Search Hotels with Connecting Rooms in Islamorada

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Check availability on Islamorada Hotels with Connecting Rooms

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Our top choices for Islamorada hotels with connecting rooms

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1004)
"Great place"
United States
Marc
The price is 3.859.555 ₫
4.342.000 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
The Pelican Key Largo Cottages

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)
"The rooms are lovely. Once the remodel is done the place will be perfect. "
United States
Deborah
The price is 3.802.781 ₫
5.112.578 ₫ total
includes taxes & fees
21 Jan - 22 Jan 2026
Dove Creek Resort & Marina, Trademark Collection by Wyndham

Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1002)
"Always a great stay"
United States
Richard
The price is 5.815.615 ₫
6.542.698 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Sunset Cove Beach Resort

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1008)
"Great location, room was spotless and perfectly met my needs. I plan to return next year."
United States
M
The price is 4.260.925 ₫
5.652.462 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Fisher Inn Resort & Marina

Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.8 out of 10, Excellent, (1000)
"Had a wonderful stay at Drop Anchor! Very adorable and super clean. Loved the amenities and the hotel staff were amazing! "
United States
Laura
The price is 3.697.176 ₫
5.080.347 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Drop Anchor

Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
8.8 out of 10, Excellent, (1000)
"Beautiful location, great views, very clean property, room was great (great bed), friendly staff."
United States
Scott
The price is 9.026.045 ₫
11.605.046 ₫ total
includes taxes & fees
19 Jan - 20 Jan 2026
Playa Largo Resort & Spa, Autograph Collection

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, (1006)
"Beautiful Hotel and Calusa Restaurant was outstanding "
United States
Darlene
The price is 10.551.789 ₫
13.321.508 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
Baker's Cay Resort Key Largo, Curio Collection by Hilton

Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1001)
"Comfortable stay. Great location. "
United States
Anand
The price is 3.913.567 ₫
5.261.420 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Hadley Resort and Marina

Rainbow Bend Resort

Rainbow Bend Resort
2.5 star property
Marathon
8.2 out of 10, Very good, (786)
"Great location, friendly service and very clean!"
United States
mike
The price is 2.974.911 ₫
4.530.917 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Rainbow Bend Resort

Hampton Inn Key Largo Manatee Bay

Hampton Inn Key Largo Manatee Bay
2.5 star property
Key Largo
8.8 out of 10, Excellent, (1007)
"Clean room, welcoming staff, nice stay."
Germany
Verena
The price is 4.618.019 ₫
5.195.271 ₫ total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn Key Largo Manatee Bay
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.

Top Islamorada Hotel Reviews

Frequently asked questions

How much do hotels with connecting rooms in Islamorada cost?
Prepare to pay from 4.342.000 ₫ to 13.321.508 ₫ 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 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.