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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.

Perfect For Family Beach Vacation! Free Breakfast - Islamorada, FL
9.7 6 reviews

Perfect For Family Beach Vacation! Free Breakfast

resort, Islamorada, Village of Islands
This Islamorada apartment, situated on a private beach within a pet-friendly resort, is a short walk (less than 1km) from the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks.
The self-catering flat offers one bedroom, one bathroom, sleeps two guests, and includes a balcony, a swimming pool, fitness centre, free parking, and daily continental breakfast and housekeeping, plus access to kayaks, paddleboards and bikes.

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.

Ocean Oasis At Ocean Pointe - Islamorada, FL
8.3 2898 reviews

Ocean Oasis At Ocean Pointe

house, Tavernier
Ocean Oasis at Ocean Pointe is situated in Tavernier, a short walk from Harry Harris Park Beach and a short drive from Pigeon Key, offering a tranquil escape in a beautiful location. The property has received very good ratings for its location, cleanliness and overall experience.
This holiday home features a well-equipped kitchen, a private balcony with sea views and a private beach for your enjoyment. Guests can also relax in the hot tub, swim in the pool, or enjoy the garden and outdoor play equipment.
Chesapeake Beach Resort - Islamorada, FL
9.0 2582 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.
Cheeca Lodge & Spa - Islamorada, FL
9.0 1989 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa is situated on a 27-acre stretch of waterfront in Islamorada, just a 20-minute drive from downtown Key Largo and 13.7 miles from Long Key State Park. The resort has received very good user ratings, with excellent scores for location and cleanliness.
The property features spacious rooms with balconies and resort views. Guests can enjoy a range of amenities, including a 9-hole golf course, spa, fishing pier, swimming pools, fitness centre, tennis courts, and watersports facilities.
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.

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.

Private Beach Resort W/ Kayaking & Bicycle Rental - Islamorada, FL
8.6 23 reviews

Private Beach Resort W/ Kayaking & Bicycle Rental

resort, Islamorada, Village of Islands
This Islamorada apartment, part of a resort with private beach access, is a short walk from the Theatre of the Sea and near Windley Key and Lignum Vitae Key Botanical State Parks.
The one-bedroom, one-bathroom unit sleeps four, offering a balcony with partial ocean views, a kitchenette with fridge and microwave, plus on-site amenities including a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast and housekeeping.
Strong Waves At Harry Harris Beach! Marina, Pool! - Islamorada, FL
No reviews

Strong Waves At Harry Harris Beach! Marina, Pool!

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.
Marina View Stay | 1 Unit | Breakfast Included! - Islamorada, FL
No reviews

Marina View Stay | 1 Unit | Breakfast Included!

resort, Islamorada, Village of Islands
This resort offers private beach access in Islamorada, Village of Islands, a short 500-meter walk from the Theater of the Sea and close to Windley Key Fossil Reef Geological State Park.
The "Strong Waves At Harry Harris Beach! Marina, Pool!" offer includes 335 sq. ft. rooms for two guests with air conditioning, Wi-Fi, a swimming pool, and on-site parking, with pets welcome.
Rare Gem! Free Parking, Breakfast, Onsite Pool - Islamorada, FL
No reviews

Rare Gem! Free Parking, Breakfast, Onsite Pool

resort, Islamorada, Village of Islands
This Islamorada resort offers direct access to a private beach and is situated conveniently close to renowned coral reefs for snorkelling and diving, Windley Key Fossil Reef Geological State Park, Lignumvitae Key Botanical State Park, the History of Diving Museum, and the Theatre of the Sea.
The "Rare Gem! Free Parking, Breakfast, Onsite Pool" offer includes accommodation for two guests with one bathroom, featuring air conditioning, internet, a pet-friendly policy with additional charges, and an on-site outdoor heated swimming pool.

Best Islamorada, FL resorts with air conditioning

2 Separate Unites W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool - Islamorada, FL
No reviews

2 Separate Unites W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool

resort, Islamorada, Village of Islands
This four-bedroom, two-bathroom holiday property, offering '2 Separate Units W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool', is located in Islamorada's Matecumbe district, near Indian Key Historic State Park and the Hurricane Monument.
The self-catering villa, sleeping up to 16 guests, boasts a pool, free Wi-Fi, and balconies with views, plus easy access to watersports such as jet skiing and kayaking in the nearby waters.
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.
Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key - Islamorada, FL
No reviews

Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key

resort, Islamorada, Village of Islands
This oceanfront villa in Islamorada, Florida, boasts private beach access and is located 2.1km from Sea Oats Beach, 9km from Upper Matecumbe Key, and 13km from the Theatre of the Sea.
This six-bedroom, four-bathroom property offers 303 square metres of living space, sleeps 20 guests, and features a heated pool, pickleball court, and well-equipped kitchen; massage treatments are available.
Aqua Lodge Houseboat "Calypso" - Islamorada, FL
9.7 74 reviews

Aqua Lodge Houseboat "Calypso"

houseboat, Tavernier
This houseboat is situated on the waterfront in Tavernier, just a short walk from Baker's Cay Resort Beach and Mariners Hospital, offering easy access to the Florida Keys Dive Center and Harry Harris Park. The property has consistently received excellent ratings for its location, cleanliness and overall experience.
The houseboat features three bedrooms and two bathrooms, providing comfortable accommodation for a family or group of friends. The spacious living area, complete with a fully equipped kitchen, air conditioning, and a private swimming pool, offers a relaxing retreat with stunning waterfront views.

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.

La Siesta Resort & Villas - Islamorada, FL
8.5 1405 reviews

La Siesta Resort & Villas

hotel, Islamorada, Village of Islands
Islander Resort - Islamorada, FL
9.1 3932 reviews

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.

One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly - Islamorada, FL
No reviews

One Bedroom Suite W/2 Queen Beds, Kitchenette, Pool, Free Parking & Pet Friendly

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.

Pines & Palms Resort - Islamorada, FL
9.2 2313 reviews

Pines & Palms Resort

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.

2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly! - Islamorada, FL
8.8 3 reviews

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

resort, Islamorada, Village of Islands
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