Search all vacation resorts in Islamorada, FL

89 available resort offers

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

89 Best resorts in Islamorada, FL

Best Islamorada, FL resorts with a jacuzzi

Among the 89 accommodations in Islamorada, FL, here are the 3 best resorts with a jacuzzi

Cheeca Lodge & Spa - Islamorada, FL
9.0 2014 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 2602 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.

Best Islamorada, FL resorts with a pool

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

King Balcony Room | 1 Mi To Theater Of The Sea - Islamorada, FL
No reviews

King Balcony Room | 1 Mi To Theater Of The Sea

resort, Islamorada, Village of Islands
This resort, offering a King Balcony Room with a 1.6 km proximity to the Theater of the Sea, is situated on a private beach in Islamorada, Village of Islands, providing direct ocean access and close proximity to world-renowned coral reefs, Windley Key Fossil Reef Geological State Park, and Lignumvitae Key Botanical State Park.
Guests can enjoy amenities such as air conditioning, Wi-Fi, a swimming pool, and parking, with the accommodation suitable for two people and offering family-friendly activities and access to the History of Diving Museum.
Matecumbe Resort - Islamorada, FL
8.7 551 reviews

Matecumbe Resort

aparthotel, 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.
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.
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.

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 (EYW) and drive about 100km, or fly into Miami International Airport (MIA) and drive about 200km. You can also take the Florida Keys Overseas Highway, which is a scenic drive that takes you over the water.
  • What are the best resorts with a swimming pool in Islamorada, FL?

    Chesapeake Beach Resort, La Jolla Resort and Pines & Palms 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 June and September to November. The weather is still warm and sunny, but the crowds are smaller and the prices are lower.
  • What are the best resorts with jacuzzi in Islamorada, FL?

    The Caribbean Resort, Topsider Resort and Cheeca Lodge & Spa 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 160km from Islamorada. You can also visit the John Pennekamp Coral Reef State Park, which is a great place to go snorkeling or diving. If you're looking for something a little different, you can check out the Dolphin Research Center in Marathon.
  • What are the best family friendly resorts in Islamorada, FL?

    The best family friendly resorts in Islamorada, FL are Chesapeake Beach Resort, La Jolla Resort and Pines & Palms 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, go for a walk on the beach, or have a romantic dinner at one of the many restaurants overlooking the water. For a truly special experience, you can book a private fishing charter or a sunset sail.
  • What are the best pet friendly resorts in Islamorada, FL?

    The best pet friendly resorts in Islamorada, FL are Chesapeake Beach Resort, Pines & Palms 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 30km away. You can also visit Key West, which is about 160km away. If you're looking for a bigger city, you can drive to Miami, which is about 200km away.
  • What are the most requested amenities in resorts in Islamorada, FL?

    Most resorts in Islamorada offer swimming pools, private beaches, and water sports activities. You can also find resorts with restaurants, bars, and spas. If you're looking for a more luxurious experience, you can book a resort with a private balcony or a beachfront villa.

Popular destinations

Best Islamorada, FL resorts with air conditioning

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
This Islamorada resort, in the Matecumbe district, offers the 'Steps Away From The Beach | Spacious 1br Suite W\/ Kitchenette' option, conveniently located near Sea Oats Beach and a short drive from the Hurricane Monument and Indian Key Historic State Park.
The 57 square metre apartment features a one-bedroom suite sleeping up to six guests, boasting a kitchenette, balcony, and access to an on-site pool, restaurant, bar, boat slips, and complimentary water sports equipment; pet-friendly accommodation is also available.
Bayside Villas By Islander Resort - Islamorada, FL
8.9 900 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.
Perfect For Family Beach Vacation! Free Breakfast - Islamorada, FL
8.9 7 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.
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.

Best Islamorada, FL resorts with a gym

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.8 495 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 3 km from Windley Key Fossil Reef Geological Park and 34 km from Key Largo. The resort has received very good ratings for user experience, location, and cleanliness.
The resort offers a range of amenities and activities, including a swimming pool, a terrace, a garden, a restaurant, a bar, and a marina. Guests can enjoy fresh seafood at the Raw Bar, charter fishing trips, or explore the surrounding area by jet ski.
Islander Resort - Islamorada, FL
9.1 3923 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.
©2026 cozycozy.com