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Islamorada Vacation Rentals

1 - 42 of 75 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
240 255 270 270 270 270 270 270 270 240 240 240 240 240 240 240 250
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
- - - - 115 120 120 120 120 99 99 99 99 99 99 99 99
Tavernier Waterfront Retreat - Islamorada, FL Vacation Rental
- 175 180 180 180 180 170 - - - - - - - - - -
Marathon Waterfront Recreational Paradise - Marathon, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Sunny Conch Getaway - Key West, FL Vacation Rental

Sunny Conch Getaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- - - 185 190 190 190 190 190 185 185 185 185 185 185 185 195
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - -
Landings of Largo Gem - Key Largo, FL Vacation Rental

Landings of Largo Gem

Key Largo, FL
2 Bed 2 Bath Sleeps 7 (4 Adults Max)
70 70 75 75 75 75 75 70 - - - - - - - 70 65
Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
- - - - 160 165 165 145 - - - - - - - - -
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - 260 - - - 275 - - - 365 385 385 365 - - -
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
99 115 120 120 120 120 120 120 120 99 99 99 99 99 99 99 99
Bright Key West Beauty - Key West, FL Vacation Rental

Bright Key West Beauty

Key West, FL
2 Bed 2.5 Bath Sleeps 5
- - - - - - - - - - - - - - - - -
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
- - - - - - - - - - - - - - - - -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
195 - - - - - - - - - - - - 230 245 245 255
Lower Keys Backcountry Escape - Sugarloaf Key, FL Vacation Rental
- - - - - - - 99 115 99 99 99 99 99 99 99 115
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
- - 195 220 220 220 220 250 250 190 190 190 190 190 195 - -
Sunnyside Canal  - Key Colony Beach, FL Vacation Rental

Sunnyside Canal

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
The Henry Flagler - Long Key, FL Vacation Rental

The Henry Flagler

Long Key, FL
2 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - 275 -
The Zane Grey - Long Key, FL Vacation Rental

The Zane Grey

Long Key, FL
2 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- - 295 295 - - - - 330 295 295 295 295 290 - - -
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- - - - - - - - 145 - - - - - - - 145
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - 185 - - - - 185 - - - - - - 150 -
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - - - 190 - - - - - - - - -
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Sweeping Atlantic View Escape - Tavernier, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
115 - - - - - - - - - - - - - - - -
Fishing and Kayaking Dream Cove - Marathon, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Ninth Street Getaway - 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
- - - - - - - - - - - - - - - - -
Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - - - - - - - - - - - - - 99 120
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
- - - - - - - 140 145 135 135 135 135 135 115 - -
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
160 - - - - - - - - - - - - - - 165 195
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- - - - - - - - 125 - - - - - - - 125
Sunlit Serenity - Key Colony Beach, FL Vacation Rental

Sunlit Serenity

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- 140 175 175 175 175 175 175 175 160 160 160 155 - - - -
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - - - 295 320 275 - - - - - - - - -
Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- 135 165 165 165 165 165 165 165 145 - - - - - - -
Downhome Cabin by the Canal - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Fisher's Paradise - Key Colony Beach, FL Vacation Rental

Fisher's Paradise

Key Colony Beach, FL
2 Bed 2 Bath Sleeps 4
- - - - - - - - - - 155 160 160 160 160 160 170
Paradise on Patricia Lane - Marathon, FL Vacation Rental

Paradise on Patricia Lane

Marathon, FL
2 Bed 2 Bath Sleeps 6
- 140 175 175 175 175 175 175 175 160 160 160 160 160 160 160 160
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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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