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

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Check availability on Islamorada Romantic Hotels

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

Our top choices for Islamorada romantic hotels

1. 4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Tavernier
United States
Donna B.
£295
includes taxes & fees
31 Aug - 1 Sept
4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

2. Ocean View 2BR Pool, Private Beach

Ocean View 2BR Pool, Private Beach
Tavernier
United States
Len
£337
includes taxes & fees
22 Sept - 23 Sept
Ocean View 2BR Pool, Private Beach

3. Ocean view condo with balcony/marina view

Ocean view condo with balcony/marina view
Tavernier
United States
Katy T.
£290
includes taxes & fees
30 Aug - 31 Aug
Ocean view condo with balcony/marina view

4. Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
Tavernier
United States
Michelle P.
£344
includes taxes & fees
6 Sept - 7 Sept
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures

5. FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
United States
Aaron G.
£372
includes taxes & fees
25 Sept - 26 Sept
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

6. Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
United States
Lauren S.
£560
includes taxes & fees
23 Sept - 24 Sept
Sunrise Escape - Ocean Front Villa - Sleeps 10

7. Key Largo Ocean Shore Villa 1 with pool & boat slip

Key Largo Ocean Shore Villa 1 with pool & boat slip
Key Largo
United States
Bonni K.
Key Largo Ocean Shore Villa 1 with pool & boat slip

8. Key Largo Villa, Kawama K5, 3/3

Key Largo Villa, Kawama K5, 3/3
Key Largo
United States
Susan S.
£434
includes taxes & fees
30 Aug - 31 Aug
Key Largo Villa, Kawama K5, 3/3

9. Bayhouse Home with Beach & Open Water Views! Amazing Sunsets!

Bayhouse Home with Beach & Open Water Views! Amazing Sunsets!
Key Largo
United States
Luke H.
£595
includes taxes & fees
9 Sept - 10 Sept
Bayhouse Home with Beach & Open Water Views! Amazing Sunsets!

10. Keys Cottage with Beach and Dockage! Bayfront Property!

Keys Cottage with Beach and Dockage! Bayfront Property!
Key Largo
United States
Julia W.
£432
includes taxes & fees
31 Aug - 1 Sept
Keys Cottage with Beach and Dockage! Bayfront Property!
View all properties

Find out more about Islamorada

Islamorada attractions for couples

Islamorada, known as the "Sport Fishing Capital of the World," offers an array of thrilling activities for discerning travellers. You can embark on a deep-sea fishing charter to catch marlin or sailfish, making memories that will last a lifetime. For those who prefer to stay on land, the History of Diving Museum provides a fascinating insight into the underwater world, showcasing artefacts and interactive exhibits that will captivate both children and adults alike. Adventure seekers can also explore the stunning waters of the Florida Keys via kayaking or paddleboarding, with the protected mangroves of the Florida Keys National Marine Sanctuary offering a serene backdrop. If relaxation is on your agenda, the picturesque beaches, such as Anne’s Beach, provide the perfect spot for a family picnic or a peaceful day in the sun. When it comes to accommodation, the charming area of Islamorada boasts several boutique hotels and resorts that focus on personalised service, ensuring your family feels pampered throughout your stay. Many of these hotels feature private beach access and waterfront dining, allowing you to indulge in fresh seafood while enjoying breathtaking sunset views over the ocean.

Find the best romantic hotels in Islamorada

For couples seeking a romantic escape in Islamorada, these exquisite hotels provide the perfect backdrop for love and relaxation. Each hotel offers charming amenities designed to enhance your romantic getaway.Sunset Inn

  • Why it's great for a couples retreat: Sunset Inn is a charming retreat for couples, featuring a high review rating of 9.4, making it a trusted choice for a romantic getaway. Guests can indulge in the beautiful garden area, perfect for intimate moments, or relax by the outdoor pool, enjoying the serene atmosphere that surrounds them.
  • Other amenities: Beyond its romantic appeal, the Inn provides several amenities that enhance the stay. Guests can expect daily housekeeping and free toiletries, ensuring comfort throughout their visit. The kitchenette facilities allow for in-room dining, while the bicycles available onsite offer a fun way to explore the picturesque surroundings together.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.9 km, Islamorada Brewery & Distillery - 0.4 km, Keys History & Discovery Center - 0.7 km

Chesapeake Beach Resort

  • Why it's great for a couples retreat: Chesapeake Beach Resort is an idyllic spot for couples looking to unwind together, a remarkable review rating of 9.2. Guests can enjoy romantic moments on their private balcony with stunning ocean views, or take a leisurely stroll along the pristine beach. With an outdoor pool and sun loungers, it's a great setting for relaxation after a day spent exploring the local area.
  • Other amenities: In addition to its romantic atmosphere, the resort offers various amenities to ensure a comfortable stay. Guests can enjoy complimentary breakfast daily, and the kitchenette in each room allows for private dining experiences. Other popular features include free off-street parking, daily housekeeping, and convenient access to boat tours, perfect for a day of adventure on the water.
  • Neighborhood: Matecumbe
  • Nearby attractions: History of Diving Museum - 0.9 km, Theater of the Sea - 1.7 km, Windley Key Fossil Reef Geological State Park - 1.8 km

Islander Resort

  • Why it's great for a couples retreat: Islander Resort presents a charming escape for couples with an excellent review rating of 9.2. This romantic hideaway offers beachfront access, allowing guests to enjoy breathtaking sunsets and tranquil walks along the shore. The resort's inviting atmosphere is complemented by its heated outdoor pool, perfect for relaxation after a day of exploration.
  • Other amenities: Couples can also take advantage of various amenities that add to their romantic experience. The resort features poolside cabanas, a premium beach bar, and complimentary beach towels. With opportunities for kayaking and nearby scuba diving, couples can enjoy adventure together. The on-site restaurant offers ocean views, ideal for intimate dinners, while the garden area provides a peaceful retreat after a busy day.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.9 km, Islamorada Brewery & Distillery - 0.8 km, Keys History & Discovery Center - 0.1 km

Pines & Palms Resort

  • Why it's great for a couples retreat: Pines & Palms Resort is a delightful choice for couples seeking romance, with a stellar review rating of 9.2. Nestled by the waterfront, this resort provides a serene atmosphere ideal for intimate getaways. Guests can unwind on their private terrace or enjoy the outdoor pool, all while being surrounded by lush landscaping that enhances the romantic vibe.
  • Other amenities: The resort also offers a variety of amenities to elevate the experience. Couples can savour in-room dining with kitchenettes available, or enjoy leisurely strolls along the beach. Other features include complimentary beach towels, daily housekeeping, and access to boat tours for those looking to explore the beautiful waters of Islamorada together. With a focus on comfort and romance, Pines & Palms Resort is a perfect retreat.
  • Neighborhood: Matecumbe
  • Nearby attractions: Bud n' Mary's Dive Center - 1 km, Indian Key Historic State Park - 0.4 km, Hurricane Monument - 1.6 km

Cheeca Lodge & Spa

  • Why it's great for a couples retreat: Cheeca Lodge & Spa is a luxurious destination for couples, featuring an impressive review rating of 9.0. This romantic paradise offers an array of couples-centric amenities including massages on the beach and intimate dining experiences tailored for two. The resort's stunning beachfront setting creates a perfect atmosphere for romance and relaxation.
  • Other amenities: In addition to its romantic offerings, Cheeca Lodge & Spa boasts an expansive range of amenities. Guests can enjoy a full-service spa, multiple dining options, and an outdoor pool with cabanas. The resort also provides complimentary bicycles for leisurely rides, and for those seeking adventure, kayaking and scuba diving are available nearby. With its elegant suites featuring private balconies, this resort ensures a memorable stay for every couple.
  • Neighborhood: Matecumbe
  • Nearby attractions: Matecumbe United Methodist Church - 0.1 km, Florida Keys Brewing Co. - 0.4 km, MoradaWay Arts & Cultural District - 0.6 km

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

10/10 Excellent
"Check-in went smoothly and the little touch of offering some champagne on arrival made me feel special! Loved the updated room! Beds comfy. Staff accommodating. Breakfast has many great hot /cold choices. Coffee was 👍One of the Pools was a little dirty but front desk had maintenance on it when I informed them .."
Janet 3-night trip
Posted 11 hours ago
Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

10/10 Excellent
"Absolutely love it here and will definitely return for another stay."
Lisa 2-night trip
Posted 15 hours ago
Cheeca Lodge & Spa
Islander Resort

Islander Resort

10/10 Excellent
"It’s a beautiful property right on the water with very nice pool area and right near everything in Islamorada"
Steven 1-night trip
Posted 16 hours ago
Islander Resort
La Siesta Resort & Villas

La Siesta Resort & Villas

10/10 Excellent
"Muy bueno nos encantó lo recomiendo al máximo . 👌👌👌👌👌"
Ivet 2-night trip
Posted 16 hours ago
La Siesta Resort & Villas
Casa Morada

Casa Morada

8/10 Good
"The room was updated, clean, and comfortable. The bed and pillows were nice. The location was perfect for us. When it’s all completed it’s going to be a really cool spot for sunsets. Overall worth the money for a one nighter on our way home from the lower keys."
Jeremy 1-night trip
Posted 2 days ago
Casa Morada
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

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

10/10 Excellent
"I’d recommend getting breakfast locally instead of the resort’s breakfast. Very friendly and helpful staff."
Dareen 3-night trip
Posted 6 days ago
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
Pines & Palms Resort

Pines & Palms Resort

8/10 Good
"Lovely location, beautifully renovated, clean room, close to everything including great restaurants. If you want peace and quiet this is the spot for you. If your idea of the keys includes loud activities this is not for you. The small beach was not accessible due to rotting sargassum. You could not even spend much time at the pool due to the smell. Not the hotels fault obviously but affected our stay negatively."
Arturo 3-night trip
Posted 6 days ago
Pines & Palms Resort
Drop Anchor

Drop Anchor

8/10 Good
"Shower didn’t get super hot & not the best water pressure. Keep blinds closed in summer as the room got very hot and the a/c unit struggled to keep the room cool even at night. Could use a shade for the kitten window to help with this. Full length mirror in the room would’ve been nice as well. Overall nice property but a little older & can use some revamping"
Jacqueline 2-night trip
Posted 8 days ago
Drop Anchor

Frequently asked questions

Searching for romantic hotels in Islamorada?
If you and your partner need some romantic time away, 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, Islamorada County Park or Founders Park. If you're interested in staying near a particular destination, you can sort by neighbourhood or distance to top landmarks, 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, take a look at these details about year-round temperatures in Islamorada: The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 22°C. Average annual precipitation for Islamorada is 1122 mm.
What is there to do in Islamorada?
There's nothing better than experiencing 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, theatre scene and fishing. If you want to spend a day exploring, you might consider stopping at Bud n' Mary's Dive Center, Islamorada County Park 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 getaway go off without a hitch: 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 centre. If you'd like to venture out around the area, consider renting a car to explore more sights.

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