Find hotels in Islamorada, FL from ￥21,388

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 prices for these dates

Tonight
Dec 15 - Dec 16
Tomorrow
Dec 16 - Dec 17
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Islamorada hotels

Sundeck
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1066)
Relax at this coastal retreat with a private beach just minutes from John Pennekamp Coral Reef State Park. Guests can paddle through scenic waters with onsite kayaking or lounge by the outdoor pool. Free WiFi and parking enhance your Keys getaway.
"Everything clean, friendly staff"
United States
Arlene
The price is ￥36,806
￥41,406 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Rock Reef Resort
On the beach, sun loungers, snorkeling, kayaking
Drift Hotel

Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1005)
Situated in Key Largo with easy access to Jimmy Johnson's Big Chill, this beach hotel offers complimentary WiFi, parking, bike rentals, and water activities including kayaking and snorkeling. Enjoy the terrace and garden while exploring nearby Pigeon Key.
"Very nice Hotel/motel reminiscent of what I imagine the old Florida Keys were like. Lovely beach, dock, and environs."
United States
Sean
Drift Hotel
Marina
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
8.8 out of 10, Excellent, (1002)
Situated near Jimmy Johnson's Big Chill, these beachfront cottages offer a serene marina and private beach. Enjoy kayaking, rowing, or canoeing adventures with free WiFi and parking. Clean rooms with microwaves and refrigerators enhance your Key Largo escape.
"The beach area was wonderful"
United States
Sonya
The price is ￥19,012
￥21,388 total
includes taxes & fees
Dec 16 - Dec 17
The Pelican Key Largo Cottages
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)
Drift into bliss at this tranquil Islamorada oceanfront retreat featuring 2 outdoor pools and a full-service marina. Complimentary breakfast, bike rentals, and spectacular sunset views create an idyllic Florida Keys getaway near diving attractions.
"Great breakfast, great location, friendly staff, nice extras."
United States
Gary
The price is ￥21,834
￥33,329 total
includes taxes & fees
Dec 16 - Dec 17
Chesapeake Beach Resort
View from property
Lime Tree Bay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1116)
Escape to this tropical resort with a private beach and complimentary kayaking along Florida's stunning coastline. 3 outdoor pools, tennis courts, and free bike rentals create endless recreation opportunities. Florida Boy restaurant serves American cuisine throughout the day.
"Great place "
United States
Oscar
Lime Tree Bay Resort
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1000)
This waterfront hotel offers an outdoor pool, complimentary kayaking, and free bike rentals to explore nearby attractions. Located near Windley Key Fossil Reef Geological State Park, guests appreciate the clean rooms and exceptional staff service.
"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
Exterior
Seafarer Key Largo

Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.4 out of 10, Exceptional, (131)
"The Seafarer stay was awesome! Great clean rooms and bathrooms! The kitchen was well equipped. The beach area was a beautiful spot to relax, swim and free kayaks to explore the beautiful water! The staff are all friendly and they keep the rooms and property super clean. Would definitely stay there again! "
United States
Laura
The price is ￥17,772
￥22,185 total
includes taxes & fees
Dec 16 - Dec 17
Seafarer Key Largo
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)
Overlooks Florida Bay with a stunning outdoor pool and private beach area. This hotel offers complimentary breakfast and parking, plus convenient access to diving spots and Windley Key Fossil Reef Geological State Park.
"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
House, 3 Bedrooms, Ocean View, Oceanfront | Lanai
La Jolla Resort

La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (1003)
Experience coastal charm at this oceanside hotel with private beach access. Enjoy the outdoor pool after a day of hiking nearby trails. Convenient to Islamorada Brewery and Keys History Center, with clean rooms and attentive staff to enhance your Florida Keys getaway.
"Great stay. Friendly staff, great accommodations, very nice complex. "
United States
Shela
La Jolla Resort
Exterior
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.6 out of 10, Good, (1003)
Experience Key Largo at this waterfront gem with a marina, outdoor pool, and hot tub. Explore John Pennekamp Coral Reef State Park nearby, or relax in the garden after a day of adventure. Includes free breakfast, WiFi, parking, and bicycles for local exploration.
"The rooms are lovely. Once the remodel is done the place will be perfect. "
United States
Deborah
The price is ￥18,518
￥25,773 total
includes taxes & fees
Dec 18 - Dec 19
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Exterior
Bayside Inn Key Largo

Bayside Inn Key Largo

Bayside Inn Key Largo
3.0 star property
Key Largo
8.6 out of 10, Excellent, (1627)
Unwind at this peaceful bayfront retreat with a private beach, kayaks, and paddleboards. Just minutes from John Pennekamp Coral Reef State Park, guests enjoy the outdoor pool, 24-hour fitness center, and excellent fishing opportunities from the dock.
"Friendly staff, clean room beautiful views from the private beach."
United States
Wanda
The price is ￥20,411
￥26,857 total
includes taxes & fees
Dec 17 - Dec 18
Bayside Inn Key Largo
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (585)
Immerse yourself in Islamorada with this beachfront aparthotel featuring a marina and outdoor pool. Clean accommodations with kitchens and free WiFi await, while Bud n' Mary's Dive Center and Hurricane Monument lie nearby.
"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 ￥14,391
￥24,266 total
includes taxes & fees
Dec 17 - Dec 18
Breezy Palms Resort
Terrace/patio
Bahia Bay Resort

Bahia Bay Resort

Bahia Bay Resort
2.5 star property
Rock Harbor
8.8 out of 10, Excellent, (125)
Just a short drive from John Pennekamp Coral Reef State Park, this hotel offers a private beach, outdoor pool, and children's splash area. After a day of exploring, unwind in the sauna while enjoying free WiFi and parking.
"Location is perfect and we just keep coming back "
United States
Jason
Bahia Bay Resort
Exterior
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1003)
Wake to ocean views at this Florida Keys retreat offering free breakfast and water activities. Enjoy kayaking, snorkeling, or cycling with complimentary equipment. Just minutes from Windley Key Fossil Reef and Rain Barrel Village, with helpful staff to enhance your stay.
"Great location, room was spotless and perfectly met my needs. I plan to return next year."
United States
M
The price is ￥17,687
￥24,982 total
includes taxes & fees
Dec 18 - Dec 19
Fisher Inn Resort & Marina
Exterior
Sunset Cove Beach Resort

Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1001)
"Always a great stay"
United States
Richard
The price is ￥24,306
￥27,344 total
includes taxes & fees
Dec 18 - Dec 19
Sunset Cove Beach Resort
25-inch flat-screen TV with digital channels, TV
Treasure Harbor

Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (117)
Experience waterfront comfort at this Florida Keys gem with an outdoor pool. Located near Rain Barrel Village and hiking trails, the hotel offers free WiFi and parking. Premium bedding ensures relaxation after a day of snorkeling adventures.
"I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore."
United States
Mary
Treasure Harbor
Outdoor pool, open 8:00 AM to 11:00 PM, sun loungers
Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo

Ocean Pointe Suites at Key Largo
3.5 star property
Tavernier
8.4 out of 10, Very Good, (1007)
This beachfront retreat in Tavernier features a private shoreline, waterfront dining at Island Grill Restaurant, and 2 outdoor tennis courts. After snorkeling nearby, unwind at the poolside bar or relax in accommodations with full kitchens.
"Just a good place to stay."
United States
William
The price is ￥21,395
￥26,874 total
includes taxes & fees
Dec 17 - Dec 18
Ocean Pointe Suites at Key Largo
Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1269)
"It was awesome, great service, staff members are helpful, clean and tidy room with excellent views!"
United States
Sami
The price is ￥30,697
￥45,051 total
includes taxes & fees
Dec 16 - Dec 17
Cheeca Lodge & Spa
Outdoor pool, free cabanas
Sunset Inn

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1001)
Explore the Florida Keys from this waterfront hotel with free bikes. The outdoor pool creates a perfect oasis after visiting nearby Islamorada Brewery & Distillery. Friendly staff and complimentary parking enhance the relaxed island experience.
"Room was clean and staff was helpful"
United States
Robert
The price is ￥18,702
￥22,792 total
includes taxes & fees
Dec 17 - Dec 18
Sunset Inn
View from property
Creekside Inn

Creekside Inn

Creekside Inn
2.5 star property
Tavernier
8.0 out of 10, Very Good, (1003)
Situated on the bay, this Keys motel offers 2 outdoor pools and marina access for water enthusiasts. Enjoy rowing, canoeing, and scuba diving onsite, plus clean rooms with refrigerators and microwaves. Florida Keys Dive Center and Mangrove Marina are nearby.
"Very comfortable stay Local dining walking distance many amenities close by Room was very clean and AC worked great "
United States
Roy
The price is ￥19,492
￥21,929 total
includes taxes & fees
Dec 18 - Dec 19
Creekside Inn
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

Great weekend hotel deals in Islamorada, FL

Showing deals for:Dec 26 - Dec 28

Image gallery for Drop Anchor

Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

3.0 star property
Islamorada
8.8/10Excellent (1,000 reviews)
10% off
Price is ￥67,537
￥162,865 total
includes taxes & fees
Drop Anchor
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Where to stay in Islamorada

Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada
Learn more about Islamorada
Islamorada showing a beach bar

Matecumbe

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Florida Keys Brewing Co. are top sights worth seeing.

Venetian Shores

Venetian Shores might not have many top sights, but Founders Park and Windley Key Fossil Reef Geological State Park are two attractions nearby that you can check out.

Lower Matecumbe Beach

Though Lower Matecumbe Beach might not have many top sights, you can venture to the surrounding area to see attractions like Anne's Beach and Fiesta Key.

Seabreeze Trailer Park

If you're looking for some top things to see and do in Seabreeze Trailer Park and surrounding area, you can visit Founders Park and Islamorada County Park.

Stay near popular Islamorada attractions

Anne\'s Beach featuring general coastal views

Anne's Beach

3.8/5 (228 reviews)
Anne's Beach offers shallow, calm waters and a scenic boardwalk winding through mangroves. Enjoy the covered pavilions for picnicking or launch your paddleboard into the crystal-clear waters of the Florida Keys.
See properties
Florida Keys Brewing Co. showing signage

Florida Keys Brewing Co.

4.6/5 (152 reviews)
The Upper Keys' first microbrewery infuses local flavors like Key lime and honey into its craft beers. Sip seasonal brews in the vibrant taproom or lush beer garden while enjoying local art and live music.
See properties

Learn more about Islamorada

The turquoise waters between the Keys offer world-class fishing that even beginners can enjoy with knowledgeable local guides. Spend mornings snorkeling coral reefs teeming with tropical fish, then unwind at waterfront restaurants where chefs cook your fresh catch.

See all hotels in Islamorada
Islamorada featuring a sunset and general coastal views

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 3 days ago
Chesapeake Beach Resort

More cheap stays in Islamorada

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

99340 Overseas Highway Key Largo FL
The price is ￥19,012 per night from Dec 16 to Dec 17
￥19,012
￥21,388 total
Dec 16 - Dec 17
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)

Frequently asked questions

Where is the best place for a stay in Islamorada?
The Caribbean Resort is ranked highly by Expedia customers. This hotel offers a marina and an outdoor pool. Other top choices based on traveler reviews include Ragged Edge Resort & Marina and Sunset Inn. See all available top hotels, or vacation rentals in Islamorada.
What are some of the best vacation home rentals in Islamorada?
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada: This highly rated vacation home rental in Islamorada offers an outdoor pool, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Other favorite homes for rent in Islamorada are Now booking late 2026 and 2027. Oceanfront - Heated Pool - Dock - Over 1 acre and Bungalow #3 - 2 Bed/1 Bath & Pool in Islamorada. See all vacation rentals in Islamorada.
If I need to cancel my hotel reservation in Islamorada, will I receive a refund?
Yes! You'll find that most hotel reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Islamorada.
Where can I learn more about changing or cancelling my trip to Islamorada?
For more details about picking new dates or cancelling your trip to Islamorada, click here.
What's the best budget-friendly accommodation in Islamorada?
Based on reviews, Chesapeake Beach Resort is a popular hotel for our travelers who want a more economical choice, and features free breakfast and free WiFi. View all budget hotels in Islamorada.
What's the best place to stay for a family vacation to Islamorada?
Cheeca Lodge & Spa is a resort with 3 outdoor pools and a private beach, and it's a top choice on Expedia for families. Other good options for your family trip include Hadley Resort and Marina and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort. Attractions in the area like John Pennekamp Coral Reef State Park and Jacob's Aquatic Center are also fun for kids of all ages. Find more child-friendly accommodations in Islamorada.
What's the best LGBTQ-friendly accommodation in Islamorada?
Hadley Resort and Marina is a top LGBTQ-friendly hotel that features a marina and a private beach. Fisher Inn Resort & Marina is another good option for your stay. See all available hotels listed as LGBTQ-friendly in Islamorada.
What's the best pet-friendly place to stay in Islamorada?
Chesapeake Beach Resort is a top hotel for people traveling with their pets, and offers 2 outdoor pools and free WiFi for its human guests. Other good options for you and your pet include Amara Cay Resort and Islander Resort. See more pet-friendly hotel accommodations in Islamorada.
Where is the best place to stay close to Florida Keys Brewing Co.?
One of the top choices for your stay is Cheeca Lodge & Spa, located next to Florida Keys Brewing Co., and this 4-star resort offers 3 outdoor pools and a full-service spa. Islander Resort and Islander Bayside Villas and Boatslips are a couple of other good options close by.
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 to stay near the beach include Chesapeake Beach Resort and Amara Cay Resort. See more stays near the beach in Islamorada.
What's the best high-end place to stay in Islamorada?
Cheeca Lodge & Spa is a luxury resort with a private beach and 3 restaurants, and it's a popular choice for Expedia travelers looking for an elegant place to stay. Find more luxury hotels in Islamorada.
How much can I expect to pay for the resort fee in Islamorada?
You'll find about 9 properties that charge a resort fee from the 913 hotels and other properties in Islamorada. The per accommodation resort fee averages USD 27.13 per night.
What are some accommodations with pools in Islamorada?
Chesapeake Beach Resort is a top hotel with 2 outdoor pools, a private beach, and free breakfast. A couple of other options with an onsite pool include Bayside Villas by Islander Resort and Drop Anchor. View all hotels with pools in Islamorada.
What is the best spa hotel in Islamorada?
Cheeca Lodge & Spa is a top beachfront spa hotel featuring 3 pools, 3 restaurants, a golf course, and a 24-hour fitness center. Treat yourself to a facial, body scrub, or detox wrap at the onsite spa. In-room massages are also available. See all spa hotels in Islamorada.
What is the best hotel near Miami International Airport (MIA)?
Miami International Airport Hotel is a popular 3-star hotel featuring a restaurant and free WiFi. It's located a short 0.1 mi (0.1 km) from Miami Intl. Airport. Other accommodations within close proximity to the airport include Ramada by Wyndham Miami Springs/Miami International Airport and Comfort Suites Miami Airport North.
What's it like staying in Islamorada?
Travelers to Islamorada give high marks for the seaside, entertainment choices, and seafood restaurants. This relaxing city also attracts tourists with its opera houses. A top sight in the city is Everglades National Park. In Islamorada, there are 913 hotels and other accommodations to choose from. Find out more about Islamorada.
What is there to see in Islamorada?
Cultural venues include History of Diving Museum and MoradaWay Arts & Cultural District. The seaside and sunsets highlight the natural beauty with places to discover including Everglades National Park, Founders Park, and Anne's Beach. Fishing is just one of the top activities, while Bud n' Mary's Dive Center and Robbie's of Islamorada are sights to visit. Check out what more to see and do in Expedia's Islamorada guide.
What's the seasonal weather like 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.

Explore a world of travel with Expedia