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Vacation rentals with a pool in Islamorada

Find and book unique homes with a pool on Airbnb

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Popular amenities for Islamorada rentals with a pool

House rentals with a pool

Guest favourite
Home in Key Largo
4.97 out of 5 average rating, 101 reviews

The Paradise 2

LeanneRating, 5 starstoday
We really enjoyed our stay. It completely matched the description, the patio was amazing, and the place was well stocked with everything we needed. It had many personal touches which made us feel at home. It was a great fit for two adults and 2 kids. Our time on the porch in the morning and relaxing in the evenings were the best part. Highly recommend!
Top guest favourite
Home in Key Largo
4.94 out of 5 average rating, 80 reviews

Large Waterfront Home, w/Efficiency, Pool, Kayaks

BrittanyRating, 5 stars1 month ago
We had everything we needed! Stu was helpful and responsive. We had a fantastic time and will be back in the future! Don’t miss a chance to stay here in Key Largo. Great location and loved keeping the boat behind the house. House is very clean and has all of the amenities you could possibly think of!! 10/10 recommend!
Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 66 reviews

Casa Solaris | Key Largo home with Private Pool!

AllisonRating, 5 stars2 weeks ago
Had a great time and the house was perfect for our group!
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars3 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Guest favourite
Home in Key Colony Beach
4.97 out of 5 average rating, 36 reviews

P23 - New 3 bedroom 2 bath duplex with private po

AndreaRating, 5 stars13 months ago
Our stay was wonderful! Key Colony is a quiet and peaceful community. Our condo was beautifully decorated and had everything we needed for the first couple days. The sheets and towels were soft The beds were very comfortable. We really enjoyed our stay and hope to go back soon again!
Guest favourite
Home in Marathon
5 out of 5 average rating, 34 reviews

Amazing Bayfront New House with Dock and Pool!

SuzieRating, 5 stars1 month ago
We had a great stay. The highlights were the view of the bay and the heated pool. The beds were comfortable and the open space was great to gather as a family. Unfortunately we didn’t catch too many fish but had a great time trying. The paddle boards were perfect for our teenage kids. Would definitely love to return.
Superhost
Home in Marathon
4.73 out of 5 average rating, 59 reviews

Gorgeous 3/2 SFH Brand-new pool&spa, 30ft dockage

BryanRating, 5 stars2 months ago
Everything about this place was perfect! The location was great, plenty to do in the immediate area and close enough for a day trip to Key West. The pool and backyard provided everything we needed for those lazy days we just wanted to stay in and enjoy the Florida weather. Boat dock was really convenient for our boat rental. Fully functional kitchen and grill allowed us to prepare meals when we wanted. Our host was available anytime we had questions. Honestly don’t have one negative thing to say!
Superhost
Home in Marathon
4.82 out of 5 average rating, 17 reviews

Sale! Pool, Hot Tub, Dock & Putting Green!

NicoleRating, 5 stars3 weeks ago
We had an amazing time! The location is perfect with so many things to do, pool, hot tub, canal, etc. The home was overall beautiful and we loved every second of it!

Condo rentals with a pool

Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 17 reviews

Resort Condo: Pool | Marina | Beach | Pickleball

SamRating, 5 stars1 week ago
This place was great for an in between Miami and Key West! The pool was perfect for relaxing at all day! Restaurants near by were all fantastic! Doable drives for day trips to key west and Miami!
Guest favourite
Condo in Tavernier
4.89 out of 5 average rating, 133 reviews

1BR - Key Largo Sun & Sand Hideaway

JosephRating, 5 stars2 days ago
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.
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.
Guest favourite
Condo in Key Largo
5 out of 5 average rating, 17 reviews

Key Lime Breeze Retreat!

SamRating, 5 stars1 week ago
Kim's place was perfect for our extended family. The full unit (kitchen, lounge, bathroom, and bedroom) downstairs was perfect for my parents to stay while my family of 4 plus my sister stayed upstairs where there is another kitchen and lounge as well as 2 bedrooms. Facilities in the complex were fantastic with a huge pool, tennis and pickle ball courts, and clubhouse. The location was great to get anywhere in Key Largo as well as the rest of the Keys. Last, but definitely not least, the hosts were extremely responsive and helpful with all the questions and things that came up during the stay. Would definitely recommend and stay again if we are back in the Keys.
Guest favourite
Condo in Tavernier
4.9 out of 5 average rating, 279 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

KristenRating, 5 stars3 days ago
My twin sister and I had such a wonderful time at Kim's home celebrating our birthday. She is super responsive and the place was exactly as described! It was so nice to sit on the patio in the morning and overlook the beautiful water. Pool is very nice and plenty to do in the property with the beach, tennis courts, BBQ, restaurant/baror just walk around in a safe, secluded environment. Condo was perfectly appointed with all the comforta and amenities of home! Can't wait to visit with Kim again! Wish I could give her 10 stars !!!!
Guest favourite
Condo in Tavernier
4.92 out of 5 average rating, 141 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

BrianRating, 5 stars1 week ago
The unit is just like the photos and was very comfortable! John was helpful and helped make for an enjoyable stay! Would happily stay here again
Top guest favourite
Condo in Tavernier
4.98 out of 5 average rating, 194 reviews

Ocean Views at Ocean Pointe

HopeRating, 5 stars3 weeks ago
Michelle was great! Very responsive and understanding when we had to make a last minute trip change. Unit was clean, bright and had a nice view. It’s a nice location between Key Largo and Islamorada making it convenient to explore both. We didn’t use any of the resort’s amenities, but there was an influx of seaweed at the small beach. Just one downside of this time of years in the Keys. But the pool looked great!
Guest favourite
Condo in Tavernier
4.9 out of 5 average rating, 120 reviews

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

JeffRating, 5 stars6 days ago
This place checked all the boxes! The location of this particular unit was awesome. Close to the pool, but not too close. A short walk to the beach area, and those views from the balcony are second to none. Largo is very responsive and very easy to communicate with. Tavernier Key is the perfect location to many activities. Our family misses this trip already.

Quick stats about vacation rentals with a pool in Islamorada

  • Total rentals

    610 properties

  • Nightly prices starting at

    $97 CAD before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Family-friendly rentals

    420 properties are a good fit for families

  • Pet-friendly rentals

    260 properties allow pets

  • Rentals with dedicated workspaces

    340 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Rentals with pools