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Islamorada Vacation Rentals

1 - 42 of 74 rentals
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White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
285 295 295 295 315 315 315 270 270 270 270 255 - - - - -
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
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Tavernier Waterfront Retreat - Islamorada, FL Vacation Rental
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Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
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Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - - - 230 - - - - - - 245 - - - -
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- 245 - - - - - 275 275 - - - - - - - -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
- - - - - - 255 270 270 270 270 270 270 270 270 270 270
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
99 99 99 99 115 99 - - - - - - - - - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
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The Henry Flagler - Long Key, FL Vacation Rental

The Henry Flagler

Long Key, FL
2 Bed 1 Bath Sleeps 6
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Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - 275 340 340 340 330 - - - - - - - 330 295
Perfect Boater's Retreat - Key Largo, FL Vacation Rental

Perfect Boater's Retreat

Key Largo, FL
3 Bed 2 Bath Sleeps 6
90 99 99 99 99 99 99 99 99 99 99 99 99 99 99 99 90
Fisherman's Canal Getaway - Key Colony Beach, FL Vacation Rental
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The Zane Grey - Long Key, FL Vacation Rental

The Zane Grey

Long Key, FL
2 Bed 1 Bath Sleeps 6
- - - - - - - - - 255 - - - - - - -
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
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White Dunes Retreat  - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - 190 195 195 195 195
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - 185 - - - - - - - - -
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
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Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - - - - - - 290 290 - - 275 - - - - 330
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
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Ninth Street Suite - Key Colony Beach, FL Vacation Rental
- - - - - - - - - 140 150 140 - - - - -
Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
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Fishing and Kayaking Dream Cove - Marathon, FL Vacation Rental
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Comfort in the Keys - Key Colony Beach, FL Vacation Rental
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No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - 165 175 175 150
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
- 225 225 225 225 - - - - - - - - - - - -
Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
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Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
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Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
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Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
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Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
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Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - - - - - 125 - - - - - - -
Eleventh Street Legacy - Key Colony Beach, FL Vacation Rental
- - - - - - 160 - - - - - - - - - -
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
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Fantastic Fifth Street - Key Colony Beach, FL Vacation Rental

Fantastic Fifth Street

Key Colony Beach, FL
4 Bed 2.5 Bath Sleeps 10
- - - 140 165 165 160 - - - - - - - - - -
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
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Oceanfront Palace - Long Key, FL Vacation Rental

Oceanfront Palace

Long Key, FL
6 Bed 5 Bath Sleeps 14
- - 580 580 580 580 580 - - - - - - - - - -
Atlantic Oasis - Tavernier, FL Vacation Rental

Atlantic Oasis

Tavernier, FL
2 Bed 2 Bath Sleeps 7 (6 Adults Max)
130 135 135 135 145 145 145 145 145 145 145 145 145 145 145 145 145
Ninth Street Splendor - Key Colony Beach, FL Vacation Rental
- - - - - - 185 195 195 165 - - - - - - -
Fisher's Paradise - Key Colony Beach, FL Vacation Rental

Fisher's Paradise

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
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About Islamorada

Islamorada rated 3.5 out of 5 based on 4 reviews Islamorada, FL

Quaint island living, plenty of fun in the sun activities, and access to world-class sport fishing are ready to greet you when you stay at one of our Islamorada vacation rentals. Islamorada is a popular destination for those seeking year-round warm weather, beautiful white sand beaches, and a laid-back island vibe. 

Things to Do in Islamorada

Located between the Florida Key islands of Key Largo to the east and Marathon Key to the west, Islamorada offers a wide range of activities from snorkeling to paragliding to landing trophy tarpon and marlin in the area’s warm coastal waters, making it well-suited for adventurers and families.

Kids will love interacting with the area’s abundant sea life at the Theater of the Sea marine mammal park, where they can toss mackerel to hungry sea lions, swim with dolphins, and get up close to endangered sea turtles. They might also enjoy learning about the island’s mangrove swamps and exotic coastal habitat aboard a Family Fun Boat Tour, where they’ll surely have close encounters with egrets, herons, gulls, and other avian residents of the island!

For more adult tastes, Islamorada offers a plethora of lively options, ranging from great dining at any of the area’s fresh-from-the-boat seafood restaurants to live reggae, bluegrass, and other music festivals throughout the year at ICE Amphitheater at Founder’s Park on Plantation Key. Whatever your vacation plans may entail, a stay in one of our Florida Keys vacation rentals in Islamorada provides an excellent home base!

Outdoor Adventures in Islamorada

For those who like to get out and explore nature, Islamorada offers unmatched access to a wide range of activities on both land and water. Take a self-guided walk through lush nature trails on 965 acres of pristine old growth mangrove, mahogany, and poisonwood marshland at Long Key State Park, or unearth buried treasure and artifacts from a Spanish ship that sunk in 1733 at Indian Key Historic State Park. If you prefer to stay dry, rent kayaks or a boat to tour the ancient coral reef and the tropical forest that thrives above at the Lignumvitae Key Botanical State Park on tiny Lignumvitae Key.

Day Trips from Islamorada, FL

On the north end of the key islands, Islamorada offers quick access to the mainland, which is only 40 miles to the north. Drive north another 40 miles to arrive in Miami, a city known for its thriving nightlife, great shopping, and Latin-focused dining. Thousands of acres of swampland that are home to alligators, cranes, snakes, and many other native species await only 53 miles away at Everglades National Park. Marathon, Big Pine, Sugarloaf, and Key West islands lie just south, and are within 80 miles of Islamorada.

For a fantastic home base in the Florida Keys, a stay in any of our Islamorada vacation rentals is one you won’t soon forget!

Photo credit: Jon Bilous via Shutterstock

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