A beach with white lounge chairs, a covered pavilion, and palm trees.

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Check availability on Islamorada Hotels with Connecting Rooms

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov

Our top choices for Islamorada hotels with connecting rooms

A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.
A resort pool with palm trees, beach chairs, and umbrellas.
A beach with palm trees, a dock, and lounge chairs.
A hotel room with a bed, a sofa, a coffee table, a desk with a lamp, and a view of the ocean.

1. Amara Cay Resort

Amara Cay Resort
Matecumbe
United States
Danielle
£183
includes taxes & fees
21 Oct - 22 Oct
Amara Cay Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.
A beach with palm trees, a thatched-roof hut, and lounge chairs.
A wooden deck with a thatched roof structure, wooden chairs, and a table, overlooking a tropical landscape with palm trees and a clear sky.
A resort with thatched-roof structures, palm trees, and a sandy beach area.

2. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
Islamorada
United States
Hailey Ritch and Patrick
£126
includes taxes & fees
26 Oct - 27 Oct
Coconut Cove Resort and Marina
A beachside patio with white furniture, palm trees, and a thatched umbrella.
A pool area with lounge chairs and a sign indicating a drop-off zone.
A wooden boardwalk leading to a building with a brick wall and a white roof.
A deck with white lounge chairs and a bench, overlooking a beach with palm trees and a thatched roof structure.

3. Drop Anchor

Drop Anchor
Islamorada
United States
Payman
£120
includes taxes & fees
19 Oct - 20 Oct
Drop Anchor
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.
A waterfront pier with wooden posts and a wooden walkway extending into the water.
A view through a door of a tropical outdoor area with a pathway leading to a beach, palm trees, and a clear sky.
A garden with various trees and a gravel path.

4. Sunset Cove Beach Resort

Sunset Cove Beach Resort
Key Largo
Canada
Alexey
£97
includes taxes & fees
21 Oct - 22 Oct
Sunset Cove Beach Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.
A pier with boats docked, a thatched-roof structure, and signs indicating tours and rentals.
A beach scene with two yellow beach chairs and a person lying on one.
An aerial view of a marina with docked boats, a building with balconies, and a beach area.

5. Hadley Resort and Marina

Hadley Resort and Marina
Matecumbe
United States
weder
£145
includes taxes & fees
9 Nov - 10 Nov
Hadley Resort and Marina
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.
A modern kitchen with a built-in stove, a large island, and a view to a balcony with outdoor seating.
A hotel room with a bed, a TV, a sofa, and a balcony with a view.
A resort with a pool, multiple buildings, and a waterfront view.

6. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham
Key Largo
United States
Omar Ahmad
£114
includes taxes & fees
26 Oct - 27 Oct
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A beach with palm trees, a dock, and a boat named "STYX".
A pathway leading to a building surrounded by lush tropical vegetation and a view of the sea.
Two purple Adirondack chairs on a sandy beach with palm trees and a clear blue sky.
A thatched-roof hut surrounded by lush greenery and vibrant red flowers.

7. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
Key Largo
United States
SUSAN
£78
includes taxes & fees
26 Oct - 27 Oct
The Pelican Key Largo Cottages
A table with a glass pitcher, a glass with a slice of lime, and a plate with raspberries and a sprig of rosemary.
A child sitting on a beach with sand toys and a green bucket nearby.
An aerial view of a resort with two large swimming pools surrounded by palm trees and lounge chairs.
A beachfront hotel with multiple balconies, a pool, and a beach area with lounge chairs.

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

Baker's Cay Resort Key Largo, Curio Collection by Hilton
Key Largo
United States
Alan
£269
includes taxes & fees
28 Oct - 29 Oct
Baker's Cay Resort Key Largo, Curio Collection by Hilton
An aerial view of a resort with a large pool, palm trees, and a beach.
A beach with clear water, a wooden pier, and lounge chairs under a tree.
A beachside patio with lounge chairs, a table, and a view of the ocean.
A pool area with lounge chairs and umbrellas, a clear sky, and palm trees.

9. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
Rock Harbor
United States
Jorge
£277
includes taxes & fees
1 Nov - 2 Nov
Playa Largo Resort & Spa, Autograph Collection
A beach with palm trees, lounge chairs, and a clear view of the ocean.
A resort with a thatched-roof structure, palm trees, and lounge chairs on a sandy beach.
A tropical garden with palm trees, various colorful plants, and a seating area with chairs.
A hotel room with a kitchenette, two beds, a desk, a television, and a ceiling fan.

10. Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
Key Largo
United States
Mee
£101
includes taxes & fees
25 Oct - 26 Oct
Hampton Inn Key Largo Manatee Bay
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

Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"We have stayed here multiple times and always have a good stay."
Michael 1-night trip
Posted 7 hours ago
Pines & Palms Resort
Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Super el hotel"
Liset 1-night trip
Posted 14 hours ago
Chesapeake Beach Resort
Hadley Resort and Marina

Hadley Resort and Marina

8/10 Good
"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was decently clean and comfy! Just noting (not complaining), the bathroom was tiny, but it worked fine for 1 person. Had a nice little kitchenette with a mini fridge, microwave, large sink, and coffee pod maker, so it was easy to save restaurant leftovers or keep a few groceries. There's a sweet little spot to sit in loungers or chairs at the end of the marina and soak up some ocean views (east-facing for sunrise is nice). It's just a quick walk to the backside of the property. It wasn't busy during my stay in early Oct., so it was easy to get a chair anytime, but note that there isn't space for more than a few people at a time. There are kayaks and other things you can use (I didn't have the time)."
Elizabeth 1-night trip
Posted 3 days ago
Hadley Resort and Marina
The Caribbean Resort

The Caribbean Resort

10/10 Excellent
"Muy bien todo excelente servicio"
Rodolfo 4-night trip
Posted 2 weeks ago
The Caribbean Resort

Frequently asked questions

How much do hotels with connecting rooms in Islamorada cost?
Prepare to pay from £78 to £277 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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