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Islamorada Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
701 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
2 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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Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast, vacation rental in Islamorada
Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast, vacation rental in Islamorada
Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast, vacation rental in Islamorada

Discover Florida Keys! Seaside Villa w/ Patio! Marina, Pool, Parking, Breakfast

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Anglers Reef- Family Friendly Community at a Fraction of the Cost., vacation rental in Islamorada
Anglers Reef- Family Friendly Community at a Fraction of the Cost., vacation rental in Islamorada
Anglers Reef- Family Friendly Community at a Fraction of the Cost., vacation rental in Islamorada

Anglers Reef- Family Friendly Community at a Fraction of the Cost.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Waterfront Townhome w/ Private Beach in the Florida Keys!, vacation rental in Islamorada
Waterfront Townhome w/ Private Beach in the Florida Keys!, vacation rental in Islamorada
Waterfront Townhome w/ Private Beach in the Florida Keys!, vacation rental in Islamorada

Waterfront Townhome w/ Private Beach in the Florida Keys!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking, vacation rental in Islamorada
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking, vacation rental in Islamorada
Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking, vacation rental in Islamorada

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly!, vacation rental in Islamorada
Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly!, vacation rental in Islamorada
Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly!, vacation rental in Islamorada

Family Getaway! 3 Tropical View Units, Outdoor Pools, Pet-friendly!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Islamorada paradise vacation home in sought after Venation shores, vacation rental in Islamorada
Islamorada paradise vacation home in sought after Venation shores, vacation rental in Islamorada
Islamorada paradise vacation home in sought after Venation shores, vacation rental in Islamorada

Islamorada paradise vacation home in sought after Venation shores

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Venetian Shores Home, vacation rental in Islamorada
Venetian Shores Home, vacation rental in Islamorada
Venetian Shores Home, vacation rental in Islamorada

Venetian Shores Home

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft, vacation rental in Islamorada
Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft, vacation rental in Islamorada
Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft, vacation rental in Islamorada

Yolo " You only live once" - Fishing Paradise in Islamorada with a 70ft

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Latitude Adjustment FLKeys, vacation rental in Islamorada
Latitude Adjustment FLKeys, vacation rental in Islamorada
Latitude Adjustment FLKeys, vacation rental in Islamorada

Latitude Adjustment FLKeys

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming Islamorada waterfront home!, vacation rental in Islamorada
Charming Islamorada waterfront home!, vacation rental in Islamorada
Charming Islamorada waterfront home!, vacation rental in Islamorada

Charming Islamorada waterfront home!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Water Views from every room in the House, vacation rental in Islamorada
Beautiful Water Views from every room in the House, vacation rental in Islamorada
Beautiful Water Views from every room in the House, vacation rental in Islamorada

Beautiful Water Views from every room in the House

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast, vacation rental in Islamorada
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast, vacation rental in Islamorada
Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast, vacation rental in Islamorada

Prime Location! Pet-Friendly Property, Free Parking, Free Breakfast

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Your Dream Escape in Islamorada! Pet-friendly Property, Swimming Pool!, vacation rental in Islamorada
Your Dream Escape in Islamorada! Pet-friendly Property, Swimming Pool!, vacation rental in Islamorada
Your Dream Escape in Islamorada! Pet-friendly Property, Swimming Pool!, vacation rental in Islamorada

Your Dream Escape in Islamorada! Pet-friendly Property, Swimming Pool!

Rental Home
1 bedroom
1 bathroom
Sleeps 4
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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2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay, vacation rental in Islamorada
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay, vacation rental in Islamorada
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay, vacation rental in Islamorada

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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�AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM, vacation rental in Islamorada
�AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM, vacation rental in Islamorada
�AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM, vacation rental in Islamorada

�AQUAMARINE OCEANVIEW⚡️FLASH SALE-OCT & DEC+”143”⭐️5 STAR REVIEWS+DOCK+POOL+GYM

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out, vacation rental in Islamorada
Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out, vacation rental in Islamorada
Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out, vacation rental in Islamorada

Coconut Palm South,1 King Bed, 2 Full Beds, 1 Pull Out

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
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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Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!, vacation rental in Islamorada
Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!, vacation rental in Islamorada
Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!, vacation rental in Islamorada

Vacation Day Is Always A Great Idea! 4 Classy Units, FREE Parking, Pets Allowed!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront, vacation rental in Islamorada
Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront, vacation rental in Islamorada
Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront, vacation rental in Islamorada

Come Create Memories w/ Fun-filled Adventures at this Paradise! Beachfront

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Upscale Waterfront Home with Private Beach & Dockage, vacation rental in Islamorada
Upscale Waterfront Home with Private Beach & Dockage, vacation rental in Islamorada
Upscale Waterfront Home with Private Beach & Dockage, vacation rental in Islamorada

Upscale Waterfront Home with Private Beach & Dockage

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Your Home Away From Home! 4 Relaxing Units, FREE Parking, Onsite Pool, vacation rental in Islamorada
Your Home Away From Home! 4 Relaxing Units, FREE Parking, Onsite Pool, vacation rental in Islamorada
Your Home Away From Home! 4 Relaxing Units, FREE Parking, Onsite Pool, vacation rental in Islamorada

Your Home Away From Home! 4 Relaxing Units, FREE Parking, Onsite Pool

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock., vacation rental in Islamorada
Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock., vacation rental in Islamorada
Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock., vacation rental in Islamorada

Islamorada waterfront gem: Total reno ‘24: 3/3.5, pool, spa & deep water dock.

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Unique 2 Bedroom Bay Front Home with Roof Top Terrace, vacation rental in Islamorada
Unique 2 Bedroom Bay Front Home with Roof Top Terrace, vacation rental in Islamorada
Unique 2 Bedroom Bay Front Home with Roof Top Terrace, vacation rental in Islamorada

Unique 2 Bedroom Bay Front Home with Roof Top Terrace

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi, vacation rental in Islamorada
Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi, vacation rental in Islamorada
Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi, vacation rental in Islamorada

Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Best Location in Islamorada!! Beach access - Boat trailer parking!, vacation rental in Islamorada
Best Location in Islamorada!! Beach access - Boat trailer parking!, vacation rental in Islamorada
Best Location in Islamorada!! Beach access - Boat trailer parking!, vacation rental in Islamorada

Best Location in Islamorada!! Beach access - Boat trailer parking!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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" Endless Summer" Awaits!, vacation rental in Islamorada
" Endless Summer" Awaits!, vacation rental in Islamorada
" Endless Summer" Awaits!, vacation rental in Islamorada

" Endless Summer" Awaits!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
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 2
Match: Sleeps
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Harbor Hideaway | Island style beach house with pool, dockage & bay views!, vacation rental in Islamorada
Harbor Hideaway | Island style beach house with pool, dockage & bay views!, vacation rental in Islamorada
Harbor Hideaway | Island style beach house with pool, dockage & bay views!, vacation rental in Islamorada

Harbor Hideaway | Island style beach house with pool, dockage & bay views!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful Townhouse in the heart of the Florida Keys, vacation rental in Islamorada
Beautiful Townhouse in the heart of the Florida Keys, vacation rental in Islamorada
Beautiful Townhouse in the heart of the Florida Keys, vacation rental in Islamorada

Beautiful Townhouse in the heart of the Florida Keys

Rental Home
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Just a Few Friends - Ocean View and Bring your Boat!, vacation rental in Islamorada
Just a Few Friends - Ocean View and Bring your Boat!, vacation rental in Islamorada
Just a Few Friends - Ocean View and Bring your Boat!, vacation rental in Islamorada

Just a Few Friends - Ocean View and Bring your Boat!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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BEAUTIFUL ISLAMORADA KEYS HOME, vacation rental in Islamorada
BEAUTIFUL ISLAMORADA KEYS HOME, vacation rental in Islamorada
BEAUTIFUL ISLAMORADA KEYS HOME, vacation rental in Islamorada

BEAUTIFUL ISLAMORADA KEYS HOME

Rental Home
1 bedroom
1 bathroom
Sleeps 20
Match: Sleeps
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Flakey's B&B in the heart of Islamorada, vacation rental in Islamorada
Flakey's B&B in the heart of Islamorada, vacation rental in Islamorada
Flakey's B&B in the heart of Islamorada, vacation rental in Islamorada

Flakey's B&B in the heart of Islamorada

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Islamorada Bay Harbour 2/2.5 Condo Free DOCK included -Rate Specials!, vacation rental in Islamorada
Islamorada Bay Harbour 2/2.5 Condo Free DOCK included -Rate Specials!, vacation rental in Islamorada
Islamorada Bay Harbour 2/2.5 Condo Free DOCK included -Rate Specials!, vacation rental in Islamorada

Islamorada Bay Harbour 2/2.5 Condo Free DOCK included -Rate Specials!

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Charming and Cozy  Townhouse in the Fl Keys with Pool and Beach Access, vacation rental in Islamorada
Charming and Cozy  Townhouse in the Fl Keys with Pool and Beach Access, vacation rental in Islamorada
Charming and Cozy  Townhouse in the Fl Keys with Pool and Beach Access, vacation rental in Islamorada

Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ultimate luxury vacation home in Islamorada, Florida!, vacation rental in Islamorada
Ultimate luxury vacation home in Islamorada, Florida!, vacation rental in Islamorada
Ultimate luxury vacation home in Islamorada, Florida!, vacation rental in Islamorada

Ultimate luxury vacation home in Islamorada, Florida!

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Hidden Gem Islamorada | 1st Floor, vacation rental in Islamorada
Hidden Gem Islamorada | 1st Floor, vacation rental in Islamorada
Hidden Gem Islamorada | 1st Floor, vacation rental in Islamorada

Hidden Gem Islamorada | 1st Floor

Condo/Apartment
2 bedrooms
2 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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Beautiful Bayfront Home with Amazing Sunsets, vacation rental in Islamorada
Beautiful Bayfront Home with Amazing Sunsets, vacation rental in Islamorada
Beautiful Bayfront Home with Amazing Sunsets, vacation rental in Islamorada

Beautiful Bayfront Home with Amazing Sunsets

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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The Villa by the Bay, Islamorada FL, vacation rental in Islamorada
The Villa by the Bay, Islamorada FL, vacation rental in Islamorada
The Villa by the Bay, Islamorada FL, vacation rental in Islamorada

The Villa by the Bay, Islamorada FL

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Harbor Front Oceanside Home on the Atlantic Ocean, vacation rental in Islamorada
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean, vacation rental in Islamorada
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean, vacation rental in Islamorada

Beautiful Harbor Front Oceanside Home on the Atlantic Ocean

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Gulf access, private dock and private neighborhood beach!, vacation rental in Islamorada
Gulf access, private dock and private neighborhood beach!, vacation rental in Islamorada
Gulf access, private dock and private neighborhood beach!, vacation rental in Islamorada

Gulf access, private dock and private neighborhood beach!

Rental Home
5 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Whole House w/ Tropical Atmosphere just Steps from the Beach - Ideal for Groups, vacation rental in Islamorada
Whole House w/ Tropical Atmosphere just Steps from the Beach - Ideal for Groups, vacation rental in Islamorada
Whole House w/ Tropical Atmosphere just Steps from the Beach - Ideal for Groups, vacation rental in Islamorada

Whole House w/ Tropical Atmosphere just Steps from the Beach - Ideal for Groups

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED, vacation rental in Islamorada
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED, vacation rental in Islamorada
TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED, vacation rental in Islamorada

TICKET TO PARADISE !!! PRIVATE POOL, OCEAN SIDE/VIEW COMPLETELY REMODELED

Rental Home
3 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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Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach., vacation rental in Islamorada
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach., vacation rental in Islamorada
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach., vacation rental in Islamorada

Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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San Remo Canal Front, vacation rental in Islamorada
San Remo Canal Front, vacation rental in Islamorada
San Remo Canal Front, vacation rental in Islamorada

San Remo Canal Front

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-50 of 701
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