Condo vacation rentals in Islamorada

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Popular amenities for Islamorada condo rentals

Weekly condo rentals

Superhost
Condo in Key Colony Beach
4.75 out of 5 average rating, 165 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

MichaelRating, 5 stars2 weeks ago
My family and I thoroughly enjoyed staying at Anne’s place! She was a great host and has a phenomenal place! We hope you check it out! Comfortable beds and enough room for my family of four (2 kids; 10 and 7). The property was very clean, well kept, and a great location! Steps away from a heated pool and private beach! We had kayaks and a stand up paddle board delivered to the rack on the private beach. Anne provided some great tips on where to explore with the kayaks. Anne was a great communicator and allowed us check in a little bit early, which was so kind. Will defiantly be back with my family! Check it out you won’t be disappointed!
Superhost
Condo in Tavernier
4.87 out of 5 average rating, 150 reviews

Reel Large END Unit in Ocean Point Suites

JohnRating, 5 stars1 week ago
Nice, clean and quiet place. pool was nice. Nice view off the balcony is of the mangroves. Beach area is nice but pretty rocky once you get into the water.
Superhost
Condo in Key Largo
4.82 out of 5 average rating, 49 reviews

Key Largo Treasure at Kawama Yacht Club

LeanneRating, 5 stars7 months ago
Even better then the pictures. Chelsea was so helpful as a Hurricane was coming in on our trip and she offered to let us come early or stay longer. Fast communication and clear instructions in the welcome and farewell email. We would absolutely stay again. We had a wonderful time and the place was perfect! Highly recommend!
Superhost
Condo in Islamorada
4.77 out of 5 average rating, 13 reviews

Den Suite Two Balconies- Islamorada

GaurangRating, 5 stars1 month ago
Great spot to spend days for vacation. Great service by office staff. They took care of all requests we had in the most friendly manner. The hotel is located right on the water, so views were great. Nice pool and great vibe. Would highly recommend.
Superhost
Condo in Tavernier
5 out of 5 average rating, 4 reviews

Gone Coastal @ Ocean Pointe

SheilaRating, 5 stars2 months ago
Loved the home and the area. Look forward to to coming back.
Guest favourite
Condo in Marathon
4.95 out of 5 average rating, 42 reviews

2-story condo w/ panoramic bay views and balconies

Eileen Rating, 5 stars3 weeks ago
Words can't really express the beauty of this rental inside and out. Fully stocked with whatever your needs are. Full sized washer and dryer were perfect. Absolutely spotless inside. Beach towels were ready to go as well. The two porches were wonderful for relaxing and taking in the breathtaking views. We saw a family of 7 manatee several days in a row. A family of parrot fish almost every day (several times a day). We saw a VERY LARGE sea turtle just hanging out in the bay. Lots of tarpon, several sharks, pinfish, yellow snapper and several conches (even one queen conch). It is worth it to snorkel feet from the porch. My daughter even caught a shark. The pier was perfect for fishing and watching all the wildlife. The landscape is beautiful. The pool is amazing (I used it almost every day for a bit and no one was down there). I cant say enough good things about this space. It's worth every single penny. We will DEFINITELY be back!
Top guest favourite
Condo in Marathon
4.96 out of 5 average rating, 100 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

JenneyRating, 5 stars1 week ago
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!
Superhost
Condo in Key Colony Beach
4.85 out of 5 average rating, 110 reviews

Beachside Unit 37 - Come Relax on the Atlantic!

ChristinaRating, 5 stars1 month ago
My little family loved our stay here. We loved the little beach and warm pool. We all wish we could stay longer and would love to come back in the near future!

Pet-friendly condo rentals

Superhost
Condo in Marathon
5 out of 5 average rating, 3 reviews

Beach/Docks Avail/3 Pools/Hot tub/Gym/Restaurants

MichaelneuroRating, 5 stars4 months ago
Great experience, great host and accommodations. Hot tub wasn't working while we were there, but repair was delayed over the holiday week which was out of the hosts' control. Very communicative and responsive.
Guest favourite
Condo in Key Largo
4.94 out of 5 average rating, 102 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

MarthaRating, 5 stars2 weeks ago
The home was immaculate, all the necessary dishes, pans, appliances. There were no extras such as coffee filters or cooking oils etc. The setting was very beautiful and well maintained and many amenities. It is a family friendly community with multiple young children. Location near restaurants and activities was great. And we really enjoyed the screened in porch. Thanks!
Guest favourite
Condo in Marathon
5 out of 5 average rating, 6 reviews

Seashells Getaway - Boat Slip, Ramp, Pool

TaraRating, 5 stars5 months ago
Hello. We Booked this place so I could be in the sun on a lounge chair and husband could fish. It was exactly what we wanted. We were able to hang out together and both get what we wanted. He caught fish like crazy! Place is beautiful and exactly how described. Getting an Uber/lyft was easy. Sombrero Beach was beautiful. Ana was excellent to communicate with. Condo bed was very comfy and the bedroom dark. The use of a cooler and beach chairs was appreciated. Would not hesitate to book again.
Top guest favourite
Condo in Key Largo
5 out of 5 average rating, 17 reviews

Key Largo Condo

BertRating, 5 stars2 weeks ago
This condo was everything it said it was. Very clean. Great location, clean and serviceable furnishings and an awesome view. One thing that really struck out for me was that the kitchen had everything that you would need without being stuffed with a lot of extra stuff you don’t need. Also the pots and pans were very clean and almost new. Michael was very responsive to all our questions and made sure that we were happy with everything. We would definitely stay here again and recommend it to anyone interested in staying in Key Largo.
Superhost
Condo in Key Largo
4.92 out of 5 average rating, 37 reviews

key Largo 3 Bedroom Townhouse Gated Community

TriciaRating, 5 stars1 month ago
Everything was great! Nice area, and easy access to local activities. we enjoyed our stay.
Condo in Homestead
4.56 out of 5 average rating, 16 reviews

Best Studio Inn

TonyRating, 5 stars2 months ago
Jamel's Airbnb is a studio suite in a hotel - it was a great value for the money. Everything was clean and soap, shampoo, and towels were all provided.
Guest favourite
Condo in Key Largo
4.91 out of 5 average rating, 77 reviews

Hidden Key Hideout

SylviaRating, 5 stars3 weeks ago
Such a lovely location along a creek with access to kayaks. We enjoyed taking them out and just watching the water from the balcony. The place had everything we needed and was a short distance from Key Largo.

Condo rentals with a pool

Guest favourite
Condo in Tavernier
5 out of 5 average rating, 24 reviews

A place in the Sun

RyanRating, 5 stars1 month ago
We really enjoyed our stay. The place was very nice. There are a lot of activities nearby ranging from kayaking, to snorkeling, to boating. The pool in the complex was great! We would definitely stay there again.
Superhost
Condo in Key Largo
4.83 out of 5 average rating, 35 reviews

Relax in Key Largo

AnthonyRating, 5 stars8 months ago
Paradise, I stayed for five weeks. July 27th-Sep 3rd. Entire Moonbay Is a condominium resort. It is huge and has everything you could ask for. The grounds are meticulously kept. The pool is gorgeous and brand heated. No one is there in August so I had the entire place to myself. The snowbirds don't return until October. kid's were in school and I was in heaven. Thank you Arthur for sharing your little slice of paradise. I will be back permanently ASAP.
Condo in Tavernier
4.83 out of 5 average rating, 35 reviews

Oceanfront condo in the keys

SusanRating, 5 stars4 weeks ago
This location is the jewel of the Keys. Private, safe and with an incredible view of the ocean and sunrise. I’ve stayed many times in the area and this is absolutely the best. Owner is extremely helpful and available for any questions. Condo has a well stocked kitchen for cooking with great restaurants nearby. Big, fluffy oversized towels are provided. Being on the second floor near the stairs made that the easiest route in and out. Great group of people we met at the pool, many returning every year for extended stays. Just a wonderful place and hoping to return again next year. Thank you so much, Jeanette!
Guest favourite
Condo in Marathon
5 out of 5 average rating, 5 reviews

2BR Spacious Condo, Balcony, Great Location

JohnRating, 5 stars3 months ago
Check in/check out was easy! Nice and clean, pool and hot tub area was clean and the pool was nice and warm. We will definitely be check CoolVacay's properties for our next vacation.
Condo in Tavernier
4.85 out of 5 average rating, 284 reviews

Condo in the Keys, Peaceful ocean view retreat!

WendyRating, 5 stars2 days ago
Loved it! The host responded so quickly to our inquiry, allowing us to book very last minute. This is a great place with wonderful amenities. We came to paddle-board and snorkel. The beach on property makes it easy! We had a wonderful weekend getaway here. Thanks so much!!
Condo in Tavernier
4.5 out of 5 average rating, 4 reviews

Ocean View 2BR - Pool, Beach – Relax. Unwind.

HeidiRating, 5 stars5 months ago
I was a little bummed out about the non refundable vacation as I thought the price I had agreed to pay was for two days…. Requested a refund and they declined the request. We found out the waves would be too big for the purpose of our trip of going on a fishing charter for our son’s 10th birthday…. Bummed we didn’t get to do that but he got sick anyways so we just enjoyed the scenery. I was a bit nervous about the vacation and the amount I paid however…. After getting there and spending the one night there we were extremely pleased with the place and how clean it was and the top quality furniture and everything else. We will be back but we will make sure we take more time off to really enjoy all that this place has to offer. Thanks again ❤️
Guest favourite
Condo in Key Largo
4.96 out of 5 average rating, 126 reviews

Kawama Suntastic @ Key Largo

Carolina BeatrizRating, 5 stars1 week ago
My family and I had an absolutely wonderful stay. We enjoyed swimming and powder boarding in the lagoon, feeding the fish, fishing off the point, relaxing poolside, and enjoying our time in Key Largo. Check-in was super easy and the owner, Cindy, was an absolute delight. Very smooth and easy, five stars, highly recommend, especially for children or anyone looking for a relaxing time.
Guest favourite
Condo in Key Largo
4.92 out of 5 average rating, 25 reviews

Serene Sunsets - Private Tropical Island Condo

JamesRating, 5 stars9 months ago
Kent's place was in a great location. We enjoyed all the amenities and beautiful sunsets every night. We will definitely be back to this location. Kent was always quick to respond to any questions I had. Great host!

Quick stats about condo rentals in Islamorada

  • Total rentals

    90 properties

  • Nightly prices starting at

    $97 CAD before taxes and fees

  • Total number of reviews

    660 reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Rentals with a pool

    80 properties have a pool

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
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