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Beachfront vacation rentals in Islamorada

Find and book unique beachfront homes on Airbnb

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Popular amenities for Islamorada beachfront rentals

Beachfront home rentals with a pool

Guest favorite
A spacious outdoor tiki living area features a thatched-roof gazebo overlooking the ocean. Two kayaks rest on the dock, with a fishing rod and tackle box nearby. The scene captures a serene sunset, reflecting light across the water and creating a tranquil ambiance.
Cottage in Key Largo
4.98 out of 5 average rating, 100 reviews

Oceanfront Getaway | Kayaks, BBQ & Stunning View!

BeckyRating, 5 stars1 week ago
Enjoyed the stay. Was very well equipped with everything we needed. We had a question about one of the keys and host was very responsive.
Guest favorite
Condo in Key Largo
4.97 out of 5 average rating, 38 reviews

PENTHOUSE SUITE - OFFERS BEST PANORAMIC OCEAN VIEW

MelissaRating, 5 stars1 month ago
Our stay was everything we could have wanted. The view was incredible. The condo had everything we could need. We will definitely come again and recommend it to family and friends.
Guest favorite
A peaceful canal scene is presented with clear blue skies and palm trees lining the water's edge. The calm water reflects the greenery and nearby structures, creating a serene atmosphere. A patterned walkway runs alongside the canal, adding to the tranquil setting.
Home in Marathon
5 out of 5 average rating, 6 reviews

Chiquita Waterfront Home

ShanaeRating, 5 stars1 week ago
My family and I really enjoyed this home the pictures do not do it justice it’s beautiful. The owners are very responsive and we were even able to check in a day early ! The canal was awesome , a boat is a must and so much fun. We saw manatees and iguanas. The private pool was fun all together a great experience.
Superhost
A serene outdoor space includes a private pool surrounded by a spacious deck. Palm trees frame the scene, casting shadows on the white tiles. A furnished sitting area can be seen nearby, offering a relaxing spot to enjoy the warm weather.
Home in Key Largo
5 out of 5 average rating, 3 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars1 week ago
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!
Guest favorite
A private pool is surrounded by a lush tropical garden, featuring tall palm trees and vibrant foliage. The clear water of the pool reflects the sunlight, while stone pathways and colorful blooming plants enhance the natural ambiance.
Home in Marathon
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars2 weeks ago
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars4 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
A spacious pool area features a large, azure swimming pool surrounded by lounge chairs and umbrella-shaded tables. Lush greenery borders the pool, enhancing the tranquil environment. Several blue umbrellas provide shade for guests enjoying the sunny Florida weather.
Condo in Tavernier
4.97 out of 5 average rating, 98 reviews

Ocean views at “Sangria Sunrise” 10% off Charters

LaurenRating, 5 stars3 weeks ago
I cannot say enough about how much we enjoyed our stay at Sangria Sunrise! The condo itself is beautiful, the property is awesome, well-maintained, and the staff are friendly and helpful! We spent most of our time at the pool and the beach. The pool bar is great and the pool is clean and refreshing. Plenty of sunny spots and lots of shaded tables, too. It’s right across from the condo so we went multiple times a day. Beautiful landscaping all around. The beach and marina area are really nice. We loved watching the boats from the balcony and seeing the sunrise over the water. Lots of fun things to do in the area within a short drive, but also plenty to do on the property if you prefer to stay put. Tracy is an excellent host and is very helpful and responsive. We will absolutely be back. Thank you for sharing your space with us, Tracy!
Superhost
Camper/RV in Key Largo
4.84 out of 5 average rating, 126 reviews

Cozy Waterfront Retreat w/ Private Boat Dock +Tiki

ShirleyRating, 5 stars1 month ago
The RV was perfect for my husband, sister and I. We especially loved the tiki dock where we hung out. Watching sunrises with our coffee was a great way to start each day’s adventures. Ramses was very communicative and made sure the check-in form was completed so everything went smoothly for us. All in all a great experience!

Pet-friendly beachfront home rentals

Superhost
A spacious living area features large glass sliding doors that open to an ocean view. The room includes a comfortable sectional sofa, a sleek coffee table, and modern chairs, creating a bright and inviting environment for relaxation.
Apartment in Islamorada
5 out of 5 average rating, 3 reviews

Ocean View Duplex Penthouse | Pool | Vista Two

AnneRating, 5 stars2 months ago
Beautiful, very clean property with a fantastic location. Excellent proximity to snorkeling, restaurants and other local attractions. Short stroll to excellent walking path that takes you along route 1 with amazing morning views of the beautiful water. Great views all around, in fact. Plenty of soft, plush towels and similarly luxurious bed linens. We had a wonderful family vacation staying at this property.
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 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!
Guest favorite
An aerial view showcases a private dock with a boat alongside a heated pool. Lounge chairs are positioned near the pool, complemented by vibrant palm trees and neatly arranged outdoor furniture. The tranquil waters reflect the bright surroundings, enhancing the overall relaxing atmosphere.
Home in Key Colony Beach
4.94 out of 5 average rating, 16 reviews

Paradise Cove!30ft Dock Pool BBQ

BryceRating, 5 stars3 weeks ago
Had a great week at Yunis place! Her house was extremely clean and had everything we needed and more especially for cooking which was nice. She had probably the most comfortable bed, sheets and pillows I’ve ever used. I loved how it was clutter free and didn’t have any breakable decorations down low around since we had our two toddlers with us. The pool was the perfect size for us and it was great to relax outdoors. We even saw Manatees swim up to the dock. 10/10 would recommend this spot.
Guest favorite
The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars3 weeks ago
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!
Superhost
A tiki bar with a thatched roof offers seating along a glass countertop. Two cocktails rest on the counter, with serene water views visible beyond. Boats are docked discreetly along the shoreline, surrounded by greenery and natural light.
Home in Key Colony Beach
4.74 out of 5 average rating, 141 reviews

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach

MichaelRating, 5 stars3 weeks ago
Great place to stay for family vacation or guys fishing trip. Plenty of dock space to park the boat and easy access to the Atlantic. House is clean and all amenities worked as they should. Would definitely recommend to a family or friend. Mary was a great host who provided all information without even requesting it.
Superhost
The outdoor area features a sandy patio surrounded by palm trees, with several blue Adirondack chairs facing a shaded seating area under a white gazebo. The spacious home stands in the background, showcasing multiple balconies and a light-colored exterior.
Home in Marathon
4.89 out of 5 average rating, 64 reviews

Gorgeous Ocean View Home!

ChristinaRating, 5 stars1 month ago
We had an amazing time with our family and a beautiful Easter dinner with our friends. The location is perfect to travel all of the keys as it's just over an hour to Key West and Key Largo. The sun rose over the top floor guest bedroom with such a beautiful view of the water every day. Morning coffee with the view was awesome. Evenings spent wrapped on the couch watching movies with really nice big TV and unwinding. Sitting down by the water in evenings before sunset hanging with family watching niece play in sand was great too. Highly recommend.
Superhost
A waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.
Apartment in Marathon
4.86 out of 5 average rating, 50 reviews

Little Venice in Marathon (in the Beautiful Keys)

AlisonRating, 5 stars2 weeks ago
We (two couples) enjoyed a great week here. Being on the canal was nice, outside sitting spots were great. The house had plenty of cooking supplies needed. Was a tad bit smaller than I expexted, but worked out just fine. Remember to bring your shampoo, body wash etc as it's not provided. Comfortable and bright, was quiet even with boats going by. Would definitely stay here again!
Guest favorite
A covered outdoor area features a dining table surrounded by white chairs. A sectional sofa is positioned against the wall, offering seating. Light blue walls complement the spacious tile flooring, which reflects natural light. A BBQ grill and other furniture are visible at the far end.
Apartment in Key Largo
4.83 out of 5 average rating, 60 reviews

Studio apartment in Calusa Resort & Campgrounds

JuanRating, 5 stars2 weeks ago
So must say 10/10 we stay in a lot of places and this one we will deff come back to over and over again it was perfect and I must say the price is a steal honestly when we first booked we were nervous because of the price was cheap and I must say dosent reflect at all it is a amazing studio super clean super comfy can’t wait to come back highly recommend

Private beachfront home rentals

Top guest favorite
An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.
Home in Marathon
5 out of 5 average rating, 17 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars1 week ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Guest favorite
A spacious outdoor area features a well-maintained dock alongside calm waters. Luce lounge chairs are arranged for comfort, with palm trees offering shade. The exterior of the duplex is visible, showcasing large windows and a patio area adjacent to the dock, enhancing the waterfront experience.
Home in Marathon
4.94 out of 5 average rating, 34 reviews

Florida Keys Oceanside Utopia

LisetteRating, 5 stars2 months ago
We spent an amazing week in the house of Kelly and Shane. The location on the waterfront is unbeatable and the house itself is super convenient, nicely remodeled and has a very cozy feel to it. We spent days in a row fishing from the dock, prepared our catch of the day on the bbq on the terrace, and caught shrimp at night which served as bait for the next day. There are great beaches, restaurants, and all kinds of day trips at hand if you wish to leave the property ;). Kelly and Shane are great hosts, with tons of tips - they clearly love the area and put great effort in the maintenance of the house and dock. They are super quick and easy in their communication and all three of us (me, husband and our 12 year old son) look forward to staying at their property again!
Top guest favorite
Condo in Key Largo
4.84 out of 5 average rating, 70 reviews

Tower 2 Master Suites 2 Kings Beds Marina Pool

ChelseaRating, 5 stars1 month ago
Pedro was an amazing host! We got in a little early and thought we were going to need to check in early and he was very accommodating! I had a few questions and he responded almost immediately which is more than impressive! The place is perfectly decorated, had a very homey feeling to it and everything we needed.
Superhost
A serene view is presented from the pool area, featuring gentle waves lapping at the shore and numerous sailboats anchored in the harbor. Two palm trees provide shade, and a well-maintained lawn borders the pool, enhancing the coastal ambiance.
Home in Marathon
5 out of 5 average rating, 8 reviews

Sandbox

MikeRating, 5 stars2 months ago
The stay experience exceeded our expectations. The only recommendation would be to have a listing of recommended restaurants, beaches, boat rental places, etc to go see in both Marathon and key west. We visited key west and found out afterwards where we should have gone.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

KCB Tropical Escape

JosephRating, 5 stars1 month ago
This was better than I expected. A very spacious 2 bedroom with large kitchen, family room. The screened in porch was huge, and a great place to have meals and watch TV and the sunrise. The fully equipped kitchen was awesome for those like us that love to cook. It was a great home away from home. This place was so comfortable and was the best we ever rented.
Top guest favorite
A tranquil beach scene features several blue lounge chairs arranged in neat rows on the sandy shore. A wooden pier extends into the water, accompanied by a thatched-roof gazebo. Lush greenery and a peaceful sky with scattered clouds complete the coastal vista.
Apartment in Tavernier
4.98 out of 5 average rating, 41 reviews

Ocean View 2br/2ba w/pool, bar and dockage 28ft

NickRating, 5 stars1 week ago
What an amazing location and you can really tell the host has thoughtfully designed the Airbnb, making it an experience. Will be back!
Top guest favorite
A private pool is situated beside a spacious deck, surrounded by tropical plants and palm trees. Comfortable lounge chairs are placed near the pool, and stairs lead to the upper level of the stilted structure. The area offers direct access to the canal.
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars2 weeks ago
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!
Guest favorite
A rattan chair with a rounded backrest is positioned against a striped wall. The chair displays decorative pillows and a light throw blanket. A small side table holds a lamp and a decorative item, contributing to a relaxed atmosphere.
Home in Marathon
4.92 out of 5 average rating, 50 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

MaxsenaRating, 5 stars1 month ago
Super nice place to stay. Very comfortable.

Quick stats about beachfront rentals in Islamorada

  • Total rentals

    280 properties

  • Nightly prices starting at

    G$16,787 GYD before taxes and fees

  • Total number of reviews

    1K reviews

  • Family-friendly rentals

    150 properties are a good fit for families

  • Pet-friendly rentals

    170 properties allow pets

  • Rentals with a pool

    220 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Beachfront rentals