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

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Check prices for these dates

Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27
In one month
Oct 9 - Oct 11
In two months
Nov 6 - Nov 8
No exact matches found, but these alternatives could be just right

Recommended hotels in Islamorada

A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

1. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"Loved this place! driving in I wasn’t too sure but when we open the door to our King suite absolutely stunning clean smelled amazing and walk right up to the water. You can paddleboard kayak. We loved our stay."
United States
Tamara
$84 nightly
The price is $95
Oct 5 - Oct 6
Total with taxes and fees
La Jolla Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,434 reviews)
"Excellent stay."
United States
Mian
$214 nightly
The price is $241
Sep 15 - Sep 16
Total with taxes and fees
Cheeca Lodge & Spa
A beach with palm trees and lounge chairs.

3. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,775 reviews)
"Excellent location, nice breakfast."
United States
Suresh
$187 nightly
The price is $211
Oct 12 - Oct 13
Total with taxes and fees
Chesapeake Beach Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

4. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
8.8 out of 10, Excellent, (743 reviews)
"Great resorts - will return again. Highly recommend"
United States
Lourdes
$111 nightly
The price is $125
Sep 13 - Sep 14
Total with taxes and fees
Breezy Palms Resort
A wooden deck with two lounge chairs, a table with two glasses of champagne and red roses, and a view of the beach and ocean.

5. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,304 reviews)
"Wonderful resort, very friendly staff, would definitely stay again!"
United States
Amy
$212 nightly
The price is $238
Sep 20 - Sep 21
Total with taxes and fees
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

6. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,113 reviews)
"Property is beautiful, staff is great and overall an amazing place to stay."
United States
Sonia
$282 nightly
The price is $317
Sep 20 - Sep 21
Total with taxes and fees
Islander Resort
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

7. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1,000 reviews)
"Love that they have a food truck on the property!"
United States
Alexandra
$147 nightly
The price is $166
Sep 21 - Sep 22
Total with taxes and fees
Fisher Inn Resort & Marina
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

8. 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, (268 reviews)
"Wonderful resort and friendly staff!"
United States
Ana
$248 nightly
The price is $279
Sep 20 - Sep 21
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A beach with rows of sun loungers and palm trees.

9. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (269 reviews)
"Great quaint stay on the water. Shower is awesome."
United States
Marianne
$92 nightly
The price is $104
Sep 20 - Sep 21
Total with taxes and fees
Ragged Edge Resort & Marina

10. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,485 reviews)
"Would stay again!"
United States
Chadwick
$208 nightly
The price is $234
Sep 15 - Sep 16
Total with taxes and fees
Lime Tree Bay Resort
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

11. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,000 reviews)
"Loved staying here and would stay again. Staff were so friendly and nice - made you feel like you knew them for years."
United States
Stephen
$268 nightly
The price is $302
Oct 1 - Oct 2
Total with taxes and fees
Pines & Palms Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.

12. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"Great location,"
United States
Marianela
$153 nightly
The price is $168
Sep 15 - Sep 16
Total with taxes and fees
Drop Anchor
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

13. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,181 reviews)
"We really enjoyed our stay there. Staff was very nice and helpful."
United States
charlotte
$110 nightly
The price is $123
Sep 13 - Sep 14
Total with taxes and fees
Rock Reef Resort
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

14. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,002 reviews)
"Very nice and clean we really enjoyed the private beach as well"
United States
Sheily
$92 nightly
The price is $104
Sep 16 - Sep 17
Total with taxes and fees
Drift Hotel
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

15. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (176 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$241 nightly
The price is $271
Oct 8 - Oct 9
Total with taxes and fees
Treasure Harbor
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

16. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (287 reviews)
"Clean room, helpful staff, very friendly and welcoming"
United States
Jasmine
$149 nightly
The price is $168
Sep 13 - Sep 14
Total with taxes and fees
Coconut Cove Resort and Marina
A beachside lounge with a wooden deck, thatched roof, and tropical plants.

17. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (460 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
$229 nightly
The price is $258
Sep 20 - Sep 21
Total with taxes and fees
Bayside Villas by Islander Resort
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

18. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,000 reviews)
"Perfect place in key largo! Definitely staying here again!"
United States
Melissa
$105 nightly
The price is $118
Sep 16 - Sep 17
Total with taxes and fees
Sunset Cove Beach Resort
A beach with palm trees, a dock, and a boat named "STYX".

19. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,000 reviews)
"Great location, perfect for relaxing. We enjoyed watching the sunset on the dock in the provided Adirondack chairs"
United States
Kim
$88 nightly
The price is $99
Oct 1 - Oct 2
Total with taxes and fees
The Pelican Key Largo Cottages
A balcony with a view of a beach, a pool, and a thatched-roof structure.

20. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,004 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
$151 nightly
The price is $170
Sep 15 - Sep 16
Total with taxes and fees
Hadley Resort and Marina
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.
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Top Islamorada Hotel Reviews

La Jolla Resort

La Jolla Resort

10/10 Excellent
"This is like an oasis along US 1 on the way down to Key West. We only stayed one night, but, in retrospect, I wish we had stayed a night or two more to take advantage of the amenities like the paddleboards and kayaks. It’s immaculately clean, everyone was so friendly, and the room was great. I can’t recommend this place more. It’s like a throwback to an earlier time, but completely updated. Plenty of restaurants to pick from nearby and the Islamorada Brewery across the street is great, and has a wonderful beer garden out back."
Michael 1-night trip
Posted 5 hours ago
La Jolla Resort

Find out more about Islamorada

Islamorada B&B information

Number of reviews
14,002
Accommodation
1 B&B
Lowest Price
$95
Highest Price
$317

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Islamorada?
Prices for B&Bs in Islamorada often vary, but you can find a great deal from $95 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Islamorada B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Islamorada?
The best time to book a B&B in Islamorada typically falls between February and April, a delightful period when the weather is pleasantly warm and ideal for outdoor activities. During these months, visitors can enjoy average temperatures ranging from the low 70s to mid-80s Fahrenheit, making it great for exploring the stunning beaches, engaging in water sports, or simply relaxing by the ocean.

This peak season attracts travelers eager to experience the vibrant marine life and lush landscapes that Islamorada is known for. Whether you're interested in snorkeling the coral reefs or embarking on a fishing charter, the conditions are often ideal, and the local atmosphere is lively with fellow adventure seekers.

If you're looking for a more budget-friendly option, consider visiting in October. This month presents an excellent opportunity to enjoy the beautiful fall weather while avoiding the larger crowds. With temperatures still warm, it's a wonderful time to take advantage of lower rates at accommodations and savor the tranquility of the islands.
What is the difference between a Islamorada Bed & Breakfast and a hotel?
Every Islamorada B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Islamorada B&Bs.

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