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

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Our top choices for Islamorada romantic hotels

1. The Islands of Islamorada

The Islands of Islamorada
5.0 star property
Matecumbe
9.6 out of 10, Exceptional, (83 reviews)
"We had an AMAZING stay! The staff was wonderful, providing excellent customer service and providing local recommendations for activities and dining. The property is pristine and gorgeous. My only critique would be a lack of on property food options. We will definitely be back."
United States
Catherine
The price is NT$21,189
NT$26,221 total
includes taxes & fees
Nov 30 - Dec 1
The Islands of Islamorada

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,804 reviews)
"Nice beach walkable property Great breakfast made to order"
United States
kent brian
The price is NT$4,924
NT$7,373 total
includes taxes & fees
Nov 2 - Nov 3
Chesapeake Beach Resort

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,159 reviews)
"The entire resort was clean, staff very friendly, bar and restaurant and pools were fabulous! Would definitely stay there again!"
United States
DEBORAH
The price is NT$7,563
NT$10,892 total
includes taxes & fees
Nov 2 - Nov 3
Islander Resort

4. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
The price is NT$4,085
NT$5,512 total
includes taxes & fees
Nov 2 - Nov 3
La Jolla Resort

5. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,494 reviews)
"Great place. Phenomenal food!"
United States
Brandon
The price is NT$5,225
NT$8,263 total
includes taxes & fees
Nov 2 - Nov 3
Cheeca Lodge & Spa

6. Casa Morada

Casa Morada
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (466 reviews)
"Very helpful staff and great location"
United States
David
The price is NT$5,985
NT$7,100 total
includes taxes & fees
Nov 2 - Nov 3
Casa Morada

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

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
4.0 star property
Islamorada
9.0 out of 10, Wonderful, (306 reviews)
"Great place to stay!"
United States
Liosbel
The price is NT$6,754
NT$9,982 total
includes taxes & fees
Nov 29 - Nov 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

8. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (468 reviews)
"Had a blast in the keys! This property gave us every reason to stay on property! Fishing provided! Bait provided! Games, bikes, excellent staff and the vibes are worth every booking moment! Definitely coming back! FYI: we stay in the townhomes and still had access to all of the amenities! Book your stay! Let’s go!"
United States
Brian
The price is NT$7,824
NT$11,185 total
includes taxes & fees
Nov 3 - Nov 4
Bayside Villas by Islander Resort

9. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,000 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
The price is NT$4,665
NT$6,312 total
includes taxes & fees
Nov 15 - Nov 16
Hadley Resort and Marina

10. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor
9.8 out of 10, Exceptional, (365 reviews)
"We will make this an annual trip. A great place. Thank you for making it a great stay"
United States
Billy
The price is NT$6,759
NT$8,521 total
includes taxes & fees
Nov 2 - Nov 3
Kona Kai Resort and Gallery - Adults Only

11. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (277 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
The price is NT$4,753
NT$5,347 total
includes taxes & fees
Nov 18 - Nov 19
Ragged Edge Resort & Marina

12. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.6 out of 10, Exceptional, (561 reviews)
"Beautiful place hidden in Tavenier Great staff and the best sunset in the keys"
United States
ED
The price is NT$7,599
NT$9,832 total
includes taxes & fees
Nov 2 - Nov 3
Coconut Palm Inn

13. Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (834 reviews)
"Excellent Stay!"
United States
Annette
The price is NT$5,091
NT$6,461 total
includes taxes & fees
Nov 3 - Nov 4
Atlantic Bay Resort

14. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,560 reviews)
"Very friendly staff, quiet and low key if that’s what you’re looking for"
United States
Mark Blair
The price is NT$4,038
NT$6,009 total
includes taxes & fees
Nov 2 - Nov 3
Lime Tree Bay Resort

15. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,199 reviews)
"cute nice place in an incredible spot. Will visit there again for sure."
United States
keith
The price is NT$2,944
NT$3,312 total
includes taxes & fees
Nov 15 - Nov 16
Rock Reef Resort

16. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (263 reviews)
"This may be my favorite place I've stayed in the Keys! So quaint and the location and breakfast were amazing. We kayaked to the mangroves, ate at the wonderful restaurant across the street (Ballyhoos), and thoroughly enjoyed the beach area"
United States
Brittany
The price is NT$4,004
NT$4,963 total
includes taxes & fees
Nov 2 - Nov 3
Seafarer Key Largo

17. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,005 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
The price is NT$3,814
NT$4,291 total
includes taxes & fees
Dec 2 - Dec 3
Sunset Cove Beach Resort

18. The Ocean View Inn & Pub

The Ocean View Inn & Pub
2.0 star property
Islamorada
9.2 out of 10, Wonderful, (34 reviews)
"Very friendly staff"
United States
Maria
The price is NT$6,073
NT$6,832 total
includes taxes & fees
Nov 16 - Nov 17
The Ocean View Inn & Pub

19. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
The price is NT$6,233
NT$8,809 total
includes taxes & fees
Nov 4 - Nov 5
Pines & Palms Resort

20. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,005 reviews)
"Loved the location and the staff were very friendly"
United States
SUSAN
The price is NT$3,255
NT$3,661 total
includes taxes & fees
Nov 22 - Nov 23
The Pelican Key Largo Cottages
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.

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

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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