20 Best B&B in Islamorada, FL - Bed and Breakfast from $113

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

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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

Matecumbe

Kayla

$113 nightly

Oct 6 - Oct 7

Total with taxes and fees

A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Matecumbe

Suresh

$186 nightly

Oct 6 - Oct 7

Total with taxes and fees

A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

3. Cheeca Lodge & Spa

Matecumbe

RAIBEL

$195 nightly

Oct 2 - Oct 3

Total with taxes and fees

A beach with palm trees, thatched-roof huts, and lounge chairs.

4. Breezy Palms Resort

Matecumbe

Zack

$107 nightly

Oct 4 - Oct 5

Total with taxes and fees

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

Matecumbe

MICHAEL

$208 nightly

Oct 5 - Oct 6

Total with taxes and fees

A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

6. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

$133 nightly

Oct 27 - Oct 28

Total with taxes and fees

A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

7. Fisher Inn Resort & Marina

Islamorada

Alexandra

$164 nightly

Oct 12 - Oct 13

Total with taxes and fees

A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

8. Pines & Palms Resort

Matecumbe

Colt

$278 nightly

Oct 15 - Oct 16

Total with taxes and fees

A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

9. Rock Reef Resort

Rock Harbor

Tia

$101 nightly

Oct 4 - Oct 5

Total with taxes and fees

An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

10. Islander Resort

Matecumbe

Steven

$334 nightly

Oct 27 - Oct 28

Total with taxes and fees

11. Lime Tree Bay Resort

Long Key

Michael

$172 nightly

Oct 4 - Oct 5

Total with taxes and fees

A beach with rows of sun loungers and palm trees.

12. Ragged Edge Resort & Marina

Islamorada

Nathalie

$168 nightly

Oct 18 - Oct 19

Total with taxes and fees

A beachside patio with white furniture, palm trees, and a thatched umbrella.

13. Drop Anchor

Islamorada

Payman

$171 nightly

Oct 4 - Oct 5

Total with taxes and fees

A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

14. Treasure Harbor

Islamorada

Laura

$254 nightly

Oct 2 - Oct 3

Total with taxes and fees

A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

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

Islamorada

Eslita

$280 nightly

Oct 18 - Oct 19

Total with taxes and fees

A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

16. Matecumbe Resort

Matecumbe

Adrian

$160 nightly

Oct 4 - Oct 5

Total with taxes and fees

A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

17. Drift Hotel

Key Largo

kelly

$100 nightly

Oct 8 - Oct 9

Total with taxes and fees

A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

18. Kona Kai Resort and Gallery - Adults Only

Rock Harbor

Karen

$270 nightly

Oct 6 - Oct 7

Total with taxes and fees

A balcony with a view of a beach, a pool, and a thatched-roof structure.

19. Hadley Resort and Marina

Matecumbe

weder

$164 nightly

Oct 18 - Oct 19

Total with taxes and fees

A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

20. Sunset Cove Beach Resort

Key Largo

Payton

$130 nightly

Oct 12 - Oct 13

Total with taxes and fees

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Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

8/10 Good

"The room was a little loud from the A/C unit but great stay"

Amara Cay Resort

8/10 Good

"This resort was absolutely beautiful!! The pool was amazing, a resort style pool. The resort had its own private beach area and a dock. Had plenty of seating everywhere, many cool sitting areas around the property. The only negative thing I could say is that the staff didn’t pick up trash and towels around the pool which seemed odd and it was off season so it wasn’t busy. It’s such a beautiful resort that I would think that would be a priority to keep it clean. Another cool thing is that they have a water taxi and shuttle to their 2 sister resorts which you can utilize all of those amenities as well. They also included bike rentals, paddle boards and kayaking on site which is convenient. You can also bring your private boat there and leave it at the dock for a fee. I would absolutely stay there again!"

Find out more about Islamorada

Islamorada B&B information

Number of reviews	12,264
Accommodation	1 B&B
Lowest Price	$113
Highest Price	$376

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 $113 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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Things to do in Islamorada

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Recommended hotels in Islamorada

1. La Jolla Resort

2. Chesapeake Beach Resort

3. Cheeca Lodge & Spa

4. Breezy Palms Resort

5. Amara Cay Resort

6. Coconut Cove Resort and Marina

7. Fisher Inn Resort & Marina

8. Pines & Palms Resort

9. Rock Reef Resort

10. Islander Resort

11. Lime Tree Bay Resort

12. Ragged Edge Resort & Marina

13. Drop Anchor

14. Treasure Harbor

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

16. Matecumbe Resort

17. Drift Hotel

18. Kona Kai Resort and Gallery - Adults Only

19. Hadley Resort and Marina

20. Sunset Cove Beach Resort

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Chesapeake Beach Resort

Islander Resort

Hadley Resort and Marina

Amara Cay Resort

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

Casa Morada

Drop Anchor

Treasure Harbor

Find out more about Islamorada

Islamorada B&B information

Frequently asked questions

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Book Islamorada Bed & Breakfast

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Recommended hotels in Islamorada

1. La Jolla Resort

2. Chesapeake Beach Resort

3. Cheeca Lodge & Spa

4. Breezy Palms Resort

5. Amara Cay Resort

6. Coconut Cove Resort and Marina

7. Fisher Inn Resort & Marina

8. Pines & Palms Resort

9. Rock Reef Resort

10. Islander Resort

11. Lime Tree Bay Resort

12. Ragged Edge Resort & Marina

13. Drop Anchor

14. Treasure Harbor

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

16. Matecumbe Resort

17. Drift Hotel

18. Kona Kai Resort and Gallery - Adults Only

19. Hadley Resort and Marina

20. Sunset Cove Beach Resort

Top Islamorada Hotel Reviews

Cheeca Lodge & Spa

Find out more about Islamorada

Islamorada B&B information

Frequently asked questions

Explore a world of travel with Expedia