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Cheap Vacations in Islamorada

Choose one or more items to build your trip:

3-night Islamorada vacations

The Reach Key West, Curio Collection by Hilton
Casa Marina Key West, A Waldorf Astoria Resort
NYAH Key West-Adults Only
The Marker Key West Harbor Resort
Island City House Hotel
The Palms Hotel
The Grand Guesthouse
Eden House
Oceans Edge Key West Resort, Hotel & Marina
Paradise Inn Key West-Adults Only
Fairfield Inn and Suites by Marriott Key West
Ibis Bay Beach Resort

4-night Islamorada vacations

The Southernmost Inn-Adults Only
Oceans Edge Key West Resort, Hotel & Marina
The Reach Key West, Curio Collection by Hilton
Paradise Inn Key West-Adults Only
NYAH Key West-Adults Only
Ibis Bay Beach Resort
Casa Marina Key West, A Waldorf Astoria Resort
The Marker Key West Harbor Resort
Island City House Hotel
The Mermaid & Alligator
The Palms Hotel
Westwinds Inn

5-night Islamorada vacations

Fashion Boutique Hotel
Sobe Lux
The L Hotel
Sheldon Hotel
Townhouse Hotel Miami Beach
Costa Hollywood Beach Resort
Club Wyndham Sea Gardens
Riptide Oceanfront Hotel
The Ritz-Carlton, South Beach
Riverside Hotel
Kimpton Angler's Hotel, an IHG Hotel
Embassy Suites Deerfield Beach - Resort & Spa

6-7 night Islamorada vacations

The Southernmost Inn-Adults Only
NYAH Key West-Adults Only
Paradise Inn Key West-Adults Only
The Reach Key West, Curio Collection by Hilton
Casa Marina Key West, A Waldorf Astoria Resort
Oceans Edge Key West Resort, Hotel & Marina
The Marker Key West Harbor Resort
Coconut Mallory Resort And Marina By Kees Vacations
DoubleTree Resort by Hilton Grand Key - Key West
Fairfield Inn and Suites by Marriott Key West
24 North Hotel Key West
Southernmost Beach Resort

Islamorada Vacation Deal FAQ's

Where to find Islamorada package deals?

On CheapTickets, you can find package deals in Islamorada as low as $463!

When is peak season in Islamorada?

July, June, August are very popular times to visit Islamorada.

When is the best time to visit Islamorada?

If you're looking for cheap vacations to Islamorada, September is the best time to visit Islamorada.

When is the worst time time to visit Islamorada?

Prices for Islamorada vacations can peak during March.

When is low season in Islamorada?

We have found December, November, October to be the least-crowded time of the year to visit Islamorada.

Where is Islamorada?

Cheap, cheap, cheap! No matter what you're searching for, we've got the best deals for your amazing vacation in Islamorada.

994 miles to the north of Islamorada is Washington. Key Largo is another nearby city, just 16 miles to the north-east.

Ready to meet some of the locals? 7,100 people call this part of Monroe County home.

Cheap Things to do in Islamorada

Don't worry about tickets, booking fees and budget-busting tourist traps! With our list of free things to see in or near Islamorada, you'll be ahead of the crowd with some of the best cheap travel hacks:

  • Eager to experience the past? If you're a fan of uncovering a slice of local history through its landmark sites, add the Hurricane Monument to your must-do list.
  • There's nothing quite like the stillness of a holy site. See if you can have a peek inside Matecumbe United Methodist Church and find out about the area's religious leanings.
  • Lignumvitae Key Botanical State Park is one of the region's most beautiful natural features. Visit to admire stunning natural views and fill your lungs with fresh air!
  • You needn't be an avid green thumb to appreciate a few hours surrounded by greenery. Harry Harris Park and Islamorada County Park are some of the best spots to take a break from the noise of the main streets.

Cheap Islamorada Vacation Package Deals

Are you over making compromises on quality just to save your cash? Relax, CheapTickets has your back. When you travel with us, there's no need to sacrifice comfort or break the bank.

Would you like a world of options on accommodations and flights? Our 500 airline partners and 500,000 global properties offer a huge array of choice. You can also save up to $290^ when you combine your bookings into a package.

Score yourself amazing value with our Price Guarantee. If you stumble upon your package for a lower rate within 48 hours of booking, we'll match that offer and reimburse the difference.

Get CheapCash

How's this for a nice perk? Our rewards program not only takes precious dollars off your next qualifying CheapTickets hotel stay, it also works together with our other promotions. All you've got to do is book those flights!

You're just a couple of clicks away from a membership with a loyalty club that actually gives you rewards you'll be keen to use! To start accruing savings on all eligible bookings, as well as unlocking exclusive bonus offers and perks, all you need to do is join CheapCash after you log in or sign up for free — being thrifty has never been simpler!

Cheap Car Rentals in Islamorada

We understand — you've already had to part with enough of your hard-earned savings on your big adventure, so you have no interest in spending a ton on cabs. Luckily for you, Islamorada has some good car rental places which should ease the load on your vacation account.

Cheap Hotels in Islamorada

You won't have any hassles snagging one of the 35 hotels in Islamorada. That said, try not to leave it too late! Your budget-friendly vacation beckons!

Our recommendations are the Cheeca Lodge & Spa and the Hadley House Islamorada for your island stay.

Flight deals to Islamorada

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Tue, May 25
ATL
Atlanta
MIA
Miami
$25
Frontier Airlines
Sat, May 29
LGA
New York
MIA
Miami
$33
Frontier Airlines
Mon, May 10
ISP
Islip
MIA
Miami
$34
Frontier Airlines
Tue, May 11 - Tue, May 18
ATL
Atlanta
MIA
Miami
$48
Frontier Airlines
Sun, May 9 - Fri, May 14
TTN
Trenton
MIA
Miami
$57
Frontier Airlines
Mon, May 17 - Thu, May 20
BOS
Boston
MIA
Miami
$67
Frontier Airlines

Top rated hotels for your Islamorada vacation

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.