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

Book Islamorada Bed & Breakfast

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22
No exact matches found, but these alternatives could be just right

Recommended hotels in Islamorada

House, 3 Bedrooms, Ocean View, Oceanfront | Lanai

1. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,005 reviews)
"The room was very nice and neat !"
United States
Leslie
$126 nightly
The price is $141
Sep 28 - Sep 29
Total with taxes and fees
La Jolla Resort
Balcony

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,450 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
$195 nightly
The price is $219
Sep 24 - Sep 25
Total with taxes and fees
Cheeca Lodge & Spa
Private beach, white sand, sun loungers, beach towels

3. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,782 reviews)
"Excellent location, nice breakfast."
United States
Suresh
$197 nightly
The price is $221
Sep 29 - Sep 30
Total with taxes and fees
Chesapeake Beach Resort
Exterior

4. Breezy Palms Resort

Breezy Palms Resort
2.5 star property
Matecumbe
9.0 out of 10, Wonderful, (749 reviews)
"It was very cozy. I was able to relax while I was celebrating my anniversary with my wife. The bed was super comfortable. The shower was excellent, and the staff was very friendly."
United States
Dionisio
$93 nightly
The price is $105
Sep 29 - Sep 30
Total with taxes and fees
Breezy Palms Resort
Exterior

5. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,123 reviews)
"Great palace to stay at a reasonable price"
United States
John
$238 nightly
The price is $268
Sep 29 - Sep 30
Total with taxes and fees
Islander Resort
Exterior

6. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,003 reviews)
"Love that they have a food truck on the property!"
United States
Alexandra
$139 nightly
The price is $156
Sep 23 - Sep 24
Total with taxes and fees
Fisher Inn Resort & Marina
Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio

7. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,507 reviews)
"Location, amenities, staff was amazing, breakfast was incredible."
United States
milayda
$172 nightly
The price is $194
Sep 24 - Sep 25
Total with taxes and fees
Lime Tree Bay Resort
Exterior

8. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (271 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
$150 nightly
The price is $168
Sep 24 - Sep 25
Total with taxes and fees
Ragged Edge Resort & Marina
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

9. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"Great location,"
United States
Marianela
$166 nightly
The price is $182
Sep 23 - Sep 24
Total with taxes and fees
Drop Anchor
Sundeck

10. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,186 reviews)
"Absolutely lovely resort, we always have a wonderful stay ♥️"
United States
Tia
$101 nightly
The price is $114
Sep 23 - Sep 24
Total with taxes and fees
Rock Reef Resort
Exterior

11. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (293 reviews)
"Excellent stay! Love this place and will definitely be back!"
United States
Hailey Ritch and Patrick
$137 nightly
The price is $154
Sep 24 - Sep 25
Total with taxes and fees
Coconut Cove Resort and Marina
Room, 1 King Bed, Balcony, Ocean View (Balcony) | Premium bedding, in-room safe, laptop workspace, iron/ironing board

12. 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, (276 reviews)
"Beautiful place Great beds Lots of dining options"
Canada
Eslita
$264 nightly
The price is $297
Sep 28 - Sep 29
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
On the beach, sun loungers, snorkeling, kayaking

13. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,005 reviews)
"Excellent location"
United States
kelly
$95 nightly
The price is $107
Sep 27 - Sep 28
Total with taxes and fees
Drift Hotel
Oceanfront Three Bedroom Villa | Premium bedding, iron/ironing board, WiFi (free), individually decorated

14. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"It was a great time staying at the resort. Really enjoyed that they had a bartender at the pool in the evenings."
United States
Colt
$179 nightly
The price is $201
Sep 23 - Sep 24
Total with taxes and fees
Pines & Palms Resort
Marina

15. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,002 reviews)
"Great place great price great location "
United States
Richard
$85 nightly
The price is $96
Oct 1 - Oct 2
Total with taxes and fees
The Pelican Key Largo Cottages
Exterior

16. Seafarer Key Largo

Seafarer Key Largo
2.0 star property
Rock Harbor
9.2 out of 10, Wonderful, (240 reviews)
"simple breakfast, older place but clean room, access to the beach - very convenient and nice!"
United States
ANDREW
$111 nightly
The price is $125
Sep 23 - Sep 24
Total with taxes and fees
Seafarer Key Largo
Balcony view

17. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,004 reviews)
"Great place"
United States
weder
$147 nightly
The price is $166
Sep 28 - Sep 29
Total with taxes and fees
Hadley Resort and Marina
Exterior

18. Sunset Cove Beach Resort

Sunset Cove Beach Resort
2.5 star property
Key Largo
9.2 out of 10, Wonderful, (1,008 reviews)
"Very pleasant stay would recommend to anyone looking for a fun get away"
United States
Payton
$109 nightly
The price is $123
Sep 23 - Sep 24
Total with taxes and fees
Sunset Cove Beach Resort
Breadfruit Suite | Terrace/patio

19. 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, (352 reviews)
"Kona Kai is truly amazing!! Best staff ever!! Grounds are gorgeous and everything well kept up. Rooms are immaculate. Definitely would go back!!"
United States
Karen
$152 nightly
The price is $171
Sep 24 - Sep 25
Total with taxes and fees
Kona Kai Resort and Gallery - Adults Only
25-inch flat-screen TV with digital channels, TV

20. Treasure Harbor

Treasure Harbor
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$234 nightly
The price is $263
Sep 23 - Sep 24
Total with taxes and fees
Treasure Harbor
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

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"Very quiet and peaceful stay. Amazing water and beach views from the balcony."
Michelle 4-night trip
Posted less than an hour ago
Chesapeake Beach Resort

Find out more about Islamorada

Islamorada B&B information

Number of reviews
12,846
Accommodation
1 B&B
Lowest Price
$96
Highest Price
$297

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 $96 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