Family-friendly holiday rentals in Lower Matecumbe Key

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Popular amenities for Lower Matecumbe Key family-friendly rentals

Family-friendly home rentals with a hot tub

Top Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 45 reviews

Florida Keys Retreat / Completly remodeled

SeanRating, 5 stars1 month ago
Perfect for our family of 5. Great outdoor area at the house for fishing and relaxing. The layout was great for us because of the separation from the master to the kitchen/living room…our baby could sleep and we didn’t have to worry about making noise and waking up the baby. KCB is in a great central location for exploring the Keys. We were also pleasantly surprised at the quality of restaurant’s nearby. The Cabana Club was crowded and has a small beach. Drinks there were good. I have nothing overly negative to say, other than that I wouldn’t look to stay in KCB or this property if you just want to hang at the pool and beach all day. But it was fine for a few easy afternoons between other activities in the area. We highly recommend and would stay again!
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 92 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

MondeRating, 5 stars2 weeks ago
Our stay in Marathon couldn’t have gone any better! I traveled with my three 20-something sons and their wives/significant others. The layout of Gerardo’s home was perfect for our needs. We had plenty of room, places to enjoy together, and space where everyone could find some peace and quiet. The location was ideal. We were within an easy driving distance of all excursions and restaurants and could even walk to Island Fish Company, which was one of our favorites. Gerardo was extremely responsive. He checked in prior to our arrival and touched base a couple of times to make sure there was nothing we needed. An excellent home I recommend to others with no hesitation!!
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Home in Marathon
4.4 out of 5 average rating, 5 reviews

One Particular Harbor ~ Pool Home, 110' Dock

DianeRating, 5 stars2 months ago
Our group of six adults loved our stay at One Particular Harbor! The property was beautiful and spacious! The pictures couldn’t do it justice. Our hosts were very helpful and attentive! We would definitely stay there again.
Superhost
Townhouse in Key Largo
4.82 out of 5 average rating, 110 reviews

Oceanfront Resort W/Indoor Pickleball - Spacious!

JulieRating, 5 stars3 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.
Superhost
Home in Duck Key
4.72 out of 5 average rating, 72 reviews

Duck Key Darling: 2-Bedroom, 2-Bath Townhouse with

SarahRating, 5 stars3 months ago
Our family of 5 enjoyed our stay on Duck Key! It was centrally located on the Keys to enjoy adventures on either side of us. The access to the Cabana Club was the best attribute of the rental. Our boys (ages 7, 8, & 10) wanted to go every day for the heated pool and beautiful beach access. We enjoyed the affordable drinks and food there, along with a safe and trusting community of people there.
Guest favourite
Condo in Tavernier
4.84 out of 5 average rating, 154 reviews

Bright & Sunny Suite w/ Magnificent Ocean Views

LisaRating, 5 stars1 month ago
Everything was as expected from the description and the pictures. Comfy beds. TVs are older and not many apps available to stream other than Netflix. Overall it was a great location and we had a great time. The poolside restaurant is open now so that was a bonus I wasn’t expecting after reading the previous reviews.
Superhost
Home in Key Colony Beach

VR44 Coral Cove

TimRating, 5 stars2 months ago
Very well laid out house. Plenty of room for our large family vacation. House was well equipped for long stay. Short walk to club which has beach access. Host left the best key lime pie for us upon arrival. The only minor thing was listing said four bikes were included. Host advised bikes had not been included for some time. Would definitely stay again.
Superhost
Townhouse in Key Largo
4.87 out of 5 average rating, 60 reviews

Family Key Largo Townhome for Fun Sun & Relaxation

DeannaRating, 5 stars3 months ago
Our group of 8 stayed Feb 2025. The home is nicely decorated, clean, and Jose supplied a starter set of toiletries for the shower, hand soap, toilet paper, paper towels, dishwashing liquid, dishwasher pods, some coffee pods, and spices for cooking. They supplied large beach towels for the pool, a small cooler, and noodles. The oasis pool and hot tub were awesome. Don’t miss the second pool by the marina that is heated and a hot tub grotto which was perfect in the evenings. 2 pools, 2 hot tubs, you just can’t beat it! This townhome is located near many restaurants and fun places for activities. You enter the home from the first floor but second floor is the main living area with full kitchen, living room, and nice balcony. Two bedrooms are on the third floor so lots of stairs but worth the trip. First floor has a private king bedroom with a pull out couch in the living area and a small kitchen. Laundry room is in a storage area outside next to the front door. We loved our stay and Jose!

Family- and pet-friendly home rentals

Superhost
Campervan/RV in Big Pine Key
4.55 out of 5 average rating, 20 reviews

Bring your own RV. Our lot your Camper B5 No Tents

KevinRating, 5 stars3 months ago
It is a great place just a little tight getting the camper in The neighbors are all very friendly and helpful
Superhost
Tiny home in Key Largo
4.67 out of 5 average rating, 284 reviews

Waterfront Pool, Beach, Dock, Kayaks, Paddleboards

RibertRating, 5 stars1 week ago
Great place to stay. Really peaceful. Thank you!
Home in Islamorada
5 out of 5 average rating, 4 reviews

75130 Overseas Highway- VR 24-0415

EricRating, 5 stars16 months ago
This Islamorada property is accurately represented on Airbnb. It is an old-school beach house with somewhat dated and kitschy decor that looks out on a gorgeous view of the gulf. Unfortunately there was construction on the neighbor’s dock that interfered with our enjoyment of that view early in our trip but we came to an agreement with the property manager that was fair. Potential renters who have mobility issues should be aware that the stairway to the 2nd-story living quarters is quite steep, but that wasn’t a problem for us. Only other possible issue for some: the beds are very, very firm. But wow, that view is spectacular, and we would happily return in the future… after confirming that there’s no additional construction next-door.
Top Guest favourite
Home in Marathon
4.89 out of 5 average rating, 37 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

LydiaRating, 5 stars9 months ago
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!
Superhost
Townhouse in Marathon
4.82 out of 5 average rating, 17 reviews

Waterfront luxury Villa (34) with sunset views and boat slip

AngelaRating, 5 stars29 months ago
Great place and location. Close to lots of restaurants. Pool was really nice! Kitchen was fully stocked and nice that they provide paper towels/toilet paper/dishwasher detergent/etc. to get you started. Had a nice bottle of champagne waiting for us upon arrival as well.
Superhost
Cottage in Key Largo
4.77 out of 5 average rating, 13 reviews

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

KlaraRating, 5 stars3 months ago
We really enjoyed our stay with Key Lime sailing club! We especially appreciated the easy access to water activities and created life long memories kayaking in the beautiful surroundings. The hosts are kind, helpful and made our stay more memorable!
Guest favourite
Home in Marathon
5 out of 5 average rating, 13 reviews

Private Keys Retreat: Waterfront, Pool, Tiki Bar &

ChristinaRating, 5 stars2 months ago
Fish Camp was spotless and the owners and property management were very communicative leading up to our trip and once we arrived. No major issues - and if we reached out they responded right away. Beach chairs would have been a great addition for our stay.
Home in Islamorada
4.94 out of 5 average rating, 16 reviews

Islamorada Waterfront Escape

ColeRating, 5 stars13 months ago
Great stay and location. Chris was super helpful with check in and had great communication

Family-friendly home rentals with a pool

Guest favourite
Villa in Islamorada
5 out of 5 average rating, 35 reviews

Anglers Reef Islamorada

KatherineRating, 5 stars1 month ago
What a great place to stay! The community was well kept and the amenities were wonderful. There are great restaurants close by and it's location is perfect. We had a wonderful time and met some really wonderful people. We plan on returning, next year!
Condo in Tavernier
4.63 out of 5 average rating, 306 reviews

Ocean view condo with Balcony/Ocean View

LauraRating, 5 stars2 weeks ago
This is our second time staying at Ron and Irma's place and we'll continue to go back! The condo is spacious, clean, modern and in a convenient location. Ron and Irma made sure to include absolutely everything you may need during your stay– down to the pots and pans. My family and I love staying here, and we highly recommend it.
Guest favourite
Condo in Key Largo
4.9 out of 5 average rating, 30 reviews

Beautiful Gateaway - Key Largo

JonahRating, 5 stars1 month ago
great place and extremely well provisioned - everything you need for a great vacation! the only negative is a bit of road noise - nothing to prevent a great stay
Top Guest favourite
Townhouse in Islamorada
4.98 out of 5 average rating, 81 reviews

Bayside Townhome in Islamorada with Boat Slip

SteveRating, 5 stars2 months ago
Claire had an emergency which caused her to forget to contact house cleaning but she was awesome to work with and went over and above to make it right when we told her of the problem. You won’t find a more beautiful private place to stay. Location is as good as it gets. Claire was a great host and we really appreciated it.
Superhost
Campervan/RV in Big Pine Key
4.73 out of 5 average rating, 130 reviews

Tropical Caribbean Paradise and pool

JawwaadRating, 5 stars2 weeks ago
Great spot and location! Nice amenities and a clean place. Captain Rick was a great host and held great communication with us.
Guest favourite
Home in Marathon
5 out of 5 average rating, 20 reviews

Keys Waterfront Pool Home - Dock - Ocean - Kayaks

MichaelRating, 5 stars1 month ago
We had an unforgettable stay at Mary’s place! The house was spotless, cozy, and truly felt like a home away from home. We spent most of our time relaxing by the pool—it was so peaceful and quiet, the perfect setting for some much-needed downtime. The location was incredibly convenient, with grocery stores and great restaurants just minutes away. One of the most special moments of our trip happened here—we got engaged! I honestly couldn't have imagined a better place to celebrate such an important moment in our lives. If I had to suggest anything, the house could get a bit warm at times with the thermostat set at 72, but it wasn’t a deal breaker at all. Mary was amazing—super responsive, helpful, and kind. We would absolutely come back. Thank you for such a memorable experience!
Home in Key Colony Beach
4.68 out of 5 average rating, 40 reviews

Lower Duplex. Canal & Dock. Pool Club included

LisaRating, 5 stars1 week ago
great location for exploring all of the different keys. beautiful quiet neighborhood. cabana beach club was a great perk. 5 minute walk, weloved the pool and the lunch menu. Havana Jack's was delicious and easy to walk to. The out side of this place was much nicer than it looks in the pictures. the inside was simple and clean. having 1 bathroom was a bit challenging with a family of 4 but I knew that going in. overall my favorite part was sitting outside and looking at the water and feeling the incredible breeze
Guest favourite
Home in Islamorada
4.85 out of 5 average rating, 60 reviews

Oceanfront community 114 Anglers Reef Islamorada

MarkRating, 5 stars1 month ago
We absolutely loved Jennifer’s home! The house was so clean and had everything we needed included towels, kid’s toys and even baby gates for the stairs. The pool was so perfect and we had a blast swimming every day. We highly recommend staying at this beautiful property and will be visiting again!

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