Family-friendly vacation rentals in Long Key

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Popular amenities for Long Key family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
Home in Key Colony Beach
5 out of 5 average rating, 45 reviews

Florida Keys Retreat / Completly remodeled

SeanRating, 5 stars2 months 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!
Superhost
Home in Cudjoe Key
4.63 out of 5 average rating, 167 reviews

Ocean Front Home in Great Location

HaroldRating, 5 stars2 weeks ago
This booking was great for what we needed, thank you to the responsive hosts and pet friendly house that made our vacation that much better.
Guest favorite
Home in Marathon
4.98 out of 5 average rating, 92 reviews

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

MondeRating, 5 stars3 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!!
Superhost
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
4.84 out of 5 average rating, 110 reviews

Oceanfront Resort W/Indoor Pickleball - Spacious!

LeoRating, 5 stars1 month ago
The Mariners Club was an excellent stay, Fernando’s property was extremely comfortable, clean and well appointed. The surrounding grounds, pools, marina and beach area were the best. Fernando was very responsive and informative making our check in and stay process work flawlessly, most appreciated, will stay again in the future, thanks for making our quick vacation a banner stay, all the best
Superhost
Townhouse in Key Largo
4.87 out of 5 average rating, 60 reviews

Family Key Largo Townhome for Fun Sun & Relaxation

DeannaRating, 5 stars4 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!
Superhost
Condo in Key Largo
4.63 out of 5 average rating, 83 reviews

The Marlin House at Mariner's Club

AndreaRating, 5 stars2 months ago
The stay was great loved the big pool and scenery. Anything we needed we felt comfortable asking. Star properties was great ! We will be back for sure
Superhost
Townhouse in Marathon
4.66 out of 5 average rating, 38 reviews

Manatee Quay-I Canal waterfront,access BEACH club!

ArnieRating, 5 stars6 months ago
Very beautiful place, quiet, so many things to do in such a short time. Loved it!!

Family- and pet-friendly home rentals

Superhost
Tiny home in Key Largo
4.67 out of 5 average rating, 285 reviews

Waterfront Pool, Beach, Dock, Kayaks, Paddleboards

BeckyRating, 5 stars4 days ago
This was our first time staying in a tiny home and found it to be very functional. The outdoor area along the water was outstanding and so relaxing. It was a great location to everything and we enjoyed sleeping well in the piece and quiet .
Top guest favorite
Home in Marathon
4.89 out of 5 average rating, 37 reviews

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

LydiaRating, 5 stars10 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 stars30 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 favorite
Villa in Marathon
4.88 out of 5 average rating, 59 reviews

New Paradise On Sombrero Beach

JenniRating, 5 stars1 month ago
The house was well equipped with all of the essentials. We had 8 adults and plenty of room. We did have to wash towels a few times, and buy more laundry soap, but the washer and dryer were conveniently located on the main level. The pool was smaller than what the pictures showed, but it perfectly suited our needs. All members of our party viewed the listing before we booked it and none of us realized it was a twin home. However, there is tons of privacy and the only times we noticed we had neighbors was when the shared dock was used. We had to buy a cooler (for poolside and the beach) and beach chairs. There were some pool floaters left behind, from previous guests that we used. The interior of the home is beautiful, with high ceilings and comfortable furniture. This is in a great location - close to grocery stores, restaurants and Sombrero beach! Monica was great to work with!
Home in Marathon
4.96 out of 5 average rating, 163 reviews

Vida De Aqua - Water Life!

BrianRating, 5 stars4 days ago
Pure paradise! This private corner-lot home on the water gave us everything we dreamed of for our Keys getaway. Our boys fished from dawn to dusk while we kicked back, relaxed, and enjoyed the incredible peace, quiet, and space—it truly felt like our home away from home. The location is unbeatable: a quiet, friendly neighborhood that’s close to everything but feels like a private retreat. Inside was spotless, comfortable, and thoughtfully equipped—perfect for cooking, bathing, sleeping, and recharging after long days outdoors. The window A/Cs in the bedrooms were loud but kept things ice cold, and the kitchen ants are just part of life in the Keys. The bait freezer in the garage was perfect for our week of fishing. We loved having use of the 1-car garage—super convenient for tossing in all our beach and fishing gear at the end of the day. There were plenty of towels, extra sheets, and everything we could possibly need in the kitchen and bathrooms. We can’t wait to come back! 5 stars!
Home in Key Colony Beach
4.68 out of 5 average rating, 40 reviews

Lower Duplex. Canal & Dock. Pool Club included

LisaRating, 5 stars2 weeks 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
Superhost
Campsite in Big Pine Key
4.73 out of 5 average rating, 120 reviews

Bring Your Own RV! Our Lot Your RV B6 No Tents

CarolynRating, 5 stars2 months ago
The RV lot was well landscaped making the space feel tropical. Access to bath and laundry facility were just a few steps from the lot.

Family-friendly home rentals with a pool

Guest favorite
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!
Home in Marathon
4.89 out of 5 average rating, 19 reviews

NEW LUXURY 4/3 SINGLE FAMILYw/HEATED P00L,BOATDOCK

BradleyRating, 5 stars10 months ago
It was an awesome place! Beautiful, clean, and cozy! You can pull your boat right up to the dock! easy access threw the canal to the ocean and a couple of restraunts! pools nice! plenty of room for a big family! All of your amenities are nearby! Grocery store, restraunts, bars if your into that, gift shops and more!
Home in Marathon
4.82 out of 5 average rating, 34 reviews

Waterfront, dock, easy ocean access, heated pool!

MelissaRating, 5 stars14 months ago
This house was a perfect spot for my partner and I and Cooper our pup. swam in the pool, sat in jacuzzi, paddle boarded ,kayaked, road the bikes, ect. we brought our boat down but unfortunately had a few issues with it so wasn't able to go out fishing as much as we'd liked. but there was plenty to do at and around this beautiful place. would definitely come back in the future:))
Superhost
Camper/RV in Big Pine Key
4.73 out of 5 average rating, 130 reviews

Tropical Caribbean Paradise and pool

JawwaadRating, 5 stars3 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 favorite
Townhouse in Key Largo
4.9 out of 5 average rating, 303 reviews

Casa Fish LLC

EmilyRating, 5 stars2 weeks ago
We had a wonderful stay and Tanya was an excellent and very responsive host. Hope to stay again in the future.
Top guest favorite
Villa in Key Largo
4.96 out of 5 average rating, 67 reviews

Oceanfront/2 Pools/Lagoon/Tennis/Picketball/Marina

EranRating, 5 stars2 months ago
We were looking for a larger stay in the keys, and Jose’s home fit the bill perfectly. It was spacious, spread over only 2 floors (vs 3 floors for most properties in Kawama). The top floor has 2 bedrooms and 2 bathrooms and is recently remodeled (incl. the kitchen and the bathrooms). The lower floor is slightly less new but still in good shape. It has the 3rd bedroom and bathroom. Provided were a club car for our use, 2 kayaks, bikes, towels, snorkeling gear… great for spending time in the lagoon (which is essentially an enclosed salt water pool). Overall great stay in Key Largo. Thank you Jose!
Guest favorite
Condo in Key Largo
4.96 out of 5 average rating, 128 reviews

Kawama Suntastic @ Key Largo

CathyRating, 5 stars5 days ago
Had an amazing 10 day stay at Cindy and Ron's Suntastic Condo. Felt right at home the minute we walked in. It has lots of kitchen supplies to prep and cook with and comfortable chairs and bedding. The location can't be beat within the Kawama complex. We especially enjoyed the lagoon right outside our door. Multiple restaurants are only a few minutes drive away. Cindy and Ron were terrific hosts and always available to answer our questions. It's a lovely home which we have plans to return to!
Condo in Islamorada
5 out of 5 average rating, 7 reviews

Sunrise Townie - Maison Matecumbe Islamorada, FL

JaneRating, 5 stars13 months ago
Beautiful place, exactly as pictured, for our family of six. We LOVED the pool and spa! The porch space was well used with lovely furniture overlooking the pool. Great location for restaurants and activities. The landscaping and grounds are beautifully maintained. Very peaceful and private during our stay.

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