Beach house holiday rentals in Islamorada

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Popular amenities for Islamorada beach house rentals

Beachfront house rentals

Superhost
Home in Marathon
4.69 out of 5 average rating, 16 reviews

#7 Waterfront 4Bed 3Bath Pool Home

CarolRating, 5 stars11 months ago
Location, location, location! Great views, nice pool area, dock space if needed. Walkable to several resorts and turtle sanctuary.
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 63 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

BarbaraRating, 5 stars1 week ago
You won’t find a better set up than this with family. Playground, beach, pool , sidewalks for walking everywhere, and great kayaking area as well. And the owner makes sure his guests have all they need.
Superhost
Home in Key Colony Beach
5 out of 5 average rating, 3 reviews

The Sandcastle - 2bed/1bath half duplex with docka

RachelRating, 5 stars11 months ago
Key Colony Beach is a quaint little village in and of itself. This duplex was exactly as the pictures show. Beds, pillows and sofa very comfortable. The kitchen was the most well stocked of all we’ve stayed in; all cooking, baking, and dining that you have at home and then some. Towels and linens were plentiful and clean. The neighbors were also kind and courteous. Having the boat dock was a big plus as we brought our boat with us. We put-in and pulled-out at the public landing across the street from the entrance, for a $25 fee each occurrence . Short, beautiful ride to our dock. Docking was easy and included an outside cleaning station and shower. Nice outdoor seating and Palms. The retractable awning above the sliding glass door was also perfect for blocking some of the afternoon sun. The location is convenient to dining, grocery and convenience stores. We loved everything about our vacay, other than having to leave. We’ll definitely be back.
Guest favourite
Home in Marathon
4.9 out of 5 average rating, 31 reviews

Viamarhe House-Private beach, Kayak, yard games

JasonRating, 5 stars3 weeks ago
Everything about this home is as described in the listing. Host is very responsive and friendly. We completely loved being there and it was incredibly peaceful and relaxing. We would love to come back again. Having the ocean for a back yard was awesome! This was probably my favorite AirBnB stay ever! We did not want to leave.
Guest favourite
Home in Key Colony Beach
4.87 out of 5 average rating, 15 reviews

Fun in the Sun!

BrentRating, 5 stars1 month ago
Great attached townhome/duplex with privacy fence between the other side. Great private pool just on the canal! The bottom story was perfect for extended family to have privacy but still be close! We even saw a manatee in the canal.
Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 85 reviews

Ocean Breeze Home

PattyRating, 5 stars2 weeks ago
We wanted a homebase to explore the keys. Perfect little home and Pamela thought of everything for our stay. We typically cook but didn’t have time but I felt like the kitchen was better stocked than ours at home! Bottled water, Keurig coffee and wine were a perfect extra bonus. Funny thing is that we locked ourselves out of the property and Pamela responded right away and was resolved immediately.
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 19 reviews

Boat Dock+King Beds & Cabana Club

RachelRating, 5 stars4 months ago
What a great week we had at this wonderful getaway! We got to watch the manatees off the dock. The neighbors were very friendly and helpful with idea of what to do in the area. We rode our rented bikes down to sunset park every evening to watch the sunset. We also found a great state park/beach just a 20 min bike ride away! The house had everything for us to use for our morning trips to the beach (coolers towels beach chairs). The house had outdoor furniture we sat at to watch the Key Colony Christmas boat parade! We will definitely be going back next year!
Guest favourite
Home in Marathon
4.89 out of 5 average rating, 18 reviews

Boaters delight! 1 min to open water, Dock & Beach

AmyRating, 5 stars2 months ago
Wonderful home on canal that opens up to gulf. The home had everything that was described and was comfortable with AC. Cannot think of anything we needed that was not there. Terrific views from balcony. Saw lots of wildlife including manatees and the iguanas were fun to watch. There was a double and a single kayak to use as well as bikes to get around as the traffic was busy. There are close neighbors next door but they were quiet. If you want a place to relax, this fits the bill.

Beach house rentals with a pool

Superhost
Home in Marathon
5 out of 5 average rating, 7 reviews

Delightful Canal Front Pool Home! Direct to Ocean!

SydneyRating, 5 stars3 months ago
This home offers so many amenities!! We thoroughly enjoyed biking, kayaking, the heated pool, grilling, and several games the host had for us. The large kitchen made it easy for our group of 6 to interact and enjoy meals together. The host was very responsive with any questions we had and checked in throughout the stay to ensure our needs were being met. This was our second year staying in Marathon, would stay at this location again.
Superhost
Home in Islamorada
5 out of 5 average rating, 3 reviews

Islamorada Cay Home. Elegant home

MarlaRating, 5 stars1 month ago
The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!
Superhost
Home in Marathon
4.79 out of 5 average rating, 34 reviews

Luxury Waterfront Retreat with Dockage & Pool

MindyRating, 5 stars1 month ago
Had an amazing stay at this house with my husband and 4 small kids. The house was spacious and clean, with lots of natural light at soon as the sun came up. The pool was so warm and had a large shallow area that was perfect for our 3 year old. Naomi was a wonderful communicator. It was so sad to have to leave.. Would definitely recommend staying here.
Guest favourite
Home in Key Colony Beach
4.92 out of 5 average rating, 12 reviews

Paradise Cove!30ft Dock Pool BBQ

MelissaRating, 5 stars1 week ago
Had a wonderful stay at Yuni’s. The home was beautiful, well appointed and clean. Yuni was very responsive to all our questions and needs, and super friendly! Thank you Yuni!
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars3 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Superhost
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars4 months ago
Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!
Guest favourite
Home in Marathon
4.87 out of 5 average rating, 23 reviews

Golf Coast Oasis

NoraRating, 5 stars2 days ago
We really enjoyed our week at Gulf Coast Oasis! The house was lovely, well-stocked, and great for our family of 5. We very VERY much enjoyed the pool and appreciated being able to heat it. Loved using the bikes and kayaks. Ate on the screened in porch. Madelyn was very helpful and responsive both in advance of and during our trip. Great stay! The only "negative" was the noise from the nearby airport -- not disruptive but worth noting.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 112 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JessicaRating, 5 stars2 days ago
Our family of 9 loved the house! The pool, corn hole, and roof deck were all huge hits with the kids. The house is perfectly situated on Marathon, close to all the restaurants. Quick drive to Bahia Honda. We will definitely will be back for another visit to Andy’s place.

Private beach house rentals

Guest favourite
Home in Marathon
4.91 out of 5 average rating, 47 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

RebeccaRating, 5 stars3 weeks ago
Giselle and Javier were awesome with communication, they gave us a ton of recommendations for food and we tried out almost all of them. Some of the best food we’d ever had and a lot of them were within walking distance of the house! The house was perfect, light, clean, and modern. We were able to catch fish off the dock and even saw a few manatees come through. Probably the best Airbnb we’ve stayed in overall!!
Superhost
Home in Cudjoe Key
4.89 out of 5 average rating, 35 reviews

Lower Keys Paradise

AhrinRating, 5 stars3 weeks ago
Great place to stay. It’s a house in a community with a lot of activities available. There’s an extra $125 fee for that, but it’s worth it.
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 58 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

ErinRating, 5 stars2 weeks ago
I can’t say how much we enjoyed this place. So private and clean. Beautiful view. Everything we needed was there. Sad to leave but back to real life. Thank you Thank you!
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 19 reviews

Keys to the Sea + Cabana Club

MarcilleRating, 5 stars2 weeks ago
Our family of 4 really enjoyed our stay! It really was the perfect getaway spot for us to rest and recharge. The amenities available were so convenient, from a well stocked kitchen, bathroom supplies, laundry, a bait freezer, to even having pool towels and a cooler available to use. Our kids ages 11 and 13 spent hours fishing off of the dock out back. We even caught our meal a couple of times! We also really enjoyed access to the Cabana Club! It had a lovely beach front along with a perfect temperature pool! Drinks and food at the club were very reasonable priced. This is our third year in a row visiting the keys and we always enjoy this area. Next year I will be looking at this rental first! Thank you again for the wonderful stay!
Top guest favourite
Home in Key Largo
4.89 out of 5 average rating, 122 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

DanielleRating, 5 stars1 month ago
FANTASTIC! We have stayed in hotels on Key Largo, but staying at Stu’s was a game changer. After our dives, it was easy to rinse off our gear then have more than enough space to relax and not feel cooped up. The entire place was extremely clean. The pool was perfect and the edge of the water was a perfect place to hang out we saw several manatees and even had a pelican visit. Stu was very responsive and we are looking forward to repeating this adventure again!
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 13 reviews

Bohemian Beach Bungalow

BonnieRating, 5 stars3 weeks ago
Karen was a lovely host and very responsive to my questions. The place was shiny clean and very comfortable with all the amenities we could have hoped for. The pool and beach were so close and it was so nice to cool off after a long day exploring Key West and the other Keys. We'd highly recommend this rental.
Superhost
Home in Key Largo
4.83 out of 5 average rating, 12 reviews

The Ultimate Bay View Home

NicoleRating, 5 stars5 months ago
I recently stayed at Adriana’s beautiful waterfront Airbnb in Key Largo while in town for a wedding, and it was everything I could’ve hoped for. The views are absolutely breathtaking – you’re right on the water, so you get to wake up and unwind with the most serene backdrop. The house itself was pristine, showing how much care and attention Adriana puts into every detail. Adriana was an amazing host, incredibly responsive and genuinely helpful from the start of our stay to the finish. She made sure everything was in perfect order and was always just a message away if we needed anything. A huge plus was being able to bring my two dogs along, which made the experience even more memorable. They loved exploring the area as much as I did! Overall, it was a fantastic experience, and I would absolutely stay here again. If you’re looking for a relaxing waterfront getaway in Key Largo, Adriana’s place is a gem!
Guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 6 reviews

Key Colony Beach Waterfront 321

JeanneRating, 5 stars8 months ago
Great place right in the heart of Key Colony. House had all we needed and more to make our 8 day stay comfortable. Great boat dock with plenty of room for 2 31 ft boats.

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