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The 10 Best Resorts in Islamorada, USA

Check out our pick of great resorts in Islamorada

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Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
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Situated in Islamorada, 3.1 km from Windley Key, Ragged Edge Resort & Marina features accommodation with free bikes, private parking, an outdoor swimming pool and a terrace. Located around 8.3 km from Upper Matecumbe Key, the resort with free WiFi is also 14 km away from Pigeon Key. Some units at the property have a balcony with a sea view.

we were delighted with the ocean view from our cottage and wonderful pool

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9.1
Superb
166 reviews
Price from
RUB 26,985
per night

This resort is situated on one-quarter mile of private beach on Long Key between Islamorada and Marathon. Bright spacious rooms and 2 swimming pools are available.

Guests can dock their boats (up to 21 feet) for free at the Lime Tree Bay Resort. A tennis court and a fishing dock are on site. Use of the sea kayaks, paddle boards, and barbecue facilities are offered. A sandy sunning beach with hammocks and loungers is available for guests' enjoyment.

Great resort! The room is neat, clean and has everything we need during our stay. The resort also provides free breakfast, and many water/land activities for the guests to ensure their can enjoy their stay. Highly recommend!

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8.6
Fabulous
2,519 reviews
Price from
RUB 20,332
per night

Positioned on 27 acres of lush gardens and 1000 feet of private waterfront, Cheeca Lodge & Spa is a luxury resort in Islamorada, Florida. It features a 9-hole par 3 golf course, on-site spa, and 525-foot fishing pier.

A beautiful large area with many activities and a beautiful beach. It is a pity that I was not able to take advantage of all this, because I was only passing through for one night.

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8.6
Fabulous
1,110 reviews
Price from
RUB 39,431
per night

Spend the afternoon lounging by the Islander's 2 on-site swimming pools. Enjoy on-site dining at Beachside Bar and Grill.

Easily discover a variety of activities only minutes from the Islander Resort, including snorkeling and scuba diving. Enjoy deep-sea fishing, sailing or browsing the local shops, also only a short distance away.

There is no other property in the upper keys like the Islander. The rooms (which are super clean) are huge and have beautiful vaulted ceilings and giant windows overlooking your own private screened-in porch and patio. The pool area is beautiful and has two pools and a full restaurant that actually serves quality food and drinks. There’s a big beautiful beach area and water sports provided by the hotel onsite. definitely Recommend!

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8.5
Very good
1,542 reviews
Price from
RUB 29,594
per night

Featuring a unique tropical atmosphere and situated on an island in the Florida Keys, this resort offers WiFi and parking to guests.

Guests of Postcard Inn Beach Resort & Marina can stop by the marina to charter a fishing trip or rent a jet ski. Guests seeking adventure will enjoy snorkeling and diving charter boats.

Very beautiful place for families and small kids.

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8
Very good
1,194 reviews

Offering an outdoor pool and sun terrace, Caloosa Cove Resort - With Full Kitchens is situated in Islamorada in the Florida Region, 9.6 km from Upper Matecumbe Key. Theater of the Sea on Islamorada is 18 km from the property.

Spotlessly clean and had everything you could need for a stay away from home.

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8.8
Fabulous
390 reviews
Price from
RUB 25,612
per night

Located adjacent to Windley Key Fossil Reef Geological State Park, this Islamorada resort features an ocean-side outdoor swimming pool. Beach towels, Kayaks, Paddle-boards & WiFi are included at this oceanfront resort and marina.

staff , canoes, paddle boards swimming pool and view pretty motel

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8
Very good
386 reviews
Price from
RUB 19,089
per night

Located on the waters of the Florida Bay, the Islander Bayside Resort is less than 5 minutes’ walk from the beach. This resort features a kitchen in every townhouse and an outdoor pool.

A flat-screen TV is included in every guest townhouse of this Islamorada resort and all units have free WiFi and laundry facilities. Kitchens offer a microwave, refrigerator and an oven.

It was right on the Bay and the pool was not crowded. Accommodations were new clean and wonderful!

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8.3
Very good
245 reviews
Price from
RUB 34,522
per night

This Islamorada resort in the Florida Keys is located near Alligator Reef. It boasts an oceanfront freshwater pool, a Tiki Bar and a private beach area. Each accommodation includes a full kitchen.

A living area with a cable TV is included in all units at Pines & Palms Resort. The traditionally styled units feature light colours and island decor. Most offer a private terrace with ocean views.

Great location clean and friendly staff

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8.7
Fabulous
848 reviews
Price from
RUB 19,921
per night

Guests at this Islamorada oceanfront resort can enjoy free WiFi access. Windley Key Fossil Reef Geological State Park is 2 miles away.

A 37-inch flat-screen cable TV and a small refrigerator are offered in each room at this Florida Chesapeake Beach Resort. Select rooms and suites have a balcony.

Chesapeake Beach Resort boasts an outdoor pool with an ocean view.

Fantastic location, right at the beach, very comfortable room with the terrace. Gorgeous restaurant with ocean view nearby. Good breakfast. Forthcoming staff. Excellent place, highly recommend.

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8
Very good
830 reviews
Price from
RUB 24,542
per night

Most booked hotels in Islamorada in the past month

Resorts that guests love in Islamorada

  • From RUB 37,808 per night
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 1,542 reviews
    Last year we stayed there and it was great, location, resort, staff and weather. This year was meh. Service at the poolside restaurant was spotty. They renamed the villages causing confusion so this year is was meh.
    Ron Moz Sr
    United States
  • From RUB 37,808 per night
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 1,542 reviews
    We loved the resort, the room was fab, modern & huge, veranda lovely & private (Refurbished rooms definitely worth paying the extra) Alisa our sever for breakfast in Elements restaurant was wonderful, so friendly & attentive.
    Morven
    United Kingdom
  • 8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 390 reviews
    Our suite was very nice and clean! It was even better than pictures. Entire resort was clean, well maintained and very quiet!
    Patricia
    United States
  • From RUB 37,808 per night
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 1,542 reviews
    The resort is beautiful and very relaxing. Enoyed everything there. Tides Beach bar and grill was the best!
    Mary
    United States
  • From RUB 19,921 per night
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 848 reviews
    I always stay at this resort every time I go to the keys. The staff is wonderful, the pool is nice and the bungalow I stayed in was facing the ocean, so relaxing! Thank you!
    Karole
    United States
  • From RUB 23,926 per night
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,039 reviews
    Location was perfect in relation to where I needed to be for scuba diving. It’s a cozy “mini resort”
    Marie Candace
    United States
  • From RUB 37,808 per night
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 1,542 reviews
    Resort in general
    A
    Anonymous
    United States
  • From RUB 79,478 per night
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 1,110 reviews
    Check lodge is an all inclusive resort with games, a fishing pier with rods and bait, paddle boards, a game room and multiple restaurants. It has a large man made beach and two pools.
    Susan
    United States
  • From RUB 17,354 per night
    7.1
    Scored 7.1
    Good
    Rated good
     · 271 reviews
    Don’t come with any grandiose expectations of this being an all inclusive luxury resort. this place was built in the 50s-70s era. ITS CLEAN AND LOCATED PERFECTLY! We had a wonderful time. if you want to stay at the resort most of your trip then spend more money.
    Franklin
    United States
  • From RUB 79,478 per night
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 1,110 reviews
    Very nice property with a golf course. Yoga, spa, etc etc. I think one of the better ones in islamorada. We stayed in one of the beach cottages . It was right above the pool and with an ocean view. Beware that music is played around the pool most of the day, you can hear it from the screened porch but the room is very well insulated so it is quiet if windows are closed. The bed was very comfortable. Ac a bit loud during the night. Updated room. Family resort. Decor and ambiance is nice with a tropical feel.
    manuela
    United States