
Condo vacation rentals in Islamorada
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Top-rated condo rentals in Islamorada
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Popular amenities for Islamorada condo rentals
Condo rentals with a pool

2 Bedroom Oceanfront Complex Heated Pool KCB
We had a great time! Awesome community with walkable restaurants and bars. We loved the local beaches. The people at the complex were super nice. Our four boys loved running from the pool to the beach. Everyone we met was very nice. Great instructions and recommendations. Loved it!

Relax in Key Largo
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.

Den Suite Two Balconies- Islamorada
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.

2BR Spacious Condo, Balcony, Great Location
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 the Keys, Peaceful ocean view retreat!
Caroline’s Airbnb was in a perfect location, it was doors away from family and we spent 3 amazing days scuba diving in Islamorada. I would definitely recommend.

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

Kawama Suntastic @ Key Largo
Went to Cynthia's place 1/18-1/21. It was better than the pictures. The Kawama community, the lagoon and Key Largo are beautiful. First time visiting Key Largo and there's much to do.,,fishing, snorkeling, biking, and visit John Pennekamp Coral Reef State Park. I went with my three sons for a long weekend for fishing and went to Key West. The lagoon is few feet from the patio to enjoy a swim. My boys loved it. Cindy kept in touch with me to see if everything was good. I had a great time and her place is is neat, clean and meticulously maintained. Go and enjoy!

Beachside Unit 39 Tiki Huts, Private Beach & Pool
We had a wonderful time here, and Cindy's accommodation was simply perfect—just right for our family with two children. The location is unbeatable... right by the small private beach, where we could watch the sunrise, and in the evening, we enjoyed the sunset at Sunset Park. Communication with Cindy was great! Thank you so much, Cindy... we wish we could have stayed much longer and will definitely be back!
Condo rentals with a hot tub

Reel Large END Unit in Ocean Point Suites
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.

Mariner's Club 126 - A SEA DWELLERS PARADISE 4 BR
Susies home was perfect for our family vacation. Comfortable, lovely views and well located within the complex.

3/3 ALLURING OCEAN VIEW - Mariner's Club Villa 521
Our unit was very nice. The gated community made us feel safe. The unit had everything we needed, including beach towels left by the entryway. We enjoyed the lanai every morning because the view was beautiful. All in all, a great vacation. Note: The jacuzzi tub was not usable during our stay because of a malfunction. That was the only disappointing feature of the unit.

Mariner's Club 522 - Don't worry Beach Happy!
The condo was beautiful and perfect for our family of 4 for the week. Lot's of great restaurants and activities near by, including a walking and biking bath right across the street. The pools and hot tub were lovely, and we loved the balcony to watch the sunrise and see the moon at night. Our only comment we be maybe getting some more functional and comfortable patio furniture so we could enjoy that even more! Thanks for a wonderful week :)

P21 - Charming 3 bedroom 3.5 bath duplex in Key C
Leslie was very responsive and addressed questions quickly. House was perfect for 6 people with each room having a private bathroom. Very spacious and comfortable.

Tequila Sunrise
This was by far the cleanest rental we have stayed in. The inside of Kathryn's place was immaculate. The grounds in general were very clean and well kept. We saw multiple workers cleaning, doing landscape work, etc. during our visit. We spoke with several people we met who said their rentals were lacking certain things. That WAS NOT the case with Kathryn's place. She has honestly thought of everything from toiletries to coolers and pool toys. Ocean Point in general was amazing. The pool was HUGE. We loved having multiple places on site to grab a drink or food. Communication both during and leading up to our visit was very timely and informative. She was very accommodating. Overall we had a great experience and are already making plans to return again next year.

Beautiful ocean view. Visit “Sangria Sunrise”!
We really enjoyed our stay! The condo was beautiful, clean and exactly as advertised. The view from the balcony was gorgeous and very peaceful! Tracy was extremely helpful and easy to communicate with. Highly recommend!

Turtle Nest 1 Ocean Point Condo “Newly Remodel”
Place was so comfortable and cozy and clean! Great view and right near everything you need to get to. The host was so responsive and welcoming. Would definitely stay again!
Weekly condo rentals

Tropical Vibes! Renovated condo in gated community
Margaret was a perfect host in a perfect condo! We walked it and was immediately impressed. The amenities were fantastic. Overall a perfect experience. Thank you!

Bayside Condo with Marina, Beach and Pool
The photos and amenities were exactly as described. The home was comfortable and Glenn is amazingly responsive. His air blasts cold, the pool was heated and the grounds were nice.

2BR oceanfront condo with open layout & pool
Beautiful location and clean home. Pool was awesome and the beach was so convenient

3 BDRM Condo on the Bay - Moonbay, Key Largo
We had a wonderful week in Key Largo! Rebecca’s condo is in a great location and has plenty of room for a family. The pool is centrally located and has plenty of chairs for sunbathing. Watching sunsets from the balcony of the condo was one of our favorite things to do. The pool, small beach and clubhouse are all very close to the condo. The third bedroom with bathroom and small kitchen on the bottom floor was convenient. Rebecca is a very responsive host and we would definitely consider coming back again.

Large 1 Bedroom Oceanview Condo With Two Balconies
Adam is a great host. The apartment is in a resort that is great. Room was nice and spacious. Would book again

Gone Coastal @ Ocean Pointe
Nice place….exactly as described…..great location….easy access to restaurants….activities….great view….would stay again!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!

2-story condo w/ panoramic bay views and balconies
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!
Quick stats about condo rentals in Islamorada
Total rentals
90 properties
Nightly prices starting at
ﺩ.ﺇ257 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
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Zoo Miami
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Biscayne National Park
- Cannon Beach
- Long Beach
- Far Beach
- Monkey Jungle
- EAA Air Museum
- Theater of the Sea
- Sea Oats Beach
- Windley Key Fossil Reef Geological State Park
- Sandspur Beach
- Cocoa Plum Beach
- Horseshoe Beach
- Everglades Alligator Farm
- Long Key State Park
- Keys' Meads