Islamorada Oceanfront Hotels

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Our Top 5

(Sorted by rating & number of reviews)

1. Pines & Palms Resort
2. Islander Resort
3. Caloosa Cove Resort
4. Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
5. La Siesta Resort & Villas

Best Oceanfront Hotels in Islamorada

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Islamorada
Aug 02, 2025 - Aug 03, 2025

Pines & Palms Resort

+ 91 photos

Located 2.1 km from Hurricane Monument, guests of 3-star Pines & Palms Resort Islamorada may find yoga classes, barbecue grills, and a garden on-site. The venue has a swimming pool, while boasting a beachfront setting in a beach area.

The property is a 5-minute drive from Michelle Nicole Lowe Art Gallery. It is 4 km from downtown Islamorada.

Pines & Palms Resort is a short ride from Matecumbe United Methodist Church.

The rooms have private bathrooms with a separate toilet, a bath, and a shower. Certain units offer views of the patio. A microwave, coffee and tea making equipment, and a fridge are also provided in the units.

A summer terrace and an outdoor pool area can be booked at Pines & Palms Resort at extra charge. Bicycle and car hire is available at this resort and the area is popular for mountain biking, parasailing, and windsurfing.

Address: 80401 Old Hwy

Islander Resort

+ 91 photos

Islander Resort Islamorada, located just near Upper Matecumbe Key Island, features fitness classes and barbecue. It is a 20-minute walk from History of Diving Museum and a 5-minute drive from Indian Key State Historic Site.

The venue is set in a beach area of Islamorada, 1 km from the city centre. The property is nestled among palm trees, and a stone's throw from the class museum "Florida Keys History and Discovery Center".

Islander Resort is a short ride from Lobster Trap Art Gift Shop and Gallery.

Many rooms offer views of the sea. They also come with private bathrooms.

Guests also have access to a swimming pool and a sundeck at an extra charge. This resort has an outdoor pool area and a fitness centre. Alternatively, you can unwind with water sports activities, snorkelling, and kayaking on-site or in the surrounding area.

Address: 82100 Overseas Highway

Caloosa Cove Resort

+ 58 photos

Situated near a private beach, Caloosa Cove Resort - With Full Kitchens Islamorada offers 33 rooms with views of the pool. Craig Key Island is a 10-minute drive from the resort and a 15-minute drive from Lower Matecumbe Key Island.

The venue is set in a beach area of Islamorada.

The bathrooms come with a separate toilet, a bath, and a shower.

Upon request and at a surcharge, a seasonal outdoor pool and a sun deck can also be provided. Other facilities include an outdoor pool area. A selection of activities are offered in the area, such as lawn tennis and fisheries.

Address: 73801 Overseas Highway

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort

+ 91 photos

Featuring hire of bicycles as well as Wi-Fi throughout the property, Postcard Inn Beach Resort & Marina is set in Islamorada, 1.2 km from Windley Key Fossil Reef Geological State Park. The centre of Islamorada is within 3 km of the venue, and Windley Key Island is about 1.5 km away.

The accommodation is placed next to white beaches. This hotel is located near the Atlantic Ocean.

You can get to History of Diving Museum in a few minutes by car.

Guests of Postcard Inn Beach Resort & Marina will enjoy use of a terrace and a community pool at additional cost. The resort also features a heated swimming pool as well as a sundeck and recreational facilities.

Address: 84457 Overseas Highway

La Siesta Resort & Villas

+ 91 photos

Set within 2.1 km from Anne s Beach, the 4-star La Siesta Resort & Villas Islamorada features Wi-Fi throughout the venue as well as parking on site. The accommodation is nestled in the business district and 4 km from the city centre.

Michelle Nicole Lowe Art Gallery is less than 2.5 km away. The hotel is based next to the own beach.

La Siesta Resort & Villas is a short ride from Indian Key Historic State Park.

This resort offers rooms with views of the garden. Moreover, they include a microwave oven, tea and coffee making equipment, and a refrigerator.

A swimming pool and a Jacuzzi can be booked at La Siesta Resort & Villas at extra charge. Various recreational opportunities and water sports facilities are available onsite. There is a fitness club with a wide range of sports.

Address: 80241 Overseas Highway