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

Book Islamorada Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15
In one month
Nov 27 - Nov 29
In two months
Dec 25 - Dec 27
No exact matches found, but these alternatives could be just right

Recommended hotels in Islamorada

A beach with palm trees and lounge chairs.

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,807 reviews)
"Great place"
United States
Phelicia
$188 nightly
The price is $212
Nov 10 - Nov 11
Total with taxes and fees
Chesapeake Beach Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

2. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,153 reviews)
"Great resort for families with children"
United States
Bryan
$273 nightly
The price is $308
Nov 15 - Nov 16
Total with taxes and fees
Islander Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

3. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (777 reviews)
"Such a great place to stay!!"
United States
Gavin
$123 nightly
The price is $138
Nov 3 - Nov 4
Total with taxes and fees
Breezy Palms Resort
A swimming pool surrounded by palm trees and lounge chairs.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,489 reviews)
"Beautiful resort"
United States
Patricia
$207 nightly
The price is $233
Nov 1 - Nov 2
Total with taxes and fees
Cheeca Lodge & Spa
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, (1,326 reviews)
"Pool side bar On the ocean Very clean and friendly"
United States
Ronald
$222 nightly
The price is $250
Nov 15 - Nov 16
Total with taxes and fees
Amara Cay Resort
A wooden deck with rustic furniture, a grill, and a view of the beach and palm trees.

6. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,003 reviews)
"Loved the beach area! Bed was comfortable, kitchenette well appointed, and there were enough electrical outlets!"
United States
Jane
$164 nightly
The price is $185
Oct 27 - Oct 28
Total with taxes and fees
La Jolla Resort
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

7. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,006 reviews)
"Excellent location"
United States
kelly
$92 nightly
The price is $103
Oct 29 - Oct 30
Total with taxes and fees
Drift Hotel
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

8. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,196 reviews)
"We loved the lagoon out back with free kayak use the room was nice with the extra large bed, microwave and refrigerator the staff was warm and friendly!"
United States
DONALD
$87 nightly
The price is $98
Oct 27 - Oct 28
Total with taxes and fees
Rock Reef Resort
A beach with palm trees, a thatched-roof structure, and kayaks.

9. Kona Kai Resort and Gallery - Adults Only

Kona Kai Resort and Gallery - Adults Only
2.5 star property
Rock Harbor
9.8 out of 10, Exceptional, (363 reviews)
"We will make this an annual trip. A great place. Thank you for making it a great stay"
United States
Billy
$129 nightly
The price is $145
Oct 27 - Oct 28
Total with taxes and fees
Kona Kai Resort and Gallery - Adults Only
A beach with rows of sun loungers and palm trees.

10. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (276 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
$144 nightly
The price is $162
Oct 29 - Oct 30
Total with taxes and fees
Ragged Edge Resort & Marina
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

11. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (303 reviews)
"Excellent stay! Love this place and will definitely be back!"
United States
Hailey Ritch and Patrick
$149 nightly
The price is $168
Oct 27 - Oct 28
Total with taxes and fees
Coconut Cove Resort and Marina
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

12. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,003 reviews)
"Very clean very quiet Close to nice restaurants and bars"
United States
Jose
$178 nightly
The price is $200
Oct 27 - Oct 28
Total with taxes and fees
Fisher Inn Resort & Marina
Terrace/patio

13. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,552 reviews)
"Very nice place the view and sunsets are amazing there is also a restaurant on the property that has great food and drinks we would definitely stay again"
United States
Christopher Michael
$179 nightly
The price is $201
Oct 27 - Oct 28
Total with taxes and fees
Lime Tree Bay Resort
A balcony with wicker chairs, a small table with drinks, and a view of the beach and ocean.

14. 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, (300 reviews)
"Great place to stay!"
United States
Liosbel
$304 nightly
The price is $342
Nov 2 - Nov 3
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A beachside patio with white furniture, palm trees, and a thatched umbrella.

15. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"Everything was nice and clean. I enjoyed my stay there."
United States
Leydis
$164 nightly
The price is $180
Oct 27 - Oct 28
Total with taxes and fees
Drop Anchor
A balcony with a view of a beach, a pool, and a thatched-roof structure.

16. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,001 reviews)
"Can’t wait to stay again in the spring. Amazing property."
United States
Jason
$158 nightly
The price is $178
Oct 27 - Oct 28
Total with taxes and fees
Hadley Resort and Marina
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

17. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,003 reviews)
"We have stayed here multiple times and always have a good stay."
United States
Michael
$229 nightly
The price is $258
Oct 27 - Oct 28
Total with taxes and fees
Pines & Palms 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, (1,003 reviews)
"Very nice clean hotel with friendly staff."
Canada
Alexey
$135 nightly
The price is $152
Nov 3 - Nov 4
Total with taxes and fees
Sunset Cove Beach Resort
A beach with a thatched umbrella, lounge chairs, and a clear view of the ocean.

19. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (180 reviews)
"A very peaceful place."
United States
angel
$160 nightly
The price is $180
Oct 27 - Oct 28
Total with taxes and fees
Matecumbe Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

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

Dove Creek Resort & Marina, Trademark Collection by Wyndham
3.0 star property
Key Largo
7.8 out of 10, Good, (1,001 reviews)
"Great place to stay"
United States
Omar Ahmad
$127 nightly
The price is $143
Oct 27 - Oct 28
Total with taxes and fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Islamorada Hotel Reviews

La Jolla Resort

La Jolla Resort

10/10 Excellent
"Place clean, comfortable and very nice. Could use some dressers for somewhere to put clothes. But I definitely would stay here again."
Daniel 4-night trip
Posted 4 hours ago
La Jolla Resort

Find out more about Islamorada

Islamorada B&B information

Number of reviews
10,121
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.

Explore a world of travel with Expedia