Search all holiday 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 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 2 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.
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 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

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.
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.
Aqua Lodge Houseboat "Calypso" - Islamorada, FL
9.7 74 reviews

Aqua Lodge Houseboat "Calypso"

resort, 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.
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.

Frequently asked questions about resorts in Islamorada, FL

  • What time of year is best to stay in a resort in Islamorada, FL?

    The best time to stay in a resort in Islamorada is during the shoulder seasons, from April to May and September to October. You'll have pleasant weather and fewer crowds. The summer months can be quite hot and humid, and the winter months can be a little cool, but it's still a great time to visit if you don't mind the crowds.
  • What are the best resorts with a swimming pool in Islamorada, FL?

    Pines & Palms Resort, Cheeca Lodge & Spa and Chesapeake Beach Resort are among the best resorts with a swimming pool in Islamorada, FL.

  • What are the most romantic activities in and around Islamorada, FL?

    For a romantic evening, you can take a sunset cruise on the water. You can also have a romantic dinner at one of the many waterfront restaurants in Islamorada. If you are looking for something more adventurous, you can go on a kayaking or paddleboarding tour through the mangroves.
  • What are the best resorts with jacuzzi in Islamorada, FL?

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

  • What are the nearest cities to explore when you are in Islamorada, FL?

    The nearest cities to Islamorada are Key West, Marathon, and Tavernier. Key West is about an hour and a half drive south, Marathon is about an hour drive north, and Tavernier is about 15 minutes north.
  • What are the best family friendly resorts in Islamorada, FL?

    The best family friendly resorts in Islamorada, FL are Pines & Palms Resort, Cheeca Lodge & Spa and Chesapeake Beach Resort.

  • What are the most requested amenities in resorts in Islamorada, FL?

    The most requested amenities in resorts in Islamorada are swimming pools, private beaches, and restaurants. Many resorts also offer watersports activities, such as kayaking, paddleboarding, and fishing.
  • 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.

Popular destinations

Best Islamorada, FL resorts with air conditioning

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

Marina View Stay | 1 Unit | Breakfast Included!

resort, Islamorada, Village of Islands
This resort offers private beach access in Islamorada, Village of Islands, a short 500-meter walk from the Theater of the Sea and close to Windley Key Fossil Reef Geological State Park.
The "Strong Waves At Harry Harris Beach! Marina, Pool!" offer includes 335 sq. ft. rooms for two guests with air conditioning, Wi-Fi, a swimming pool, and on-site parking, with pets welcome.
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.
Best Place To Unwind! 2 Units, Pool & Breakfast! - Islamorada, FL
No reviews

Best Place To Unwind! 2 Units, Pool & Breakfast!

resort, Islamorada, Village of Islands
This Islamorada apartment complex boasts private beach access and is within walking distance of the Theatre of the Sea, and close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks.
Offering two separate 290 sq ft (approx. 27 sq m) units, each with two queen-size beds, this pet-friendly property sleeps eight, and includes a heated pool, kayaks, paddleboards, bike rentals, daily continental breakfast, and complimentary parking for one car.
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.

Best Islamorada, FL resorts with a gym

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.
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