A beach with white lounge chairs, a covered pavilion, and palm trees.

Find Romantic Hotels in Islamorada, FL

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Check availability on Islamorada Romantic Hotels

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Find out more about Islamorada

Islamorada attractions for couples

Islamorada, nestled in the Florida Keys, is a haven for adventurous families seeking both thrilling activities and luxurious accommodation. Start your journey at the iconic Theater of the Sea, where you can swim with dolphins, interact with sea lions, and enjoy captivating marine shows, making it an unforgettable experience for both kids and adults. For a taste of the area's natural beauty, explore the stunning waters of the Florida Keys National Marine Sanctuary, perfect for snorkeling among vibrant coral reefs filled with tropical fish. If you’re looking to reel in some excitement, the world-renowned fishing charter services here, like Robbie's of Islamorada, offer family-friendly deep-sea fishing excursions that can create lasting memories. Don't miss the chance to visit the History of Diving Museum, which engages visitors with fascinating exhibits on underwater exploration—an educational and inspiring experience for the whole family. After a day filled with adventure, unwind in the picturesque area of Islamorada Village, where boutique hotels and waterfront resorts provide a blend of comfort and luxury. Many accommodations feature private balconies with ocean views, infinity pools, and on-site dining options that serve fresh local seafood. With attentive guest service and a focus on creating memorable experiences, your stay in Islamorada promises to be both relaxing and filled with excitement.

Find the best romantic hotels in Islamorada

For couples seeking a romantic escape in Islamorada, Florida, these hotels provide the perfect backdrop for love and relaxation. Each offers unique amenities tailored for romantic getaways.Sunset Inn

  • Why it's great for a couples retreat: The Sunset Inn offers a charming and romantic atmosphere for couples, rated highly with a guest review score of 9.4. Set in the picturesque Matecumbe neighborhood, this intimate hotel features an inviting outdoor pool where guests can relax and reconnect while surrounded by lush gardens. The peaceful ambiance makes it a perfect retreat for lovebirds looking to escape the hustle and bustle of everyday life.
  • Other amenities: In addition to the beautiful setting, the hotel provides convenient amenities such as kitchenettes in the rooms, allowing couples to enjoy breakfast in bed or prepare a romantic dinner. Guests can also take advantage of bicycles available on-site for leisurely rides along the scenic coast. The hotel's self-parking and daily housekeeping ensure a stress-free stay, making it easy for couples to focus on each other and their time together.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.53 miles, Islamorada Brewery & Distillery - 0.24 miles, Keys History & Discovery Center - 0.47 miles

Chesapeake Beach Resort

  • Why it's great for a couples retreat: Chesapeake Beach Resort is an ideal choice for romantic travelers looking to unwind together in a serene setting. With an impressive guest review rating of 9.2, this beachfront resort offers stunning ocean views and a beautiful private beach where couples can enjoy peaceful moments together. The outdoor pool and poolside sun loungers provide a relaxing atmosphere to soak up the sun and enjoy each other's company.
  • Other amenities: Additional features include complimentary breakfast, a concierge service for personalized planning, and on-site boat tours for a day of adventure. Guests can also take advantage of kitchenette facilities for intimate in-room dining, while the nearby snorkeling opportunities allow couples to explore the vibrant underwater world together. Enjoy the gorgeous resort design and comfortable accommodations, perfect for creating lasting memories with your loved one.
  • Neighborhood: Matecumbe
  • Nearby attractions: History of Diving Museum - 0.56 miles, Theater of the Sea - 1.08 miles, Windley Key Fossil Reef Geological State Park - 1.11 miles

Islander Resort

  • Why it's great for a couples retreat: The Islander Resort is a romantic haven for couples looking to enjoy the beauty of Islamorada, receiving an impressive guest review rating of 9.2. Set against a stunning beachfront, this resort offers a relaxing atmosphere where couples can unwind together by the pool or on the sandy shores. The resort's charming setting, complete with a beachfront restaurant, allows guests to enjoy intimate meals with a view.
  • Other amenities: In addition to its picturesque location, the resort features amenities such as pool cabanas for added privacy, concierge services for personalized experiences, and complimentary beach towels. Guests can also explore local attractions, enjoy water sports like kayaking and scuba diving, or simply relax on the beach with sun loungers. The Islander Resort is designed to create unforgettable moments for couples looking to strengthen their bond in a beautiful setting.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.53 miles, Islamorada Brewery & Distillery - 0.51 miles, Keys History & Discovery Center - 0.09 miles

Pines & Palms Resort

  • Why it's great for a couples retreat: Pines & Palms Resort offers a charming and intimate atmosphere for romantic travelers, a solid guest review rating of 9.2. Nestled along the waterfront, this resort invites couples to enjoy breathtaking views and serene surroundings. The outdoor pool and beach access provide perfect settings for relaxation and connection, making it a fantastic choice for a romantic getaway in Islamorada.
  • Other amenities: The resort features a variety of amenities, including kitchenettes for in-room dining, complimentary beach towels, and water sports equipment for adventurous couples. Guests can indulge in relaxing yoga classes on the beach or enjoy a sunset picnic on the private beach area. With its beautiful accommodations and access to a range of outdoor activities, Pines & Palms Resort is a great choice for couples seeking both relaxation and adventure.
  • Neighborhood: Matecumbe
  • Nearby attractions: Bud n' Mary's Dive Center - 0.62 miles, Indian Key Historic State Park - 0.23 miles, Hurricane Monument - 1.0 miles

Cheeca Lodge & Spa

  • Why it's great for a couples retreat: Cheeca Lodge & Spa is the epitome of luxury for romantic travelers, a stellar review rating of 9.0. This upscale resort offers couples a variety of intimate experiences, including massages on the beach and private dining options. The tranquil spa features couples treatment rooms for ultimate relaxation and pampering, making it a perfect spot for a romantic getaway or special occasion.
  • Other amenities: Beyond its romantic offerings, the lodge provides an array of amenities such as a hot tub, poolside bar, and on-site dining with ocean views. Guests can indulge in water activities like snorkeling and kayaking, or enjoy a round of golf on the nearby course. With its luxurious accommodations, beautiful beachfront, and attentive service, Cheeca Lodge & Spa is a top choice for couples seeking romance and relaxation in Islamorada.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.06 miles, Florida Keys Brewing Co. - 0.28 miles, MoradaWay Arts & Cultural District - 0.34 miles

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"They offer a free breakfast which is super convenient/ The rooms are clean and the common areas are well maintained."
Rob 2-night trip
Posted less than an hour ago
Chesapeake Beach Resort
Coconut Cove Resort and Marina

Coconut Cove Resort and Marina

10/10 Excellent
"Our stay here was wonderful. Though some things may need updated the overall ambiance of the resort over rode that. The managing staff are very helpful & hardworking. It’s a beautiful piece of oceanfront property & so easy to navigate whether you want to swim, boat, fish or just relax."
louise 8-night trip
Posted 7 hours ago
Coconut Cove Resort and Marina
Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

8/10 Good
"We had a nice stay at Fisher Inn. The location was great, the rooms were spacious, and having two king beds was a bonus. The bathroom was on the small side, but it was clean. We also appreciated the Keurig coffee maker in the room, especially having dark roast coffee available, and there were some nice breakfast options. The evening staff member was great, and the fire pits were a lovely amenity and a great place to relax. There were a couple of things that could have been better. Our accommodation included a cocktail promotion, but when we asked about redeeming it, the employee told us it wasn’t their promotion and then offered us a pop instead. The response felt dismissive and left us feeling that the advertised perk wasn’t being honoured. We would have appreciated a more helpful explanation and a genuine effort to resolve the issue, rather than simply being offered a soda or water. Also, we only saw three bikes available, which really isn’t enough for a property of this size. It would have been helpful to have clearer information about the limited availability. Overall, a great location with spacious, clean rooms and some nice amenities, but a little more attention to guest service and clearer communication about the included perks and available bikes would have made the experience even better."
Jennifer 2-night trip
Posted 16 hours ago
Fisher Inn Resort & Marina
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

10/10 Excellent
"We've stayed at many places over the years . This place and the room that we had were the best . Waking up in bed to a view of the ocean can't be beat. It is situated on the most luxurious of all the keys.. can't wait to return ."
Tim 3-night trip
Posted 2 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort

Pines & Palms Resort

10/10 Excellent
"We have stayed here multiple times and always have a good stay."
Michael 1-night trip
Posted 4 days ago
Pines & Palms Resort
Casa Morada

Casa Morada

10/10 Excellent
"."
angela 3-night trip
Posted 4 days ago
Casa Morada

Frequently asked questions

Searching for romantic hotels in Islamorada?
If you and your partner need a romantic escape, we've got just the ticket. Our guests also love Islamorada for its top seafood restaurants, fishing, and beautiful ocean views. You might consider checking out some of the nearby sights and attractions such as Bud n' Mary's Dive Center, Robbie's of Islamorada, or Anne's Beach. If you'd like to stay close to a particular destination, you can sort by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Islamorada?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Islamorada: The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches.
What is there to do in Islamorada?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Islamorada. Couples looking for a little of everything will enjoy Islamorada for its opera houses, theater scene, and fishing. If you want to spend a day exploring, you might consider a stop at Bud n' Mary's Dive Center, Robbie's of Islamorada, or Anne's Beach.
What's the best way to get to Islamorada and around town during my romantic getaway?
This information about transportation options in Islamorada might help your romantic trip get off to a smooth start: Make your way to Islamorada with a flight to Marathon, FL (MTH-Florida Keys Marathon), which is the closest major airport located 30 mi (48.2 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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