
Holiday rentals with a pool in Lower Matecumbe Key
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Top-rated rentals with a pool in Lower Matecumbe Key
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Popular amenities for Lower Matecumbe Key rentals with a pool
House rentals with a pool

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
We booked this home last minute and now have our go-to vacation spot in Marathon! Alida is a friendly host with great communication. The home is very clean. Beds are very comfortable. Kitchen is well stocked with pots, pans, etc. The kayaks and paddle board made our vacation even more special! The steet is very quiet and peaceful. The setting in the back yard is very private, as is the long dock. We had a 23' rental boat for our stay. The view is amazing and the sunsets are a special treat each evening. I very much appreciated the ample, comfortable seating everywhere - inside and outside of the home. Thank you Alida. We made great family memories here!

Cancellation Deal: 08/02 thru 08/09
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

Beautiful Anglers Reef - 2/2.5 - Pool+Marina+Beach
Our first time at Angler's Reef and renting from Doug & Mary and we can't have asked for a better trip. First, Doug & Mary were great in providing everything we needed in advance and very responsive during our stay, couldn't have asked for a better host. The Lucky Lobster is well appointed; had everything we needed. All appliances appeared newer and functioned as they should, overall, the place was very clean and perfect for the five of us. The pool was very nice, and the area offers plenty to do. We rented a boat and went snorkeling at a couple of different sites and then hung out at the sand bar (which is extremely close to Angler's Reef). Anyway, we couldn't have had a better week and highly recommend The Lucky Lobster to anyone visiting Islamorada...

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

Private Pool! Luxury Paradise Pointe, Pet Friendly
Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!

Waterview from three sides, Cabana Club, 30' Docks
A Perfect Getaway! Our stay at this fabulous Airbnb was nothing short of amazing! The house was beautiful, clean, and offered breathtaking panoramic views of the open water. Waking up to the sunrise over the water was absolutely unforgettable. Brad, our host, was fantastic—super responsible, quick to respond, and incredibly easy to communicate with. He made the entire experience smooth and enjoyable from start to finish. The location was ideal for anyone who loves peace, nature, and especially fishing. We had plenty of opportunities to fish right from the property, which was a huge bonus. Highly recommend this place to anyone looking for a relaxing waterfront escape. We can't wait to come back!.
Apartment rentals with a pool

1BR - Key Largo Sun & Sand Hideaway
Had a great time at this spot in the Keys! Location: Short drive to many great restaurants and outdoor activities. Nice to be in the upper Keys to reach out flight back to Miami Accommodation: unit was clean, well equipped, and A/C worked great during a summer visit Amenities: the property was walkable, plenty of parking, and while the beach was there, we loved the late hours of the pool for a cool down swim before bed Host: incredibly detailed, proactive information so no surprises. Made for easy arrival. No crazy asks of guests like some AirBnb's too. Would gladly return!

Reel Large END Unit in Ocean Point Suites
Something for the whole family to do right at location. Pool was great.

Gorgeous lagoon-front 2BR Townhouse with 2 pools
This place was just what we needed. It was the perfect size for our 4 plus a dog for 2 nights. It’s located in a nice community and close to a lot. I would stay here again!

Ocean Views at Ocean Pointe
We had a fantastic stay at this condo in Tavernier! The location was ideal—close to everything we wanted to see and do in the Keys. The unit was clean, comfortable, and well-stocked, with a beautiful view of the ocean that made every morning feel like a dream. The host was extremely responsive and made everything easy from check-in to check-out. Highly recommend this place—we’d love to come back!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
We really enjoyed our stay Beautiful condo extremely clean clear instructions wonderful place to stay pool and hot tub area are amazing. You can swim anytime which is really nice. Most places the pool closes at dusk. There is a nice poolside little restaurant and also a restaurant right by the beach area really convenient would go back there anytime

Tropical Getaway
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!

Modern and Coastal 3212 is Across from Pool
This is the perfect place to stay to explore the areas of Key Largo and Islamorada. The unit is very clean and nicely decorated. We had no issues and would stay there again. Highly recommend!
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Coral Castle
- Cannon Beach
- Conch Key
- Calusa Beach & Loggerhead Beach
- Everglades Alligator Farm
- Theater of the Sea
- EAA Air Museum
- Cocoa Plum Beach
- Long Beach
- Far Beach
- Horseshoe Beach
- Long Key State Park
- Windley Key Fossil Reef Geological State Park
- Keys' Meads