Search Condos Rentals in Islamorada from CA $272

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Jan 31 - Feb 2
In two weeks
Feb 7 - Feb 9
In one month
Feb 21 - Feb 23
In two months
Mar 21 - Mar 23

Browse Select Islamorada Condo Rentals

Chesapeake Beach Resort
Private beach, white sand, sun loungers, beach towels

Chesapeake Beach Resort

2.5 star property
9.0 out of 10, Wonderful, (1385)
"Very clean! Nice staff!"
The price is CA $343
CA $457 total
includes taxes & fees
Jan 23 - Jan 24
Chesapeake Beach Resort
Cheeca Lodge & Spa
Private beach, sun loungers, beach umbrellas, beach towels

Cheeca Lodge & Spa

5.0 star property
9.0 out of 10, Wonderful, (1025)
"High-end resort with beautiful facilities but the restaurant wasn’t to the same standard. I thought the food was expensive and came out cold. The side order of mushrooms came out on a stone cold skillet, you could hold the skillet with your hand. The special that night I order was the seabass and risotto which was lukewarm. The restaurant wasn’t that busy so not sure how they let my food get cold. On a better note the king suit was amazing, so spacious and bathroom huge. The checkin staff were...
The price is CA $429
CA $579 total
includes taxes & fees
Jan 23 - Jan 24
Cheeca Lodge & Spa
Amara Cay Resort
Exterior

Amara Cay Resort

4.0 star property
8.8 out of 10, Excellent, (1210)
"A little help with baggage and getting a cart would have been super appreciated "
The price is CA $429
CA $578 total
includes taxes & fees
Jan 26 - Jan 27
Amara Cay Resort
La Siesta Resort & Villas
Outdoor pool, sun loungers

La Siesta Resort & Villas

4.0 star property
8.6 out of 10, Excellent, (1001)
"I understood that the place was pet friendly. However, nowhere in the booking process was I made aware that I would have to pay $50.00 per dog per night for the stay. Cost an extra $200.00 upon arrival. Somewhere in the process this was not made clear in any way that I saw. "
The price is CA $396
CA $540 total
includes taxes & fees
Jan 26 - Jan 27
La Siesta Resort & Villas
Islander Resort
Exterior

Islander Resort

4.0 star property
9.0 out of 10, Wonderful, (1003)
"Best 5 star resort in Florida keys, from the rooms, pools, beach area and staff. The staff at the hotel were so friendly, helpful and generous. A kind member of staff gave us an extra 25 cent for the laundry after helping to explain how it works. The rooms had modern facilities but the beautiful layout was classical beach house designed to make you feel completely relaxed. The pools were all heated/temperature controlled, so even if it was slight cold outside you can still enjoy a swim. Out of...
The price is CA $412
CA $553 total
includes taxes & fees
Jan 23 - Jan 24
Islander Resort
Coconut Cove Resort and Marina
Outdoor pool, sun loungers

Coconut Cove Resort and Marina

2.5 star property
7.4 out of 10, Good, (699)
"The property itself is amazing. The room was very clean and comfortable. The staff and property manager are incredible - super friendly, helpful and accommodating. We’d definitely stay again!"
The price is CA $271
CA $305 total
includes taxes & fees
Jan 23 - Jan 24
Coconut Cove Resort and Marina
Drop Anchor
Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view

Drop Anchor

3.0 star property
8.8 out of 10, Excellent, (1001)
"Good value for the money. Enjoyed using the kayaks and paddle boards. Friendly staff. Very good location on the water."
The price is CA $260
CA $343 total
includes taxes & fees
Jan 23 - Jan 24
Drop Anchor
Hadley Resort and Marina
Dock

Hadley Resort and Marina

3.5 star property
8.0 out of 10, Very good, (1001)
"Room is clean and staffs are very friendly. Ocean view room is worth the price."
The price is CA $270
CA $350 total
includes taxes & fees
Jan 23 - Jan 24
Hadley Resort and Marina
Fisher Inn Resort & Marina
Exterior

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1001)
"We had such a great experience! Nice room with a great view, friendly staff, dog friendly. The bikes, kayaks and paddle boards were a nice touch too!"
The price is CA $269
CA $349 total
includes taxes & fees
Jan 26 - Jan 27
Fisher Inn Resort & Marina
Treasure Harbor
25-inch flat-screen TV with digital channels, TV

Treasure Harbor

2.0 star property
9.2 out of 10, Wonderful, (48)
"Relaxing stay in a quiet lagoon. We enjoyed the manatees swimming in front of our houseboat every day. The facility was clean the staff were very friendly and restaurants were in easy walking distance. "
The price is CA $218
CA $490 total
includes taxes & fees
Jan 26 - Jan 27
Treasure Harbor
La Jolla Resort
View from property

La Jolla Resort

2.5 star property
9.0 out of 10, Wonderful, (1000)
"We had a great time at this resort. The amenities were perfect, kayaks, hammocks, snacks and don’t forget Felix the cat who made us feel more at home. My next trip I will book my full stay at LaJolla. It’s also walking distance to a few good happy hour locations. "
The price is CA $214
CA $281 total
includes taxes & fees
Jan 26 - Jan 27
La Jolla Resort
Sunset Inn
Outdoor pool, free cabanas

Sunset Inn

3.0 star property
9.2 out of 10, Wonderful, (1000)
"This is a nice hotel. It’s a old property but they keep it up very nice. No smells when you walk in, nice pool area , friendly front desk staff location is good. I would stay here again "
The price is CA $230
CA $275 total
includes taxes & fees
Jan 28 - Jan 29
Sunset Inn
Sands of Islamorada
Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio

Sands of Islamorada

2.5 star property
8.8 out of 10, Excellent, (354)
"The birds, I love the birds. I kept wanting to feed them "
The price is CA $307
CA $394 total
includes taxes & fees
Jan 23 - Jan 24
Sands of Islamorada
Ragged Edge Resort & Marina
Exterior

Ragged Edge Resort & Marina

2.5 star property
9.4 out of 10, Exceptional, (154)
"Love this property! We paid a little more for our stay as it was peak season. However, we felt it was worth every penny. I recommend to stay here. "
The price is CA $360
CA $405 total
includes taxes & fees
Jan 27 - Jan 28
Ragged Edge Resort & Marina
Pines & Palms Resort
Poolside bar

Pines & Palms Resort

3.0 star property
9.2 out of 10, Wonderful, (974)
"Place was under heavy construction, when booking stay know one mentioned the whole resort is under reconstruction. Besides the construction the location was beautiful setting "
The price is CA $227
CA $367 total
includes taxes & fees
Jan 28 - Jan 29
Pines & Palms Resort
Islander Bayside Villas and Boatslips
Outdoor pool, pool umbrellas, sun loungers

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 CA $388
CA $527 total
includes taxes & fees
Feb 4 - Feb 5
Islander Bayside Villas and Boatslips
Casa Morada
Outdoor pool, pool umbrellas, sun loungers

Casa Morada

3.5 star property
9.4 out of 10, Exceptional, (375)
"Staff very friendly and helpful. Beautiful grounds and very private. A great place to relax and unwind. "
The price is CA $540
CA $716 total
includes taxes & fees
Jan 29 - Jan 30
Casa Morada
The Caribbean Resort
Exterior

The Caribbean Resort

3.5 star property
10.0 out of 10, Exceptional, (149)
"Staff is always great. Rooms are beautiful & clean. Feels like I am at home"
The Caribbean Resort
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
3 outdoor pools, a heated pool, pool umbrellas, sun loungers

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 CA $559
CA $724 total
includes taxes & fees
Jan 29 - Jan 30
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort
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
Sign in
Sign up, it's free

Other property types in Islamorada

Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (398)
"This is a great little place to stay at a very good rate. It is walking distance to some amazing restaurants. The room had been updated, it was clean. Staff was friendly but I wouldn’t say they go out of their way. The beach is good for relaxing at but it’s pretty shallow a long way out so not much for swimming. The pool was nice but you lose the sun early due to placement. I’d stay here again."
The price is CA $222
CA $324 total
includes taxes & fees
Jan 26 - Jan 27
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (44)
"This property was immaculate, a great blend of an upscale hotel feel with a vacation rental. We loved all the amenities. Would highly recommend!"
The price is CA $655
CA $816 total
includes taxes & fees
Feb 11 - Feb 12
The Islands of Islamorada
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
Beach

Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip

10.0 out of 10, Exceptional, (5)
"We had a wonderful visit. We come every Thanksgiving. Anglers is wonderful place to stay."
Beautiful Waterfront Villa 133 Anglers Reef with On-Site Boat Slip
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

How much do condos in Islamorada cost?
The price range for condos in Islamorada is CA $272 to CA $368 per night. No matter your budget, you’re sure to find someplace that suits your pocket — as well as your entire crew! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Islamorada?
Islamorada has 354 condos. To help you book a place that’s perfect, make use of our filters to search for the amenities or perks you need.
Are there any family-friendly condos in Islamorada?
Take the crew to Topsider Resort By Capital Vacations and make your visit to Islamorada a comfortable one. This family-friendly condo has a 3.5-star rating and conveniences like a nearby waterfront and a terrace. After checking in and chilling out together in your cozy new digs, it’s time to head out and discover some of the local sights. Theater of the Sea and Anne’s Beach are top family-friendly attractions in Islamorada.
Why book your condo in Islamorada with Expedia?
Vacationing should be hassle-free, so if you’re after condos at an affordable price, Expedia has got your back. Save cash and check in to something small and cozy, or book a 5-star condo and really spoil your crew. Use our search filters to find a property in Islamorada that suits your needs.
How can I find cheap condos in Islamorada?
Expedia can help you track down cheap condos in Islamorada. To lock in the perfect stay in a matter of clicks, simply use our handy filter tool to refine your search by budget, star rating and amenities.
What is there to do in Islamorada near my condo?
Islamorada has enough activities and experiences to keep you on the hop for weeks (or months!), beginning with Theater of the Sea. Anne’s Beach, Florida Keys Brewing Co. and Windley Key Fossil Reef Geological State Park are other impressive attractions. If you’re in town for longer, Sunset Drive Beach and Indian Key Historic State Park will round off your itinerary nicely.