Find Beach Hotels in Islamorada, FL

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Islamorada Beach Hotels

Our top choices for Islamorada beach hotels

Exterior
Drop Anchor

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1000)
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
United States
Laura
The price is ￥12,981
￥20,057 total
includes taxes & fees
Dec 17 - Dec 18
Drop Anchor
In-room safe, individually decorated, individually furnished
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (115)
"Beautiful place to stay"
United States
Jonathan
The price is ￥37,239
￥52,236 total
includes taxes & fees
Dec 17 - Dec 18
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Private beach, fishing
La Jolla Resort

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (1003)
"Great stay. Friendly staff, great accommodations, very nice complex. "
United States
Shela
La Jolla Resort
Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1595)
"Great breakfast, great location, friendly staff, nice extras."
United States
Gary
The price is ￥19,850
￥31,097 total
includes taxes & fees
Dec 17 - Dec 18
Chesapeake Beach Resort
Aerial view
Pines & Palms Resort

Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1001)
"Very nice place to stay "
United States
Joan
Pines & Palms Resort
View from room
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1004)
"This resort is beautiful and the rooms are decorated so tastefully. I highly recommend The Islander Resort for family fun and couples get aways alike. "
United States
Suzanne
The price is ￥74,789
￥94,655 total
includes taxes & fees
Dec 22 - Dec 23
Islander Resort
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (585)
"we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff "
United States
Terry
The price is ￥13,685
￥23,473 total
includes taxes & fees
Dec 17 - Dec 18
Breezy Palms Resort
Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room
Amara Cay Resort

Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1265)
"very nice staff, quiet and comfortable"
United States
Dana
The price is ￥28,009
￥41,854 total
includes taxes & fees
Dec 18 - Dec 19
Amara Cay Resort
Exterior
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (150)
"Great place to stay! Clean, great location and great customer service. Very easy to check in, front desk was so sweet! Highly recommended!!! Had a great experience overall"
United States
Elaysi
The price is ￥20,291
￥22,827 total
includes taxes & fees
Dec 17 - Dec 18
Coconut Cove Resort and Marina
Outdoor pool, sun loungers
La Siesta Resort & Villas

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1000)
"Great stay and beautiful space"
United States
Amir
The price is ￥25,926
￥39,510 total
includes taxes & fees
Dec 18 - Dec 19
La Siesta Resort & Villas
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.
View all properties

Beach hotels with pools in Islamorada

Sundeck
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1066)
The price is ￥36,806
￥41,406 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Rock Reef Resort
View all properties

Beach hotels with ocean views in Islamorada

Sundeck
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1066)
The price is ￥36,806
￥41,406 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Rock Reef Resort
View all properties

Beach hotels with free breakfast in Islamorada

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

Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1595)
The price is ￥19,850
￥31,097 total
includes taxes & fees
Dec 17 - Dec 18
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.
View all properties

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Room was great. Staff was awesome views amazing !!!!!"
Jeff 7-night trip
Posted 4 days ago
Chesapeake Beach Resort

Explore a world of travel with Expedia

Frequently asked questions

What is Islamorada like for travelers who love the beach?
Known for its snorkeling and diving spots, Islamorada has a lot to offer the traveler planning a beach vacation.
What's the best place to stay near the beach in Islamorada?
Cheeca Lodge & Spa is a top resort located on the beach. Other good options for your beach trip include Chesapeake Beach Resort and Amara Cay Resort.
How many beach hotels should I expect to find in Islamorada?
Choose from one of Expedia's 77 hotels in Islamorada for your beachside break.
When's the best time for a beach vacation in Islamorada?
Plan your trip to the beach with a look at year-round temperatures in Islamorada: The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.
What is there to see and do around Islamorada?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. Beach lovers can head straight to Anne's Beach or Sunset Drive Beach for some quality time by the water. Take advantage of the area's diving and snorkeling, and make time for local attractions like Everglades National Park and Florida Keys Brewing Co.. Other things to see and do in the area are Bud n' Mary's Dive Center and Founders Park.
What's the best way to get to my beach hotel in Islamorada?
Here's some information to help you get to and around your beach accommodation in Islamorada with ease. To get to Islamorada, book a flight to Marathon, FL (MTH-Florida Keys Marathon), the closest major airport, which is located 30 mi (48.2 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.