Search all holiday resorts in Islamorada, FL

89 available resort offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Islamorada, FL resorts
Choose the perfect holiday 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 1 best resorts with a jacuzzi

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.

Best Islamorada, FL resorts with a pool

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

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

Island Getaway In Islamorada! Parking! Breakfast!

resort, Islamorada, Village of Islands
This apartment is located in Islamorada, a charming seaside village known for its stunning coral reefs, and is just a short walk from the Theater of the Sea and nearby tropical forests like Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. This property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a private beach, a heated pool with ocean views, a private boat ramp, kayaks, stand-up paddleboards, bicycles, and a daily continental breakfast.
Islander Resort - Islamorada, FL
9.1 3917 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.

Frequently asked questions about resorts in Islamorada, FL

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

    It's pretty straightforward. You can fly into Key West International Airport (EYW) and then drive about an hour and a half north. Or you can fly into Miami International Airport (MIA) and drive down the Overseas Highway, which is a scenic drive that takes about four hours.
  • What time of year is best to stay in a resort in Islamorada, FL?

    The best time to visit is during the shoulder seasons, from April to May or September to October. The weather is still good, but the crowds are smaller and the prices are lower.
  • What are the best daytrips from Islamorada, FL?

    You could take a day trip to Key West, which is about an hour and a half drive south. You can also visit the John Pennekamp Coral Reef State Park, which has great snorkeling and diving opportunities. Or you could head to the Dolphin Research Center in Marathon, where you can learn about and interact with dolphins.
  • What are the most romantic activities in and around Islamorada, FL?

    A sunset cruise on the water is always a winner. You can also take a private fishing charter and enjoy a romantic dinner at a restaurant on the water. For something a bit more adventurous, you could go kayaking or paddleboarding at sunset.
  • What are the nearest cities to explore when you are in Islamorada, FL?

    The closest city is Marathon, which is about 20 minutes away. You can also visit Key West, which is about an hour and a half drive away. And if you're looking for a bigger city, Miami is about four hours away.
  • What are the most requested amenities in resorts in Islamorada, FL?

    Most resorts offer private balconies or patios with views of the water, swimming pools, and restaurants. Some also offer spa services, fitness centres, and water sports activities.

Popular destinations

Best Islamorada, FL resorts with air conditioning

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.
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, offering the "Beachfront Estate - Two Villas Heated Pools Docks Dolphin Mahi Key" package, is located in Islamorada, Village of Islands, 2.25 kilometres from Sea Oats Beach and 9 kilometres from Upper Matecumbe Key.
This property comprises two private villas featuring heated swimming pools, on-site docking, fully equipped kitchens, and air conditioning, accommodating up to 27 guests with direct sea access and balconies.
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 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.
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.

Best Islamorada, FL resorts with a gym

Bayside Villas By Islander Resort - Islamorada, FL
8.9 897 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.
©2026 cozycozy.com