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.

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

Marina View Stay | 1 Unit | Breakfast Included!

resort, Islamorada, Village of Islands
The Modish Unit Steps To Windley Key Fossil Reef! Pool is a holiday let situated in a private beach area of Islamorada, Village of Islands, offering direct access to coral reefs ideal for diving and snorkelling, and is a short walk to the Theater of the Sea.
This pet-friendly accommodation, suitable for two guests, features a private beach, an outdoor heated swimming pool, air conditioning, complimentary toiletries, a kitchen, and on-site parking, with rooms measuring 31 square metres.

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
9.0 1946 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.
Chesapeake Beach Resort - Islamorada, FL
9.0 2589 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.

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.
Ragged Edge Resort & Marina - Islamorada, FL
9.3 372 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.
Matecumbe Resort - Islamorada, FL
8.7 544 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.
Premium Villa, Ocean Views, Patio, Pool, Breakfast - Islamorada, FL
No reviews

Premium Villa, Ocean Views, Patio, Pool, Breakfast

resort, Islamorada, Village of Islands
This resort in Islamorada offers the Premium Villa with Ocean Views, featuring direct access to a private beach and proximity to world-class diving reefs, the History of Diving Museum, and Windley Key Fossil Reef Geological State Park.
This one-bedroom villa accommodates up to four guests and includes air conditioning, Wi-Fi, a swimming pool, and parking, with family-friendly activities available nearby.

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 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.
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.
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.
Two Balcony Rooms W/ Breakfast & Pool Access - Islamorada, FL
No reviews

Two Balcony Rooms W/ Breakfast & Pool Access

resort, Islamorada, Village of Islands
This Islamorada resort offers two-balcony rooms with breakfast and pool access, situated on a private beach within easy reach of coral reefs, Windley Key Fossil Reef Geological State Park, and Lignumvitae Key Botanical State Park, just 700 metres from the History of Diving Museum and a short walk to the Theater of the Sea. This accommodation provides private beach access, swimming pool, garden, air conditioning, internet, and parking for up to eight guests across two bedrooms and two bathrooms, with nearby opportunities for snorkelling and scuba diving.

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
8.9 457 reviews

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

resort, Islamorada, Village of Islands
Bayside Villas By Islander Resort - Islamorada, FL
8.9 896 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.

Pines & Palms Resort - Islamorada, FL
9.2 2310 reviews

Pines & Palms Resort

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.

Cheeca Lodge & Spa - Islamorada, FL
9.0 1946 reviews

Cheeca Lodge & Spa

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

Cheeca Lodge & Spa

resort, Islamorada, Village of Islands
Islander Resort - Islamorada, FL
9.1 3910 reviews

Islander Resort

resort, Islamorada, Village of Islands
Pines & Palms Resort - Islamorada, FL
9.2 2310 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.

Matecumbe Resort - Islamorada, FL
8.7 544 reviews

Matecumbe Resort

resort, Islamorada, Village of Islands
©2026 cozycozy.com