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Featured Islamorada Romantic Hotels

See all 206 Hotels in Islamorada
Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82, Islamorada
    4.0 out of 5.0
     
     
    4.4 out of 5 (1,440 reviews)
    Fantastic hotelOn arrival we were given complementary champagne and told we can keep the glasses as well. The staff were so friendly and helpful and the rooms were lovely and beds comfortable. This is probably my favourite ever hotel and definitely ticks all the boxes and I would highly recommend this hotel to ...
    May 18, 2018

    Cheeca Lodge & Spa$220

    Cheeca Lodge & Spa$220
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada
      2.5 out of 5.0
       
       
      3.7 out of 5 (587 reviews)
      didn't have beach access due to Hurricane Irma damage, but centrally located to restaurants and moderately priced.
      May 21, 2018

      Chesapeake Beach Resort$111

      Chesapeake Beach Resort$111
      Amazing Sunsets, Amazing Amenities, & Amazing Value

      Amazing Sunsets, Amazing Amenities, & Amazing Value

      , Islamorada
         
         
        4.8 out of 5 (9 reviews)
        Great little condoThe condo was great, the pool was warm, and the weather was beautiful. Right in the middle of everything we wanted to do.
        Dec 6, 2017
        Ocean House

        Ocean House

        82885 Old Hwy, Islamorada
          3.5 out of 5.0
           
           
          4.7 out of 5 (6 reviews)

          Ocean House$425

          Ocean House$425
          Oceanfront Paradise W/ Large Screened Porch & Cable Internet::special Aug 1000

          Oceanfront Paradise W/ Large Screened Porch & Cable Internet::special Aug 1000

          , Tavernier
             
             
            4.7 out of 5 (13 reviews)
            Beautiful oceanfront condoWe loved our stay in this beautiful oceanfront condo. The location was perfect – very convenient to all that the Keys has to offer. Jeanette went out of her way to make sure we were comfortable. We were close to many great restaurants and Jeanette provided great recommendations. I would definitely ...
            Apr 3, 2018
            Amara Cay Resort

            Amara Cay Resort

            80001 Overseas Hwy, Islamorada
              3.5 out of 5.0
               
               
              4.3 out of 5 (1,299 reviews)
              Pelican Cove Resort & Marina

              Pelican Cove Resort & Marina

              84457 Overseas Highway, Islamorada
                3.0 out of 5.0
                 
                 
                3.9 out of 5 (1,100 reviews)
                Wonderful stay! Nice beach with fun amenities My husband and I had a wonderful time at Pelican Cove. Hotel is clean, modern and well situated in Islamorada. Best feature was the resort beach and free amenities like: free paddle boards, snorkel gear, kayaks and water floats that add to your stay. Free Continental breakfast is just OK but poolside ...
                May 8, 2018

                Pelican Cove Resort & Marina$195

                Pelican Cove Resort & Marina$195
                Casa Morada

                Casa Morada

                136 Madeira Road, Islamorada
                  3.5 out of 5.0
                   
                   
                  4.7 out of 5 (54 reviews)
                  Absolutely beautiful setting! We adored Hazel at the front desk and the amazing sunsets!
                  May 7, 2018
                  Islander Resort

                  Islander Resort

                  82100 Overseas Highway, Islamorada
                    3.0 out of 5.0
                     
                     
                    4.2 out of 5 (1,745 reviews)
                    Our favorite hotel in the keys!Classic keys motel...feels like we are transported back to the 1950s when we are on property...with a modern twist and Guy Harvey artwork abound. Lots of time in the pool (with drinks served poolside) or cooking out on the backyard grills with the kids. You are only a few steps from the ocean with ...
                    Sep 13, 2017

                    Islander Resort$221

                    Islander Resort$221
                    Drop Anchor Resort and Marina

                    Drop Anchor Resort and Marina

                    84959 Overseas Highway, 222, Islamorada
                      3.0 out of 5.0
                       
                       
                      4.2 out of 5 (886 reviews)
                      Vert cute motel with a waterfront area with a great view, plenty of seating. and a small pool. Our room, number 9 was clean and spacious. I would however not return as smoking is permitted in all outside areas. Ashtrays all over the resort. Lots of heavy smokers. If you are bothered by second hand ...
                      May 19, 2018

                      Drop Anchor Resort and Marina$135

                      Drop Anchor Resort and Marina$135
                      Pines & Palms Resort

                      Pines & Palms Resort

                      80401 Old Hwy, Islamorada
                        3.0 out of 5.0
                         
                         
                        4.4 out of 5 (380 reviews)
                        We had a great experience here. The staff was helpful with all of our questions and gave a great recommendation for breakfast and dinner out. The pool is amazing and Chris the bartender was super nice.i would stay here again.
                        May 14, 2018
                        Smuggler's Cove Resort and Marina

                        Smuggler's Cove Resort and Marina

                        85500 Overseas Highway, Islamorada
                          2.5 out of 5.0
                           
                           
                          2.9 out of 5 (209 reviews)

                          Smuggler's Cove Resort and Marina$119

                          Smuggler's Cove Resort and Marina$119
                          Postcard Inn Beach Resort & Marina

                          Postcard Inn Beach Resort & Marina

                          84001 Overseas Hwy, Islamorada
                            3.0 out of 5.0
                             
                             
                            3.8 out of 5 (1,198 reviews)
                            The hotel was nice. On the beach and has beautiful views.
                            Sep 5, 2017

                            Postcard Inn Beach Resort & Marina$223

                            Postcard Inn Beach Resort & Marina$223
                            La Siesta Resort & Marina

                            La Siesta Resort & Marina

                            80241 Overseas Highway, Islamorada
                              3.0 out of 5.0
                               
                               
                              3.8 out of 5 (653 reviews)
                              Every year i stay at la siesta and its just perfect the only thing is they closed down the jacuzzi which i really liked especially if it was being a little cold outside. The pool heater i guess its either not working or really low because the pool was cold this past weekend for mothers day. And the ...
                              May 18, 2018
                              Bayside Townhomes and Boatslips

                              Bayside Townhomes and Boatslips

                              81450 Overseas Highway, Islamorada
                                3.5 out of 5.0
                                 
                                 
                                4.6 out of 5 (160 reviews)
                                Usually stay at the cheeca Just as nice without the restaurant and tiki bar
                                Oct 27, 2017
                                Coconut Cove Resort and Marina

                                Coconut Cove Resort and Marina

                                84801 Overseas Highway, Islamorada
                                  2.0 out of 5.0
                                   
                                   
                                  3.3 out of 5 (173 reviews)
                                  Super friendly office staff. When we booked our reservation, we originally had it down for myself and my husband. We ended up bringing the kids with us and at no extra charge, we were upgraded to a cottage so that we would all be able to fit in one room. The pool area was super nice and the rooms ...
                                  May 14, 2018
                                  Harbor Lights

                                  Harbor Lights

                                  84951 Overseas Hwy, Islamorada
                                    2.0 out of 5.0
                                     
                                     
                                    2.9 out of 5 (855 reviews)
                                    Creekside Inn Islamorada

                                    Creekside Inn Islamorada

                                    90611 Old Highway, Islamorada
                                      2.5 out of 5.0
                                       
                                       
                                      3.6 out of 5 (745 reviews)
                                      Stay at Creekside InnNice stop on our way to Key West. Clean and comfortable for a reasonable price.
                                      May 18, 2018

                                      Creekside Inn Islamorada$116

                                      Creekside Inn Islamorada$116
                                      Lookout Lodge Resort

                                      Lookout Lodge Resort

                                      87770 Overseas Hwy, Islamorada
                                        2.5 out of 5.0
                                         
                                         
                                        3.8 out of 5 (78 reviews)
                                        Map

                                        Recently booked Romantic Hotels in Islamorada

                                        Chesapeake Beach Resort
                                        2.5 out of 5.0
                                        Last booking: 21 minutes ago
                                        Amara Cay Resort
                                        3.5 out of 5.0
                                        Last booking: 8 hours ago
                                        Postcard Inn Beach Resort & Marina
                                        3.0 out of 5.0
                                        Last booking: 9 hours ago
                                        Drop Anchor Resort and Marina
                                        3.0 out of 5.0
                                        Last booking: 12 hours ago
                                        Conch On Inn Motel
                                        2.0 out of 5.0
                                        Last booking: 13 hours ago
                                        Cheeca Lodge & Spa
                                        4.0 out of 5.0
                                        Last booking: 14 hours ago
                                        Pelican Cove Resort & Marina
                                        3.0 out of 5.0
                                        Last booking: 16 hours ago
                                        La Jolla Resort
                                        2.5 out of 5.0
                                        Last booking: 20 hours ago
                                        Casa Morada
                                        3.5 out of 5.0
                                        Last booking: 21 hours ago

                                        Romantic Islamorada Hotels Information

                                        Light the candles, put on some sultry music, and create the path of petals: You are on your way toward a legendary affair. Whether you have a remarkable weekend upcoming or need a break from a hectic life schedule, you'll say "ooh la la" as soon as you lay eyes on our romantic accommodation in Islamorada. We make it simple to search 3 romantic hotels in Islamorada, regardless of the reason you can hardly wait for this trip.

                                        Islamorada Romantic Accommodation Is Just the First Step

                                        What do you desire when it comes to tales of romance? Islamorada hotels with private rooms or in-room indulgences for a relaxing couples massage could be right around the corner. The area establishments will be happy to provide for candlelit meals where you can gaze deeply into your sweetheart's eyes. Perhaps you will keep the fun times going at a nearby watering hole before you head back to your lodging.

                                        You can also understand what to look forward to, because you'll discover lots of verified reports on Islamorada's romantic lodging.

                                        • 81% of visitors were delighted about Islamorada romantic hotels, and would recommend them to friends and family.
                                        • In fact, average satisfaction gathered lofty scores.
                                        • These rooms are so comfortable, you and your darling may never feel the need to leave.
                                        • You're in the correct town for exceptional service and skillful employees.
                                        • The well cultivated grounds invite date night walks under the moon and stars.

                                        It's Now a Great Moment to Get Top Discounts and Choices

                                        Yes, you will soon realize why guests come back so often. Islamorada has had a 2,269% rise in bookings over the last twelve months. And you will have plenty of money left over thanks to Expedia's bargains. Let us help you today, and you'll soon be swooning all over again.