Vacation rentals in Upper Matecumbe Key

4.96 out of 5 average rating, 115 reviews

Paradise Casa Bayfront sunsets,pool,King bed ,dock

KimRating, 5 stars1 week ago

We really enjoyed our time at Paradise Casa. A great spot to get to Pennekamp quickly and enjoy each sunset right outside the RV. The inside was well laid out and our family of 5 was very comfortable. Everything was very clean and user friendly. We spent a lot of time outdoors looking over the water, listening to the palm fronds sway in the breeze and relaxing. Just know that the empty lot next door does become the local fishing spot. Overall the stay was wonderful

Vacation home in Key Largo

A bright, open-concept living area features a light-colored sofa adorned with decorative pillows and a wooden coffee table. A dining table with white chairs is positioned near large windows, while a modern kitchen with stainless steel appliances is visible in the background. A rattan chair adds a touch of texture.

4.94 out of 5 average rating, 116 reviews

Ocean Shores Villa 3 with pool and boat slip

KellyRating, 5 stars1 week ago

We stayed for 3 days for kids spring break to travel down to the different Keys and eventually hit Key West. We were on the 3rd floor unit. The space was very clean. Kitchen had everything you need to make a basic meal. Small balcony to overlook the waterfront. There were little toys for the kids to play. There’s a communal storage room that had all sorts of goodies: life jackets, fishing rods, electric scooter, ice maker. We didn’t have time to use the bikes and kayaks. The kids enjoyed the pool. Noodles were provided as well. The neighborhood was nice. There’s a seafood market/eatery across the street. One small thing but it didn’t affect our stay as much: the lights kept flickering. It was a cozy stay overall and I would definitely come back!

A serene waterfront scene is depicted, featuring a calm body of water reflecting the soft hues of dusk. A thatched-roof structure and a boat are aligned along the shore, surrounded by lush greenery and rocky formations.

4.92 out of 5 average rating, 26 reviews

146 RV Vacation Rental n Key Largo Kampground, FL

SusanRating, 5 stars3 weeks ago

Julie’s place was great as a snowbird escape! The weather in Key Largo is fantastic and her location is great! The pool was heated and had plenty of deck chairs. The sandy beaches at the campground made it super easy to launch our kayaks and get to the mangrove kayak trails super fast. There are so many restaurants in town to try, and Publix grocery store is super close (walkable if needed). Her outside patio is super relaxing and has an outside tv (where we watched the Super Bowl). The bikes at her site were a great amenity too! We loved our time at Julie’s place!!!

4.93 out of 5 average rating, 155 reviews

A serene waterway is framed by lush greenery, with the calm surface reflecting the surrounding trees and structures. Boats are docked at a well-maintained pier, with the gentle morning light casting a warm glow on the scene.

Apartment in Key Largo

2/1 Oceanfront Apartment with Dockage

GabbyRating, 5 stars3 days ago

This was my favorite Airbnb I have ever stayed in. The unit is stunning inside and very modern. The view is beyond gorgeous. The location is perfect and only a short walk to fantastic beach side restaurants. The hosts were very accommodating and made our stay very memorable. The unit is very clean and the furniture is also in great condition.

4.99 out of 5 average rating, 106 reviews

Condo in Tavernier

Modern and Coastal Ocean Pointe 2307

LeahRating, 5 stars1 month ago

Exactly as pictured! Beautiful getaway in the Keys! It was very clean, even up to my picky healthcare expectations! Had everything we needed! A few more towels would have been great but we made it work. Kitchen stocked with all we needed. It was great to know what amenities and products were included and how much up front. The recommendation book was awesome! Beds were comfortable, all tvs worked well. Nice to have cable included too! The pool was absolutely beautiful, especially at night. Very clean facility outdoors as well. The beach area was probably the only disappointment, and out of their control. Just wasn’t as sandy etc. as we thought from pictures. Still very nice. It was also so nice to have a door code and not worry about a key. The neighborhood was welcoming too and safe to go for a morning run. All in all we would highly recommend this condo for your Keys vacation, family or couple! Our family of 6 fit :). Thanks for a great home away from home!

5 out of 5 average rating, 34 reviews

A covered outdoor area features a billiards table, surrounded by tropical landscaping and views of a pool. Comfortable seating is arranged nearby, with a small dining set on a lush green lawn. Palm trees and a tranquil atmosphere are prominent in the background.

Home in Marathon

Waterfront Escape -VACA-23-408

KimberlyRating, 5 stars4 days ago

To say this house was awesome is an understatement. We went with our adult children and grandson. There were so many fun activities for all of us, not to mention a large dock for our boat with a beautiful view. We even had a visit from two adorable manatees! Will definitely stay there again! Thanks Carmen

4.84 out of 5 average rating, 69 reviews

Townhouse in Key Largo

VOTED TRIPADVISOR'S #1 DESTINATION, POOL, TENNIS

KristinRating, 5 stars1 month ago

Pedro was extremely helpful and very responsive with communication. We had a few hiccups but Pedro was able to help sort it out. Beautiful house! Beautiful neighborhood! Very relaxing and accommodating for all ages and families! We had our 3 year old and 7 month old with their grandma and we all had a blast. Would definitely return!

4.64 out of 5 average rating, 111 reviews

A serene waterfront scene features calm turquoise waters with gentle waves. A thatched-roof gazebo extends over the water's edge, providing a shaded area. In the background, a row of palm trees sways slightly under the bright blue sky, adding to the tranquil atmosphere.

Cottage in Cudjoe Key

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

Elizabeth CarmenRating, 5 stars1 month ago

Jason’s place was a great place to stay in the keys!! Jason is great at responding great location, clean house only the couch could use a cleaning. It would have been nice if there were trash bags, extra hand soap and extra toilet paper. Other then that it was perfect!!

A relaxing outdoor seating area is surrounded by vibrant blue chairs facing a calm waterway. A central table features a fire pit, and string lights hang above. Lush greenery can be seen along the shoreline, creating a tranquil atmosphere.

4.78 out of 5 average rating, 18 reviews

A motorhome in paradise

RachelRating, 5 stars1 month ago

We stayed here over spring break 2025- and it was very fun. It has such close proximity to John Pennekamp State Park.. so if you are an avid snorkeler, this is the place for you. My kids loved the pool, and went for night swims every night. It's very safe, and the neighborhood can be a little loud at night, but if you close the windows it's so peaceful. We weren't here often ( out doing adventures on the Florida Keys) but it was a nice place to come back to after a long day. The hammocks are very very nice and the marina has a gorgeous view. Thank you!

4.82 out of 5 average rating, 110 reviews

Townhouse in Key Largo

Oceanfront Resort W/Indoor Pickleball - Spacious!

JulieRating, 5 stars2 months ago

We had a nice stay at the condo. The place was very clean and spacious. The beds were comfortable. There are 3 levels and another outdoor staircase to get up on to the rooftop area. The outdoor patio was nice to sit on in the morning and evening. The grounds and the pools at the resort were great. We spent most of the days outside. The condo is located in a busy area and close to restaurants and grocery stores. There are some basic supplies like small shampoo bottles and some spices for cooking but you will need to bring or buy your own. There are plenty of dishes and cookware between the 2 kitchens but no plastic cups to take outside.

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Popular amenities for Upper Matecumbe Key vacation rentals

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Free parking on premises

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Other great vacation rentals in Upper Matecumbe Key

5 out of 5 average rating, 5 reviews

Home in Key Colony Beach

Huge Swim Spa~ Incredible Special Fall Pricing

MatthewRating, 5 stars1 month ago

We really enjoyed our stay. The host, Sherry, gave timely information and quickly responded to messages. We were pleasantly surprised by the number of amenities that were available to us at the house. The Cabana Club was a real hit with my teenage daughters. It had reasonably priced drinks and lunch type meals. They enjoyed just laying by the pool or beach and sun tanning. We saw manatees one of the evenings right in the backyard of the home.

4.95 out of 5 average rating, 136 reviews

A wooden dock extends into clear turquoise waters, providing access to the surrounding landscape. Lush greenery and palm trees frame the serene view, while a brightly colored patio umbrella adds a pop of color nearby. The peaceful atmosphere is enhanced by the open sky above.

Villa in Marathon

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

StefanieRating, 5 stars2 weeks ago

My family and I stayed for a week and the house had everything we needed and more! The space was clean, comfortable and had lots of extras for the outside like pool floats, bikes, paddle boards, kayaks and more. The added touches inside like dish soap, hand soap, cleaning supplies, shampoo and conditioner was unexpected and a huge help. I was slightly surprised that this was an attached home, but there was still plenty of privacy and the location was extremely convenient. The hosts were very friendly and responsive and we would definitely recommend to others.

5 out of 5 average rating, 7 reviews

An outdoor space features colorful chairs arranged near a covered area, with palms swaying in the gentle breeze. A pathway of pavers winds through the landscape, leading to a hammock under a shade sail, surrounded by lush greenery and gravel.

Townhouse in Key Largo

Tropical Paradise at Moon Bay Key Largo, Florida

TomRating, 5 stars12 months ago

Great place to stay. Kitchen was well stocked. Had plenty of room for our family of 6. Steps from the pool. Gorgeous sunsets. Great location close to many local dive centers.

4.97 out of 5 average rating, 37 reviews

Paradise Key Largo

DeannaRating, 5 stars4 weeks ago

Our family of 5 just returned from vacation. My toddlers loved the pool and all the hammocks near the water. Niurka was responsive to any questions we had and gave local recommendations on where to take the kids. We had a great time and will definitely return.

4.75 out of 5 average rating, 4 reviews

Home in Marathon

SeaEsta! Bring your boat & 1 block to the beach!

KellyRating, 5 stars1 month ago

Our stay at John's place was amazing. The location was perfect as we went up and down the Keys spending time in Islamorada and a day in Key West. We walked the neighborhood and to Sombrero Beach. The set up for our boat was fabulous. We were able to leave it in the water to use everyday. The best part of John's house was the outdoor area in back. We stayed out there more than anywhere, of course the weather was perfect. Thank you for sharing your place with us John. We hope to be back!

4.94 out of 5 average rating, 16 reviews

A sandy beach area features several palm trees swaying gently in the breeze. A covered pavilion with picnic tables is visible, providing a shaded spot for relaxation. The calm water stretches into the distance, under a bright blue sky with scattered clouds.

Home in Key Largo

Key Largo Village getaway

WestonRating, 5 stars1 month ago

If you are looking for a place to stay in the Keys, look no further. To start things off, Jenn is the best host you can ask for!! She was extremely responsive and incredibly sweet throughout the whole stay. She would always check in on us at the perfect times and really helped us feel right at home. Best experience I have ever had with a host!! As for the AirBnB itself, it was absolutely perfect for what we were looking for. It is tucked in a private family-friendly neighborhood that does a good job of drowning out any noise from the roads. It was exceptionally clean when we arrived and the amenities were fantastic. Really felt like a home away from home. The location was also very convenient and made our day trips to Miami and Key West a cinch. It is also near lots of amazing local beaches, snorkeling and kayaking spots, and restaurants. We will definitely be staying with Jenn again anytime we are in the area!!

5 out of 5 average rating, 10 reviews

A serene view of the private pool is framed by lush palm trees and vibrant greenery. The clear water of the pool reflects the blue sky, while the calming canal is visible in the background, enhancing the peaceful surroundings.

Home in Key Colony Beach

Sleeps 8, 3 bedroom, 4 full bath, pool, 37.5' dock

JeffreyRating, 5 stars7 months ago

Excellent location in a quiet upscale neighborhood. The house was like new, everything was clean and fresh. Very well equipped kitchen and baths. Lots of space indoors and out, with a beautiful small pool! Would definitely recommend this property for a peaceful getaway in the heart of the Florida Keys!!!