Find Hotels with Connecting Rooms in Islamorada, FL

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Check availability on Islamorada Hotels with Connecting Rooms

Tonight
Nov 26 - Nov 27
Tomorrow
Nov 27 - Nov 28
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Top Islamorada Hotels with Connecting Rooms

Marina
The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

2.0 star property
Key Largo
8.8 out of 10, Excellent, (1014)
"We were delighted with everything The Pelican said it was. The staff was friendly and courteous throughout the property. THE VIEWS were stunning! "
United States
Ramiro
$97 nightly
The price is $110
Nov 30 - Dec 1
Total with taxes and fees
The Pelican Key Largo Cottages
Aerial view
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Dove Creek Resort & Marina, Trademark Collection by Wyndham

3.0 star property
Key Largo
7.6 out of 10, Good, (1002)
"clean room nice balcony view nice staff nice breakfast"
United States
Manuel
$121 nightly
The price is $136
Dec 3 - Dec 4
Total with taxes and fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
Dock
Hadley Resort and Marina

Hadley Resort and Marina

3.5 star property
Matecumbe
7.8 out of 10, Good, (1005)
"Azaya at the front desk was GREAT!! Boat launch on property free for guests. Perfect location comfy rooms! "
United States
Jeff
$129 nightly
The price is $145
Nov 30 - Dec 1
Total with taxes and fees
Hadley Resort and Marina
Gazebo
Sunset Cove Beach Resort

Sunset Cove Beach Resort

2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1006)
"Always a great stay"
United States
Richard
$147 nightly
The price is $166
Dec 3 - Dec 4
Total with taxes and fees
Sunset Cove Beach Resort
Outdoor pool, cabanas (surcharge), pool umbrellas
Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection

4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1003)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
$288 nightly
The price is $324
Dec 3 - Dec 4
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection
32-inch LCD TV with satellite channels, TV, iPod dock
Baker's Cay Resort Key Largo, Curio Collection by Hilton

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

4.0 star property
Key Largo
8.6 out of 10, Excellent, (1003)
"Beautiful and relaxing stay "
Sweden
Pauline
$286 nightly
The price is $322
Dec 3 - Dec 4
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view
Drop Anchor

Drop Anchor

3.0 star property
Islamorada
8.8 out of 10, Excellent, (1004)
"Beautiful property and the staff was amazing."
United States
John
$130 nightly
The price is $142
Nov 30 - Dec 1
Total with taxes and fees
Drop Anchor
Room, 1 King Bed, Bay View | Beach/ocean view
Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay

2.5 star property
Key Largo
8.8 out of 10, Excellent, (1024)
"Great resort"
United States
david
$111 nightly
The price is $125
Dec 3 - Dec 4
Total with taxes and fees
Hampton Inn Key Largo Manatee Bay
Outdoor pool, open 7:00 AM to 11:00 PM, pool umbrellas, sun loungers
Holiday Inn Key Largo by IHG

Holiday Inn Key Largo by IHG

3.0 star property
Key Largo
8.6 out of 10, Excellent, (1010)
"Excellent place to stay for a weekend "
United States
Carlos
$143 nightly
The price is $161
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Key Largo by IHG
View from room
Rainbow Bend Resort

Rainbow Bend Resort

2.5 star property
Marathon
8.2 out of 10, Very Good, (767)
"Loved the beach area and view. Good breakfasts, too."
United States
Kelly
$128 nightly
The price is $145
Nov 29 - Nov 30
Total with taxes and fees
Rainbow Bend Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Find out more about Islamorada

Discover top Islamorada attractions

Islamorada, a jewel in the Florida Keys, is perfect for adventurous families seeking quality experiences. Begin your exploration at the History of Diving Museum, where children and adults alike can marvel at fascinating exhibits detailing the evolution of underwater exploration. Next, head to the beautiful Anne's Beach, known for its shallow waters and family-friendly atmosphere, making it ideal for children to splash and play. For the thrill-seekers, the Florida Keys Kayak Tours offers guided adventures through mangroves, where you can spot manatees and dolphins in their natural habitat. Don’t miss the iconic Robbie's of Islamorada, where you can feed wild tarpon—a memory your kids will cherish! Finally, unwind at the Morada Bay Beach Café, a perfect spot to enjoy sunset views while dining on fresh seafood. When it comes to accommodations, consider staying at a waterfront resort like the Cheeca Lodge & Spa, which offers luxurious amenities and attentive service, ensuring your family feels pampered after a day of adventures. With spacious rooms and direct beach access, it’s an excellent base for exploring all that Islamorada has to offer.

Find the best hotels with connecting rooms in Islamorada

For travelers seeking accommodations in Islamorada that offer connecting rooms, these hotels provide the perfect blend of comfort and convenience for families or groups. Each hotel features spacious options to enhance your stay.

The Caribbean Resort

  • Why it's great for extra space: The Caribbean Resort is an exceptional choice for travelers in need of connecting rooms, a remarkable review rating of 9.8. This hotel combines luxury and convenience, offering spacious rooms that are perfect for families or groups. Guests can enjoy an outdoor pool and a relaxing hot tub, making it a fantastic escape in paradise.
  • Other amenities: Guests will appreciate the ocean views and the resort's nearby the beach. The hotel features convenient amenities such as a fully-equipped kitchen, complimentary toiletries, and daily housekeeping. Enjoy onsite water sports, secure parking, and a lovely terrace for outdoor relaxation. With its family-friendly services like cribs and highchairs, this resort ensures a comfortable stay for everyone.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.34 miles, Florida Keys Brewing Co. - 0.5 miles, Keys History & Discovery Center - 0.48 miles

Amara Cay Resort

  • Why it's great for extra space: Amara Cay Resort is an excellent choice for travelers needing connecting rooms, an excellent guest review rating of 8.8. This resort not only offers the convenience of connecting rooms but also features a beautiful beachfront location, perfect for family gatherings and relaxation. Guests can enjoy a variety of amenities including a refreshing outdoor pool, a poolside bar, and daily housekeeping to ensure a comfortable stay.
  • Other amenities: In addition to the connecting rooms, guests will appreciate the resort's numerous features such as a restaurant with ocean views, complimentary breakfast, and access to water sports like kayaking and snorkeling. The resort also offers premium bedding for a restful night, a fitness center, and beach towels for fun in the sun. For those traveling with young ones, cribs and playpens are available free of charge, making it a family-friendly choice.
  • Neighborhood: Matecumbe
  • Nearby attractions: Bud n' Mary's Dive Center - 0.21 miles, Indian Key Historic State Park - 0.67 miles, Hurricane Monument - 1.4 miles

Drop Anchor

  • Why it's great for extra space: Drop Anchor stands out with its inviting atmosphere and flexibility for travelers seeking connecting rooms, earning a solid review rating of 8.2. This charming hotel offers a cozy retreat with easy access to Islamorada's stunning beaches, making it an ideal spot for families or groups wanting to stay close together. The outdoor pool provides a great space for relaxation and leisure.
  • Other amenities: Beyond connecting rooms, guests will find a kitchenette equipped with essential appliances, a patio for outdoor enjoyment, and a yard for kids to play. Enjoy the convenience of housekeeping and free self-parking, along with beach umbrellas and sun loungers for beach days. The hotel also provides opportunities for water activities such as snorkeling and boating nearby, ensuring a fun-filled stay.
  • Nearby attractions: Theater of the Sea - 0.34 miles, Windley Key Fossil Reef Geological State Park - 0.23 miles, Rain Barrel Village - 1.73 miles

Hadley Resort and Marina

  • Why it's great for extra space: Ideal for travelers looking for connecting rooms, Hadley Resort and Marina offers a comfortable stay with a review rating of 7.6. Nestled in the scenic Matecumbe area, this resort delivers a welcoming atmosphere with easy access to the beach and various water sports. The connecting rooms provide ample space for families or groups wanting to enjoy their time together in a relaxed setting.
  • Other amenities: Guests can enjoy free breakfast daily, a marina for boating adventures, and an outdoor pool perfect for cooling off. Additional features include free parking, a playground for children, and access to kayaking and scuba diving nearby. With a range of dining options including a restaurant offering kids' meals, this resort is well-equipped for family enjoyment.
  • Neighborhood: Matecumbe
  • Nearby attractions: History of Diving Museum - 0.38 miles, Islamorada Brewery & Distillery - 0.3 miles, Keys History & Discovery Center - 0.79 miles

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Room was very clean, view was amazing, breakfast was great, and restaurants and activities nearby. Only issue was hot tub not working. Would’ve enjoyed that amenity! "
Deborah 2-night trip
Posted 2 days ago
Chesapeake Beach Resort

Frequently asked questions

How much do hotels with connecting rooms in Islamorada cost?
Prepare to pay from $110 to $324 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 8.4.
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 organizing 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 favorite. Once you've checked in and unpacked, there's no shortage of family-friendly attractions to see around Islamorada. Theater of the Sea and Anne's Beach are two of our top suggestions.
Why book your hotel with connecting rooms in Islamorada with Expedia?
Traveling 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. Theater 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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