Search all holiday resorts in Islamorada, FL

89 available resort offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Islamorada, FL resorts
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.

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.

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.

Chesapeake Beach Resort - Islamorada, FL
9.0 2591 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 1963 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.

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.

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.
Proximity Ats Its Best! 2 Units, Pool + Breakfast! - Islamorada, FL
10 3 reviews

Proximity Ats Its Best! 2 Units, Pool + Breakfast!

resort, Islamorada, Village of Islands
This Islamorada apartment rental is situated on a private beach, within walking distance of the Theatre of the Sea and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks.
The 606 sq ft property comprises two bedrooms, two bathrooms, sleeps eight guests, and offers amenities including a heated pool, kayaks, paddleboards, bicycles, and complimentary continental breakfast.
Beachside Unit With Free Breakfast - Islamorada, FL
10 1 review

Beachside Unit With Free Breakfast

resort, Islamorada, Village of Islands
This Islamorada beachfront apartment offers direct beach access, a short walk (less than 1 km) from the Theatre of the Sea and near Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks.
The 37 square metre self-catering flat sleeps four guests, boasting two queen beds, a sofa bed, a kitchenette, a balcony, and access to an on-site heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast and housekeeping.
Matecumbe Resort - Islamorada, FL
8.7 553 reviews

Matecumbe Resort

resort, Islamorada, Village of Islands
The Matecumbe Resort is situated in Islamorada, a short distance from Sea Oats Beach, Upper Matecumbe Key, and Windley Key, offering a convenient base to explore the beautiful Florida Keys. This 2-star aparthotel consistently receives very good user ratings for its cleanliness, location, and overall experience.
Each self-catering apartment comes equipped with a kitchen, including a fridge, microwave, and other essentials. Guests can enjoy a range of amenities, including a swimming pool, a terrace, a garden, free parking, and Wi-Fi, as well as access to a private beach.

Best Islamorada, FL resorts with air conditioning

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 beach bungalow, part of the "2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay" offer, is located in Matecumbe, Islamorada, within 2 kilometres of Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park, with MoradaWay Arts & Cultural District and Keys History & Discovery Center also nearby.
Each 2-bedroom, 2-bathroom unit accommodates up to six guests, featuring a full kitchen, private washer/dryer, complimentary use of kayaks and bicycles, and direct access to a private beach, alongside on-site amenities including a pool, hot tub, fishing pier, and boat ramp with a complimentary slip.
Bayside Villas By Islander Resort - Islamorada, FL
8.9 894 reviews

Bayside Villas By Islander Resort

resort, Islamorada, Village of Islands
Islander Bayside Villas & Boatslips is located in Islamorada, Florida, just a short walk from the beach and a short drive from Windley Key Fossil Reef Park. The resort has received very good ratings for user experience, location, and cleanliness.
The villas offer a comfortable and convenient stay with fully equipped kitchens, flat-screen TVs, free WiFi, and laundry facilities. Guests can enjoy a refreshing dip in the outdoor pool, rent bicycles, and explore the nearby water sports activities.
Aqua Lodge Houseboat "Calypso" - Islamorada, FL
9.7 73 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.
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 self-contained units, boasts private beach access with a boat ramp and is within walking distance of the Theatre of the Sea, and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park.
Each 93 square metre (301 sq ft) unit features two queen-size beds, a balcony with partial ocean views, and the property includes a heated pool, kayaks, paddleboards, bicycles, barbecue facilities, and accommodates up to sixteen guests.

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.

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.9 102 reviews

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

resort, Islamorada, Village of Islands
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.9 450 reviews

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

Spacious 1br Suite W/kitchenette, Outdoor Pool, Free Parking & Pet Friendly - Islamorada, FL
10 1 review

Spacious 1br Suite W/kitchenette, Outdoor 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.

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.9 102 reviews

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

resort, Islamorada, Village of Islands
Pines & Palms Resort - Islamorada, FL
9.2 2317 reviews

Pines & Palms Resort

resort, Islamorada, Village of Islands
Islander Resort - Islamorada, FL
9.1 3931 reviews

Islander Resort

resort, Islamorada, Village of Islands
Ragged Edge Resort & Marina - Islamorada, FL
9.3 377 reviews

Ragged Edge Resort & Marina

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 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
©2026 cozycozy.com