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Vacation rentals in Islamorada

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Top-rated vacation rentals in Islamorada

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

Escape to the Seaside - Pulpo Cottage
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Escape to the Seaside - Pulpo CottageOur one bedroom studio features a queen size bed and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large studio with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it’s your home.
TROPICAL PARADISE Ocean Condo - Cabana Daydreamin'
Entire condominium (condo) · 6 guests · 3 beds · 2 baths
TROPICAL PARADISE Ocean Condo - Cabana Daydreamin'TROPICAL PARADISE Oceanfront Condo-CABANA DAYDREAMIN’ Fully Renovated & equipped 2 bedroom, 2 bath condo with gorgeous ocean views This unit had over 60 five star reviews with the previous owner! And we've made it even BETTER!! Updated tropical decor, new sofa, more open layout, new twin over full bunk beds, rod storage and more!!!Marina,Beach, Pool, etc... Located on 60 acres in Tavernier, nestled in between Islamorada and Key Largo! Private Ocean Pointe grounds offers a tropical paradise.
Escape to the Seaside - Manta Cottage
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath
Escape to the Seaside - Manta CottageOur one bedroom suite features separate bedroom and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large in-suite space with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it's your home.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Islamorada vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Islamorada

SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside - Tiburon Cottage
$160 per night
  1. Entire residential home
  2. Key Largo
Cary’s Oceanside
$221 per night
  1. Entire residential home
  2. Islamorada
Your Keys Get Away - B
$218 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Tavernier
Best View Ocean Pointe Beach Pool Marina Key Largo
$175 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Tavernier
Oct 18-Nov 13 Discount *Pool Closure* Sea View
$221 per night
SUPERHOST
  1. Entire bungalow
  2. Islamorada
House - Waterview, Kayak, Snorkel
$195 per night
  1. Entire residential home
  2. Key Largo
Beautiful NEW Home in Key Largo Resort
$193 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Tavernier
Welcome to Warmer Weather★Key Lime Pie+Ocean Views
$197 per night
SUPERHOST
  1. Entire residential home
  2. Tavernier
OCEAN FRONT WITH AMAZING VIEW AND PRIVATE BEACH
$229 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Tavernier
Toes in the Sand - 2 Bedroom Condo Sleeps 4
$158 per night
SUPERHOST
  1. Entire residential home
  2. Islamorada
Beach Cottage with pool, Dock and beach access
$384 per night
SUPERHOST
  1. Entire rental unit
  2. Key Largo
Escape to the Seaside!
$300 per night

Your guide to Islamorada

All About Islamorada


How do I get around Islamorada?

If you’re flying in, the fastest way to get to Islamorada is by landing at Miami International Airport (MIA) and driving 90 minutes south. Fort Lauderdale-Hollywood International (FLL) isn’t too much further away, and will still take fewer than two hours. And if that’s not fast enough, the Florida Keys Marathon Airport (MTH) is about 40 minutes down the Keys and has charter flights from select Florida cities. For drivers, take the Florida Turnpike south toward Key West — once you start island hopping (in the form of driving over the Overseas Highway’s 42 bridges), US-1 South will take you to all the major Florida Keys destinations. Shuttle bus services also run between Miami and Fort Lauderdale and the Keys.


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.