TOP Hotels with Connecting Rooms in Islamorada, FL for 2026

Q: What are the best hotels with connecting rooms in Islamorada?

We recommend The Caribbean Resort . Kick back at this 3.5-star stay which features a terrace and individually decorated rooms. Pines & Palms Resort is another hotel with connecting rooms worth considering. Unpack your suitcase at this 3-star option and take advantage of conveniences like pool sun loungers and individually decorated rooms. You'll have your pick of multiple hotels with connecting rooms in Islamorada with a total average guest review rating of 8.5.

Q: Are there any family-friendly hotels with connecting rooms in Islamorada?

Settle in at The Caribbean Resort , a 3.5-star option just a short drive from town. Amenities here include water sports equipment and housekeeping services. Another family-friendly hotel with connecting rooms is Amara Cay Resort . Beach loungers and laundry facilities help make this 4-star escape a guest favourite. Once you've checked in and unpacked, there's no shortage of family-friendly attractions to see around Islamorada. Theatre of the Sea and Anne's Beach are two of our top suggestions.

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Our top choices for Islamorada hotels with connecting rooms

Sunset Cove Beach Resort

Key Largo

Anna

includes taxes & fees

15 Apr - 16 Apr

The Pelican Key Largo Cottages

Key Largo

Beth

includes taxes & fees

12 May - 13 May

Hadley Resort and Marina

Matecumbe

Ashley

includes taxes & fees

5 May - 6 May

Baker's Cay Resort Key Largo, Curio Collection by Hilton

Key Largo

Jessica

includes taxes & fees

27 Apr - 28 Apr

Suite, 1 Bedroom, Balcony, Marina View | Pillow-top beds, in-room safe, individually decorated

Courtyard by Marriott Key Largo

Key Largo

Thomas

includes taxes & fees

10 May - 11 May

Tropical Cottages

Marathon

jennifer

includes taxes & fees

14 May - 15 May

View all properties

Find out more about Islamorada

Discover top Islamorada attractions

Islamorada, nestled in the Florida Keys, offers a unique blend of relaxation and adventure perfect for families seeking quality experiences. Begin your journey at the Florida Keys History & Discovery Center, where interactive exhibits bring local history to life, making it an educational yet fun outing for children and adults alike. For a taste of the area's vibrant marine life, the world-renowned Theater of the Sea is a must-visit; here, you can enjoy spectacular marine shows and even swim with dolphins, creating unforgettable memories for the whole family. If your crew is up for a bit of adventure, embark on a snorkeling or diving excursion at the nearby Alligator Reef, where colourful coral gardens and tropical fish await just beneath the surface. Anglers will be delighted by the fishing opportunities, with charter services available for both deep-sea and backcountry fishing, ensuring a thrilling day on the water. After a day of exploration, consider staying in the charming area of Plantation Key, where family-friendly resorts offer spacious rooms and stunning views of the sunset over the bay. Enjoy the convenience of on-site dining and water sports, ensuring every moment of your stay is filled with ease and enjoyment. With attentive guest service and a focus on quality, your family will feel pampered throughout your stay.

Find the best hotels with connecting rooms in Islamorada

For families or friends travelling together to Islamorada, these hotels offer the perfect blend of comfort and convenience with connecting rooms that enhance your stay. Discover your ideal retreat in this beautiful destination.

The Caribbean Resort

Why it's great for extra space: The Caribbean Resort stands out as an exceptional option for those seeking connecting rooms, catering perfectly to families or larger groups. With an impressive review rating of 10.0, this Matecumbe gem ensures a memorable stay with spacious rooms and a host of amenities. The outdoor pool and hot tub offer relaxation, while the waterfront location enhances the overall charm of the resort.
Other amenities: Guests can enjoy free cribs and highchairs, alongside modern conveniences like a fully equipped kitchen. With daily housekeeping, premium bedding, and air conditioning, comfort is paramount. The resort also provides a variety of water activities, including motorboating and snorkeling, ensuring fun for everyone. Explore the nearby shopping district and enjoy the beautiful gardens surrounding the resort.
Neighborhood: Matecumbe
Nearby attractions: Matecumbe United Methodist Church - 0.5 km, Florida Keys Brewing Co. - 0.8 km, Keys History & Discovery Center - 0.8 km

Amara Cay Resort

Why it's great for extra space: Amara Cay Resort is an excellent choice for travelers seeking connecting rooms, ideal for families or groups. With a guest review rating of 8.8, this upscale hotel in Matecumbe features spacious rooms with connecting options, ensuring everyone stays close. Guests can enjoy a beachfront restaurant, outdoor pool, and complimentary breakfast, enhancing the overall experience for those travelling together.
Other amenities: Additional features include free cribs and rollaway beds, a terrace for relaxation, and a fitness centre for maintaining your routine. The hotel offers a range of water activities, including scuba diving and nearby boat tours. With air conditioning, premium bedding, and Egyptian cotton sheets, comfort is assured. Enjoy ocean views from your room and take advantage of the resort's shuttle service for easy exploration of the area.
Neighborhood: Matecumbe
Nearby attractions: Bud n' Mary's Dive Center - 0.3 km, Indian Key Historic State Park - 1.1 km, Hurricane Monument - 2.3 km

Drop Anchor

Why it's great for extra space: Drop Anchor provides a welcoming atmosphere for travelers who prefer connecting rooms, making it a fantastic option for families or groups visiting Islamorada. With a solid review rating of 8.8, this charming hotel ensures that guests can enjoy their privacy while being just a room away from loved ones. The hotel features an outdoor pool and easy access to the beach, perfect for sun-soaked days together.
Other amenities: Guests can enjoy a kitchenette in their rooms, making meal preparations convenient. The hotel offers free housekeeping, beach towels, and access to sun loungers. Enjoy the beautiful views from your balcony or patio, and take advantage of nearby water sports such as kayaking and snorkeling. The hotel also includes a marina for boating enthusiasts and free off-street parking.
Nearby attractions: Theater of the Sea - 0.5 km, Windley Key Fossil Reef Geological State Park - 0.4 km, Rain Barrel Village - 2.8 km

Hadley Resort and Marina

Why it's great for extra space: Hadley Resort and Marina is a delightful choice for those needing connecting rooms, providing ample space for families or groups. With a review rating of 7.8, this hotel in Matecumbe ensures a comfortable stay with essential amenities. Guests can enjoy daily complimentary breakfast and have easy access to the beach, perfect for group outings.
Other amenities: The resort features an outdoor pool, complimentary beach towels, and a playground for children to enjoy. Guests have access to water sports like kayaking and fishing right onsite. With options for early check-in and late check-out, flexibility is offered for all visitors. The hotel also provides air conditioning, a terrace area, and local attractions nearby for exploration.
Neighborhood: Matecumbe
Nearby attractions: History of Diving Museum - 0.6 km, Islamorada Brewery & Distillery - 0.5 km, Keys History & Discovery Center - 1.3 km

Top Islamorada Hotel Reviews

Fisher Inn Resort & Marina

10/10 Excellent

"Perfect views! Clean exterior and well kept property. Staff was awesome when we interacted, helpful and courteous. The breakfast was decent. Food vendor on site was delicious for sure! Very nice people too. Parking was really convenient although, spaces seemed to be limited, we always found a spot. Our room was.. nice. The flooring was a bit rough and needs to be replaced. I would and will, 100% stay here again! "

Chesapeake Beach Resort

10/10 Excellent

"We enjoyed our stay. Nice staff, nice looking property, nice room, very good breakfast which was included and the omelette chef worked very hard to accommodate us and the other guests. Walked to a restaurant for dinner at Wahoos Seafood Bar and Grill, very good, about 200 yards from the resort. "

Frequently asked questions

How much do hotels with connecting rooms in Islamorada cost?

Prepare to pay from £107 to £334 per night for hotels with connecting rooms in Islamorada. No matter your budget, an ideal stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What are the best hotels with connecting rooms in Islamorada?

We recommend The Caribbean Resort. Kick back at this 3.5-star stay which features a terrace and individually decorated rooms. Pines & Palms Resort is another hotel with connecting rooms worth considering. Unpack your suitcase at this 3-star option and take advantage of conveniences like pool sun loungers and individually decorated rooms. You'll have your pick of multiple hotels with connecting rooms in Islamorada with a total average guest review rating of 8.5.

How many hotels with adjoining rooms are there in Islamorada?

Take your pick of 11 hotels with adjoining rooms in Islamorada. Whether you're taking a trip with the little ones or organising a weekend escape with your buddies, Expedia can help you find the best space for your whole crew.

Are there any family-friendly hotels with connecting rooms in Islamorada?

Settle in at The Caribbean Resort, a 3.5-star option just a short drive from town. Amenities here include water sports equipment and housekeeping services. Another family-friendly hotel with connecting rooms is Amara Cay Resort. Beach loungers and laundry facilities help make this 4-star escape a guest favourite. Once you've checked in and unpacked, there's no shortage of family-friendly attractions to see around Islamorada. Theatre of the Sea and Anne's Beach are two of our top suggestions.

Why book your hotel with connecting rooms in Islamorada with Expedia?

Travelling with the family should be stress-free, so if you're seeking hotels with connecting rooms at an affordable rate, Expedia has your back. Save money and pick a comfy motel with connecting rooms, or splurge on a 5-star hotel and really spoil your crew. Use our search filters to secure a property in Islamorada that matches your needs.

How can I find cheap hotels with connecting rooms in Islamorada?

Expedia is here to help you look for cheap hotels with connecting rooms in Islamorada. To book a fantastic stay in a few quick keystrokes, use our handy filter tool to refine your search by budget, star rating and amenities.

What is there to do in Islamorada near my hotel with connecting rooms?

Whatever your interests, Islamorada has plenty to keep you entertained. Theatre of the Sea, Anne's Beach and Florida Keys Brewing Co. are on most visitors' lists. Don't head home without exploring Windley Key Fossil Reef Geological State Park, Sunset Drive Beach and Indian Key Historic State Park either. With Expedia's Islamorada hotel deals, you'll be able to discover even more popular attractions like these with the money you save.

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