Condo holiday rentals in Islamorada

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Popular amenities for Islamorada condo rentals

Weekly condo rentals

Guest favourite
Condo in Tavernier
4.87 out of 5 average rating, 31 reviews

Sea Side Whimsy Ocean Pointe -06

MartinRating, 5 stars6 days ago
We had a lovely overnight stay, Jennifer and Mark were so accommodating, the condo was perfect for what we wanted and we had a very comfortable stay. Thank you both for letting us stay in your piece of paradise.
Top Guest favourite
Condo in Key Largo
4.84 out of 5 average rating, 70 reviews

Tower 2 Master Suites 2 Kings Beds Marina Pool

ChelseaRating, 5 stars1 month ago
Pedro was an amazing host! We got in a little early and thought we were going to need to check in early and he was very accommodating! I had a few questions and he responded almost immediately which is more than impressive! The place is perfectly decorated, had a very homey feeling to it and everything we needed.
Guest favourite
Condo in Tavernier
4.91 out of 5 average rating, 22 reviews

Condo Resort: Pool, Beach, Marina, Pickleball

ThomasRating, 5 stars6 days ago
We had a great time. Condo was amazing. Everything we expected and more. Will definitly be back.
Top Guest favourite
Condo in Marathon
5 out of 5 average rating, 20 reviews

*NEW LUXURY*Sea Glass-Beach/Pool

NicoRating, 5 stars1 week ago
Great, clean and well organized apartment. Great little pool a good beach and some restaurants and bars in walkable distance. Yuni responded very quickly to our messages and took care of the online little thing that wasn’t perfect right away. The location on marathon is also great as there are many things to do and see in a 5-10 minute drive. Great stay. Would absolutely do again and recommend. Thank you Yuni!
Guest favourite
Condo in Key Largo
4.97 out of 5 average rating, 38 reviews

PENTHOUSE SUITE - OFFERS BEST PANORAMIC OCEAN VIEW

MelissaRating, 5 stars1 month ago
Our stay was everything we could have wanted. The view was incredible. The condo had everything we could need. We will definitely come again and recommend it to family and friends.
Top Guest favourite
Condo in Key Largo
5 out of 5 average rating, 17 reviews

Stylish & Secluded | Pool, Dock, Key Largo Living

AprilRating, 5 stars2 weeks ago
Great place for a family vacation, and perfect for kids! The lagoon is extremely convenient and fun for everyone. The fire pits and jetty are great for fishing and a relaxing night. The condo was just as pictured, extremely clean, and has everything you could need and more. It is located just around the corner from a ton of amazing restaurants. Would definitely come back again!
Superhost
Condo in Key Largo
4.93 out of 5 average rating, 72 reviews

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

BillRating, 5 stars1 week ago
Location of unit is beautiful! Amenities were also wonderful and resort like. Host provided a prompt response regarding some questions about the unit and addressed any concerns presented. Thank you for a relaxing stay!
Guest favourite
Condo in Key Largo
4.94 out of 5 average rating, 50 reviews

Million dollar view in Key Largo!

DarrylRating, 5 stars2 months ago
The condo was very nice. Lots of room, clean and easy to access. We loved the balcony, and spent a lot of time there. We enjoyed the kayaks a couple of different times as well. Our first time to The Keys and we enjoyed this spot.

Pet-friendly condo rentals

Condo in Islamorada

180 Degrees of Ocean Views, Lagoon and Florida Bay

NatashaRating, 5 stars5 months ago
The house was exactly what we needed for our family vacation. We all felt super at home. The kids made their space on the patio and loved the outdoor TV. We fished from the pier and beach, took day trips, and enjoyed dinner nightly on the patio. overall, exceed expectations.
Superhost
Condo in Marathon
5 out of 5 average rating, 3 reviews

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

MichaelneuroRating, 5 stars5 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 Layton
4.86 out of 5 average rating, 14 reviews

Keys Getaway- 2 bedrooms w/Boat Dock, Pet Friendly

DorothyRating, 5 stars2 weeks ago
Sea Bird Marina is the place you want to go if you have a boat. Plenty of slips and great help by TONY❣️❣️ everyone at the marina is very helpful. Plenty of great restaurants. We loved it there and will definitely be going back ❣️❣️
Guest favourite
Condo in Marathon
5 out of 5 average rating, 6 reviews

Seashells Getaway - Boat Slip, Ramp, Pool

TaraRating, 5 stars7 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.
Superhost
Condo in Key Largo
4.86 out of 5 average rating, 86 reviews

Oceanside Key Largo 3/3 kayaks included

StephRating, 5 stars1 week ago
We had a great stay at Rich's place. There were 6 of us (and our dog) so we were able to sleep on the first and third floors and then hang out together, watch TV, eat, etc. on the second floor. There was a lot to do in the complex (e.g., paddleboard the in the lagoon and fish off the jetty), and we were close to a ton of restaurants and places to do other activities as well. Rich was very responsive and checked on us often. We felt very safe. Would return again!
Top Guest favourite
Condo in Key Largo
5 out of 5 average rating, 19 reviews

Key Largo Condo

MykenzieRating, 5 stars2 weeks ago
This was hands down the best airbnb I have ever stayed at. It had EVERYTHING we needed besides basic groceries. It was also extremely clean when we arrived, everything worked properly and was in incredible condition. The pool was amazing - they play great music down there and there was even such a good food truck right outside the condo we went to a couple of times. The sunrise and view was so stunning each morning! I don’t have a single negative comment about our stay or the place! Thank you Michael!
Superhost
Condo in Key Largo
4.92 out of 5 average rating, 37 reviews

key Largo 3 Bedroom Townhouse Gated Community

TriciaRating, 5 stars3 months ago
Everything was great! Nice area, and easy access to local activities. we enjoyed our stay.
Guest favourite
Condo in Key Largo
4.89 out of 5 average rating, 80 reviews

Hidden Key Hideout

LaurenRating, 5 stars3 weeks ago
Diane's place was perfect for us. The views from the balcony, kitchen, master bedrooms om, and even master bath were beautiful! So much beautiful sunshine, and the place was so cute and clean. We loved being right on the canal, and the available kayaks and paddle board were super convenient and appreciated. We were sad to leave and would absolutely go back! Diane was a very fast communicator, and most of the communication was proactive. Very happy with that too!

Condo rentals with a pool

Top Guest favourite
Condo in Key Largo
5 out of 5 average rating, 20 reviews

Newly Renovated Piece ofParadise

WolfgangRating, 5 stars2 weeks ago
We had such a wonderful stay at Todd’s Airbnb in beautiful Key Largo! The place was modern, spotless, and thoughtfully decorated—it felt like a true home away from home. The kitchen was well stocked with everything we needed, which made cooking a breeze. There were so many fun things to do on the property, from grilling out on the BBQs to relaxing in the hammocks, and playing foosball or ping pong. The pool was awesome, and the marina was absolutely stunning—especially at sunset. Todd was an incredible host, full of helpful information and spot-on recommendations that made our trip even better. We’d highly recommend his place to anyone looking for a fun, comfortable, and well-located home base in Key Largo. Can’t wait to come back!
Top Guest favourite
Condo in Islamorada
5 out of 5 average rating, 27 reviews

Luxury condo with boat slip overlooking the bay

KerrinRating, 5 stars1 month ago
We have stayed at Lee and Loretta’s home several times over the past few years and it never disappoints! Clean, spacious, well appointed and comfortable - both Lee and Loretta are extremely responsive with any questions we have had during our stay - we love it there!
Condo in Tavernier
4.89 out of 5 average rating, 122 reviews

500 Burton Drive Tavernier, Key Largo

BettyRating, 5 stars1 month ago
My sister's and I absolutely enjoyed our stay! There were so many things to do close by - short and easy drive! The pool on site was fantastic & the bartender at the beach restaurant was Wonderful! She gave us tips, ideas and suggestions! The weather was awesome - a bit rainy on last morning. We stumbled on an amazing food tour - Craigsfoodtour at Islamorada & it was a MUST DO!!!! Thank you Dave for sharing this wonderful space! WE are all relaxed, connected & left with smiles & memories! Thank you Betty
Guest favourite
Condo in Key Largo
4.91 out of 5 average rating, 46 reviews

Key Largo Oasis

StefanRating, 5 stars1 month ago
We as a family are very satisfied with Michelle's condo. Our children are 5 & 9 years old and the condo and the community had a lot to offer for the. Everything from a beach area with kayak, a great heated pool, docks where we were watching shark fishing at night and the manatees came cruising by. The condo itself had everything we could wish for and was as described in the listing. Everything you need for the stay, even fishing gear is available in the condo. This is a great listing and the host was very quick to answer the questions we had. If you're planning to visit the Keys with kids, this condo is a great place!
Condo in Tavernier
5 out of 5 average rating, 3 reviews

Key Largo 2BR w/ Partial Ocean Views & Pool

KelseyRating, 5 stars2 months ago
Great place to stay! Check in part was a bit of a hassle as you have to check in at a different location down the road. All in all it was a beautiful spot and we enjoyed our time!
Top Guest favourite
Condo in Key Colony Beach
5 out of 5 average rating, 16 reviews

Private Beach in Marathons Key Colony Beach

KimberlyRating, 5 stars1 month ago
This was a repeat stay with us at Darene's place, and we will come again. Darene is great with communication and responds quickly. Her place is great! The ocean view never gets old. The beach at the condos is perfect, and the proximity to the pool is also perfect! The condo is nice and accomodating. The beds are very comfortable. We had everything that we needed during our stay, and we can't wait to return again! Thank you Darene!
Guest favourite
Condo in Tavernier
4.98 out of 5 average rating, 111 reviews

Modern and Coastal Ocean Pointe 2307

JimRating, 5 stars3 weeks ago
Clean, comfortable, nicely decorated, and in a nice complex. Love the pickleball courts. Condo is conveniently located for exploring the Keys with plenty of services nearby. Host’s managers are friendly and responsive. Strongly recommended
Top Guest favourite
Condo in Tavernier
5 out of 5 average rating, 5 reviews

Oceanfront 2 bdrm, 2 bath, View, Pool, Islamorada

MichalRating, 5 stars6 months ago
We stayed here for the Thanksgiving week. The place was nice, clean, and quiet. My kids enjoyed the playroom and the pool. The condo had plenty of board games to keep the kids entertained. The Keys have lots to offer, so there is always plenty to do. Donna was very responsive, the check-in was very simple, and we had a great time. Thank you for hosting us.

Quick stats about condo rentals in Islamorada

  • Total rentals

    90 properties

  • Nightly prices starting at

    $117 NZD 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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