Search for Cheap Deals on
Romantic Hotels in Islamorada

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!


Featured Islamorada Romantic Hotels

Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Cheeca Lodge & Spa
Chesapeake Beach Resort
Chesapeake Beach Resort
2.5 out of 5
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
Book a stay at this beach hotel in Islamorada. Enjoy 2 outdoor pools, a private beach, and a 24-hour front desk. Our guests praise the breakfast and the pool ...
Chesapeake Beach Resort
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
Amara Cay Resort
Casa Morada
Casa Morada
3.5 out of 5
136 Madeira Road, Islamorada, FL
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Casa Morada
Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. ...
Islander Resort
Drop Anchor
Drop Anchor
3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
Drop Anchor
Pines & Palms Resort
Pines & Palms Resort
3 out of 5
80401 Old Hwy, Islamorada, FL
Stay at this 3-star beach hotel in Islamorada. Enjoy free WiFi, a private beach, and a marina. Our guests praise the helpful staff in our reviews. Popular attractions ...
Pines & Palms Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3 out of 5
84001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
Stay at this 3-star beach resort in Islamorada. Enjoy free WiFi, a private beach, and a marina. Our guests praise the helpful staff and the clean rooms in our ...
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
La Siesta Resort & Villas
La Siesta Resort & Villas
4 out of 5
80241 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
Stay at this 4-star beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious ...
La Siesta Resort & Villas
Islander Bayside Villas and Boatslips
Islander Bayside Villas and Boatslips
3.5 out of 5
81450 Overseas Highway, Islamorada, FL
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Hurricane Monument and MoradaWay ...
Islander Bayside Villas and Boatslips
Coconut Cove Resort and Marina
Coconut Cove Resort and Marina
2.5 out of 5
84801 Overseas Highway, Islamorada, FL
Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free parking, and a marina. Our guests praise the pool and the helpful staff in our reviews. ...
Coconut Cove Resort and Marina
Fisher Inn Resort & Marina
Fisher Inn Resort & Marina
3.5 out of 5
84951 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
Stay at this 3.5-star beach motel in Islamorada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in ...
Fisher Inn Resort & Marina
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.

Hotels with Hot Tubs in Islamorada

Islander Resort
Islander Resort
4 out of 5
82100 Overseas Highway, Islamorada, FL
Stay at this 4-star beach hotel in Islamorada. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff in our reviews. ...
Islander Resort
Sands of Islamorada
Sands of Islamorada
2.5 out of 5
80051 Overseas Highway, Islamorada, FL
Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument ...
Sands of Islamorada
Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Cheeca Lodge & Spa
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.

Luxury Hotels in Islamorada

Cheeca Lodge & Spa
Cheeca Lodge & Spa
5 out of 5
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ...
Cheeca Lodge & Spa
Amara Cay Resort
Amara Cay Resort
4 out of 5
80001 Overseas Hwy, Islamorada, FL
Stay at this 4-star beach resort in Islamorada. Enjoy free parking, 2 restaurants, and a private beach. Our guests praise the pool and the bar in our reviews. ...
Amara Cay Resort
Drop Anchor
Drop Anchor
3 out of 5
84959 Overseas Highway, 222, Islamorada, FL
Stay at this 3-star hotel in Islamorada. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
Drop Anchor
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.

Romantic Hotels in Islamorada

Looking to pop the big question? Book a romantic hotel. Digging yourself out of the doghouse? Book a romantic hotel. Regardless of the reason for spoiling your partner, a romantic hotel in Islamorada will do the trick.

What’s love got to do with it?

Pick a flirty place with a secluded pool and private cabanas or go for one with an in-room hot tub and a swanky restaurant on-site. Some hotels in Islamorada even offer romantic packages, so you can really crank up the heat. Did someone say couple’s massages? Yes, please!

Maybe it’s the little things like a ridiculously good view from your balcony or the bottle of bubbly waiting for you when you arrive, but whatever it is, your sweetie is going to flip when they see the romantic resort you booked in Islamorada. Just imagine the fun you’ll have with a place all to yourselves.

Love your hotel; love your savings

You’ll find yourself falling for a lot more than your honey when you book a romantic hotel in Islamorada. You and your partner will have hearts in your eyes when you set your sights on our swoon-worthy hotel rates. Filter hotels by:

  • Hotwire Hot Rates: Snag a Hotwire Hot Rate and you’ll find out the name of your hotel after you book. It’s like the best blind date ever.

  • Price: With rooms starting at $182, your heart may skip a beat when you see how low our prices go on Romantic hotels.

  • Amenities: Room with a view? Fancy restaurant? Room service? Sort through our amenities to find whatever puts you two in the mood.

We’re no doctor of love, but we’ve got some advice for you, don’t wait for a reason to book a romantic hotel. Surprise your honey with a getaway to Islamorada for no reason at all. Spice it with up a Hotwire Hot Rate—after all, every good relationship loves a little mystery.