Vacation rentals with a pool in Islamorada

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Popular amenities for Islamorada rentals with a pool

House rentals with a pool

Superhost
Home in Marathon
4.76 out of 5 average rating, 25 reviews

Sunset Views, Pool and Dock

GregRating, 5 stars3 weeks ago
Thank you Frank for a great place to stay! Close to restaurants, quite neighborhood, nice pool, a dock to swim and fish from, and beautiful sunsets. We had everything we needed.
Guest favorite
Home in Key Largo
4.94 out of 5 average rating, 72 reviews

Casa Solaris | Key Largo home with Private Pool!

JessicaRating, 5 stars1 month ago
My family had a wedding in Key Largo and wanted a nice space to hold 6 people with a private pool. This place matched our needs perfectly! It's incredibly spacious, has amazing amenities and of course had the most beautiful pool and spa. I loved how there was a separate downstairs area with a kitchenette so my husband and I could have extra space as well. It was also close distance to restaurants and grocery stores. Sean always answered quickly and offered help if we ever needed it. It was the perfect house for our little getaway.
Guest favorite
Home in Marathon
4.89 out of 5 average rating, 75 reviews

Dream Vacation KCB Marathon with private pool !

AlexsisRating, 5 stars1 week ago
Alfonso, place was great to stay! beautiful view, my son was able to give a manatee water from the dock. we saw tarpon, snappers, needle fish and much more from the deck. Friendly neighbors! very peaceful surroundings. Alfonso, was very responsive and polite . Worth the price, my family loved it!
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars4 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.
Superhost
Home in Islamorada
4.86 out of 5 average rating, 7 reviews

Venetian Tropics private heated pool at 82 degrees

JessicaRating, 5 stars8 months ago
I’d like to start this review with JoAn is amazing and super responsive. If you need anything, she will ensure that you will get it. This house is the epitome of what you would expect for a Florida keys home. If you’re looking for a house with a lot of character, in a phenomenal location for Atlantic access and fuel, this is the place. We throughly enjoyed our time staying here and will be back next year. The pool was nice to get into after diving every day, there was a fresh water hose on the dock, a freshwater outside shower and even a fish cleaning station. There is a deep freezer for ice and a tiki bar outside with a sink. Couldn’t be any happier with the house or the host. Thanks again JoAn for letting us use your house.
Guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 84 reviews

“La casa azul” step 3’ to a private pool

RickRating, 5 stars3 days ago
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.
Superhost
Home in Key Colony Beach
4.83 out of 5 average rating, 12 reviews

P22 - Updated 3 bedroom 2 bath duplex with private

BrittanyRating, 5 stars32 months ago
We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.
Guest favorite
Home in Marathon
4.96 out of 5 average rating, 113 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JasonRating, 5 stars3 days ago
We really enjoyed this home in Marathon. Sitting by the canal for morning coffee, swimming in the pool on a hot afternoon, having dinner on the covered porch, or plying corn hole on the roof… it was all super enjoyable. Andy even dropped off some wonderful bagels one morning! The location is super close to all that Marathon has to offer. We would recommend this home to anyone

Condo rentals with a pool

Guest favorite
Condo in Tavernier
4.95 out of 5 average rating, 20 reviews

Resort Condo: Pool, Beach, Marina, Pickleball

WilliamRating, 5 stars3 weeks ago
That’s great enjoy we had a good time. Thank you once again and I would recommend it.
Guest favorite
Condo in Tavernier
4.89 out of 5 average rating, 133 reviews

1BR - Key Largo Sun & Sand Hideaway

JosephRating, 5 stars1 month 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.
Guest favorite
Condo in Key Largo
4.93 out of 5 average rating, 107 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

JodiRating, 5 stars3 weeks ago
Would definitely rent again! Relaxing with plenty of outdoor spaces to enjoy. Comfortable condo with everything you need.
Superhost
Condo in Key Largo
4.81 out of 5 average rating, 36 reviews

Relax in Key Largo

AnthonyRating, 5 stars9 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 Marathon
5 out of 5 average rating, 5 reviews

*NEW* Finer Things-Beach/Pool

Michael StephenRating, 5 stars1 week ago
I would love to stay here every year for my anniversary! Yuni was a great host. The place was clean and quiet and perfect. My husband and I loved it. Hoping to get to go again in 2026.
Guest favorite
Condo in Key Largo
5 out of 5 average rating, 20 reviews

Key Lime Breeze Retreat!

LisaRating, 5 stars1 month ago
Loved our stay!!! Close to great restaurants!! The condo was beautiful, extremely spacious loved the studio apartment. That space provided much needed space for family of 8; Very clean, beautiful pool with grill.
Guest favorite
Condo in Key Largo
4.96 out of 5 average rating, 127 reviews

Kawama Suntastic @ Key Largo

AveryRating, 5 stars2 weeks ago
Cindy’s place was even better than the pictures! The location was quiet and serene. The condo itself was immaculate. Cindy was a very helpful and responsive host. We loved the walkway around the saltwater lagoon and our children kept busy with swimming, kayaking, SUP, etc. This is a place we will definitely visit again. Highly recommend for families or a couple looking for a peaceful getaway!
Guest favorite
Condo in Key Largo
4.88 out of 5 average rating, 162 reviews

Tropical Getaway

TrevorRating, 5 stars2 weeks ago
We had a great stay at Kawama, Key Largo Everything was as described in the listing and photos. Great location, good facilities with the pools, creek and beach options. We enjoyed sitting in the shade by the beach having a drink and snacks as the sun went down. Also really handy for snorkelling at John Pennekamp. Would highly Recommend Many thanks Gladys!

Quick stats about vacation rentals with a pool in Islamorada

  • Total rentals

    610 properties

  • Nightly prices starting at

    $70 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