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Top hotels

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

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

3.5 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
This Art Deco resort features a private beach, a marina, and 4 restaurants. Enjoy a day at the beach snorkeling, or relax with sun loungers. Families will appreciate ...
"This is a stunning property with so many amenities and restaurants! I can’t say enough about the friendliness and cooperation of the staff! Alondra at the front desk in particular! She went out of her way to accommodate our needs! Well done, Three Waters! The only complaint is that our stay wasn’t ..."

Reviewed on Jun 17, 2025

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

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
A private beach, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind ...
"Very accommodating staff."

Reviewed on Jun 21, 2025

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
This luxury resort features a private beach, a golf course, and a full-service spa. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...
"This is a beautiful resort and the staff is very friendly and competent."

Reviewed on Jun 19, 2025

Cheeca Lodge & Spa
Islander Resort

Islander Resort

4 out of 5
82100 Overseas Highway, Islamorada, FL
This hotel features a private beach, a golf course, and 3 restaurants. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Families will appreciate ...
"We loved our stay! Room was clean, comfortable; staff was friendly and very helpful. We really like the feeling of being"

Reviewed on Jun 22, 2025

Islander Resort
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy, Islamorada, FL
A private beach, 2 restaurants, and an outdoor pool are all featured at this resort. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a ...
"The property was very nicely landscaped and the pool and beach areas had comfortable furniture and were very inviting. The chickee huts provided nice shade. There is a seawall on the beach that separates the sand and water areas. There were pretty fire pits and music in the courtyard area which also ..."

Reviewed on Jun 23, 2025

Amara Cay Resort
La Jolla Resort

La Jolla Resort

2.5 out of 5
82216 Overseas Highway, Islamorada, FL
A private beach and an outdoor pool are featured at this smoke-free hotel. WiFi in public areas is free. A garden, a picnic area, and concierge services are ...
"The place has been updated. Access to the beach is awesome. Tons of things to do - such as paddleboard and kayak. Sunsets are amazing. Chill! Pool is small and no view but not what we came for."

Reviewed on Jun 20, 2025

La Jolla Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

4 out of 5
80241 Overseas Highway, Islamorada, FL
The private beach and marina are among the highlights at this resort. Enjoy the outdoor pool and perks like a free area shuttle. There's a poolside bar on site, ...
"Pretty view."

Reviewed on Jun 24, 2025

La Siesta Resort & Villas
Hadley Resort and Marina

Hadley Resort and Marina

3.5 out of 5
82749 Overseas Hwy, Islamorada, FL
This traditional hotel's private beach and marina are among the highlights. Enjoy a day at the beach kayaking, or relax with sun loungers. Families will appreciate ...
"Front desk had everything ready for me and it was quick and easy check in."

Reviewed on Jun 20, 2025

Hadley Resort and Marina
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
A private beach and an outdoor pool are featured at this Art Deco motel. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. ...
"Our stay was nice. Nobody cleaned our room. We had to go to the office to get towels daily. The continental breakfast has gone downhill big time since my last visit. Not enough coffee for each of us. Nothing but toast and bagels with no butter."

Reviewed on Jun 19, 2025

Fisher Inn Resort & Marina
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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.

Cheap Islamorada hotels

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.

Islamorada Hotel & Travel Guide

If you need nice rooms in the Islamorada area, you'll be excited to find there is a large range of options on offer. Travelocity's up-to-date database includes 22 hotels that are within a 6-mile (10-kilometer) distance of downtown Islamorada.

Hoping to discover a Travelocity-listed hotel that can be reached on foot from the urban core of Islamorada? The Moorings Village and Spa and The Caribbean Resort will fit the bill.

Islamorada features some lower-priced hotel and apartment options that will be sure to satisfy even the thriftiest travelers. 2 miles (3 kilometers) away from Islamorada's downtown you'll find the Amara Cay Resort. The Chesapeake Beach Resort is just 2 miles (4 kilometers) away. The La Siesta Resort & Marina and the Postcard Inn Beach Resort & Marina are another two lower priced hotels worth checking out.

0.7 miles (1.2 kilometers) outside of central Islamorada, you will find the Cheeca Lodge & Spa. Alternatively, the Duck Key Vacation Rentals @ Hawks Cay Resort is approximately 20 miles (32 kilometers) away. Two more hotel options close by are the Mariner's Resort Villas & Marina, a Keys Caribbean Resort along with the Hawks Cay Resort.

If you have the time, why not spread your wings and discover the myriad attractions located around South Florida during your stay in the area? Get to know South Florida's lighthouses. Nature lovers should make the time to relish the region's beaches and everglades. In this fascinating part of United States of America adventurous visitors might partake in hiking and cycling.

20 miles (32 kilometers) away from Islamorada, you'll find Key Largo, where you can find Dolphins Plus Bayside and John Pennekamp Coral Reef State Park. Should you wish to spend any time in Key Largo, be sure to check out the Key Largo Bay Marriott Beach Resort and Courtyard by Marriott Key Largo. 11 miles (17 kilometers) to the northeast of Islamorada, you'll find Tavernier, which features the Dove Creek Lodge, an Ascend Hotel Collection Member and Ocean Pointe Suites at Key Largo. When you stay in Tavernier, a couple of sights worth adding to your itinerary are the Harry Harris Park and Florida Keys Wild Bird Center.

Miami International Airport is located 65 miles (104 kilometers) from central Islamorada. Enlightened travelers who desire to find accommodation nearby can easily secure a convenient option in the EB Hotel Miami or Hyatt Regency Coral Gables.

Top reasons for your vacation to Islamorada

  • Outdoor Activities: Islamorada offers a variety of outdoor activities such as fishing, diving, and snorkeling, making it the perfect destination for adventure enthusiasts.
  • Beautiful Beaches: With its stunning landscapes and beach paradise, Islamorada boasts beautiful beaches where you can relax, swim, and enjoy the crystal-clear waters.
  • Breathtaking Sunsets: Witness the awe-inspiring sunsets in Islamorada, providing a picturesque backdrop for romantic walks along the beach.
  • Local Entertainment: Experience the local entertainment scene in Islamorada, from snorkeling adventures to opera performances and theater shows.
  • Delicious Seafood: Indulge in mouthwatering seafood delicacies in Islamorada, satisfying the cravings of any seafood lover.

Find your favorite hotels in Islamorada

If you're planning a vacation to Islamorada, Florida, you'll find a variety of hotel accommodations to choose from. Whether you're looking for a beachfront hotel or a hotel near the beach, there are options available to suit your needs. Islamorada offers a range of top hotels that provide a comfortable and enjoyable stay for you and your family. These hotels serve as a perfect base for exploring the outdoor attractions and activities that Islamorada has to offer.

Hotel nameTypeStarsDescription
Chesapeake Beach ResortHotel2.5This 2.5-star rated hotel offers a close proximity to various outdoor activities such as rowing, canoeing, fishing, skydiving, and snorkeling. It also has a marina and tennis facilities, making it an ideal choice for your outdoor vacation.
Cheeca Lodge & SpaResort4.0As a 4.0-star rated resort, Cheeca Lodge & Spa is perfect for those seeking a luxurious outdoor getaway. With its close proximity to fishing spots, yoga classes, tennis courts, and kayaking opportunities, you can indulge in outdoor activities while enjoying the serene views. The resort also offers a steam room and friendly staff.
La Siesta Resort & VillasResort2.5This 2.5-star rated resort is situated near a marina, offering easy access to fishing and sailing. You can also enjoy kayaking, relaxing by the sea, and outdoor pool entertainment. With its proximity to wedding venues, it's a good option for outdoor enthusiasts planning a wedding in a scenic location.

Explore the best activities and sights in Islamorada

When visiting Islamorada, Florida, there are plenty of outdoor activities for the whole family to enjoy. With its close proximity to the sea, fishing, diving, and snorkeling are popular options. You can also relax on the beautiful beaches and witness breathtaking sunsets. For entertainment, there are options like opera and theater. If you're a seafood lover, Islamorada offers delicious seafood options. Explore the Florida Keys and visit Islamorada Fishing Resorts, Treasure Harbor, and enjoy Bluewater Adventure. With so many attractions, Islamorada is the perfect destination for an outdoor vacation.

  1. Anne's Beach: Anne's Beach is a picturesque beach destination that offers a serene and tranquil atmosphere. With its crystal-clear turquoise waters, soft white sand, and swaying palm trees, it provides the perfect setting for a relaxing day at the beach. The gentle waves are ideal for swimming and paddleboarding, while the shallow areas are great for kids to splash around. Enjoy the stunning sunsets that paint the sky with vibrant hues, creating a magical ambiance. Anne's Beach is a hidden gem that allows you to unwind and connect with nature in a peaceful and idyllic setting.
  2. Bud n' Mary's Dive Center: Bud n' Mary's Dive Center is a paradise for outdoor enthusiasts and nature lovers. Situated by the sea, this marina offers a wide range of activities to enjoy. Embark on a thrilling fishing expedition and catch some of the most exotic fish species in the area. Admire the breathtaking sunsets as you relax on the beautiful sandy beach. Explore the rich marine life through diving and snorkeling adventures. Indulge in delicious seafood delicacies at the onsite restaurant. With its stunning scenery and family-friendly atmosphere, Bud n' Mary's Dive Center is the perfect destination for an unforgettable outdoor adventure.
  3. Florida Keys Brewing Co.: Florida Keys Brewing Co. is a charming and romantic brewery that offers a unique experience for beer enthusiasts. Immerse yourself in the cozy ambiance as you sip on a variety of handcrafted beers. The brewery's rustic décor and warm lighting create an intimate atmosphere, perfect for a relaxed evening out. Enjoy live entertainment and engage in lively conversations with fellow beer lovers. The friendly staff will guide you through the brewing process, allowing you to appreciate the art behind each beer. Whether you're a beer connoisseur or simply looking for a fun night out, Florida Keys Brewing Co. promises an entertaining and unforgettable experience.

Where to stay in Islamorada

Experience the enchanting beauty of Islamorada, Florida, on your outdoor vacation. With its postcard-worthy views, stunning landscapes, and beach paradise, this hidden gem offers a perfect escape from the hustle and bustle. Explore the beaten path and discover the thrill of fishing in the crystal-clear waters, dive into the vibrant sea life, or simply relax and soak in the breathtaking sunsets. Indulge in the local entertainment scene, from snorkeling adventures to opera performances and theater shows. Don't miss the chance to savor mouthwatering seafood delicacies that will leave your taste buds craving for more. Unwind, recharge, and create unforgettable memories in Islamorada.

  1. Matecumbe: Matecumbe is a popular neighborhood in Islamorada known for its unique charm and local atmosphere. With its beautiful beaches, stunning sunsets, and excellent fishing opportunities, it offers a perfect outdoor vacation experience for families. You can relax on the sandy shores, indulge in water activities like snorkeling and diving, or simply enjoy the breathtaking views. The neighborhood also boasts a vibrant entertainment scene, with theaters and opera performances to keep you entertained. Don't forget to savor the delicious seafood that the area is famous for.
  2. Venetian Shores: Venetian Shores is another popular neighborhood in Islamorada that should not be missed. With its picturesque canals and waterfront homes, it provides a unique experience for outdoor enthusiasts. Families can enjoy activities like boating, kayaking, and paddleboarding in the serene waters. The neighborhood's scenic beauty and peaceful ambiance make it an ideal spot for relaxation and family bonding.
  3. Lower Matecumbe Beach: Lower Matecumbe Beach is a must-visit neighborhood in Islamorada for outdoor lovers. This area is known for its stunning beaches, clear waters, and vibrant marine life, making it perfect for fishing, snorkeling, and diving. You can also enjoy breathtaking sunsets while relaxing on the sandy shores. The neighborhood offers a range of entertainment options, including theaters and seafood restaurants, ensuring a memorable family vacation.

Best times to go to Islamorada

The travel seasons of Islamorada

Trips to Islamorada show a small change in popularity throughout the year. The peak season to visit is from February to April, with March being the highest month. Off-peak season starts from October to December, and October sees the least travelers.

Islamorada has something in store for you whenever you visit. January is the coldest month of the year, while August is hottest, with average temperatures up to 84.4 degrees Fahrenheit. The wettest month in Islamorada is September, so pack accordingly.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationcloud iconCloudiness
January70.0°F (21.1°C)No Rain (Dry)Mostly Sunny
February71.8°F (22.1°C)No Rain (Dry)Mostly Sunny
March72.9°F (22.7°C)No Rain (Dry)Mostly Sunny
April76.6°F (24.8°C)No Rain (Dry)Mostly Sunny
May79.3°F (26.3°C)Light RainMostly Sunny
June82.4°F (28.0°C)Light RainMostly Sunny
July83.8°F (28.8°C)Light RainMostly Sunny
August84.4°F (29.1°C)Light RainMostly Sunny
September83.3°F (28.5°C)Light RainMostly Sunny
October80.2°F (26.8°C)Light RainMostly Sunny
November75.9°F (24.4°C)Light RainMostly Sunny
December72.9°F (22.7°C)No Rain (Dry)Mostly Sunny

Food and dining in Islamorada

When visiting Islamorada, you will be delighted by the distinctive local cuisines available in the area. One popular restaurant is Lazy Days Restaurant, known for its highly rated North American dishes. Another great option is Wahoo's Bar & Grill, where you can indulge in delicious North American fare. If you're in the mood for pizza and seafood specialties, Whale Harbor Restaurant Marina is a fantastic choice. For a unique dining experience, make sure to check out Habanos Restaurant. With its diverse offerings and fantastic restaurants, Islamorada is a paradise for food lovers.

How do I find a great hotel with Travelocity?

Give your entire crew a vacation they'll never forget. Find the perfect accommodations with our family-friendly badge, which highlights hotels that offer additional amenities for children. Our custom filters make it easy to narrow down your options to hotels that are conveniently located near top attractions, provide enhanced cleaning services, and fit within your budget.

Why should I book with Travelocity?

Conference calls, to-do lists and, of course, football practice. Busy lives and packed schedules call for trips that are hassle-free. Our aim is to provide worry-free travel every time you and your family book with us so that you can spend less time fretting and more time creating lasting memories. To achieve that, we will assist you in finding and planning your ideal trip, along with offering transparent pricing and authentic reviews, as well as 24/7 guaranteed customer support before, during, and after your vacation.

How can I save money on my trip to Islamorada?

If you're planning a trip to Islamorada with your family, consider visiting during the off-peak season from October to December to save money. To further save, bundle your flights, hotel, and car bookings together for a discounted price. While in Islamorada, you can enjoy affordable activities such as fishing, relaxing on the beach, and snorkeling. These local attractions offer inexpensive options for family fun without breaking the bank.

Frequently asked questions

What are the top kid-friendly hotels in Islamorada?
From well-thought-out amenities to bigger rooms, kid-friendly hotels are equipped with features that can help transform a routine family vacation into a sensational one. These Islamorada options make traveling with young ones child's play: Your crew will enjoy staying at Bayside: 1st Floor Apartment in Native Hammock on Florida Bay. A playground and a nearby theme park are among the things that help make this property a winner. Mitchells Keys Villa - private, secluded bayfront home is another excellent choice. After a big day of exploring, come back home to your comfortable room and amenities like a water park and a playground.
Where can I find cheap hotels in Islamorada?
At Travelocity you'll find really nice hotels in Islamorada at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Islamorada rather than in Islamorada. We may find you even better rates, too.
How do I find the best Islamorada hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Islamorada then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Islamorada?
The cheapest hotel in Islamorada is . This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Islamorada?
There are 2,181 hotels in Islamorada on Travelocity.
What are the best hotels in Islamorada?
Islamorada has so many great hotels to choose from at Travelocity --- and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Islamorada for you!
When is the best time to visit Islamorada?
If you want the joy of a fun-filled trip in peak season, visit Islamorada during November, December and January. If you'd prefer the peace of off-season, book a stay during quieter months, such as April, September and October.
When is the cheapest time to stay in Islamorada?
Based on historic data is usually the cheapest month to visit Islamorada. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Islamorada?
There are multiple hotels in Islamorada that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Islamorada. We have plenty of kid-friendly hotels in Islamorada to choose from on Travelocity!
Why book a hotel in Islamorada through Travelocity?
Because we have the top hotels in Islamorada! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Islamorada on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

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