Find hotels in Islamorada, FL from ₩234,789

  • 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
Jan 13 - Jan 14
Tomorrow
Jan 14 - Jan 15
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Islamorada hotels

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, (1,631 reviews)
"The hotel is in a perfect location, and offers so much on premise"
United States
Nancy
The price is ₩277,656
₩394,975 total
includes taxes & fees
Jan 28 - Jan 29
Chesapeake Beach Resort
Balcony
Cheeca Lodge & Spa

Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,292 reviews)
"Breakfast was fantastic "
Canada
Craig
The price is ₩398,309
₩555,503 total
includes taxes & fees
Jan 28 - Jan 29
Cheeca Lodge & Spa
Exterior
Islander Resort

Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,008 reviews)
"Rooms are clean, staff is friendly and the place is beautifull"
United States
James
The price is ₩422,983
₩574,993 total
includes taxes & fees
Jan 29 - Jan 30
Islander 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, (1,261 reviews)
"Great Location, Friendly Staff"
United States
HECTOR
The price is ₩314,183
₩460,161 total
includes taxes & fees
Jan 19 - Jan 20
Amara Cay Resort
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio
Lime Tree Bay Resort

Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.2 out of 10, Wonderful, (1,136 reviews)
"Great sunsets, convenient restaurant next door, great staff."
United States
Kris
Lime Tree Bay Resort
Sundeck
Rock Reef Resort

Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,077 reviews)
"Would stay here again!"
United States
James
Rock Reef Resort
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, (125 reviews)
"Beautiful chilled out hotel"
United Kingdom
Jacqueline
The price is ₩435,687
₩587,640 total
includes taxes & fees
Jan 21 - Jan 22
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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, (1,656 reviews)
"Spotless rooms, staff is so friendly and helpful! Amazing place to stay."
Canada
Jeannie
The price is ₩231,998
₩297,476 total
includes taxes & fees
Jan 15 - Jan 16
Bayside Inn Key Largo
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, (1,008 reviews)
"Yes my family had a great stay and will absolutely be returning in the future. "
United States
Sarah
Drift Hotel
Exterior
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1,001 reviews)
"Courteous staff, clean, many extra like hot chocolate bar, s’mores station and coffee station. Nice stay!"
United States
Kelley
The price is ₩703,503
₩872,409 total
includes taxes & fees
Jan 27 - Jan 28
Playa Largo Resort & Spa, Autograph Collection
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, (1,009 reviews)
"This place is amazing "
United States
cindy
La Jolla Resort
Marina
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,004 reviews)
"We had a wonderful stay! Our room was spotless and well-maintained, and the staff was friendly, helpful, and made us feel welcome. Would definitely stay here again!"
United States
Elena
The Pelican Key Largo Cottages
Exterior
Breezy Palms Resort

Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (607 reviews)
"Property was nice and easy to navigate, ocean view room was extra nice to have!"
United States
Lisa
The price is ₩219,892
₩323,508 total
includes taxes & fees
Jan 14 - Jan 15
Breezy Palms Resort
Outdoor pool, free cabanas
Sunset Inn

Sunset Inn

Sunset Inn
3.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,001 reviews)
"Good beds, clean room close to Loreleis for sunset dinner. Easy location for Islamorada activities"
United States
Celeste
The price is ₩241,496
₩288,206 total
includes taxes & fees
Jan 14 - Jan 15
Sunset Inn
Suite, 1 King Bed with Sofa bed, Ocean View | Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe
La Siesta Resort & Villas

La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,005 reviews)
"Great accommodations, very peaceful setting "
United States
Susan
The price is ₩434,879
₩596,644 total
includes taxes & fees
Jan 14 - Jan 15
La Siesta Resort & Villas
Property grounds
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,007 reviews)
"One of the nicest hotels we have stayed at. Amazing staff, food, activities and property "
United States
Sara
The price is ₩516,656
₩662,206 total
includes taxes & fees
Jan 22 - Jan 23
Baker's Cay Resort Key Largo, Curio Collection by Hilton
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, (1,005 reviews)
"Beautiful location and staff is amazing. Would definitely recommend!"
United States
Zachary
The price is ₩250,735
₩330,000 total
includes taxes & fees
Jan 19 - Jan 20
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, (1,001 reviews)
"I enjoyed staying here, very cute hotel on the beach "
United States
Emi
The price is ₩265,558
₩298,753 total
includes taxes & fees
Jan 19 - Jan 20
Sunset Cove Beach 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, (1,000 reviews)
"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 ₩265,307
₩349,874 total
includes taxes & fees
Jan 19 - Jan 20
Drop Anchor
Oceanfront Three Bedroom Villa | Premium bedding, individually decorated, individually furnished
Pines & Palms Resort

Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,008 reviews)
"Staff are excellent, resort has been recently upgraded. Best describe his quaint, comfortable and cozy."
Canada
scott
Pines & Palms 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

Great weekend hotel deals in Islamorada, FL

Showing deals for:Jan 23 - Jan 25

Image gallery for The Islands of Islamorada

On the beach, sun loungers, beach umbrellas, beach towels

The Islands of Islamorada

4.0 star property
Islamorada
9.8/10Exceptional (70 reviews)
10% off
Price is ₩2,523,356
₩5,839,476 total
includes taxes & fees
The Islands of Islamorada
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 Sunset Drive Beach.

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
"The check in was easy. The front desk employee was very kind. Our room was spotless. We spent the afternoon on the beach and used the kayak. We enjoyed breakfast. The omelet chef was awesome. Overall I was very happy with my stay "
Nancy 1-night trip
Posted 1 day ago
Chesapeake Beach Resort

More cheap stays in Islamorada

Creekside Inn

Creekside Inn

90611 Old Highway Tavernier FL
The price is ₩248,207 per night from Jan 14 to Jan 15
₩248,207
₩279,232 total
Jan 14 - Jan 15
includes taxes & fees
7.8/10 Good! (1,001 reviews)

Frequently asked questions

Where is the best place for a stay in Islamorada?
Ragged Edge Resort & Marina is ranked highly by Expedia customers. This guesthouse offers an outdoor pool and free parking. Other top choices based on traveler reviews include Sunset Inn and Coconut Cove Resort and Marina. See all available top hotels, or 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 La Siesta Resort & Villas. 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?
Chesapeake Beach Resort is a top hotel located on the beach. Other good options to stay near the beach include Cheeca Lodge & Spa 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 912 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 Drop Anchor and Bayside Villas by Islander Resort. 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 912 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.