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

$200 nightly

Nov 19 - Nov 20

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

$224 nightly

Nov 16 - Nov 17

Total with taxes and fees

A covered outdoor area with wooden furniture, a table with a candle, and a view of the ocean.

3. La Jolla Resort

Matecumbe

Jane

$160 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hotel courtyard with palm trees, a tiled walkway, and a building entrance.

4. Cheeca Lodge & Spa

Matecumbe

Nicholas

$290 nightly

Nov 16 - Nov 17

Total with taxes and fees

A beachside patio with wooden furniture, a thatched roof, and a view of the ocean.

5. Islander Resort

Matecumbe

DEBORAH

$250 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

Patricia

$130 nightly

Nov 17 - Nov 18

Total with taxes and fees

A beach with thatched umbrellas, palm trees, and lounge chairs.

7. Breezy Palms Resort

Matecumbe

Gavin

$141 nightly

Nov 15 - Nov 16

Total with taxes and fees

A covered outdoor seating area with wicker chairs and a table, overlooking a beach with palm trees and a wooden deck.

8. Fisher Inn Resort & Marina

Islamorada

Susan

$189 nightly

Nov 17 - Nov 18

Total with taxes and fees

A beachside lounge with a thatched roof, lounge chairs, and a view of the ocean.

9. Ragged Edge Resort & Marina

Islamorada

Nathalie

$132 nightly

Nov 18 - Nov 19

Total with taxes and fees

A seaside resort with a glass balustrade, outdoor seating, and a mural of tropical leaves.

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

Cassi

$103 nightly

Nov 17 - Nov 18

Total with taxes and fees

A spacious living area with a large island, wooden furniture, and a ceiling fan.

12. Lime Tree Bay Resort

Long Key

Donald

$182 nightly

Nov 29 - Nov 30

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

Dec 2 - Dec 3

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 sun loungers and umbrellas, palm trees, and a clear sky.

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

Key Largo

ruben

$137 nightly

Nov 18 - Nov 19

Total with taxes and fees

A beachside seating area with Adirondack chairs and a table, palm trees, and a view of the ocean.

17. Atlantic Bay Resort

Tavernier

Annette

$206 nightly

Dec 1 - Dec 2

Total with taxes and fees

A beach scene with colorful Adirondack chairs, a blue umbrella, and a view of the ocean.

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 waterfront patio with outdoor seating, a yellow umbrella, and a view of the water.

20. Creekside Inn

Tavernier

MARIO

$132 nightly

Dec 14 - Dec 15

Total with taxes and fees

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Top Islamorada Hotel Reviews

Caloosa Cove Resort by CoolVacay

8/10 Good

"The night watchman was very helpful"

Coconut Cove Resort and Marina

10/10 Excellent

"This is my second time staying here. It's a laid-back, extremely quiet place, so if you're looking for the party vibe, definitely not for you. The "beach" is really no more than a mangrove swamp, but that's typical of the Keys. For beaches, look elsewhere in Florida. The pool makes up for it, though. It is absolutely beautiful, with a waterfall and a chiller, so the water is always cool and refreshing even at the height of summer. And best of all: the pool is open 24 hours! This place is super safe; I left my sliding glass door unlocked the whole time I was here and had no problems. They offer a free, very basic "grab and go" breakfast in the lobby every morning (toast, muffins, cereal, yogurt, coffee and OJ). There is no restaurant or bar on the premises, but plenty of options nearby. The people who own and run this place are some of the nicest, most helpful people you will ever meet. A friend of mine who joined us midway through our stay had booked his room for the wrong date (totally his fault), and they helped him straighten everything out and got him a room at no extra charge!"

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."

Find out more about Islamorada

Islamorada B&B information

Number of reviews	7,518
Accommodation	1 B&B
Lowest Price	$115
Highest Price	$327

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

Room 1

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

Treasure Harbor

Coconut Cove Resort and Marina

Fisher Inn Resort & Marina

Hadley Resort and Marina

La Siesta Resort & Villas

Drop Anchor

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

Breezy 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

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