Relaxing Units! FREE Breakfast, FREE Parking, Onsite Pool, Pets Allowed!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK, vacation rental in Islamorada
Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK, vacation rental in Islamorada
Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK, vacation rental in Islamorada

Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Coastal Retreat ~ Brand New 4-Bedroom Home in the Heart of Islamorada, vacation rental in Islamorada
Coastal Retreat ~ Brand New 4-Bedroom Home in the Heart of Islamorada, vacation rental in Islamorada
Coastal Retreat ~ Brand New 4-Bedroom Home in the Heart of Islamorada, vacation rental in Islamorada

Coastal Retreat ~ Brand New 4-Bedroom Home in the Heart of Islamorada

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,, vacation rental in Islamorada
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,, vacation rental in Islamorada
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,, vacation rental in Islamorada

Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Ocean Harbor Paradise in Islamorada, vacation rental in Islamorada
Ocean Harbor Paradise in Islamorada, vacation rental in Islamorada
Ocean Harbor Paradise in Islamorada, vacation rental in Islamorada

Ocean Harbor Paradise in Islamorada

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!, vacation rental in Islamorada
Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!, vacation rental in Islamorada
Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!, vacation rental in Islamorada

Dive Into Your Dream Vacation! 3 Spacious Units, Onsite Pool, FREE Breakfast!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life!, vacation rental in Islamorada
Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life!, vacation rental in Islamorada
Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life!, vacation rental in Islamorada

Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life!

Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite!, vacation rental in Islamorada
Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite!, vacation rental in Islamorada
Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite!, vacation rental in Islamorada

Cozy Coastal Haven for Relaxation! With Pools and Water Sports Onsite!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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2 Spacious Garden Suite w/ Kitchenette | Outdoor Pool + Beach Access, vacation rental in Islamorada
2 Spacious Garden Suite w/ Kitchenette | Outdoor Pool + Beach Access, vacation rental in Islamorada
2 Spacious Garden Suite w/ Kitchenette | Outdoor Pool + Beach Access, vacation rental in Islamorada

2 Spacious Garden Suite w/ Kitchenette | Outdoor Pool + Beach Access

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage, vacation rental in Islamorada
Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage, vacation rental in Islamorada
Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage, vacation rental in Islamorada

Romantic Studio Cottage Nestled in Lush Landscaping with Pool and Dockage

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Florida Keys' Jewel - Executive Bay Club, vacation rental in Islamorada
Florida Keys' Jewel - Executive Bay Club, vacation rental in Islamorada
Florida Keys' Jewel - Executive Bay Club, vacation rental in Islamorada

Florida Keys' Jewel - Executive Bay Club

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed, vacation rental in Islamorada
Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed, vacation rental in Islamorada
Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed, vacation rental in Islamorada

Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun, vacation rental in Islamorada
Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun, vacation rental in Islamorada
Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun, vacation rental in Islamorada

Islamorada HappyTarpon House:Private Heated Pool - Private Boat Dock- Family Fun

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Malayan Palm North 2 Bedrooms, 1 Bath, Garden View, vacation rental in Islamorada
Malayan Palm North 2 Bedrooms, 1 Bath, Garden View, vacation rental in Islamorada
Malayan Palm North 2 Bedrooms, 1 Bath, Garden View, vacation rental in Islamorada

Malayan Palm North 2 Bedrooms, 1 Bath, Garden View

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
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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Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool, vacation rental in Islamorada
Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool, vacation rental in Islamorada
Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool, vacation rental in Islamorada

Everything You Need For The Perfect Vacation! 3 Sleek Units, Beachfront, Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Beach Dream House, relax and enjoy the clear waters of Islamorada  FL, vacation rental in Islamorada
Beach Dream House, relax and enjoy the clear waters of Islamorada  FL, vacation rental in Islamorada
Beach Dream House, relax and enjoy the clear waters of Islamorada  FL, vacation rental in Islamorada

Beach Dream House, relax and enjoy the clear waters of Islamorada FL

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Executive Bay Club Bayfront/Beachfront paradise, vacation rental in Islamorada
Executive Bay Club Bayfront/Beachfront paradise, vacation rental in Islamorada
Executive Bay Club Bayfront/Beachfront paradise, vacation rental in Islamorada

Executive Bay Club Bayfront/Beachfront paradise

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!, vacation rental in Islamorada
Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!, vacation rental in Islamorada
Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!, vacation rental in Islamorada

Relax and Unwind Near Robbie's of Islamorada! FREE Parking & Breakfast, Pool!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View, vacation rental in Islamorada
Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View, vacation rental in Islamorada
Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View, vacation rental in Islamorada

Harbor house 2 Bedrooms, 2 Baths, Partial Ocean View

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out, vacation rental in Islamorada
Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out, vacation rental in Islamorada
Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out, vacation rental in Islamorada

Princess Palm South Poolside,1 King Bed, 2 FullBeds, 1 Pull Out

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Venetian Shores 5bed 7b, Pool , Spa, Boat lifts, open for Oct 2024, vacation rental in Islamorada
Venetian Shores 5bed 7b, Pool , Spa, Boat lifts, open for Oct 2024, vacation rental in Islamorada
Venetian Shores 5bed 7b, Pool , Spa, Boat lifts, open for Oct 2024, vacation rental in Islamorada

Venetian Shores 5bed 7b, Pool , Spa, Boat lifts, open for Oct 2024

Rental Home
5 bedrooms
8 bathrooms
Sleeps 10
Match: Sleeps
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Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed, vacation rental in Islamorada
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed, vacation rental in Islamorada
Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed, vacation rental in Islamorada

Convenient Stay in Florida! Free Parking, Free Breakfast, Pool, Pets Allowed

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming 2 Bedroom Ground Level Home with Bay Views, vacation rental in Islamorada
Charming 2 Bedroom Ground Level Home with Bay Views, vacation rental in Islamorada
Charming 2 Bedroom Ground Level Home with Bay Views, vacation rental in Islamorada

Charming 2 Bedroom Ground Level Home with Bay Views

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock, vacation rental in Islamorada
Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock, vacation rental in Islamorada
Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock, vacation rental in Islamorada

Sunset Reef - 4 bdrm, Bayside Private Gated Estate, Pool, Spa, Deep Water Dock

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Malayan Palm East 1 Bedroom, 1 Bath Garden View, vacation rental in Islamorada
Malayan Palm East 1 Bedroom, 1 Bath Garden View, vacation rental in Islamorada
Malayan Palm East 1 Bedroom, 1 Bath Garden View, vacation rental in Islamorada

Malayan Palm East 1 Bedroom, 1 Bath Garden View

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fantastic ocean front conch house on the ocean with 160’ dock., vacation rental in Islamorada
Fantastic ocean front conch house on the ocean with 160’ dock., vacation rental in Islamorada
Fantastic ocean front conch house on the ocean with 160’ dock., vacation rental in Islamorada

Fantastic ocean front conch house on the ocean with 160’ dock.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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