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

This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

Find out more about Islamorada

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

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
"Resort is amazing. Gets better every year. Beach, 2 pools, water sports place is amazing."
Michael 5-night trip
Posted less than an hour ago
Chesapeake Beach Resort

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 Everglades National Park, Bud n' Mary's Dive Center, or Founders Park. 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 Everglades National Park, Bud n' Mary's Dive Center, or Founders Park.
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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