20 Best B&B in Islamorada, FL - Bed and Breakfast from $98

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

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Recommended hotels in Islamorada

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Matecumbe

Dianne

$175 nightly

Oct 26 - Oct 27

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.

2. Amara Cay Resort

Matecumbe

Danielle

$208 nightly

Oct 21 - Oct 22

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

Kristin

$232 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

4. Islander Resort

Matecumbe

Clara

$276 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

5. La Jolla Resort

Matecumbe

Brett

$152 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

6. Breezy Palms Resort

Matecumbe

Gavin

$123 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

7. Rock Reef Resort

Rock Harbor

Jared

$87 nightly

Oct 21 - Oct 22

Total with taxes and fees

A beach with rows of sun loungers and palm trees.

8. Ragged Edge Resort & Marina

Islamorada

Nathalie

$174 nightly

Oct 18 - Oct 19

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.

9. Coconut Cove Resort and Marina

Islamorada

Hailey Ritch and Patrick

$149 nightly

Oct 26 - Oct 27

Total with taxes and fees

10. Lime Tree Bay Resort

Long Key

Christopher Michael

$132 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

11. Sunset Cove Beach Resort

Key Largo

Alexey

$108 nightly

Oct 21 - Oct 22

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.

12. Kona Kai Resort and Gallery - Adults Only

Rock Harbor

Billy

$186 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

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

Islamorada

Liosbel

$304 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

14. Drop Anchor

Islamorada

Payman

$158 nightly

Oct 18 - Oct 19

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.

15. Drift Hotel

Key Largo

kelly

$110 nightly

Oct 21 - Oct 22

Total with taxes and fees

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

16. Fisher Inn Resort & Marina

Islamorada

Robyn

$188 nightly

Oct 18 - Oct 19

Total with taxes and fees

A beach with lounge chairs, palm trees, and a view of the water.

17. Atlantic Bay Resort

Tavernier

Annette

$159 nightly

Oct 27 - Oct 28

Total with taxes and fees

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

18. Matecumbe Resort

Matecumbe

angel

$141 nightly

Oct 27 - Oct 28

Total with taxes and fees

A beachside lounge with two blue umbrellas, a hammock, and lounge chairs.

19. Seafarer Key Largo

Rock Harbor

Soraya

$139 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

20. Treasure Harbor

Islamorada

Laura

$244 nightly

Oct 18 - Oct 19

Total with taxes and fees

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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

10/10 Excellent

"Excellent location we had a Waterview room, which was extremely clean well maintained with a beautiful view of the ocean and beach from our balcony. Both swimming pools were well maintained. Only glitch was hot tub was not working.. would definitely stay again ."

Breezy Palms Resort

10/10 Excellent

"This property is a nice old Florida style hotel with a nice pool, a small beach and marina. The room was very clean and comfortable with a strong air conditioner. Islamorada it’s still hot in October. We got the room with ocean view and a kitchen. Is a spacious space with a pretty nice stove, lots of utensils, dishes, cups, cutlery, pans and appliances like a toaster, a drip coffee maker (all’americana machine) it even had a blender! It had a few frying pans, bowls for salad, a colander, pots for pasta with the steamer, I think it lacked a water jug because water is potable in the Florida keys and I hate buying plastic bottles, but I’m not complaining because I used the blender vase to chill water and the glass pot, the coffee carafe, too. On top of everything, this room also has two ice cubes trays. The room we got has everything you need in the kitchen. We didn’t really cooked but brought a small bottle of olive oil to make breakfast with eggs, toasts or sandwiches in the morning. Very close is CAO bakery and we had a very good Cuban espresso there every day."

Hadley Resort and Marina

8/10 Good

"Lovely gem of a place and in a great location to explore either direction in the Keys! Helpful and friendly staff! I stayed in the room units closer to the road and next to the main lobby, so I can't compare them to the larger suites or ocean-view spots--which I'm guessing are fancier. The room was decently clean and comfy! Just noting (not complaining), the bathroom was tiny, but it worked fine for 1 person. Had a nice little kitchenette with a mini fridge, microwave, large sink, and coffee pod maker, so it was easy to save restaurant leftovers or keep a few groceries. There's a sweet little spot to sit in loungers or chairs at the end of the marina and soak up some ocean views (east-facing for sunrise is nice). It's just a quick walk to the backside of the property. It wasn't busy during my stay in early Oct., so it was easy to get a chair anytime, but note that there isn't space for more than a few people at a time. There are kayaks and other things you can use (I didn't have the time)."

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Islamorada B&B information

Number of reviews	11,512
Accommodation	1 B&B
Lowest Price	$98
Highest Price	$342

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 $98 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. Chesapeake Beach Resort

2. Amara Cay Resort

3. Cheeca Lodge & Spa

4. Islander Resort

5. La Jolla Resort

6. Breezy Palms Resort

7. Rock Reef Resort

8. Ragged Edge Resort & Marina

9. Coconut Cove Resort and Marina

10. Lime Tree Bay Resort

11. Sunset Cove Beach Resort

12. Kona Kai Resort and Gallery - Adults Only

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

14. Drop Anchor

15. Drift Hotel

16. Fisher Inn Resort & Marina

17. Atlantic Bay Resort

18. Matecumbe Resort

19. Seafarer Key Largo

20. Treasure Harbor

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Fisher Inn Resort & Marina

Breezy Palms Resort

Islander Resort

Caloosa Cove Resort by CoolVacay

Hadley Resort and Marina

Treasure Harbor

La Jolla Resort

Pines & Palms Resort

Find out more about Islamorada

Islamorada B&B information

Frequently asked questions

Explore a world of travel with Expedia

Book Islamorada Bed & Breakfast

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Recommended hotels in Islamorada

1. Chesapeake Beach Resort

2. Amara Cay Resort

3. Cheeca Lodge & Spa

4. Islander Resort

5. La Jolla Resort

6. Breezy Palms Resort

7. Rock Reef Resort

8. Ragged Edge Resort & Marina

9. Coconut Cove Resort and Marina

10. Lime Tree Bay Resort

11. Sunset Cove Beach Resort

12. Kona Kai Resort and Gallery - Adults Only

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

14. Drop Anchor

15. Drift Hotel

16. Fisher Inn Resort & Marina

17. Atlantic Bay Resort

18. Matecumbe Resort

19. Seafarer Key Largo

20. Treasure Harbor

Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Find out more about Islamorada

Islamorada B&B information

Frequently asked questions

Explore a world of travel with Expedia