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Tonight Nov 28 - Nov 29
Next weekend Dec 4 - Dec 6

Top Islamorada Romantic Getaways & Hotels

$139
Cheeca Lodge & Spa

Cheeca Lodge & Spa

4.0 out of 5.0 81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
4/5
(20 Reviews)
This romantic resort features a private beach, a golf course, and a full-service spa. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and an arcade/game room, and families will appreciate the picnic area.
$137
Chesapeake Beach Resort

Chesapeake Beach Resort

2.5 out of 5.0 83409 Overseas Hwy, Islamorada, FL
3.5/5
(45 Reviews)
This smoke-free resort's private beach and 2 outdoor pools are some of the highlights. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a spa tub on site, and a 24-hour front desk and a terrace are also provided.
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Large Screened Porch, Professional Cleaning, Wifi: Special Aug & Sep 1000/week

Large Screened Porch, Professional Cleaning, Wifi: Special Aug & Sep 1000/week

Tavernier, FL
A sauna is featured at this condo, along with barbecue grills.

Hotels in Islamorada with Hot Tubs

$146
Islander Resort

Islander Resort

3.0 out of 5.0 82100 Overseas Highway, Islamorada, FL
4.5/5
(16 Reviews)
Nestled on the beach, this Islamorada resort is 0.6 mi (1 km) from Florida Keys Brewing Co. and 2.7 mi (4.3 km) from Theater of the Sea. Hurricane Monument and History of Diving Museum are also within 1 mi (2 km).
$130
Sands of Islamorada

Sands of Islamorada

2.5 out of 5.0 80051 Overseas Highway, Islamorada, FL
4.2/5
(5 Reviews)
Situated by the sea, this hotel is 0.3 mi (0.5 km) from Bud n' Mary's Dive Center and 3 mi (4.8 km) from History of Diving Museum. Theater of the Sea and Windley Key Fossil Reef Geological State Park are also within 6 mi (10 km).
$139
Cheeca Lodge & Spa

Cheeca Lodge & Spa

4.0 out of 5.0 81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
4/5
(20 Reviews)
Nestled on the beach, this Islamorada resort is 0.3 mi (0.5 km) from Florida Keys Brewing Co. and 2.9 mi (4.7 km) from Theater of the Sea. Hurricane Monument and Indian Key Historic State Park are also within 1 mi (2 km).
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Recent Islamorada Hotel Reviews By Fellow Wanderers

Islamorada Romantic Hotels

Is your anniversary quickly approaching? Maybe you’re looking for the perfect honeymoon getaway? Or, has it just been too long since you and yours had some quality alone time away from the hectic schedule of everyday life? Take a steamy trip and stay at one of the most romantic hotels in Islamorada.

Remember the feeling of first meeting your significant other? You were nervous and excited. It felt like talking to your first crush on the playground. Re-ignite those feelings with an unforgettable stay to one of the Islamorada romantic hotels. Treat your loved one to a perfect day with breakfast in bed, a day at the spa and then a sultry dinner at a top restaurant in Islamorada. After dinner, take a moonlit walk through one of the city’s beautiful parks, because nothing says romance like a stroll under the stars. Whether you have been together for a few weeks or 50 years, the romantic hotels in Islamorada are the perfect weekend getaway for you and your loved one. 

You’ll also be feeling affectionate toward Travelocity when you browse our vast selection of accommodations that cater to couples. We have unbelievable deals on the best romantic hotels in Islamorada, so you don’t have to worry about breaking the bank for your trip. Book now and let the honeymoon begin.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.