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Islamorada Vacation Rentals

1 - 42 of 80 rentals
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Ocean Oasis - Islamorada, FL Vacation Rental

Ocean Oasis

Islamorada, FL
4 Bed 3 Bath Sleeps 10
- - - - - - - - - - - - - - - 560 590
Hawksbill Cottage - Islamorada, FL Vacation Rental

Hawksbill Cottage

Islamorada, FL
1 Bed 1 Bath Sleeps 3 (2 Adults Max)
- - - - - - - - - - - - - - - - -
Kemp's Cottage - Islamorada, FL Vacation Rental

Kemp's Cottage

Islamorada, FL
1 Bed 1 Bath Sleeps 2
- - - - - - - - - - - - - - - - -
Turtle Key Complex - Islamorada, FL Vacation Rental

Turtle Key Complex

Islamorada, FL
6 Bed 6 Bath Sleeps 22 (20 Adults Max)
- - - - - - - - - - - - - - - - -
Green Turtle Cottage - Islamorada, FL Vacation Rental

Green Turtle Cottage

Islamorada, FL
2 Bed 1 Bath Sleeps 6 (4 Adults Max)
- - - - - - - - - - - - - - - - -
Leatherback Cottage - Upper Unit - Islamorada, FL Vacation Rental
- - - - - - - - - - - - - - - - -
White Sands in Paradise - Islamorada, FL Vacation Rental

White Sands in Paradise

Islamorada, FL
2 Bed 2 Bath Sleeps 6
215 195 - - - - - - - - 190 190 - - - - -
Summer Sea Luxury - Islamorada, FL Vacation Rental

Summer Sea Luxury

Islamorada, FL
1 Bed 1 Bath Sleeps 4
85 90 90 99 99 99 99 99 99 99 99 99 99 99 99 99 99
Tavernier Waterfront Retreat - Islamorada, FL Vacation Rental
135 165 165 150 160 160 160 160 185 185 160 160 160 160 160 185 185
The Ocean is Calling  - Marathon, FL Vacation Rental

The Ocean is Calling

Marathon, FL
5 Bed 3 Bath Sleeps 12
- - - - - - - - - - - - - - - - -
Breezy Palms & Tropical Charm - Key Colony Beach, FL Vacation Rental
- - - - - - - - - - - - - - - - -
Marathon Waterfront Recreational Paradise - Marathon, FL Vacation Rental
- - 460 485 - - - - - - - - - - - - 495
Sweet Serenity - Key Largo, FL Vacation Rental

Sweet Serenity

Key Largo, FL
3 Bed 2 Bath Sleeps 8
65 65 65 65 65 65 65 65 65 65 65 65 65 65 65 65 65
Million Dollar View - Marathon, FL Vacation Rental

Million Dollar View

Marathon, FL
4 Bed 3 Bath Sleeps 8
- - - - - - - - - - - - - - - - 455
Pelico Paradise - Sugarloaf Key, FL Vacation Rental

Pelico Paradise

Sugarloaf Key, FL
5 Bed 3.5 Bath Sleeps 10
- - - - 190 195 190 - - - 190 195 195 190 - - -
Waterfront Playground - Key Largo, FL Vacation Rental

Waterfront Playground

Key Largo, FL
3 Bed 2.5 Bath Sleeps 8
99 99 99 99 99 99 99 99 99 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
260 235 - - - - - - - 190 225 225 225 215 - - -
Boater's Dream Come True - Marathon, FL Vacation Rental

Boater's Dream Come True

Marathon, FL
4 Bed 2.5 Bath Sleeps 12
- - - - - - 220 230 195 - - - - - - - 190
Hemingway Hideaway - Key West, FL Vacation Rental

Hemingway Hideaway

Key West, FL
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - 220 230 220 - -
Key Lime on Fifth Street - Key Colony Beach, FL Vacation Rental
130 135 135 145 135 135 135 135 115 - - - - - - - 115
Dolphin Retreat - Marathon, FL Vacation Rental

Dolphin Retreat

Marathon, FL
3 Bed 3 Bath Sleeps 8
180 235 235 195 180 180 180 180 220 220 180 180 180 180 180 220 220
Sweeping Atlantic View Escape - Tavernier, FL Vacation Rental
155 195 195 175 185 185 185 185 215 215 185 185 185 185 185 215 215
No Worries on Ninth Street - Key Colony Beach, FL Vacation Rental
- 145 155 160 155 145 - - - - - - - - - - -
Duck Key Retreat - Marathon, FL Vacation Rental

Duck Key Retreat

Marathon, FL
3 Bed 2.5 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Bay Point Serenity - Key West, FL Vacation Rental

Bay Point Serenity

Key West, FL
3 Bed 3 Bath Sleeps 8
230 240 240 255 195 195 195 195 195 195 195 195 195 195 195 195 195
The Fish Wrangler - Marathon, FL Vacation Rental

The Fish Wrangler

Marathon, FL
2 Bed 2 Bath Sleeps 6
- - - - 160 170 170 170 145 - - - - - - - -
Ninth Street Cabana - Key Colony Beach, FL Vacation Rental

Ninth Street Cabana

Key Colony Beach, FL
3 Bed 2.5 Bath Sleeps 10
215 225 225 240 240 240 240 240 195 - - - - - - 225 240
Fisherman's Prime - Marathon, FL Vacation Rental

Fisherman's Prime

Marathon, FL
2 Bed 2 Bath Sleeps 6
150 - - - - - - - 155 - - - - - - - 165
Oasis in the Keys - Marathon, FL Vacation Rental

Oasis in the Keys

Marathon, FL
3 Bed 2.5 Bath Sleeps 8
- - - - - 250 265 265 265 265 265 265 265 265 265 265 265
The Zane Grey - Long Key, FL Vacation Rental

The Zane Grey

Long Key, FL
2 Bed 1 Bath Sleeps 6
- - - 240 250 240 - - - - - 225 - - - - -
Tropical Treasure - Key Colony Beach, FL Vacation Rental

Tropical Treasure

Key Colony Beach, FL
3 Bed 2 Bath Sleeps 8
- - - - - - - - - 175 195 195 195 195 190 - -
Ninth Street Suite - Key Colony Beach, FL Vacation Rental
- - - 140 150 150 150 150 150 150 150 140 - - - - -
Ninth Street Getaway - Key Colony Beach, FL Vacation Rental
- - 130 160 160 160 160 160 160 160 160 160 160 160 160 160 160
Dockside Delight - Key Colony Beach, FL Vacation Rental

Dockside Delight

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 6
- - 155 195 185 185 185 185 185 185 185 185 185 185 185 185 185
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)
65 70 70 65 65 65 65 65 70 70 65 65 65 65 65 70 70
Comfort in the Keys - Key Colony Beach, FL Vacation Rental
- - - - - - - 145 155 155 155 155 155 155 155 155 155
Sombrero Beach Place - Marathon, FL Vacation Rental

Sombrero Beach Place

Marathon, FL
2 Bed 2 Bath Sleeps 5
145 155 155 160 155 155 155 155 155 155 145 - - - - - -
Perfect Diver's and Fisherman's Pad - Marathon, FL Vacation Rental
- - - - - - 115 120 99 - - - - - - - 99
Captain's Haven - Key Colony Beach, FL Vacation Rental

Captain's Haven

Key Colony Beach, FL
3 Bed 3 Bath Sleeps 9
- - - - - - - - - - - - - - - - -
The Atlantic Lookout  - Marathon, FL Vacation Rental

The Atlantic Lookout

Marathon, FL
2 Bed 2 Bath Sleeps 6
165 175 175 185 170 170 170 170 170 160 - - - - - - -
Canal-side Charisma - Key Colony Beach, FL Vacation Rental
- 99 - - - - - - - - - - - - - - -
Seventh Street on the Water - Key Colony Beach, FL Vacation Rental
- 99 99 - - - - - - - 99 99 99 99 99 99 99
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About Islamorada

Islamorada rated 3.8 out of 5 based on 5 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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