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Islamorada, FL resorts
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89 Best resorts in Islamorada, FL

Best Islamorada, FL resorts with air conditioning

Rare Gem! 4 Units, Free Parking, Pool + Breakfast! - Islamorada, FL
9.5 4 reviews

Rare Gem! 4 Units, Free Parking, Pool + Breakfast!

resort, Islamorada, Village of Islands
This Islamorada resort, offering four separate 301-square-foot units, boasts private beach access and is within walking distance of the Theater of the Sea, near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks.
Each unit features two queen beds, a kitchenette, dining area, and balcony with partial ocean views, accommodating up to 16 guests with on-site amenities including a heated pool, kayaks, paddleboards, bike rentals, and a daily continental breakfast.
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay - Islamorada, FL
No reviews

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

resort, Islamorada, Village of Islands
This 2-bedroom, 2-bathroom beach bungalow, offered as the "2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay," is located in the Matecumbe neighborhood of Islamorada, putting it within 1 mile of Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park.
This resort features direct private beach access, a pool, hot tub, fishing pier, complimentary boat slip, and free use of kayaks and bicycles, accommodating up to 6 guests with a full kitchen and in-unit laundry.
2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed! - Islamorada, FL
10 1 review

2 Bedroom Suite In Islamorada! Swimming Pool, Kitchenette, Pets Allowed!

resort, Islamorada, Village of Islands
This beachfront villa in Matecumbe, Islamorada, offers direct ocean access and is a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Center, with Hurricane Monument and Florida Keys Brewing Co. less than 1.2 miles away.
This 1,070-square-foot property features two bedrooms, two bathrooms, accommodates eight guests, and includes a pool, terrace, concierge service, parking, and a fully equipped kitchen with a refrigerator and microwave.
Aqua Lodge Houseboat "Calypso" - Islamorada, FL
9.7 74 reviews

Aqua Lodge Houseboat "Calypso"

resort, Tavernier
This houseboat is located in Tavernier, a 15-minute walk from Baker's Cay Resort Beach and Mariners Hospital, and within 3 miles of Florida Keys Dive Center and Harry Harris Park. The property has received excellent ratings for user experience, location, and cleanliness.
The houseboat has three bedrooms and two bathrooms, and offers a private pool, a kitchen with a fridge, microwave, and dishwasher, and air conditioning. This waterfront property offers access to swimming, sunbathing, diving, snorkeling, and exploring the natural beauty of the area.

Check Out Resorts with a Gym in Islamorada, FL

Every resort in Islamorada, FL on this list includes an on-site gym, making it easy to fit a coastal workout into your daily vacation routine.

Cheeca Lodge & Spa - Islamorada, FL
9.0 1953 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa is a luxurious hotel located in Islamorada, Florida, just a 20-minute drive from downtown Key Largo. The resort has consistently received excellent ratings for its location, cleanliness, and overall experience.
The hotel sits on 27 acres of lush gardens, offering a tranquil and secluded atmosphere. Guests can enjoy a variety of amenities and activities, including a 9-hole golf course, a fishing pier, swimming pools, a fitness center, tennis courts, and a full-service spa.
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.9 455 reviews

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

resort, Islamorada, Village of Islands
The Postcard Inn Beach Resort & Marina is located on an island in the Florida Keys, just a short drive from Windley Key Fossil Reef Geological Park and Key Largo. The resort is highly rated by travelers, with excellent location, very good cleanliness, and very good overall ratings.
This resort offers a unique tropical atmosphere with a marina for fishing, jet ski rentals, and water sports. Guests can enjoy the on-site Raw Bar, WiFi, parking, cable TV, private bathrooms, and safety deposit boxes in each room.
Islander Resort - Islamorada, FL
9.1 3917 reviews

Islander Resort

resort, Islamorada, Village of Islands
Islander Resort is located directly on the beach in Islamorada, Village of Islands, offering easy access to the area's many attractions and activities. The resort has received excellent ratings for location, cleanliness, and overall experience.
The resort offers spacious rooms with private porches and lanais, allowing guests to enjoy the beautiful views and relax in comfort. The resort features amenities such as two swimming pools, a spa, a fitness center, a restaurant, and a bar, providing plenty of opportunities for relaxation and entertainment.
Cheeca Lodge & Spa - Islamorada, FL
8.8 219 reviews

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Cheeca Lodge & Spa is a resort located in Islamorada, Village of Islands, with direct access to a beach.
This establishment offers a swimming pool, a spa, a fitness center, and on-site dining, with accommodations featuring air conditioning and balconies.

Frequently Asked Questions about resorts in Islamorada, FL

  • What are the top attractions in and around Islamorada, FL?

    Islamorada is known for its beautiful beaches and watersports. You can't miss the Theater of the Sea, a marine park where you can see dolphins, sea lions, and other marine animals. For a taste of the local culture, visit the Islamorada History Museum. If you are looking for something more adventurous, you can go snorkeling or diving at the nearby reefs.
  • 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.

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

    Islamorada is located on the Overseas Highway, which is easily accessible by car. The drive from Miami International Airport takes about 1 hour and 45 minutes. You can also fly into Key West International Airport, which is about a 1 hour and 30 minute drive from Islamorada.
  • What are the best resorts with jacuzzi in Islamorada, FL?

    Chesapeake Beach Resort, Cheeca Lodge & Spa and The Caribbean Resort Malayan Palm East are the best resorts with a jacuzzi in Islamorada, FL.

  • What are the best daytrips from Islamorada, FL?

    You can easily take a day trip to Key West, which is about a 1 hour and 30 minute drive from Islamorada. You can also visit the John Pennekamp Coral Reef State Park, which is located just a short drive from Islamorada. This park offers opportunities for snorkeling, diving, and kayaking.
  • 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 most romantic activities in and around Islamorada, FL?

    Islamorada is a great place for a romantic getaway. You can take a sunset cruise on the water, have dinner at a waterfront restaurant, or go for a walk on the beach. If you are looking for something more unique, you can take a private fishing charter or go on a dolphin watching tour.
  • 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 nearest cities to explore when you are in Islamorada, FL?

    The nearest major city to Islamorada is Miami, which is about a 1 hour and 45 minute drive. You can also visit Key West, which is about a 1 hour and 30 minute drive from Islamorada. Both cities offer a wide variety of attractions, restaurants, and nightlife.
  • What are the most requested amenities in resorts in Islamorada, FL?

    Resorts in Islamorada often offer a variety of amenities, including swimming pools, private beaches, restaurants, and bars. Many resorts also offer water sports activities, such as snorkeling, diving, and kayaking. If you are looking for a more luxurious experience, you can find resorts with spa services, fitness centers, and other amenities.

Popular destinations

Best Islamorada, FL resorts with a jacuzzi

Among the 89 accommodations in Islamorada, FL, here are the 1 best resorts with a jacuzzi

Chesapeake Beach Resort - Islamorada, FL
9.0 2586 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, offering easy access to both the beach and nearby attractions. The resort consistently receives very good ratings for its location, cleanliness, and overall experience.
The resort offers a variety of rooms and suites, all featuring comfortable furnishings and modern amenities. Guests can enjoy a refreshing swim in the outdoor pool, relax in the hot tub, or take advantage of the on-site restaurant, bar, and room service.

Best Islamorada, FL resorts with a pool

Among the 89 accommodations in Islamorada, FL, here are the 4 best resorts with a pool

Island Getaway In Islamorada! Parking! Breakfast! - Islamorada, FL
9.3 51 reviews

Island Getaway In Islamorada! Parking! Breakfast!

resort, Islamorada, Village of Islands
This Islamorada apartment is located on a private beach with direct ocean access, just a short walk from Theater of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This rental has excellent ratings for location, cleanliness, and user experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. Enjoy amenities such as a heated pool with ocean views, free Wi-Fi, daily continental breakfast, and on-site kayaks, stand-up paddleboards, and bicycles for exploring the surrounding area.
Ragged Edge Resort & Marina - Islamorada, FL
9.3 372 reviews

Ragged Edge Resort & Marina

resort, Islamorada, Village of Islands
Ragged Edge Resort & Marina sits in Islamorada, just a short drive from Windley Key and Upper Matecumbe Key, offering easy access to the area's natural beauty and attractions. Guests consistently rate the resort excellent for its location, cleanliness, and overall experience.
The resort features a variety of accommodations, including rooms with kitchens and balconies with ocean views. Guests can enjoy the outdoor swimming pool, terrace, free bikes, on-site grill, and free parking and Wi-Fi, making it an ideal choice for families and couples looking for a relaxing and enjoyable stay.
4 Units! Free Breakfast & Parking! Pets Allowed. - Islamorada, FL
No reviews

4 Units! Free Breakfast & Parking! Pets Allowed.

resort, Islamorada, Village of Islands
This Islamorada vacation rental boasts four bedrooms and four bathrooms, comfortably accommodating up to 16 guests, and is situated on a private beach, within walking distance of the Theater of the Sea and near Windley Key Fossil Reef and Lignumvitae Key Botanical State Parks.
The property offers on-site amenities including a heated pool with ocean views, kayak and paddleboard rentals, bike rentals, a daily continental breakfast, and 24/7 front desk service; pet-friendly with boat ramp access (fees may apply).
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
This beachfront estate, the "Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key," offers direct sea views in Islamorada, Village of Islands, just 1.4 miles from Sea Oats Beach and 5.6 miles from Upper Matecumbe Key.
This expansive property features two villas with heated pools, seven bedrooms, seven bathrooms, and accommodations for up to 27 guests, complete with on-site docking facilities, fully equipped kitchens, and balconies with ocean vistas, plus available massage services.

Search Coastal Resorts near Islamorada, FL

Experience relaxing maritime vibes at seaside resorts in Islamorada, FL, positioned short distances from the local beach towns.

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

Explore 5-Star Resorts in Islamorada, FL

Experience the height of comfort in Islamorada, FL. These luxury resorts offer high-end service and a prime setting for your stay.

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

Best Family Resorts in Islamorada, FL

Getting the resort right makes all the difference for a family trip to Islamorada, FL, with every option offering beach access and room to spread out.

Pines & Palms Resort - Islamorada, FL
9.2 2313 reviews

Pines & Palms Resort

resort, Islamorada, Village of Islands

Search Pet-Friendly Resorts in Islamorada, FL

Your dog is just as welcome as you are; every pet-friendly waterfront resort in Islamorada, FL features dog-friendly beaches and pet washing stations.

Bayside Villas By Islander Resort - Islamorada, FL
8.9 897 reviews

Bayside Villas By Islander Resort

resort, Islamorada, Village of Islands

Top-Rated Resorts with Wellness in Islamorada, FL

Spa access at every resort near the water in Islamorada, FL ensures that waterside wellness is a central part of your vacation.

Matecumbe Resort - Islamorada, FL
8.7 548 reviews

Matecumbe Resort

resort, Islamorada, Village of Islands
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