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Islamorada, FL resorts
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69 Best resorts in Islamorada, FL

Best Islamorada, FL resorts with a jacuzzi

Among the 69 accommodations in Islamorada, FL, here are the 1 best resorts with a jacuzzi

Chesapeake Beach Resort - Islamorada, FL
9.0 2594 reviews
Islamorada, FL
28/06 – 01/07
NZ$1469/nighttotal: NZ$4407 (3 )

Chesapeake Beach Resort

1 5
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 69 accommodations in Islamorada, FL, here are the 4 best resorts with a pool

Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key - Islamorada, FL
Islamorada, FL
17/10 – 26/10
NZ$7131/nighttotal: NZ$64179 (9 )

Private Beach Pickleball Court And Tiki Bar Heated Pool Designated Paradise Key

6 6
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.
2 Comfortable Units, Onsite Pool, Pets Allowed - Islamorada, FL
9.3 3 reviews
Islamorada, FL
18/07 – 22/07
NZ$855/nighttotal: NZ$3420 (4 )

2 Comfortable Units, Onsite Pool, Pets Allowed

2 4
resort , Islamorada, Village of Islands
This Islamorada apartment complex, situated on a private beach, offers easy walking access to the Theatre of the Sea and is close to Windley Key Fossil Reef and Lignum Vitae Key Botanical State Parks.
Two 290 sq ft (approx. 27 sq m) units, each sleeping up to eight guests, feature two bedrooms, two bathrooms, a swimming pool, fitness centre, parking, and daily housekeeping, plus kayaks, paddleboards and bike rentals are available on-site.
Strong Waves At Harry Harris Beach! Marina, Pool! - Islamorada, FL
Islamorada, FL
23/07 – 26/07
NZ$499/nighttotal: NZ$1497 (3 )

Strong Waves At Harry Harris Beach! Marina, Pool!

1 2
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.
Florida Keys Tour! Private Beach Access W/ Marina! - Islamorada, FL
8.0 1 review
Islamorada, FL
30/07 – 06/08
NZ$463/nighttotal: NZ$3241 (7 )

Florida Keys Tour! Private Beach Access W/ Marina!

1 2
resort , Islamorada, Village of Islands
This Islamorada apartment, 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, offers convenient access to local attractions. This one-bedroom, one-bathroom flat sleeps four guests comfortably, boasting two queen-size beds, a private beach, on-site amenities including a heated pool, kayaks, paddleboards, bicycles, daily continental breakfast, daily housekeeping, and free parking.

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.

Destinations nearby

Best Islamorada, FL resorts with air conditioning

4 Spacious Units! Free Parking, Pets Allowed - Islamorada, FL
Islamorada, FL
16/10 – 18/10
NZ$1832/nighttotal: NZ$3664 (2 )

4 Spacious Units! Free Parking, Pets Allowed

4 12
resort , Islamorada, Village of Islands
This Islamorada resort, offering a four-bedroom apartment, boasts private beach access 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.
The 1160 sq ft property sleeps up to 16 guests, features four bathrooms, a private boat ramp (fee applies), daily housekeeping, a complimentary continental breakfast, and access to an on-site heated pool, kayaks, paddleboards, and bike rentals.
2 Pet-friendly Units, Free Breakfast, Pool - Islamorada, FL
Islamorada, FL
28/06 – 01/07
NZ$705/nighttotal: NZ$2115 (3 )

2 Pet-friendly Units, Free Breakfast, Pool

2 5
resort , Islamorada, Village of Islands
This resort offers two-bedroom, two-bathroom holiday accommodation for eight guests, situated on a private beach in Islamorada, Village of Islands, a short walk from the Theater of the Sea and near Windley Key Fossil Reef Geological State Park and Lignumvitae Key Botanical State Park. Enjoy the "2 Pet-friendly Units, Free Breakfast, Pool" offer, which includes access to a heated outdoor swimming pool, complimentary toiletries, and on-site parking, with pet-friendly options available for an additional charge, whilst being close to coral reef snorkelling and scuba diving.
Pines & Palms Resort - Islamorada, FL
9.2 2444 reviews
Islamorada, FL
23/07 – 26/07
NZ$618/nighttotal: NZ$1854 (3 )

Pines & Palms Resort

1 2
resort , Islamorada, Village of Islands
Pines & Palms Resort is located in Islamorada, close to Alligator Reef and less than a mile from Miss Islamorada Fishing Charters, with John Pennekamp Coral Reef State Park a short 30-minute drive away. This resort has very good user ratings, an excellent location rating and a very good cleanliness rating.
The resort offers a range of apartments with full kitchens and ocean views. Guests can enjoy a private beach, an oceanfront pool, a Tiki Bar, kayak and bike rentals, private boat docks, a covered cabana with a barbecue grill, and premium sport fishing areas.
Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly - Islamorada, FL
Islamorada, FL
09/08 – 14/08
NZ$1902/nighttotal: NZ$9510 (5 )

Two Bedrooms Suite W/ocean View, Pool, Free Parking & Pet Friendly

2 2
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
8.3 758 reviews
Islamorada, FL
16/10 – 18/10
NZ$3790/nighttotal: NZ$7580 (2 )

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

3 12
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
9.0 4004 reviews
Islamorada, FL
30/07 – 06/08
NZ$580/nighttotal: NZ$4060 (7 )

Islander Resort

1 2
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.
Bayside Villas By Islander Resort - Islamorada, FL
8.8 873 reviews
Islamorada, FL
02/07 – 05/07
NZ$1428/nighttotal: NZ$4284 (3 )

Bayside Villas By Islander Resort

1 5
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.
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