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

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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

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

1. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,002 reviews)
"The room was very nice and neat !"
United States
Leslie
$105 nightly
The price is $118
Sep 29 - Sep 30
Total with taxes and fees
La Jolla Resort
A beach with palm trees and lounge chairs.

2. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,781 reviews)
"Excellent location, nice breakfast."
United States
Suresh
$197 nightly
The price is $221
Oct 20 - Oct 21
Total with taxes and fees
Chesapeake Beach 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, (753 reviews)
"Great Florida style resort, clean and nice staff. Close to everything in Islamorada!"
United States
Debra
$107 nightly
The price is $120
Oct 1 - Oct 2
Total with taxes and fees
Breezy Palms Resort
A bathroom with a large bathtub, a window with curtains, and a view of palm trees and the sea.

4. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,454 reviews)
"Excellent hotel to spend good time with friends and family, just amazing."
United States
RAIBEL
$190 nightly
The price is $214
Oct 4 - Oct 5
Total with taxes and fees
Cheeca Lodge & Spa
A modern kitchen with a central island, a dining area with a view, and a living space with a balcony overlooking the ocean.

5. 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
$268 nightly
The price is $302
Oct 1 - Oct 2
Total with taxes and fees
Pines & Palms Resort
A beachfront hotel with a pool, beach chairs, and a view of the ocean at sunset.

6. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very good, (1,000 reviews)
"Love that they have a food truck on the property!"
United States
Alexandra
$156 nightly
The price is $175
Sep 28 - Sep 29
Total with taxes and fees
Fisher Inn Resort & Marina
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.

7. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,320 reviews)
"amazing clean stay."
United States
MICHAEL
$220 nightly
The price is $247
Sep 30 - Oct 1
Total with taxes and fees
Amara Cay Resort
An aerial view of a resort with two swimming pools surrounded by palm trees and sun loungers.

8. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,125 reviews)
"Great palace to stay at a reasonable price"
United States
John
$270 nightly
The price is $304
Sep 27 - Sep 28
Total with taxes and fees
Islander Resort
A clear blue pool surrounded by palm trees and a thatched-roof structure, with a view of the ocean in the background.

9. 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
Oct 1 - Oct 2
Total with taxes and fees
Coconut Cove Resort and Marina
A beach hut with a thatched roof, surrounded by lounge chairs and a picnic table, overlooking a calm sea.

10. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,188 reviews)
"Absolutely lovely resort, we always have a wonderful stay ♥️"
United States
Tia
$93 nightly
The price is $104
Sep 27 - Sep 28
Total with taxes and fees
Rock Reef Resort
A beach with rows of sun loungers and palm trees.

11. Ragged Edge Resort & Marina

Ragged Edge Resort & Marina
2.5 star property
Islamorada
9.6 out of 10, Exceptional, (273 reviews)
"Incredible place, ample room and everything you need to cook and to bbq."
United States
Nathalie
$142 nightly
The price is $159
Sep 27 - Sep 28
Total with taxes and fees
Ragged Edge Resort & Marina
A beachside patio with white furniture, palm trees, and a thatched umbrella.

12. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,000 reviews)
"Great location,"
United States
Marianela
$167 nightly
The price is $183
Sep 28 - Sep 29
Total with taxes and fees
Drop Anchor

13. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,515 reviews)
"Location, amenities, staff was amazing, breakfast was incredible."
United States
milayda
$172 nightly
The price is $194
Sep 27 - Sep 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, (278 reviews)
"Beautiful place Great beds Lots of dining options"
Canada
Eslita
$272 nightly
The price is $306
Oct 6 - Oct 7
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, (175 reviews)
"We loved sitting in the deck in the evening and again in the morning."
Canada
Molly
$244 nightly
The price is $275
Sep 28 - Sep 29
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, (1,009 reviews)
"Very pleasant stay would recommend to anyone looking for a fun get away"
United States
Payton
$130 nightly
The price is $146
Oct 1 - Oct 2
Total with taxes and fees
Sunset Cove Beach Resort
A balcony with a view of a beach, a pool, and a thatched-roof structure.

17. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,001 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
A beach with lounge chairs and a blue umbrella, a pier with boats, and a mural of wings on a wall.

18. Drift Hotel

Drift Hotel
2.5 star property
Key Largo
9.0 out of 10, Wonderful, (1,000 reviews)
"Excellent location"
United States
kelly
$92 nightly
The price is $104
Sep 28 - Sep 29
Total with taxes and fees
Drift Hotel
A view through a window with metal bars, featuring a beach with palm trees, a thatched umbrella, and a wooden dock.

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 28 - Sep 29
Total with taxes and fees
Kona Kai Resort and Gallery - Adults Only
A beach with palm trees, a dock, and a boat named "STYX".

20. The Pelican Key Largo Cottages

The Pelican Key Largo Cottages
2.0 star property
Key Largo
9.0 out of 10, Wonderful, (1,004 reviews)
"Great place great price great location "
United States
Richard
$86 nightly
The price is $96
Sep 27 - Sep 28
Total with taxes and fees
The Pelican Key Largo Cottages
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.
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Top Islamorada Hotel Reviews

Chesapeake Beach Resort

Chesapeake Beach Resort

8/10 Good
"Very nice property even though they have some remodeling going on, the place is agreeable. The staff in general was amazing, at least my experience was great. I visited the place few days after an accident with some limitations and my mother, an elderly person, they went an extra step to assist us and make our stay memorable at all times. My villa was spacious, clean and well located."
Mariateresa 7-night trip
Posted 3 hours ago
Chesapeake Beach Resort

Find out more about Islamorada

Islamorada B&B information

Number of reviews
10,673
Accommodation
1 B&B
Lowest Price
$96
Highest Price
$306

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.

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