Question 1

What is the best area to stay in Islamorada?

Accepted Answer

The best area to stay in Islamorada is along the Overseas Highway (US-1), particularly in the stretch between Windley Key and Upper Matecumbe Key. This central corridor offers convenient access to most of Islamorada's attractions and amenities.

Couples often find this area ideal for a relaxing and activity-filled vacation. Along this main road, you'll find a variety of resorts and boutique hotels, many with private beach access, on-site dining, and water sports rentals. It's easy to arrange fishing charters, snorkeling trips, or simply enjoy the ocean views from your accommodation. The area is also home to several much-loved restaurants and art galleries, making it simple to plan evenings out.

For those looking for a more secluded and quiet experience, the northern end of Upper Matecumbe Key, away from the immediate highway, provides a more residential feel with vacation rentals and smaller, intimate resorts.

Question 2

What are the best hotels in Islamorada that travelers recommend?

Accepted Answer

Two of the best hotels in Islamorada that receive consistently high recommendations from travelers are the Cheeca Lodge & Spa and the Islander Resort.

The 5-star Cheeca Lodge & Spa, with an outstanding 9.2 rating, provides a luxurious experience with amenities such as 24-hour room service, massages on the beach, and a private beach location. Guests frequently praise the friendly staff, beautiful rooms, and excellent service. It is conveniently located near the MoradaWay Arts & Cultural District, just 0.3 miles away.

Another highly recommended option is the 4-star Islander Resort, which also has an impressive 9.2 rating. This resort offers a beachfront restaurant, evening entertainment, and a poolside bar. Travelers often highlight the friendly staff, beautiful, clean rooms, and the large, beautiful pool. It is very close to the Keys History & Discovery Center, only 0.1 miles away.

Other excellent choices include the 4-star Amara Cay Resort, rated 8.8, known for its comfortable suites and private beach, and the 4-star La Siesta Resort & Villas, also rated 8.8, which offers private beach access and designer toiletries. The 3-star Pines & Palms Resort, with a 9.2 rating, is another great option, offering a heated pool and private beach.

Question 3

What are the best family hotels in Islamorada?

Accepted Answer

For families traveling to Islamorada, two highly-rated options are the Cheeca Lodge & Spa and The Caribbean Resort.

The 5-star Cheeca Lodge & Spa, with an excellent 9.2 rating, offers a wealth of amenities designed for families. These include toys for children and babies, a kids' meal option, a gated pool, and a children's club with free access. The hotel also provides babysitting and childcare services on-site, complimentary cribs, beach toys, a playground, and free rollaway extra beds. Guests consistently praise the friendly staff, beautiful and clean rooms, and amazing amenities and service. It is conveniently located near the MoradaWay Arts & Cultural District and the Keys History & Discovery Center.

Another outstanding choice is The Caribbean Resort, which boasts a great 10.0 rating. This 3.5-star resort provides playpens, connecting rooms, highchairs, sofa beds, a gated pool, and complimentary cribs, ensuring a comfortable stay for families. Guests often highlight the helpful staff and the beautiful, clean rooms. The resort is also close to the MoradaWay Arts & Cultural District and the Keys History & Discovery Center. Find more child-friendly accommodations in Islamorada

Question 4

What are the best 5-star hotels in Islamorada?

Accepted Answer

For a luxurious 5-star experience in Islamorada, consider the Cheeca Lodge & Spa.

The Cheeca Lodge & Spa, with an impressive 9.2 rating, offers an exceptional stay. Guests consistently praise the friendly and amazing staff, beautiful and clean rooms, and excellent service. This resort provides a wealth of amenities including 24-hour room service, designer toiletries, premium bedding, and a rainfall showerhead. For relaxation, you can enjoy a deep soaking bathtub, a private pool, or a private outdoor hot tub. Dining options include a beachfront restaurant and couples dining experiences, complemented by champagne service and a poolside bar. Active guests will appreciate the on-site golf course and outdoor tennis courts. The resort is also conveniently located near the Morada Way Arts & Cultural District and the Keys History & Discovery Center. Find more luxury hotels in Islamorada

Question 5

What are the best spa hotels in Islamorada?

Accepted Answer

For an exceptional spa experience in Islamorada, consider the luxurious Cheeca Lodge & Spa or the highly-rated Casa Morada.

The 5-star Cheeca Lodge & Spa, with an outstanding 9.2 rating, offers an array of spa treatments including deep tissue massage, aromatherapy, body scrubs, body wraps, and hot stone massage. Guests can also enjoy amenities such as a full-service spa with a steam room, sauna, and couples' treatment rooms. Reviewers consistently praise the friendly and amazing staff, the beautiful and clean rooms, and the great amenities.

Another excellent option is the 3.5-star Casa Morada, boasting an impressive 9.4 rating. While offering a more focused selection of spa services like Swedish, sports, and deep tissue massages, it is also highly regarded for its excellent and comfortable rooms, good facilities, and helpful staff. Guests also benefit from a complimentary continental breakfast. See all spa hotels in Islamorada

Question 6

Which beach resorts in Islamorada do travelers love?

Accepted Answer

For highly-rated beach resorts in Islamorada, travelers frequently recommend Cheeca Lodge & Spa, Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, Amara Cay Resort, La Siesta Resort & Villas, and Matecumbe Resort.

The 5-star Cheeca Lodge & Spa, with an impressive 9.2 rating, offers a luxurious experience with a private beach, ocean views, and amenities like 24-hour room service and a rainfall showerhead. Guests particularly appreciate the golf course on-site and the beachfront restaurant. It is conveniently located near the MoradaWay Arts & Cultural District.

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, rated 9.0, provides a great experience with a private beach, ocean views, and an outdoor pool with sun loungers. This 3.5-star resort is close to the History of Diving Museum and Windley Key Fossil Reef Geological State Park.

The 4-star Amara Cay Resort, with an 8.8 rating, also features a private beach and ocean views. Guests often praise the friendly staff and the clean, comfortable rooms. It's located just 2 miles from Indian Key Historic State Park.

Also rated 8.8, the 4-star La Siesta Resort & Villas provides a private beach, ocean views, an outdoor pool, and a poolside bar. It's situated near the MoradaWay Arts & Cultural District.

Matecumbe Resort, with an 8.8 rating, is another excellent option offering a private beach, ocean views, and an outdoor pool. Many rooms also include a kitchen, providing extra convenience for guests. It is located just over a mile from Robbie's of Islamorada. See more stays near the beach in Islamorada

Question 7

What hotels in Islamorada offer free breakfast?

Accepted Answer

For hotels in Islamorada that offer free breakfast, consider Casa Morada, Chesapeake Beach Resort, Coconut Cove Resort and Marina, Fisher Inn Resort & Marina, and Hadley Resort and Marina.

The 3.5-star Casa Morada, with an excellent 9.4 rating, offers free continental breakfast and free breakfast. Guests frequently praise its comfortable rooms, good facilities, and excellent reception. The hotel also features an outdoor pool with a poolside bar and sun loungers. It's conveniently located near the Islamorada Brewery & Distillery, just 0.2 miles away.

Another great option is the 3.5-star Chesapeake Beach Resort, rated 9.2. This hotel provides free breakfast and free continental breakfast. Travelers highlight the friendly and great staff, comfortable and clean rooms, and excellent breakfast. The beautiful location is also a frequent point of praise.

The 3-star Coconut Cove Resort and Marina, with a 9.0 rating, also offers free breakfast and free continental breakfast. Guests appreciate the friendly and helpful staff, comfortable and clean rooms, and the great outdoor pool. Many rooms offer ocean views, and the hotel is located very close to the sea.

The 3.5-star Fisher Inn Resort & Marina, rated 8.2, includes free breakfast and free to-go breakfast. Reviewers often mention the nice and clean rooms, excellent and friendly staff, and the great location. The hotel also has an outdoor pool with sun loungers.

Finally, the 3.5-star Hadley Resort and Marina, with a 7.6 rating, offers free breakfast and free to-go breakfast. Guests praise the nice and clean rooms, friendly and amazing staff, and the convenient location. The hotel is situated very close to the ocean and features a private beach. Find more hotels with free breakfast in Islamorada

Question 8

What are the top pet-friendly hotels in Islamorada?

Accepted Answer

For top pet-friendly hotels in Islamorada, consider the Fisher Inn Resort & Marina, Sands of Islamorada, Bayside Villas by Islander Resort, Chesapeake Beach Resort, and Amara Cay Resort.

The 3.5-star Fisher Inn Resort & Marina, with an 8.2 rating, welcomes dogs and is praised by guests for its nice and clean rooms, excellent staff, and superb location. It is conveniently located just 0.2 miles from Windley Key Fossil Reef Geological State Park.

Sands of Islamorada, rated 8.8, is a great option that permits both dogs and cats and provides food and water bowls. Guests frequently mention its beautiful and convenient location and clean rooms. It is 2.1 miles from Indian Key Historic State Park.

Another excellent choice is the 3.5-star Bayside Villas by Islander Resort, which has an 8.8 rating and allows dogs. It is situated 0.3 miles from MoradaWay Arts & Cultural District and 1.0 mile from Keys History & Discovery Center.

The 3.5-star Chesapeake Beach Resort, with an impressive 9.2 rating, permits pets and offers free continental breakfast. Guests consistently highlight the friendly staff, comfortable rooms, and excellent breakfast. It is 1.2 miles from Windley Key Fossil Reef Geological State Park.

Finally, the 4-star Amara Cay Resort, rated 8.8, welcomes dogs and provides food and water bowls. Guests often praise the friendly staff, beautiful location, and comfortable rooms. It is located 2.0 miles from Indian Key Historic State Park. See more pet-friendly hotels in Islamorada

Question 9

What are the top boutique hotels in Islamorada?

Accepted Answer

For top boutique hotels in Islamorada, consider the Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, the Fisher Inn Resort & Marina, and the Drop Anchor.

The 3.5-star Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort, with a 9.0 rating, offers guests a poolside bar and a lovely outdoor pool with sun loungers. Many rooms provide beautiful sea, ocean, or marina views, and the property also features a private beach location. Guests often highlight the great food available.

Another excellent choice is the 3.5-star Fisher Inn Resort & Marina, rated 8.2. This resort boasts a heated outdoor pool with sun loungers and umbrellas, and guests consistently praise the nice, clean rooms and the excellent, friendly staff. Its location is frequently described as great and great, and the amenities are considered perfect.

The 3-star Drop Anchor, with an 8.8 rating, also offers a fantastic experience. Guests appreciate the spacious, clean rooms and the comfortable, great pool. The staff is consistently described as excellent and friendly, and the location is noted as beautiful and great. Many rooms offer beach or ocean views, and some even include a kitchen. See all boutique hotels in Islamorada

Question 10

What are the best budget hotels in Islamorada?

Accepted Answer

Two of the best budget hotels in Islamorada are the Sunset Inn and Pines & Palms Resort.

The 3-star Sunset Inn, with an outstanding 9.4 rating, is praised for its spacious and clean rooms, as well as its friendly and helpful staff. Guests appreciate its central location, warm outdoor pool, and excellent free self-parking. It is conveniently located near the Keys History & Discovery Center and the Islamorada Brewery & Distillery.

Another excellent choice is the 3-star Pines & Palms Resort, which has a 9.2 rating. Travelers frequently mention its beautiful location and clean rooms. This resort offers free WiFi, free self-parking, and suites, along with a private beach access and ocean views.

Other highly-rated budget options include Coconut Cove Resort and Marina, Sands of Islamorada, and Drop Anchor.

The 3-star Coconut Cove Resort and Marina, rated 9.0, provides free continental breakfast, free self-parking, and an outdoor pool with sun loungers. Customers consistently highlight the friendly and helpful staff, comfortable and clean rooms, and a great pool. It is located near Windley Key Fossil Reef Geological State Park.

Sands of Islamorada, with an 8.8 rating, offers free WiFi, free self-parking, and an outdoor pool. Guests often comment on its beautiful and convenient location, clean rooms, and phenomenal staff.

The 3-star Drop Anchor, rated 8.8, features free WiFi, free self-parking, and offers beach and ocean views. It is praised for its excellent and friendly staff, spacious and clean rooms, and great location. It is also close to Windley Key Fossil Reef Geological State Park. View all budget hotels in Islamorada

Question 11

What are the most romantic hotels in Islamorada for couples?

Accepted Answer

For a romantic getaway in Islamorada, couples have several excellent choices, including The Caribbean Resort, Casa Morada, Chesapeake Beach Resort, Cheeca Lodge & Spa, and Islander Resort.

The Caribbean Resort, with a great 10.0 rating, offers beautiful, clean rooms and helpful staff. Guests can enjoy the outdoor pool and stunning ocean views, providing a serene backdrop for a romantic stay. It is conveniently located near the Islamorada Brewery & Distillery and Matecumbe United Methodist Church.

Casa Morada, rated 9.4, provides excellent and comfortable rooms, good facilities, and an excellent reception. This hotel offers a free continental breakfast and a poolside bar, making it ideal for relaxing together. It's also close to the Islamorada Brewery & Distillery.

Chesapeake Beach Resort, with a 9.2 rating, is praised for its friendly and great staff, comfortable and clean rooms, and an excellent breakfast. The beautiful location and clean pool add to its appeal for couples. It's situated near Windley Key Fossil Reef Geological State Park and Theater of the Sea.

The 5-star Cheeca Lodge & Spa, rated 9.2, is a luxurious option with amazing staff, beautiful and clean rooms, and excellent service. Couples can indulge in massages on the beach, private dining experiences, and enjoy amenities like a 24-hour room service, a private beach, and private hot tubs. The resort also features an on-site golf course and beachfront restaurant. It is located close to the Matecumbe United Methodist Church.

Islander Resort, a 4-star hotel rated 9.2, offers beautiful and clean rooms, as well as a beautiful and large pool. With its private beach and ocean views, it provides a wonderful setting for couples seeking a peaceful escape. It is located near the Islamorada Brewery & Distillery. See all romantic hotels in Islamorada

Question 12

What are the best hotels in Islamorada near MoradaWay Arts & Cultural District?

Accepted Answer

For hotels in Islamorada near the MoradaWay Arts & Cultural District, consider the Cheeca Lodge & Spa, The Caribbean Resort, and the Islander Resort.

The 5-star Cheeca Lodge & Spa, with a 9.2 rating, is an excellent choice, located just 0.3 miles from the district. This hotel is particularly well-suited for families, offering amenities such as toys, games, a children's club, a playground, and babysitting services. Guests frequently praise the friendly and amazing staff, beautiful and clean rooms, and great amenities.

The Caribbean Resort, a 3.5-star accommodation with a superb 10.0 rating, is situated 0.5 miles from the MoradaWay Arts & Cultural District. This resort provides family-friendly amenities like playpens, highchairs, and cribs, along with a pool. Reviews highlight the helpful and great staff, as well as beautiful and clean rooms.

Another great option is the 4-star Islander Resort, rated 9.2, and located 0.6 miles from the district. This resort offers a beautiful pool, free cribs and rollaway extra beds, and boasts ocean and beach views, with a private beach on site. Guests frequently mention the friendly staff, beautiful and clean rooms, and great service.

Question 13

When is the best time to go to Islamorada?

Accepted Answer

The best time to visit Islamorada is during the dry season, from November to April, for optimal weather and outdoor activities.

During these months, you'll experience pleasant temperatures, typically ranging from the mid-70s to low 80s Fahrenheit, with lower humidity and less chance of rain. This makes it ideal for enjoying water sports like fishing, snorkeling, and diving, as well as relaxing on the beaches.

Couples looking for a romantic getaway will appreciate the comfortable climate for sunset cruises and dining al fresco. The cooler, drier air also enhances outdoor excursions to places like the Indian Key Historic State Park or Theater of the Sea.

Families traveling with children will find the conditions superb for all-day beach activities and exploring the area's natural attractions without the intense heat and humidity of the summer months.

Question 14

Can I cancel my hotel reservation on Expedia?

Accepted Answer

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Islamorada.

Question 15

How can I save on a Islamorada hotel booking with Expedia?

Accepted Answer

With Expedia, you earn OneKeyCash™* on eligible Islamorada hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It’s free to join, and you’ll unlock our lowest Member Prices as soon as you’re signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

Question 16

How much is the nightly rate at a Islamorada hotel?

Accepted Answer

Prices for hotels in Islamorada often vary, but you can find a great deal from $207 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

Month	Price
January	$503
February	$373
March	$386
April	$348
May	$319
June	$288
July	$278
August	$263
September	$225
October	$241
November	$258
December	$328

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	70.0°F (21.1°C)	No Rain	Mostly Sunny	Average	Average
February	71.8°F (22.1°C)	No Rain	Mostly Sunny	Average	Slightly High
March	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
April	76.6°F (24.8°C)	No Rain	Mostly Sunny	Moderately High	Slightly High
May	79.3°F (26.3°C)	Light Rain	Mostly Sunny	Average	Average
June	82.4°F (28.0°C)	Light Rain	Mostly Sunny	Average	Average
July	83.8°F (28.8°C)	Light Rain	Mostly Sunny	Moderately High	Average
August	84.4°F (29.1°C)	Light Rain	Mostly Sunny	Average	Average
September	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	80.2°F (26.8°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
November	75.9°F (24.4°C)	Light Rain	Mostly Sunny	Moderately Low	Slightly Low
December	72.9°F (22.7°C)	No Rain	Mostly Sunny	Moderately Low	Average

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Chesapeake Beach Resort

Cheeca Lodge & Spa

Islander Resort

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Sunset Inn

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Dove Creek Resort & Marina, Trademark Collection by Wyndham

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Gilbert's Resort

Siesta Motel

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