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Islamorada, FL resorts
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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 2595 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

Convenient Stay, Superb Location, Free Breakfast - Islamorada, FL
No reviews

Convenient Stay, Superb Location, Free Breakfast

resort, Islamorada, Village of Islands
This Islamorada resort offers a "Convenient Stay, Superb Location, Free Breakfast" package, situated on a private beach just 200 metres from the History of Diving Museum and within easy reach of Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park.
This family-friendly accommodation, suitable for up to four guests, features air conditioning, Wi-Fi, an outdoor heated swimming pool, and allows pets for an additional fee, with complimentary parking available.
Premium Suites W/ Kitchenette! Pool, Breakfast! - Islamorada, FL
No reviews

Premium Suites W/ Kitchenette! Pool, Breakfast!

resort, Islamorada, Village of Islands
This resort in Islamorada, Village of Islands, offers premium suites with kitchenettes and is situated on a private beach, within 500 meters of the Theater of the Sea and close to Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park.
These pet-friendly lodgings provide 31 square meters of space for two guests, featuring air conditioning, internet, and access to a heated outdoor swimming pool and gardens, with complimentary parking available.
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.
Island Getaway In Islamorada! Parking! Breakfast! - Islamorada, FL
9.3 53 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.

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 an hour and a half, or fly into Miami International Airport (MIA) and drive about four hours. If you're driving, you'll be taking the Overseas Highway (US 1), which is a scenic drive with plenty of stops along the way.
  • 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 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 and September to October. The weather is still pleasant, the crowds are smaller, and the prices are often lower.
  • What are the best resorts with jacuzzi in Islamorada, FL?

  • What are the best daytrips from Islamorada, FL?

    From Islamorada, you can easily take day trips to nearby destinations. Key West is a popular choice, known for its vibrant nightlife and historic architecture. You can also visit Dry Tortugas National Park, a remote island with a 19th-century fort and stunning coral reefs. For a more laid-back day, head to Marathon, a charming town with a variety of restaurants and shops.
  • 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 romantic activities in and around Islamorada, FL?

    Islamorada is a great place for a romantic getaway. Take a sunset cruise on a sailboat or catamaran, enjoy a private picnic on Anne's Beach, or go kayaking at Indian Key Historic State Park. You can also indulge in a couples massage at one of the many spas in the area.
  • 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 nearest cities to explore when you are in Islamorada, FL?

    Islamorada is located in the heart of the Florida Keys, so you'll be close to a variety of cities. Key West is about an hour and a half drive south, while Marathon is about 30 minutes north. If you're looking for a bigger city, Miami is about a four-hour drive.
  • What are the most requested amenities in resorts in Islamorada, FL?

    Resorts in Islamorada are known for their beautiful beaches, so you'll find many offer private beach access, swimming pools, and water sports like kayaking and paddleboarding. Other popular amenities include restaurants, bars, and spas.

Popular destinations

Best Islamorada, FL resorts with air conditioning

2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly! - Islamorada, FL
8.0 4 reviews

2 Bedroom Suite W/ Kitchenette, Outdoor Pool, Free Parking & Pet Friendly!

resort, Islamorada, Village of Islands
This beachfront villa in Matecumbe, Islamorada, enjoys a central location, less than 2km from Hurricane Monument and the Florida Keys Brewing Company, and a 15-minute walk from Indian Key Historic State Park and Bud n' Mary's Dive Centre.
The 125 square metre property offers two bedrooms, one bathroom, sleeps eight guests, and includes a swimming pool, terrace, and concierge service, alongside amenities such as Wi-Fi and parking.
Best Place To Stay In Florida! Free Breakfast - Islamorada, FL
No reviews

Best Place To Stay In Florida! Free Breakfast

resort, Islamorada, Village of Islands
This Islamorada hotel offers direct access to a private beach, placing you within 500 metres of the Theatre of the Sea and a short distance from Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park.
Guests can enjoy complimentary breakfast and Wi-Fi in this pet-friendly accommodation, which features air conditioning, a heated outdoor pool, and is ideally situated for exploring nearby coral reefs for snorkelling and scuba diving.
Proximity Ats Its Best! 2 Units, Pool + Breakfast! - Islamorada, FL
10 4 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.
2 Separate Unites W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool - Islamorada, FL
No reviews

2 Separate Unites W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool

resort, Islamorada, Village of Islands
This four-bedroom, two-bathroom holiday property, offering '2 Separate Units W/ 2 Bedrooms, Kitchenette, Pool, Free Parking & Pool', is located in Islamorada's Matecumbe district, near Indian Key Historic State Park and the Hurricane Monument.
The self-catering villa, sleeping up to 16 guests, boasts a pool, free Wi-Fi, and balconies with views, plus easy access to watersports such as jet skiing and kayaking in the nearby waters.

Best Islamorada, FL resorts with a gym

Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort - Islamorada, FL
8.8 489 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 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.
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