Islamorada vacation rentals

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Top-rated vacation rentals in Islamorada

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Cottage in Islamorada
*Key Lime Cottage* charming 2 BR w/pool near beach
Your slice of Islamorada awaits at the Key Lime Cottage! Located in the heart of the Florida Keys yet set in its own oasis, this charming 2 bedroom, 1 bath home with a full kitchen, access to a gorgeous (heated) community pool with only 6 other homes, outside seating with grill, beach chairs and key lime treats - there is something for everyone! Located 1 mile from the world famous Robbie's and numerous restaurants, breweries, marinas and shops in a 5-10 min drive. Anne's beach is 5 min drive.
$253 per night
Cottage in Islamorada
Islamorada bungalow 2 bed & pool
Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina
$391 per night
Bungalow in Islamorada
Lost in Paradise! King Master, Queen Guest, Pool
Castaway Island! Luxury In paradise! This hidden gem is your piece of paradise waiting! Fully remodeled and furnished from the floor up. All new furniture, fixtures and furnishings await. One of the most well appointed and private Bungalows in Islamorada. Perfect for the honeymooners and special occasion couples and small families. Private outside spaces. Room for boats and trailers. Even a private and locked boat ramp for our guests. Bikes, SUP's, Kayaks, beach chairs and more await you.
$374 per night

Stay near Islamorada's top sights

Photo of Theater of the Sea
Theater of the Sea140 locals recommend
Photo of Robbie's
Robbie's165 locals recommend
Photo of Whale Harbor Seafood Buffet
Whale Harbor Seafood Buffet14 locals recommend
Photo of Rain Barrel Village
Rain Barrel Village21 locals recommend
Photo of Lorelei Restaurant & Cabana Bar
Lorelei Restaurant & Cabana Bar73 locals recommend
Photo of Lazy Days Restaurant
Lazy Days Restaurant76 locals recommend

Islamorada house rentals

Home in Islamorada
Tropical Getaway 3/3 with 100’ boat dock and pool
$449 per night
SUPERHOST
Home in Islamorada
4 Bedroom Private Oceanfront House - Bahia
$699 per night
Home in Islamorada
Oceanfront 114 Anglers Reef Islamorada Fla Keys
$549 per night
Home in Marathon
Oceanfront Tiny Villa | Dog Friendly
$364 per night
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Home in Key Colony Beach
Private Corner Lot, Wide Water Views, 30' Dock
$329 per night
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Home in Islamorada
The Russell Estate, 2 Acrs on OCEAN, tropical 3/2
$700 per night
Home in Key Largo
Your Keys Getaway!
$159 per night
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Home in Key Colony Beach
Captain’s Quarters Ahoy Mateys! Florida, Keys
$367 per night
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Home in Key Colony Beach
Waterfront Home 37.5-ft dock, Cabana Club Included
$275 per night
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Home in Key Colony Beach
P37 - 200 11th Street
$318 per night
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Home in Key Colony Beach
P38 - 210 11th street
$229 per night
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Home in Islamorada
Tranquility Cove
$199 per night

Islamorada condo rentals

Condo in Islamorada
Amazing Sunsets, Beach, Offices, 50% Off Feb & Mar
$399 per night
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Condo in Key Colony Beach
Beachside Unit 07 - Come Enjoy Our Private Beach
$253 per night
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Condo in Key Colony Beach
Beachside Unit 14 -Tiki Huts, Beach, Pool...Oh My!
$253 per night
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Condo in Tavernier
Amazing newly remodeled Coastal Condo w Ocean view
$222 per night
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Condo in Tavernier
It's Tiki Time in the Keys! Mid-Mod 1 Br/1Ba
$302 per night
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Condo in Tavernier
Epic Views from Ocean Front Condo in Key Largo
$260 per night
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Condo in Tavernier
Best View Ocean Pointe Beach Pool Marina Key Largo
$212 per night
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Condo in Tavernier
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
$305 per night
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Condo in Tavernier
Florida Keys Getaway - Slps 5 - Ocean View
$172 per night
Condo in Tavernier
Key Largo Getaway★Instaworthy Views★Ace Location
$246 per night
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Condo in Tavernier
Impeccably Designed Oceanfront Condo in Key Largo
$239 per night
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Condo in Islamorada
Two bedroom Oasis, steps from pool and Ocean
$135 per night
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Islamorada beach vacation rentals

Cottage in Islamorada
Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 4
$352 per night
Condo in Tavernier
Impressive coastal hideaway for ocean enthusiasts
$328 per night
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Condo in Key Colony Beach
Coastal Keys Condo, Oceanfront Complex Sleeps 4
$282 per night
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Condo in Tavernier
Turtle Nest 2 @ Ocean Pointe Suites Unit 1308
$299 per night
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Condo in Key Colony Beach
Bright Cheery Condo, Ocean Views in Key Colony
$331 per night
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Condo in Tavernier
TROPICAL PARADISE Ocean Condo - Cabana Daydreamin'
$279 per night
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Condo in Tavernier
Welcome to Warmer Weather★Key Lime Pie+Ocean Views
$250 per night
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Condo in Key Colony Beach
Beachside Unit 28 - Private Beach, Pool & Paradise
$245 per night
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Condo in Key Colony Beach
Beachside Unit 23 - Tropical Paradise on Atlantic
$253 per night
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Condo in Key Colony Beach
Key Lime Condo - Key Colony Oceanfront - Sleeps 4
$245 per night
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Condo in Key Colony Beach
Ocean Oasis - Steps to Ocean and Pool Key Colony
$245 per night
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Cottage in Islamorada
Islamorada Bungalow 2 Bed/1 Bath & Pool Unit 3
$441 per night

Your guide to Islamorada

All about Islamorada

Islamorada’s beaches make for a great retreat, but the area is also known for its water sports. Whether you’re an angler looking to go tarpon fishing, an adventurer hoping to go dolphin spotting, or a boater who wants to cruise the backwaters before heading back to the Islamorada Marina’s protected dockage, there’s a getaway with your name on it. Known as the Village of Islands, Islamorada comprises five islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and Indian Key. Approximately halfway between Miami and Key West in the Florida Keys, it’s about 10 miles south of Tavernier, 16 miles south of Key Largo, and 81 miles north of Key West.


When is the best time to stay in a vacation rental in Islamorada?

Summertime in the Keys and the living is easy — but scorching hot. High temperatures are in the upper 80s to 90s Fahrenheit, while lows hover around the mid-70s. Along with the warm weather comes humidity, which can often feel oppressive, so opt for lightweight, comfortable clothing. Hurricane season runs from June through November, so keep an eye on the forecast, since there is only one road in and out of the Keys, and you’ll want to plan ahead if conditions get extreme. Spring and fall may be the more comfortable times of year to visit, when it’s between the upper 60s and 80s. But winters are also lovely in the mid-60s to upper 70s — and with less rain.


What are the top things to do in Islamorada?

Founders Park

This 45-acre park is the most popular of the village’s parks, especially because of its shallow beach on the bay side. In addition to tiki huts, picnic tables, volleyball courts, and a playground, there’s also an Olympic-size pool, walking trails, a driving range, and courts for basketball, tennis, and pickleball.

Windley Key Fossil Reef Geological State Park

Walk along the eight-foot-high walls of the former quarry, formed of Key Largo limestone (fossilized coral). The land was once owned by the Florida East Railroad, a company that helped build the Overseas Railroad in the early 20th century, connecting the mainland to Key West — but it was eventually damaged by hurricanes and shut down.

Alligator Reef Lighthouse

The namesake for the 136-foot-tall lighthouse, built in 1873, is not the reptile, but rather the USS Alligator, whose remains are deep underwater. Nowadays, the area is known for its reef with 500 sea life species, including barracudas and spiny lobsters.

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