Family-friendly vacation rentals in Islamorada

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Popular amenities for Islamorada family-friendly rentals

Family-friendly home rentals with a pool

Guest favorite
Condo in Key Largo
4.95 out of 5 average rating, 80 reviews

Key Largo Sunsets Penthouse on the Ocean

KimberlyRating, 5 stars1 week ago
Jose was an amazing host! His son was super helpful with local recommendations, also. Very easy and quick to reply. The condo was super clean (I'm very picky) and had everything that we needed to be comfortable and "at home." They even had a book on what to do in the Florida Keys- we did many activities listed in the book. The condo location was close to everything we did- snorkeling, deep sea fishing, restaurants etc. The lagoon was SO AWESOME! The fish would swim around the kids! The parrot fish were beautiful. The kids had so much fun! We also watched the iguanas climbing the trees. One would sleep on the top of the palm tree outside of our 5th floor balcony! The view of the sunsets are phenomenal. We would absolutely stay here again!
Guest favorite
Apartment in Key Largo
5 out of 5 average rating, 52 reviews

Key Largo, Florida - Gem by the Sea

ErinRating, 5 stars5 months ago
We had a great time at Diana’s place. We loved being able to use the available kayaks and fishing gear! Diana was super responsive and gave us some great recommendations. Moon bay was the perfect choice for our family of 5! Thanks Diana
Superhost
A spacious four-bedroom, three-bath home is elevated on stilts, featured with a welcoming porch and white railings. Adjacent, a private heated pool reflects a clear blue sky, surrounded by lounge chairs, offering a relaxing outdoor space near the dock and beach area.
Home in Marathon
4.85 out of 5 average rating, 33 reviews

( #3)Beautiful 4 Bed 3 Bath Pool Home w Free Dock

ShaneRating, 5 stars6 days ago
Amazing stay at Keys Cove, team on site were all great from buggy rental to dock assistance to general helpfulness about anything we needed. We will 100% be staying here again!
Superhost
A private pool is showcased, surrounded by lush greenery and palm trees. The clear blue water invites relaxation, while a spacious deck provides seating options for outdoor enjoyment. The background features a glimpse of the home, enhancing the tranquil, outdoor atmosphere.
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.
Guest favorite
Townhouse in Key Largo
4.94 out of 5 average rating, 154 reviews

Your island home away from home!

MannyRating, 5 stars1 month ago
Lucia’s place is exactly as described. Beautiful location in one of the most beautiful areas of the country. I highly recommend walking down to the marina and taking a siesta under one of the cabanas facing the bay. The other thing I appreciated about Lucia’s place was the simplicity of the close out. An excellent choice I highly recommend to all.
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
A serene outdoor space is revealed, featuring a heated pool surrounded by lush greenery and lounge chairs. A blue poolside sitting area enhances relaxation, while a spacious patio with dining options is visible in the background, framed by palm trees under a clear sky.
Home in Marathon
4.72 out of 5 average rating, 47 reviews

Blue Paradise

SabrinaRating, 5 stars11 months ago
Great house for a family vacation. Lots of room and great indoor and outdoor kitchens for preparing large meals. Off street parking was adequate for 4 large vehicles. The pool was very relaxing and there were nets and games for the kids too. Amazing hosts!
Superhost
A spacious living area features a leather sofa, a large television, and a coffee table, with tropical decor enhancing the environment. Natural light brightens the room from surrounding windows, and a dining area with woven chairs is visible in the background, contributing to an open layout.
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

Family-friendly home rentals with air conditioning

Guest favorite
A two-story villa features a cheerful yellow exterior, showcasing a spacious front porch with white railings. Lush green landscaping surrounds the entrance, with vibrant plants adding color. The well-maintained structure stands alongside other similarly styled homes in a serene and inviting neighborhood.
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!
Villa in Key Largo
4.9 out of 5 average rating, 20 reviews

Lux Villa for Spring Break: Pool, Kayak & Marriott

JillRating, 5 stars2 weeks ago
Beautiful home with amazing access to amenities
A bright yellow, two-story home is surrounded by lush greenery and swaying palms. The spacious deck features white railings, offering seating for relaxation. Large windows allow ample natural light, while a paved pathway leads up to the entrance, enhancing accessibility.
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
Top guest favorite
A serene outdoor seating area features two woven chairs facing a sunset over the bay. A small metallic table sits between the chairs, and palm trees are visible in the distance, framing the tranquil water view.
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.
An outdoor tiki hut provides a shaded seating area with comfortable wicker furniture. Decorative cushions adorn the sofas, and a hammock hangs nearby. Lush greenery surrounds the space, offering a relaxing spot for gathering or unwinding.
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!
Guest favorite
A spacious backyard features a heated swimming pool surrounded by colorful tropical landscaping. Sun loungers line the poolside, with palm trees offering shade. A hammock is visible in the background, and a canal can be seen just beyond the pool area.
Home in Marathon
5 out of 5 average rating, 21 reviews

Keys Waterfront Pool Home - Dock - Ocean - Kayaks

MichaelRating, 5 stars2 months 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!
Guest favorite
A serene waterfront view is presented, featuring several white Adirondack chairs positioned along a sandy beach. The calm water reflects a clear blue sky, with lush greenery visible in the background, creating an inviting space for relaxation.
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!
Superhost
A spacious pool area is framed by lounge chairs that overlook the sea. Lush greenery surrounds the pool, with palm trees and a shaded seating area in the background. Sailboats can be seen in the distance against a clear blue sky.
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!

Family-friendly home rentals with Wifi

A vibrant sunset is captured over the ocean, with hues of orange, purple, and pink blending in the sky. Silhouetted palm trees frame the scene, creating a serene tropical atmosphere that highlights the natural beauty of the Florida Keys.
Condo in Tavernier
4.63 out of 5 average rating, 306 reviews

Ocean view condo with Balcony/Ocean View

LauraRating, 5 stars3 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.
Top guest favorite
A view from the balcony reveals tranquil waters of the Atlantic Ocean stretching towards the horizon. A thatched-roof structure is visible nearby, with a dock extending into the water, surrounded by lush greenery.
Home in Marathon
5 out of 5 average rating, 14 reviews

Casita Mar Canal, Direct Ocean 2/2 Book Summer Now

ErinRating, 5 stars1 month ago
We enjoyed our time. It was great being centrally located to visit both Key West and Islamorada. The home was super clean and the couches and bed were very comfortable. The kitchen has everything you need and having a bbq grill was an added perk! The neighbors are quiet and friendly. We never knew anyone was around unless we saw someone coming and going. The view to the ocean was great!
A serene sunset is captured over calm waters, with the sun reflecting warm hues across the surface. Silhouetted against the horizon is a small islet, while distant markers are visible along the waterway, creating a sense of tranquility.
Condo in Tavernier
4.83 out of 5 average rating, 6 reviews

Oceanfront with unbelievable views

MegRating, 5 stars2 months ago
The view is beautifully tropical with the ocean water alternating turquoise blues! The white sand beach, palm trees and sparkling pool added to the ambience. The condo had everything we needed, beach towels, umbrella and beach chairs were a plus. There is a high school next door so you can expect high school activities. As it was our first experience in the keys, the location worked well for us. We could go back and forth across all the keys and experience what they had to offer.
A two-story waterfront home is depicted, featuring a light green exterior with white trim. Surrounding vegetation includes low shrubs and small trees. A sandy area is visible, and a swimming pool can be seen in the background, suggesting a relaxing outdoor environment.
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!
Guest favorite
An aerial view showcases the community's vibrant grounds, featuring a 65-slip marina with boats docked alongside red-roofed buildings. Lush greenery surrounds the area, leading to the tranquil blue waters of the bay, complemented by the distant shoreline and open sky.
Condo in Islamorada
4.76 out of 5 average rating, 66 reviews

Bayside Condo with Marina, Beach and Pool

SammyRating, 5 stars2 weeks ago
Easy to find, easy to contact and reach glenn, and he was very helpful, would definitely stay here again.
A serene waterfront view is captured, showcasing calm waters framed by lush greenery and palm trees. The scene includes a glimpse of a dock area with boats visible in the distance, enhancing the peacefulness of this tropical setting.
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:))
The exterior of the Yellowtail houseboat is shown, featuring a modern design with large glass doors and a welcoming entryway. A lifebuoy is mounted on the wall, and air conditioning units are visible on both the houseboat and nearby units. The deck leads to the dock, enhancing accessibility.
Boat in Tavernier
4.88 out of 5 average rating, 48 reviews

Aqua Lodge Houseboat "Yellow Tail "

SaraRating, 5 stars2 months ago
We stayed at this wonderful houseboat as we began our trip to the Florida Keys and it was perfect! We saw manatees, enjoyed dinner at the outdoor bar with locals, and had a beautiful view of the sunset. Great location with a wonderful host!
A shaded pathway lined with lush tropical plants and palm trees leads to an open gazebo. Bright green and reddish foliage creates a natural border on either side. Soft sunlight filters through the leaves, casting gentle shadows on the walkway.
Home in Islamorada
4.85 out of 5 average rating, 39 reviews

Anglers Reef is Oceanfront, Blue Marlin House2/2.5

JulieRating, 5 stars19 months ago
Very nice house. Very clean. Only downside is the noise from the road behind the house. You don’t pay any attention to it until you try and sleep. The place is very beautiful. Swimming pool was very nice. We used the kayaks and bikes. It was a quiet community. What we were looking for and it was gated. We would definitely stay there in the future.

Quick stats about vacation rentals that are family-friendly in Islamorada

  • Total rentals

    610 properties

  • Nightly prices starting at

    G$16,727 GYD before taxes and fees

  • Total number of reviews

    4.9K reviews

  • Pet-friendly rentals

    270 properties allow pets

  • Rentals with a pool

    420 properties have a pool

  • Rentals with dedicated workspaces

    330 properties have a dedicated workspace

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