
Waterfront vacation rentals in Stock Island
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Stock Island
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Stock Island waterfront rentals
Waterfront apartment rentals

"O" Fish Ally Paradise @Ocean Isle Fishing Village
Beautiful development, loved the fishing dock and the pool. It was close to grocery stores and restaurants.

*NEW* Sea La Vie - Pool & Beach
Great spot for our family with young kids! With the beach and pool, we never had to leave to find entertainment. They had the best time, and we could relax a little! Clean space, friendly people, fantastic view!

Beachside Unit 22 - Private Beach on Atlantic
We enjoyed our stay at the Key Colony Continental Inn. The environment and location was described accurately by Cindy, as stated there were endless amenities nearby which made the stay feel like home. The beach at the condo was nice although we discovered a nice public beach nearby named Sombrero Beach. Overall, Cindy was a great host whom responded quickly to our questions. We would definitely comeback to visit again and again.

#1 Island Hideaway 89 - OCEAN FRONT
We had a great week! The condo was a perfect size for my husband and I. We loved the location and looking right at the ocean.

Hyatt Windward Pointe! Great Location!
Beautiful place with a well stocked unit…close enough to all the places we wanted to visit, yet far enough away for a quiet, relaxing day. We loved the area and our stay here. Thank you, Chris.

Ocean Side Paradise Awaits!
Great stay at Ocean Isles. The unit was exactly as shown and was immaculate. We really appreciated how clean and spacious it is. The community is completely secure, quiet, and extremely well maintained. People were friendly. The pool is very big, clean, and warm. Plenty of room to lounge by the pool or at the waterfront. Location is convenient to restaurants and stores. We experienced lots of nearby outdoor adventures. I mean, it’s in the middle of the Florida flipping Keys, so it’s paradise! Frank was easy to communicate with and accommodating. He is an excellent host. We hope to return soon and would be very happy with the same unit.

Henry's Penthouse On The Ocean
We arrived early on the day of check-in, and because previous guests has left early, we were able to check in first thing in the morning! Henry happened to be in Key West, working around his property, so he very kindly gave us a full tour of the apartment, the parking area, the grounds, pool, and beach. The apartment is whimsically decorated with pastel colors to fit the Key West vibe, and has lots of cute details. Amazingly, all the small appliances, dishes, glasses, and tableware are in the pink/rose colored family. Literally every appliance is pink (Cuisenart, coffee maker, toaster, Keurig, blender, tableware, and more). It gave the place a unified cozy feel. The living room is spacious, with lots of couch room for a family to watch TV together. The kitchen is eat-in, and the bathrooms and bedrooms are super nice. We felt very at-home in Henry's place, and appreciate the details he provides about checking in, keys, garage parking, etc. We had a great time.

Dock POOL Kayaks Bikes Beach2mi WalkToStores
We absolutely loved our stay. All the gear was there for everything - biking, beach time, games with family, kayaking, paddle boarding, swimming in the pool. Seriously so happy we stayed there. Absolutely a great stay. Great location. I hate to say so many positive things as I want the place to be my little secret for a return visit. But seriously good. It is a duplex, but the upstairs guests were amazing to be friend and hang out with. And knowing it has two spaces for rent will be nice if I can get more of my family to go to Florida and we can book both spaces in the duplex. Loved our stay.
Waterfront house rentals

Seaside Sunrise. Newly remodeled waterfront
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.

Dock, Beach Club, January avail., tennis, golf
We loved our stay at Jeffery's house. It is spacious and very comfortable. My husband appreciated the proximity to the pickleball courts - we could see them from our bedroom windows- and my son enjoyed fishing off the dock. The upper suite was wonderful for privacy and quiet when the older kids stayed up later than the adults. Jeffery was super helpful and responsive. We would love to stay here again!

Luxury Waterfront Retreat with Dockage & Pool
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.

Waterfront home with direct Atlantic Ocean access
Our first stay at this property was truly unforgettable, and we can't wait to return! Francisco is an outstanding host, always quick to respond and attentive to every detail. The house exceeded our expectations—it was spotless, fully equipped, and conveniently located near stores and restaurants. The outdoor area was a peaceful and inviting space, thoughtfully designed with a refrigerator, sink, hot tub, gas fire pit, and ceiling fans to keep you comfortable. The soft lighting added a warm and welcoming ambiance, perfect for evening gatherings or simply relaxing under the stars. We especially loved the canal, which was incredibly easy to navigate and provided quick access to the ocean—a paradise for fishing enthusiasts! We even caught fish right in the canal, but the absolute highlight was spotting manatees from the dock. If you're looking for the perfect getaway, look no further. Book your stay with Francisco—you won’t regret it

Dream Vacation KCB Marathon with private pool !
Alfonso is a very responsive host who provided clear details, local recommendations (multiple of which we used), and provided a place in a great location. Neighbors are friendly. Place was clean. Perfect for our family with a 14 and 6 year old.

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK
Had a wonderful, peaceful stay. We fished off the dock area, enjoyed time at the cabana, walked every morning enjoying the views and participated in the sunset community almost every night at the park! Great vacation for our multigenerational needs!

Easy Ocean Access 30' Dock House Pool Cabana Club
Doraida was very responsive from initially booking throughout the duration our stay. All of the communication was clear, the instructions were easy to understand, check-in was easy, and the accommodations were very modern with all needed amenities found on site.

Private 174ft Dock, Boat Launch, Sombrero Beach
We had a great stay here, beds were comfortable and bathrooms were clean. Kids loved fishing off the dock - although the boat ramp was unavailable, we were able to use the ramp at the marina down the block ($30 each drop). Hosts were easy to communicate with and very helpful when we had a question. Wed definitely stay here again next time in Marathon.
Waterfront condo rentals

Condo de Paradise/Salt Water Pool/Boat Dock
Peaceful location just a short drive to Key West. The views were beautiful and the condo was just like the pictures! Very spacious and comfortable with everything you'd need. It was the perfect space for our family of four. Cynthia was great. Very responsive and friendly!

Oceanfront 3 bed condo Ocean Edge w/ optional slip
A beautiful condo in a resort community close to many Key West adventures and restaurants. The balcony offers absolutely incredible views of the tranquil water, birds, and stars at night. The views of the sunrise and sunset were stunning. Condo was very nicely furnished and beds were comfortable. Pool was great too. Would love to stay here again!

Oceanfront and Sunrise Views!
This condo was absolutely wonderful! It’s in a beautiful location and safe, walkable neighborhood. It had everything we needed to feel comfortable and at home. Yolanda went above and beyond as a host. She was very responsive and communicated well. We were there during the wildfire in the Everglades and the internet went out in all of the Keys. She called right away to let us know what was going on and when she found out that we were stuck on the mainland until 9pm due to the highway being closed for 5 and a half hours, she stayed in touch to make sure we finally were able to get back to Duck Key safely that night. She generously offered us an extra night to make up for the inconvenience. I can’t say enough good things about Yolanda and the condo. We had a great vacation and will be back!

P80 - Coral Lagoon 3bd/2.5ba townhome with large c
Expect a nice, relaxing time. Beautiful scenery and lots to do in Marathon Key.

Anchor Drop modern elegance upgrades throughout vi
We loved everything about this place. It was super clean and fresh. The bedding was very comfortable and felt expensive. We drank coffee on the balcony every morning watching the ocean. The oceanfront pool area was clean and well taken care of. The unit was stocked and well labeled with all that we would need and more. The garage door opener for inside private parking was amazing. We watched the Tyson fight in the living room on the BIG tv! Had a great vacation. Thank you.

Key Wes't Best- Upgraded condo 5 mins to Smathers
Excellent place. Highly recommend. Great location, walk 1 min to nearby beach. Parking is free for our rental car which is hugely helpful. The place looks just like the photos. Kitchen is big, clean, functional with many utensils, pans. Throughout the home there are abundance of daily needed items such as additional towels, bedsheets, plates, pans, dishwashers which make it very convenient. Looking forward to coming back to this place again.

Paradise @ MM61 - Waterfront 1 BR / 1 Bath Condo
We had a wonderful stay at this location. I recommend it highly. The setting is quiet. Sitting outside on the patio, drinking morning coffee, looking at the ocean, was definately a highlight. The unit was very clean and well stocked with bedding, towels,etc. Duck Key is great for walking. Resturants are easy to get to. We fished most of the time. There is a marina to rent boats less that a 1/2 mile away on Duck Key.

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Great place to stay in Marathon. Close to grocery stores, gas stations, souvenir shops, etc. Very clean, well kept living space and lovely balcony for morning coffee. Pool area is great to relax in. If you are looking for a home base to have while enjoying all that the Keys offer, this is a great place to stay!
Quick stats about waterfront rentals in Stock Island
Total rentals
50 properties
Nightly prices starting at
$110 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
30 properties have a pool
Destinations to explore
- Key West Vacation rentals
- Florida Keys Vacation rentals
- Havana Vacation rentals
- Miami Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Bay Vacation rentals
- St Petersburg Vacation rentals
- Seminole Vacation rentals
- Tampa Vacation rentals
- Central Florida Vacation rentals
- Condo rentals Stock Island
- Apartment rentals Stock Island
- Rentals with a fire pit Stock Island
- House rentals Stock Island
- Rentals with a washer and dryer Stock Island
- Beachfront rentals Stock Island
- Fitness-friendly rentals Stock Island
- Rentals with a hot tub Stock Island
- Kid-friendly rentals Stock Island
- Rentals with a patio Stock Island
- Family-friendly rentals Stock Island
- Rentals with pools Stock Island
- Rentals with a kayak Stock Island
- Rentals with an EV charger Stock Island
- Rentals with outdoor seating Stock Island
- Rentals with beach access Stock Island
- Hotel rentals Stock Island
- Pet-friendly rentals Stock Island
- Waterfront rentals Monroe County
- Waterfront rentals Florida
- Waterfront rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes