Search Cottages in Islamorada

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Cottages in Islamorada and around

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1215)
"Stay here was nice, rooms are pretty clean, stairwells & doors are dirty. Food and drink are ridiculously expensive, and no vending machines. I ended up going offsite & buying beer & snacks. No microwaves in room. And no real beach. Its just a drop off with stairs to water. Room was very comfortable and pool was great. Thats about it. For the price of admission, you'd think a free breakfast every morning woul be included. Again, we went off site for that. It was very relaxing and quiet however."
The price is €415
includes taxes & fees
11 Feb - 12 Feb
Amara Cay Resort

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1395)
"The resort is very clean and the staff are amazing. We encountered many staff during our stay and they were very friendly. Chef Chris in the Sunrise room created delicious made to order omelets. Breakfast was great."
The price is €374
includes taxes & fees
10 Feb - 11 Feb
Chesapeake Beach Resort

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1032)
"We spent 3 fab nights at Cheeca Lodge and we had a great time. Only problem with such a lovely resort is that you don’t want to go and explore the islands (although we did) and to do so means not using the ample facilities enough. The beach and pier area was beautiful and peaceful, the gym was just about right and the room was ideally sized. We heard one lady moaning about their TV not working so we checked and ours wasn’t either - so if you want to stay in your room and watch tv…!! We...
The price is €391
includes taxes & fees
23 Feb - 24 Feb
Cheeca Lodge & Spa

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1003)
"."
The price is €390
includes taxes & fees
23 Feb - 24 Feb
La Siesta Resort & Villas

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1007)
"Islander Resort is a great place to relax in Islamorada. It has several on site restaurants, a pool, a private beach, a fishing pier, and water sports options. I went in January and the weather was a bit chilly, but I would return in hotter weather to take full advantage of it. They were very accommodating to my service dog. Friendly and helpful staff."
The price is €319
includes taxes & fees
23 Feb - 24 Feb
Islander Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
8.0 out of 10, Very good, (1008)
"Was great for a resort. Onsite restaurants have great food and amazing views. Contstant piped in music (all throughout the resort— on the beaches, the pools, the walkways, etc) was a downside but they might be par for the course on a resort. Biggest downside was that there is no hot tub on the premises. This might change as some of the resort is still under construction. Biggest upside is the amazing views and the wonderful staff. Everyone was not only polite, but helpful, and friendly. "
The price is €452
includes taxes & fees
11 Feb - 12 Feb
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Hadley Resort and Marina

3.5 star property
8.0 out of 10, Very good, (1004)
"When we arrived our room was ready and the staff was very friendley."
The price is €236
includes taxes & fees
10 Feb - 11 Feb
Hadley Resort and Marina

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1001)
"Small hotel, nice and quiet staff was great"
The price is €350
includes taxes & fees
20 Feb - 21 Feb
Drop Anchor

Coconut Cove Resort and Marina

2.5 star property
7.4 out of 10, Good, (714)
"It's like it came out of a time capsule from the 70's. Reminded me of old Florida. Its very quit and centrally located."
The price is €260
includes taxes & fees
13 Feb - 14 Feb
Coconut Cove Resort and Marina

Sunset Inn

3.0 star property
9.2 out of 10, Wonderful, (1002)
"Highly recommend "
The price is €284
includes taxes & fees
23 Feb - 24 Feb
Sunset Inn

Treasure Harbor

2.0 star property
9.2 out of 10, Wonderful, (52)
"Stayed a couple of days prior to our cruise. The boats were nice and we would most definitely stay there again. Could use some refreshing or deep cleaning some things were in need of repair, but dont let that deture you. It is a nice place with lots of things to do around the area along with some great food stops. "
The price is €365
includes taxes & fees
22 Feb - 23 Feb
Treasure Harbor

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1004)
"All good. Nice pool and beach area"
The price is €325
includes taxes & fees
10 Feb - 11 Feb
Fisher Inn Resort & Marina

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1000)
"Friendly staff"
The price is €407
includes taxes & fees
20 Feb - 21 Feb
La Jolla Resort

The Caribbean Resort

3.5 star property
10.0 out of 10, Exceptional, (150)
"Staff is always great. Rooms are beautiful & clean. Feels like I am at home"
The Caribbean Resort

Ragged Edge Resort & Marina

2.5 star property
9.4 out of 10, Exceptional, (157)
"This property is peaceful and calming. April is so nice. "
Ragged Edge Resort & Marina

Islander Bayside Villas and Boatslips

3.5 star property
8.8 out of 10, Excellent, (358)
"We booked here because of the full kitchen plus living areas; the kitchen was pretty sparse regarding cookware/appliances, but the front desk bent over backwards to get us the missing items we requested. One of the selling points was access to their resort property, just up the street. However, that property was almost deserted due to a lot of construction work. The resort pool was closed (the Bayside Villas pool was open). Overall this was a pleasant stay for us."
The price is €430
includes taxes & fees
11 Feb - 12 Feb
Islander Bayside Villas and Boatslips

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (355)
"Loved the location of our room-we could easily get coffee and head out to sit and watch the sunrise. Ice machine broken so that was a bummer but the staff was phenomenal especially when allowing us to check in early."
The price is €293
includes taxes & fees
11 Feb - 12 Feb
Sands of Islamorada

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (381)
"We stayed in the ocean front Shangri-La room. Beautiful views and the most comfortable bed of our trip. Enjoyed lounging on the island. Our room only had a bathtub, no shower, which was unexpected but we made due. Lovely manicured grounds. Nice continental breakfast."
The price is €558
includes taxes & fees
26 Feb - 27 Feb
Casa Morada

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (977)
"Staff was friendly"
The price is €488
includes taxes & fees
10 Feb - 11 Feb
Pines & Palms Resort

The Ocean View Inn & Pub

2.0 star property
8.0 out of 10, Very good, (1)
The Ocean View Inn & Pub
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.
Don't see what you're looking for?
See all available properties in Islamorada
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Islamorada

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (403)
"nice warm pool, nice ocean views."
The price is €190
includes taxes & fees
12 Feb - 13 Feb
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (49)
"Lovely room with friendly staff. "
The price is €701
includes taxes & fees
2 Mar - 3 Mar
The Islands of Islamorada

WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!

9.6 out of 10, Exceptional, (76)
"Great and clean place to stay. Chris was the perfect host. "
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
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.

Frequently asked questions

Why book your cottage in Islamorada with Expedia?
We think that a holiday should be a piece of cake, so if you’re on the lookout for cottages in Islamorada at a great price, Expedia delivers. Stick to the budget and check in to an economical option surrounded by nature, or splurge on a luxury cottage to spoil your favourite people.
How can I find cheap cottages in Islamorada?
With Expedia’s useful filter tool, comparing cheap cottages in Islamorada couldn’t be simpler. To find stays that’ll make your wallet smile, refine your search by amenities, budget and star rating.
What is there to do in Islamorada near my cottage?
Islamorada has enough sights and experiences to entertain you for weeks (or months!), starting with Theatre of the Sea. Anne’s Beach, Florida Keys Brewing Co. and Windley Key Fossil Reef Geological State Park are other awesome attractions. If you have more time, Sunset Drive Beach and Indian Key Historic State Park are nice final touches to your itinerary.