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
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20
No exact matches found, but these alternatives could be just right

Recommended hotels in Islamorada

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

1. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,152 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 and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.4 out of 10, Exceptional, (1,805 reviews)
"Great location"
United States
Dianne
$188 nightly
The price is $212
Nov 4 - Nov 5
Total with taxes and fees
Chesapeake Beach Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

3. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,486 reviews)
"Beautiful resort"
United States
Patricia
$226 nightly
The price is $246
Nov 19 - Nov 20
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.

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,323 reviews)
"Pool side bar On the ocean Very clean and friendly"
United States
Ronald
$220 nightly
The price is $248
Nov 15 - Nov 16
Total with taxes and fees
Amara Cay Resort
A beach with palm trees, thatched-roof huts, and lounge chairs.

5. 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 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, (1,002 reviews)
"Nice hotel."
United States
Brett
$184 nightly
The price is $207
Oct 27 - Oct 28
Total with taxes and fees
La Jolla Resort
A beach with rows of sun loungers and palm trees.

7. 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
$150 nightly
The price is $168
Oct 29 - Oct 30
Total with taxes and fees
Ragged Edge Resort & Marina
A beach with palm trees, a thatched-roof structure, and kayaks.

8. 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, (362 reviews)
"We will make this an annual trip. A great place. Thank you for making it a great stay"
United States
Billy
$137 nightly
The price is $154
Oct 27 - Oct 28
Total with taxes and fees
Kona Kai Resort and Gallery - Adults Only
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

9. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,193 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 beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

10. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,002 reviews)
"Very clean very quiet Close to nice restaurants and bars"
United States
Jose
$178 nightly
The price is $200
Oct 26 - Oct 27
Total with taxes and fees
Fisher Inn Resort & Marina
Terrace/patio

11. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,551 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
$182 nightly
The price is $204
Oct 28 - Oct 29
Total with taxes and fees
Lime Tree Bay Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

12. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (302 reviews)
"Excellent stay! Love this place and will definitely be back!"
United States
Hailey Ritch and Patrick
$149 nightly
The price is $168
Oct 26 - Oct 27
Total with taxes and fees
Coconut Cove Resort and Marina
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

13. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,004 reviews)
"Excellent location"
United States
kelly
$84 nightly
The price is $95
Oct 29 - Oct 30
Total with taxes and fees
Drift Hotel
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, (299 reviews)
"Great place to stay!"
United States
Liosbel
$304 nightly
The price is $342
Nov 1 - Nov 2
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
A modern kitchen with white cabinets, a microwave, and a dining area with a table and chairs.

15. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (180 reviews)
"Had a very enjoyable stay at Hemingway House. The place was spotless! All staff were very friendly and helpful. Would highly recommend staying here!"
United States
Diane
$244 nightly
The price is $275
Oct 26 - Oct 27
Total with taxes and fees
Treasure Harbor
A beach with thatched umbrellas, wooden chairs, and a wooden pier extending into the water.

16. 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.

17. Matecumbe Resort

Matecumbe Resort
2.0 star property
Matecumbe
9.0 out of 10, Wonderful, (177 reviews)
"A very peaceful place."
United States
angel
$160 nightly
The price is $180
Oct 26 - Oct 27
Total with taxes and fees
Matecumbe Resort
A beach with lounge chairs, palm trees, and a view of the water.

18. Atlantic Bay Resort

Atlantic Bay Resort
3.0 star property
Tavernier
9.4 out of 10, Exceptional, (832 reviews)
"Excellent Stay!"
United States
Annette
$172 nightly
The price is $193
Oct 26 - Oct 27
Total with taxes and fees
Atlantic Bay Resort
A beach with hammocks under palm trees, a sandy beach, and a clear blue sky.

19. 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
$137 nightly
The price is $154
Oct 26 - Oct 27
Total with taxes and fees
Dove Creek Resort & Marina, Trademark Collection by Wyndham
A row of beachside cottages with colorful exteriors, each with a beach chair and umbrella.

20. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,001 reviews)
"Great place to stay!"
United States
Brianne
$237 nightly
The price is $266
Nov 15 - Nov 16
Total with taxes and fees
La Siesta Resort & Villas
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

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Every thing excellent"
HECTOR 2-night trip
Posted 1 day ago
Fisher Inn Resort & Marina

Find out more about Islamorada

Islamorada B&B information

Number of reviews
6,130
Accommodation
1 B&B
Lowest Price
$95
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 $95 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