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

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Recommended hotels in Islamorada

1. Chesapeake Beach Resort

Chesapeake Beach Resort
3.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,771 reviews)
"Spectacular, beautiful view, excellent amenities, a quiet and beautiful place, very attentive staff, and the breakfast is exquisite—I’ll be back as soon as I can"
United States
alicia
$198 nightly
The price is $223
Aug 25 - Aug 26
Total with taxes and fees
Chesapeake Beach Resort

2. Cheeca Lodge & Spa

Cheeca Lodge & Spa
5.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,388 reviews)
"Wonderful stay! Friendly staff, clean rooms, highly recommend!"
United States
Jessica
$214 nightly
The price is $241
Aug 13 - Aug 14
Total with taxes and fees
Cheeca Lodge & Spa

3. Islander Resort

Islander Resort
4.0 star property
Matecumbe
9.4 out of 10, Exceptional, (1,101 reviews)
"Can't wait to stay there again!"
United States
Sarah
$277 nightly
The price is $312
Sep 2 - Sep 3
Total with taxes and fees
Islander Resort

4. Amara Cay Resort

Amara Cay Resort
4.0 star property
Matecumbe
8.8 out of 10, Excellent, (1,306 reviews)
"Beautiful hotel, amazing views , very friendly staff, I will definitely return to Amara cay"
United States
Estefani
$216 nightly
The price is $243
Aug 16 - Aug 17
Total with taxes and fees
Amara Cay Resort

5. 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, (247 reviews)
"Wonderful resort and friendly staff!"
United States
Ana
$272 nightly
The price is $306
Aug 19 - Aug 20
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

6. Coconut Cove Resort and Marina

Coconut Cove Resort and Marina
3.0 star property
Islamorada
9.0 out of 10, Wonderful, (280 reviews)
"Amazing staff! Clancy is great! This place is so cute family oriented and friendly! I cant wait to stay here again!"
United States
Lisa C
$149 nightly
The price is $168
Aug 30 - Aug 31
Total with taxes and fees
Coconut Cove Resort and Marina

7. La Jolla Resort

La Jolla Resort
2.5 star property
Matecumbe
9.2 out of 10, Wonderful, (1,001 reviews)
"Good location and great staff"
United States
adrian
$127 nightly
The price is $143
Aug 25 - Aug 26
Total with taxes and fees
La Jolla Resort

8. Lime Tree Bay Resort

Lime Tree Bay Resort
3.5 star property
Long Key
9.4 out of 10, Exceptional, (1,451 reviews)
"Great place to stay!!"
United States
Javier
$172 nightly
The price is $194
Aug 16 - Aug 17
Total with taxes and fees
Lime Tree Bay Resort

9. La Siesta Resort & Villas

La Siesta Resort & Villas
4.0 star property
Matecumbe
8.6 out of 10, Excellent, (1,005 reviews)
"Great place to stay!"
United States
Brianne
$237 nightly
The price is $266
Aug 18 - Aug 19
Total with taxes and fees
La Siesta Resort & Villas

10. Fisher Inn Resort & Marina

Fisher Inn Resort & Marina
3.5 star property
Islamorada
8.2 out of 10, Very Good, (1,020 reviews)
"We stay here once or twice a year, the staff is very friendly. The amenities are perfect and the location is right where you want to be."
United States
MARC
$147 nightly
The price is $166
Aug 31 - Sep 1
Total with taxes and fees
Fisher Inn Resort & Marina

11. Bayside Villas by Islander Resort

Bayside Villas by Islander Resort
3.5 star property
Matecumbe
9.0 out of 10, Wonderful, (455 reviews)
"Nice place very clean , quiet . Was great stay for us , thank you"
United States
beata
$322 nightly
The price is $362
Aug 23 - Aug 24
Total with taxes and fees
Bayside Villas by Islander Resort

12. Drop Anchor

Drop Anchor
3.0 star property
Islamorada
8.6 out of 10, Excellent, (1,012 reviews)
"Great location,"
United States
Marianela
$140 nightly
The price is $153
Aug 16 - Aug 17
Total with taxes and fees
Drop Anchor

13. Playa Largo Resort & Spa, Autograph Collection

Playa Largo Resort & Spa, Autograph Collection
4.5 star property
Rock Harbor
9.0 out of 10, Wonderful, (1,003 reviews)
"Lovely resort and very pet friendly which we loved!"
United States
Emily
$288 nightly
The price is $324
Aug 30 - Aug 31
Total with taxes and fees
Playa Largo Resort & Spa, Autograph Collection

14. Coconut Palm Inn

Coconut Palm Inn
3.0 star property
Tavernier
9.6 out of 10, Exceptional, (553 reviews)
"So happy with the stay, everything was clean and spacious. This is a little treasure nested in the keys. Can’t wait to be back"
United States
judith
$239 nightly
The price is $268
Aug 23 - Aug 24
Total with taxes and fees
Coconut Palm Inn

15. Pines & Palms Resort

Pines & Palms Resort
3.0 star property
Matecumbe
9.2 out of 10, Wonderful, (1,004 reviews)
"I had an excellent stay at the resort. and look forward to returning!"
United States
Isabel
$209 nightly
The price is $235
Aug 13 - Aug 14
Total with taxes and fees
Pines & Palms Resort

16. The Islands of Islamorada

The Islands of Islamorada
4.0 star property
Matecumbe
9.6 out of 10, Exceptional, (79 reviews)
"Love this property! Our family had the most amazing time in the villas. The location is great and the property is really well kept with amazing staff. We enjoyed the pool, the kids game area, pickle ball and relaxing in the home. Highly recommend!!"
United States
Christian
$441 nightly
The price is $496
Aug 16 - Aug 17
Total with taxes and fees
The Islands of Islamorada

17. Hadley Resort and Marina

Hadley Resort and Marina
3.5 star property
Matecumbe
7.6 out of 10, Good, (1,003 reviews)
"Nice pet friendly hotel, clean, nice staff, good continental breakfast."
United States
RAIBEL
$153 nightly
The price is $172
Sep 6 - Sep 7
Total with taxes and fees
Hadley Resort and Marina

18. Creekside Inn

Creekside Inn
2.5 star property
Tavernier
7.8 out of 10, Good, (1,010 reviews)
"Great place to stay!!!!"
United States
Cristy
$137 nightly
The price is $154
Aug 16 - Aug 17
Total with taxes and fees
Creekside Inn

19. Baker's Cay Resort Key Largo, Curio Collection by Hilton

Baker's Cay Resort Key Largo, Curio Collection by Hilton
4.0 star property
Key Largo
8.6 out of 10, Excellent, (1,149 reviews)
"My family and I really enjoyed our stay."
United States
Jennifer
$302 nightly
The price is $340
Aug 24 - Aug 25
Total with taxes and fees
Baker's Cay Resort Key Largo, Curio Collection by Hilton

20. Rock Reef Resort

Rock Reef Resort
2.5 star property
Rock Harbor
9.2 out of 10, Wonderful, (1,170 reviews)
"The best place i ever stayed in the Florida Keys by far ,the staff is amazing, the premises are gorgeous and well maintained , a real family vacation resort we already have plans to return in 5 weeks"
United States
Martin
$119 nightly
The price is $134
Aug 13 - Aug 14
Total with taxes and fees
Rock Reef Resort
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Top Islamorada Hotel Reviews

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Islamorada B&B information

Number of reviews
5,945
Accommodation
1 B&B
Lowest Price
$109
Highest Price
$312

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 $109 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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