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Islamorada, FL resorts
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89 Best resorts in Islamorada, FL

Browse Coastal Resorts in Islamorada, FL, United States

Walk straight out of your luxury suite directly onto the powdery white sand at spectacular seashore resorts in Islamorada, FL, United States.

Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly - Islamorada, FL
No reviews

Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly

resort, Islamorada, Village of Islands
This pet-friendly beachside apartment, offering the 'Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly', is situated in Islamorada's Matecumbe district, close to parks and easily accessible to the Morada Way Arts & Cultural District and Keys History & Discovery Centre.
The two-bedroom suite boasts an ocean view, private balcony, and accommodates up to eight guests, with amenities including Wi-Fi, a pool, and proximity to water sports such as jet skiing and scuba diving at Bud n' Mary's Dive Center.

Browse Resorts with a Hot Tub in Islamorada, FL, United States

Listen to the rustle of palms from the comfort of a private tropical hot tub at island resorts in Islamorada, FL, United States.

Cheeca Lodge & Spa - Islamorada, FL
8.8 219 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa, a resort in Islamorada, Village of Islands, offers direct access to a nearby beach, ideal for exploring the coastal beauty of the Florida Keys.
This establishment provides a comprehensive range of amenities including an on-site spa, swimming pool with a poolside bar, fitness centre, and convenient parking, with express check-in/check-out services available.
Chesapeake Beach Resort - Islamorada, FL
9.0 2604 reviews

Chesapeake Beach Resort

resort, Islamorada, Village of Islands
Chesapeake Beach Resort is located in Islamorada, Florida, just two miles from Windley Key Fossil Reef Geological State Park and directly on the oceanfront, offering stunning ocean views and easy access to the beach. The resort has received very good ratings for location, cleanliness, and overall user experience.
The resort offers a range of rooms and suites, all featuring a 37-inch flat-screen cable TV and a small refrigerator. Guests can enjoy an outdoor pool with ocean views, a Jacuzzi, a terrace or balcony, a garden, and a restaurant and bar on-site.

Frequently asked questions about resorts in Islamorada, FL

  • How easy is it to get to Islamorada, FL?

    Getting to Islamorada is pretty straightforward. You can fly into Key West International Airport and then drive about an hour and a half, or you can drive down from Miami, which takes about four hours. If you're driving, you'll be on the famous Overseas Highway, which is a scenic drive over bridges and through islands.
  • What are the best resorts with a swimming pool in Islamorada, FL?

    Pines & Palms Resort, Chesapeake Beach Resort and Islander Resort are among the best resorts with a swimming pool in Islamorada, FL.

  • What time of year is best to stay in a resort in Islamorada, FL?

    The best time to visit Islamorada is during the shoulder seasons, from April to May or September to October. The weather is still great, but the crowds are smaller and prices are usually lower. The summer months can get hot and humid, and hurricane season runs from June to November.
  • What are the best resorts with jacuzzi in Islamorada, FL?

  • What are the most romantic activities in and around Islamorada, FL?

    Islamorada is a perfect destination for a romantic getaway. You can take a sunset cruise on a sailboat, have a romantic dinner at one of the many waterfront restaurants, or spend a day exploring the Indian Key Historic State Park, which is a beautiful and secluded spot. There are also lots of opportunities for fishing, kayaking, and paddleboarding.
  • What are the best family friendly resorts in Islamorada, FL?

    The best family friendly resorts in Islamorada, FL are Pines & Palms Resort, Chesapeake Beach Resort and Islander Resort.

  • What are the nearest cities to explore when you are in Islamorada, FL?

    The nearest city to Islamorada is Marathon, which is about 30 minutes away. You can also easily drive to Key West (about two hours), Miami (about four hours), and Fort Lauderdale (about four and a half hours).
  • What are the best pet friendly resorts in Islamorada, FL?

    The best pet friendly resorts in Islamorada, FL are Pines & Palms Resort, Chesapeake Beach Resort and Islander Resort.

  • What are the most requested amenities in resorts in Islamorada, FL?

    The most requested amenities in Islamorada resorts are private balconies or patios, swimming pools, and waterfront views. Many resorts also offer on-site restaurants, bars, and spa services.

Popular destinations

Browse Resorts with a Pool in Islamorada, FL, United States

Float the day away in a crystal-clear infinity pool right beside the ocean waves at island resorts featuring a pool in Islamorada, FL, United States.

Islander Resort - Islamorada, FL
9.1 3918 reviews

Islander Resort

resort, Islamorada, Village of Islands
Islander Resort is situated directly on the beach in Islamorada, offering easy access to the beautiful waters of the Florida Keys and the area's attractions. The resort has received very good ratings for its overall experience, with excellent marks for its location and cleanliness.
The resort provides spacious rooms with private porches or lanais, perfect for enjoying the tropical ambiance. Guests can enjoy a range of amenities including swimming pools, a bar and restaurant, a spa, a fitness centre, and a concierge service.
Islamorada Stay! Free Breakfast | Pool & Parking! - Islamorada, FL
No reviews

Islamorada Stay! Free Breakfast | Pool & Parking!

resort, Islamorada, Village of Islands
This Islamorada resort offers a prime location in the Village of Islands, approximately 160 kilometres south of Miami, known for its upscale, small-town atmosphere and natural beauty.
The accommodation provides a 2-bedroom, 1-bathroom unit for up to 4 guests, featuring air conditioning, free Wi-Fi, a swimming pool, complimentary breakfast and parking, and welcomes pets for an additional nightly charge under the "Islamorada Stay! Free Breakfast | Pool & Parking!" offer.
Pines & Palms Resort - Islamorada, FL
9.2 2299 reviews

Pines & Palms Resort

resort, Islamorada, Village of Islands
Pines & Palms Resort is located in Islamorada, close to Alligator Reef and less than a mile from Miss Islamorada Fishing Charters, with John Pennekamp Coral Reef State Park a short 30-minute drive away. This resort has very good user ratings, an excellent location rating and a very good cleanliness rating.
The resort offers a range of apartments with full kitchens and ocean views. Guests can enjoy a private beach, an oceanfront pool, a Tiki Bar, kayak and bike rentals, private boat docks, a covered cabana with a barbecue grill, and premium sport fishing areas.
Strong Waves At Harry Harris Beach! Free Breakfast - Islamorada, FL
No reviews

Strong Waves At Harry Harris Beach! Free Breakfast

resort, Islamorada, Village of Islands
This Islamorada apartment is situated on a private beach, a short walk from the Theatre of the Sea and close to Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks.
The 301 sq ft (28 sq m) self-catering unit sleeps four, features two queen beds, a balcony, daily housekeeping, and includes a fridge, microwave, dishwasher, and a Keurig coffee maker; on-site amenities comprise a heated pool, kayaks, paddleboards, bike rentals, and a daily continental breakfast.

Best Islamorada, FL resorts with air conditioning

2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly! - Islamorada, FL
8.0 4 reviews

2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly!

resort, Islamorada, Village of Islands
This beachfront villa in Matecumbe, Islamorada, enjoys a central location, less than 2km from Hurricane Monument and the Florida Keys Brewing Company, and a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Centre.
The 125 square metre property offers two bedrooms, one bathroom, sleeps eight guests, and includes a swimming pool, terrace, and concierge service, alongside amenities such as Wi-Fi and parking.
King Room W/ Balcony, Breakfast & Pool - Islamorada, FL
No reviews

King Room W/ Balcony, Breakfast & Pool

resort, Islamorada, Village of Islands
This Islamorada resort offers private beach access and is situated close to renowned coral reefs, Windley Key Fossil Reef Geological State Park, Lignumvitae Key Botanical State Park, the History of Diving Museum, and the Theater of the Sea.
The "King Room W/ Balcony, Breakfast & Pool" accommodation accommodates two guests and features air conditioning, internet, parking, a swimming pool, and is pet-friendly.
Ragged Edge Resort & Marina - Islamorada, FL
9.5 382 reviews

Ragged Edge Resort & Marina

resort, Islamorada, Village of Islands
Ragged Edge Resort & Marina is located in Islamorada, just a short drive from Windley Key and Upper Matecumbe Key, offering easy access to the area's natural beauty. The resort has consistently received excellent ratings for location, cleanliness, and overall experience.
The accommodation features a mix of rooms and suites, some with balconies offering sea views. Guests can enjoy amenities such as a swimming pool, terrace, free bikes, a communal grill, and free Wi-Fi.
1 Bedroom Suite W/kitchenette, Pool View, Free Parking & Pet Friendly - Islamorada, FL
8.0 1 review

1 Bedroom Suite W/kitchenette, Pool View, Free Parking & Pet Friendly

resort, Islamorada, Village of Islands
This beachfront suite, ‘Beachside Retreat In Islamorada - Suite W/ Pool View Queen | Family Ready’, is situated in Matecumbe, Islamorada, within a 2.4km walk of Indian Key Historic State Park and Bud n' Mary's Dive Centre, and under 1.6km from the Hurricane Monument and Florida Keys Brewing Co.
The 42 square metre self-catering apartment offers a queen-size bed, one bathroom, sleeps six, and includes a pool, terrace, and concierge service, providing easy access to Islamorada's attractions.

Browse Resorts with a Gym in Islamorada, FL, United States

Keep up with your workouts steps from your room with professional equipment at resorts near the ocean with a gym in Islamorada, FL, United States.

Bayside Villas By Islander Resort - Islamorada, FL
8.9 899 reviews

Bayside Villas By Islander Resort

resort, Islamorada, Village of Islands

Escape to Our Hand-Picked Luxury Resorts in Islamorada, FL, United States

Bask in five-star tropical luxury with overwater villas and white sand at luxury island resorts in Islamorada, FL, United States.

Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key - Islamorada, FL
No reviews

Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key

resort, Islamorada, Village of Islands

Discover Ultimate Family Resorts in Islamorada, FL, United States

Keep everyone happy with children's clubs, splash pools, and family dining at family resorts near the ocean in Islamorada, FL, United States.

Islander Resort - Islamorada, FL
9.1 3918 reviews

Islander Resort

resort, Islamorada, Village of Islands
Bayside Villas By Islander Resort - Islamorada, FL
8.9 899 reviews

Bayside Villas By Islander Resort

resort, Islamorada, Village of Islands
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.8 510 reviews

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

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa - Islamorada, FL
8.8 219 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands

Check Out Resorts with Parking in Islamorada, FL

Drive up and settle straight into holiday mode; book a resort in Islamorada, FL offering convenient parking alongside every resort perk.

Best Place To Unwind! 2 Units, Pool & Breakfast! - Islamorada, FL
No reviews

Best Place To Unwind! 2 Units, Pool & Breakfast!

resort, Islamorada, Village of Islands
Two Balcony Rooms W/ Breakfast & Pool Access - Islamorada, FL
No reviews

Two Balcony Rooms W/ Breakfast & Pool Access

resort, Islamorada, Village of Islands
Trademark Collection By Wyndham Dove Creek Resort & Marina - Islamorada, FL
No reviews

Trademark Collection By Wyndham Dove Creek Resort & Marina

resort, Key Largo
Pet-friendly King Stay| Pool Access & Free Parking - Islamorada, FL
No reviews

Pet-friendly King Stay| Pool Access & Free Parking

resort, Islamorada, Village of Islands

Browse Resorts with Free Breakfast in Islamorada, FL, United States

Head down to the sand completely fueled up and ready for water sports with island resorts featuring free breakfast in Islamorada, FL, United States.

Island Getaway In Islamorada! Parking! Breakfast! - Islamorada, FL
9.3 53 reviews

Island Getaway In Islamorada! Parking! Breakfast!

resort, Islamorada, Village of Islands
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