Islamorada Hotels from S$143

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12 Jul - 13 Jul
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Top 10 trending Islamorada hotels

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

Chesapeake Beach Resort

3.5 star property
9.2 out of 10, Wonderful, (1489)
"Super nice staff! Great place to stay! "
The price is S$426
includes taxes & fees
23 Jul - 24 Jul
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.
Showing deals for:25 Jul - 27 Jul

Image gallery for Condo in the Keys

Indoor/outdoor pool

Condo in the Keys

5.0 star property
Tavernier
9.0/10Wonderful (7 reviews)
7% off
Price is S$649
S$324 per night
includes taxes & fees
Condo in the Keys
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Where to stay in Islamorada

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

Matecumbe

6 out of top 10 points of interest in this area

If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Anne's Beach are top sights worth seeing.

Venetian Shores map

Venetian Shores

Though Venetian Shores may not have many top sights, you can venture to the surrounding area to see attractions like Islamorada County Park and Founders Park.

Lower Matecumbe Beach map

Lower Matecumbe Beach

While Lower Matecumbe Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Anne's Beach and Sunset Drive Beach.

Seabreeze Trailer Park map

Seabreeze Trailer Park

While there might not be top attractions in Seabreeze Trailer Park, you can explore the larger area and discover places like Founders Park and Islamorada County Park.

Learn more about Islamorada

Relaxing Islamorada is calling! Discover its fishing, sunsets, entertainment and more.

See all hotels in Islamorada
Islamorada which includes a beach and tropical scenes

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 traveller reviews include Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort and Ragged Edge Resort & 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, the majority of room reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which is usually within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and be given a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Islamorada.

What's the best place to stay on a budget in Islamorada?

Based on reviews, Chesapeake Beach Resort is a popular hotel for our travellers who want a more economical choice, and features free breakfast and free Wi-Fi. View all budget hotels in Islamorada.

What's the best family accommodation in Islamorada?

Amara Cay Resort is a resort with a private beach and an outdoor pool, and it's a top choice on Expedia for families. Other options for your child-friendly holiday include Cheeca Lodge & Spa and Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort. Also, attractions in the area such as John Pennekamp Coral Reef State Park and Jacob's Aquatic Center are fun for children of all ages. Find more child-friendly accommodations in Islamorada.

What's the best accommodation for a romantic holiday in Islamorada?

Cheeca Lodge & Spa is a favourite resort for couples, and features a full-service spa and a private beach. Other good choices for your romantic getaway include La Siesta Resort & Villas and Amara Cay Resort. See all romantic hotels 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 holiday. See all available hotels listed as LGBTQ-friendly in Islamorada.

What's the best dog-friendly place to stay in Islamorada?

Chesapeake Beach Resort is a top hotel for people travelling with their pets, and offers 2 outdoor pools and free WiFi for its human guests. Two other good options for you and your pet's trip include Amara Cay Resort and Islander Resort. See more pet-friendly hotel accommodations in Islamorada.

What's the best hotel to stay near the beach in Islamorada?

Chesapeake Beach Resort is a top hotel located on the beach . Other good options for your beach trip include Amara Cay Resort and Islander Resort. See more stays near the beach in Islamorada.

What's the best luxury hotel in Islamorada?

Cheeca Lodge & Spa is a luxury resort with a private beach and 3 restaurants, and it's a popular choice for Expedia travellers looking for an elegant place to stay. Find more luxury hotels in Islamorada.

What's the best boutique hotel in Islamorada?

Amara Cay Resort is a favourite 3.5-star hotel with Expedia travellers looking for stylish accommodation, and features a private beach and 2 restaurants. Casa Morada and Drop Anchor are other choices for a boutique stay.

What are some accommodation options with pools in Islamorada?

Chesapeake Beach Resort is a top hotel with 2 outdoor swimming pools, a private beach and free breakfast. A couple of other options that offer an on-site pool include Islander Bayside Villas and Boatslips 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 centre. Treat yourself to a facial, body scrub or detox wrap at the on-site spa. In-room massages are also available. See all spa hotels in Islamorada.

What's it like to stay in Islamorada?

Travellers 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 905 hotels and other accommodation options to choose from. Find out more about Islamorada.

What are the top places to visit in Islamorada?

Cultural venues include History of Diving Museum and MoradaWay Arts & Cultural District. Landmarks like Matecumbe United Methodist Church and Hurricane Monument might be worth a visit. The seaside and sunsets highlight the natural beauty with places to discover including Everglades National Park, Islamorada County Park and Founders Park. Take a look at what more there is to see and do in Expedia's Islamorada guide.

What's the weather like in Islamorada?

The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.