Hotels in Islamorada

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Where to stay in Islamorada?

Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1385)
The price is $218
includes taxes & fees
$199 per night
Dec 8 - Dec 9
Chesapeake Beach Resort
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.
On a rooftop patio, a person leans back in a lounge chair while reading a magazine. Skyscrapers are visible in the distance.

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Top neighborhoods in Islamorada

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Venetian Shores

The Venetian Shores neighborhood offers attractions such as Everglades National Park and Baker's Cay Resort Beach.

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Venetian Shores

Top landmarks in Islamorada

Theater of the Sea

Theater of the Sea

Take the kids to visit the sea life you'll find at Theater of the Sea during your trip to Islamorada. Take in the entertainment choices and beautiful sunsets in this family-friendly area.

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Theater of the Sea

Frequently asked questions

What accommodations do travelers recommend in Islamorada?
The Caribbean Resort, Ragged Edge Resort & Marina and Treasure Harbor are all accommodations that are popular with guests.
Where can I find free parking with my stay in Islamorada?
These hotels offer the perk of free parking: Cheeca Lodge & Spa, Islander Resort and Islander Bayside Villas and Boatslips. There are 5 options you may want to check out on our site.
Can I book refundable hotels in Islamorada?
If you’re looking for the flexibility to change your plans to Islamorada, most hotels provide refundable* bookable rates. You can see these properties by searching our site and using the “fully refundable” filter to narrow down the results.
Where can I stay with my pet in Islamorada?
Your animal companion is welcome at these pet-friendly hotels: Chesapeake Beach Resort, La Siesta Resort & Villas, and Amara Cay Resort. There are 24 options on our site to choose from.
Which Islamorada hotels do our guests like for their terrific location?
Our guests love Chesapeake Beach Resort for its great location.
Where should I stay in Islamorada if I want an affordable accommodation?
Coconut Cove Resort and Marina is an accommodation you might want to consider that’ll save you money.
Where can I stay in Islamorada if I want a vacation rental instead of a traditional hotel?
If you want to find a good alternative to a hotel, review our selection of 598 vacation homes. In addition, there are 81 apartments and 117 condos.
Where can I stay if I'm traveling to Islamorada for a family-friendly vacation?
Parents traveling with children may want to consider Cheeca Lodge & Spa, Amara Cay Resort and Hadley Resort and Marina. You can also check out 5 available options on our site.
Where should I stay in Islamorada for a vacation with my partner?
Cheeca Lodge & Spa, La Siesta Resort & Villas and Amara Cay Resort are a few good options for a romantic getaway with your special someone.
Where should I stay in Islamorada if I'm looking for a luxury hotel?
An option for a luxury stay is Cheeca Lodge & Spa.
What will the weather in Islamorada be like during my trip?
With an average temperature of 72°F during the coldest months, Islamorada is a great place to visit any time of year.
Why should I book my Islamorada hotel with Hotels.com?
There are lots of reasons to book your Islamorada trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.