20 Best B&B in Islamorada, FL - Bed and Breakfast from $115

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

Olga Vasiliy

$199 nightly

Nov 15 - Nov 16

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

Amir

$222 nightly

Nov 29 - Nov 30

Total with taxes and fees

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

3. La Jolla Resort

Matecumbe

Jane

$169 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

4. Cheeca Lodge & Spa

Matecumbe

Nicholas

$314 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

5. Islander Resort

Matecumbe

DEBORAH

$253 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

6. Sunset Cove Beach Resort

Key Largo

Alexey

$130 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

7. Breezy Palms Resort

Matecumbe

Gavin

$141 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

8. Fisher Inn Resort & Marina

Islamorada

Susan

$189 nightly

Nov 29 - Nov 30

Total with taxes and fees

Three Adirondack chairs facing a sunset over a body of water.

9. Ragged Edge Resort & Marina

Islamorada

Nathalie

$135 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

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

Islamorada

Stephen

$272 nightly

Nov 29 - Nov 30

Total with taxes and fees

A covered outdoor area with a view of a beach and palm trees.

11. Rock Reef Resort

Rock Harbor

keith

$103 nightly

Nov 17 - Nov 18

Total with taxes and fees

12. Lime Tree Bay Resort

Long Key

Donald

$182 nightly

Nov 16 - Nov 17

Total with taxes and fees

A beach with palm trees, a thatched-roof hut, and beach chairs.

13. Drop Anchor

Islamorada

Valerie

$164 nightly

Nov 24 - Nov 25

Total with taxes and fees

A beach with palm trees, a dock, and a boat named "STYX".

14. The Pelican Key Largo Cottages

Key Largo

SUSAN

$102 nightly

Nov 29 - Nov 30

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.

15. Coconut Cove Resort and Marina

Islamorada

Tiffany

$169 nightly

Nov 15 - Nov 16

Total with taxes and fees

A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

16. Dove Creek Resort & Marina, Trademark Collection by Wyndham

Key Largo

ruben

$126 nightly

Nov 19 - Nov 20

Total with taxes and fees

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

17. Atlantic Bay Resort

Tavernier

Annette

$206 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

18. Seafarer Key Largo

Rock Harbor

Brittany

$122 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

19. Treasure Harbor

Islamorada

Diane

$262 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden dock extending over calm turquoise water, lined with white railings and palm trees.

20. Creekside Inn

Tavernier

MARIO

$132 nightly

Dec 13 - Dec 14

Total with taxes and fees

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Top Islamorada Hotel Reviews

Caloosa Cove Resort by CoolVacay

8/10 Good

"Un lugar muy pero muy tranquilo y la playa no esta buena para bañarse"

Hadley Resort and Marina

8/10 Good

"Good for a single night . We were allowed early check-in at 2pm which was nice. Unfortunately charged with a resort fee in addition to what we have already paid through Hotels.com. Informed at check in that the pool was not operable, but we could use another resort pool down the road ice machine in the building didn’t work, but they were accommodating and gave us a free bag of ice when I asked . Room was very clean, bed was not very comfortable but fine for a night."

Cheeca Lodge & Spa

10/10 Excellent

"The room was clean and spacious. We stayed in a King suite, garden view. Staff throughout the property were friendly and accommodating. We had breakfast, lunch and dinner at the resort. Food was excellent at the pool and main restaurant. Drinks at the resort were pricey but delicious! Pool areas were clean with nicely maintained chairs. The grounds were gorgeous and well maintained. The free amenities included fishing, paddle boards, tennis, golf and a basketball court. My only complaint was that a wall in the building where our suite was located had cracks, scrapes and holes on it."

Chesapeake Beach Resort

10/10 Excellent

"I loved having a balcony to sit on to view the water. It was perfect for morning coffee or an afternoon to read. The breakfast every morning was perfect, and provided healthy options like fruit and yogurt. I tried a bite of my husband’s omelette and it was excellent. All the staff was friendly and helpful. Thank you for a nice stay!"

Treasure Harbor

10/10 Excellent

"I never do reviews but felt like I had to this time. Jen was absolutely amazing. She was very helpful regarding our boat rental, was very patient and answered all our questions. Having the snorkel and fishing gear was super handy and saved us time and money. Everything was very clean. I highly recommended staying here."

Find out more about Islamorada

Islamorada B&B information

Number of reviews	12,587
Accommodation	1 B&B
Lowest Price	$115
Highest Price	$353

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 $115 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. La Jolla Resort

4. Cheeca Lodge & Spa

5. Islander Resort

6. Sunset Cove Beach Resort

7. Breezy Palms Resort

8. Fisher Inn Resort & Marina

9. Ragged Edge Resort & Marina

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

11. Rock Reef Resort

12. Lime Tree Bay Resort

13. Drop Anchor

14. The Pelican Key Largo Cottages

15. Coconut Cove Resort and Marina

16. Dove Creek Resort & Marina, Trademark Collection by Wyndham

17. Atlantic Bay Resort

18. Seafarer Key Largo

19. Treasure Harbor

20. Creekside Inn

Top Islamorada Hotel Reviews

Caloosa Cove Resort by CoolVacay

Fisher Inn Resort & Marina

Hadley Resort and Marina

La Siesta Resort & Villas

Cheeca Lodge & Spa

Chesapeake Beach Resort

Coconut Cove Resort and Marina

Drop Anchor

Treasure Harbor

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. La Jolla Resort

4. Cheeca Lodge & Spa

5. Islander Resort

6. Sunset Cove Beach Resort

7. Breezy Palms Resort

8. Fisher Inn Resort & Marina

9. Ragged Edge Resort & Marina

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

11. Rock Reef Resort

12. Lime Tree Bay Resort

13. Drop Anchor

14. The Pelican Key Largo Cottages

15. Coconut Cove Resort and Marina

16. Dove Creek Resort & Marina, Trademark Collection by Wyndham

17. Atlantic Bay Resort

18. Seafarer Key Largo

19. Treasure Harbor

20. Creekside Inn

Top Islamorada Hotel Reviews

Caloosa Cove Resort by CoolVacay

Find out more about Islamorada

Islamorada B&B information

Frequently asked questions

Explore a world of travel with Expedia