Condo vacation rentals in Islamorada

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Popular amenities for Islamorada condo rentals

Condo rentals with a pool

Superhost
Condo in Key Colony Beach
4.75 out of 5 average rating, 164 reviews

2 Bedroom Oceanfront Complex Heated Pool KCB

RobertRating, 5 stars4 weeks ago
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!
Superhost
Condo in Key Largo
4.83 out of 5 average rating, 35 reviews

Relax in Key Largo

AnthonyRating, 5 stars7 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.
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.
Guest favorite
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, 282 reviews

Condo in the Keys, Peaceful ocean view retreat!

DavidRating, 5 stars2 weeks ago
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.
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 favorite
Condo in Key Largo
4.96 out of 5 average rating, 124 reviews

Kawama Suntastic @ Key Largo

VincenzoRating, 5 stars3 months ago
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!
Guest favorite
Condo in Key Colony Beach
4.91 out of 5 average rating, 140 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

ChristianRating, 5 stars1 month ago
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

Superhost
Condo in Tavernier
4.87 out of 5 average rating, 150 reviews

Reel Large END Unit in Ocean Point Suites

JohnRating, 5 stars1 day 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.
Guest favorite
Condo in Key Largo
4.9 out of 5 average rating, 30 reviews

Mariner's Club 126 - A SEA DWELLERS PARADISE 4 BR

AnnetteRating, 5 stars2 months ago
Susies home was perfect for our family vacation. Comfortable, lovely views and well located within the complex.
Guest favorite
Condo in Key Largo
4.93 out of 5 average rating, 15 reviews

3/3 ALLURING OCEAN VIEW - Mariner's Club Villa 521

SusanRating, 5 stars3 months ago
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.
Superhost
Condo in Key Largo
4.94 out of 5 average rating, 69 reviews

Mariner's Club 522 - Don't worry Beach Happy!

MeganRating, 5 stars1 week ago
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 :)
Superhost
Condo in Key Colony Beach
4.57 out of 5 average rating, 7 reviews

P21 - Charming 3 bedroom 3.5 bath duplex in Key C

KevinRating, 5 stars22 months ago
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.
Top guest favorite
Condo in Tavernier
5 out of 5 average rating, 46 reviews

Tequila Sunrise

DeannaRating, 5 stars1 week ago
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.
Superhost
Condo in Tavernier
4.97 out of 5 average rating, 97 reviews

Beautiful ocean view. Visit “Sangria Sunrise”!

DianaRating, 5 stars2 weeks ago
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!
Superhost
Condo in Tavernier
4.87 out of 5 average rating, 83 reviews

Turtle Nest 1 Ocean Point Condo “Newly Remodel”

SamanthaRating, 5 stars2 days ago
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

Guest favorite
Condo in Key Largo
4.98 out of 5 average rating, 57 reviews

Tropical Vibes! Renovated condo in gated community

MichelleRating, 5 stars4 months ago
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!
Guest favorite
Condo in Islamorada
4.75 out of 5 average rating, 64 reviews

Bayside Condo with Marina, Beach and Pool

HeatherRating, 5 stars2 months ago
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.
Guest favorite
Condo in Marathon
5 out of 5 average rating, 14 reviews

2BR oceanfront condo with open layout & pool

FaithRating, 5 stars2 weeks ago
Beautiful location and clean home. Pool was awesome and the beach was so convenient
Condo in Key Largo
4.86 out of 5 average rating, 37 reviews

3 BDRM Condo on the Bay - Moonbay, Key Largo

SaraRating, 5 stars6 months ago
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.
Condo in Islamorada
5 out of 5 average rating, 3 reviews

Large 1 Bedroom Oceanview Condo With Two Balconies

HaikoRating, 5 stars9 months ago
Adam is a great host. The apartment is in a resort that is great. Room was nice and spacious. Would book again
Superhost
Condo in Tavernier
5 out of 5 average rating, 3 reviews

Gone Coastal @ Ocean Pointe

GaryRating, 5 stars3 months ago
Nice place….exactly as described…..great location….easy access to restaurants….activities….great view….would stay again!
Top guest favorite
Condo in Marathon
4.96 out of 5 average rating, 100 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

JenneyRating, 5 stars2 days ago
Great little place for our family of 4! Very clean and the location was perfect for us. Would definitely stay again!
Guest favorite
Condo in Marathon
4.95 out of 5 average rating, 41 reviews

2-story condo w/ panoramic bay views and balconies

Eileen Rating, 5 stars2 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!

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

Destinations to explore

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  4. Monroe County
  5. Islamorada
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