
Waterfront vacation rentals in Stock Island
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Top-rated waterfront rentals in Stock Island
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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
Enjoyed our stay! Yuni answered all our questions in a timely manner. The home was spotless! Location is very peaceful and relaxing! We would highly recommend staying here and hope to come back again someday!

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 have traveled to the Keys many times and this has been our favorite stay. Beautiful location (pictures could not capture all the beauty of this location). Everyone was so friendly at this location, felt safe and right at home. We were amazed at how quiet this location was. Ocean steps away. Loved our sunrise and sunset views on the patio. We truly enjoyed the music and dance the last night we stayed. This will be our return trip next year, doubling days of stay for sure! Thank you again:)

Hyatt Windward Pointe! Great Location!
Beautiful condo with amazing ocean views. Front desk staff was amazing and offered us everything that we needed. Would definitely stay again with Chris.

Best Catch on Grouper LN at Ocean Isles
We had a great week stay here. Easy to get in and out of this gated community. Condo seemed very new, pretty, clean and comfortable. Kitchen had everything we could possibly need. Pool and view was great and it was a nice central location as we visited places from Key West to Key Largo

Little Venice in Marathon (in the Beautiful Keys)
Very cute place. Nice outdoor patio area with lighting. You could put your boat right in front. Very well thought of with things like a grill, fish cleaning area with a water supply, beach towels and indoor laundry. Nearby homes had activity but nobody was loud, even the nearby charter boat was very quiet. We didn't even hear them drive by in the morning. We would stay here again.

Dock POOL Kayaks Bikes Beach2mi WalkToStores
Luna Bay Breeze was the most family friendly “resort” stay we’ve had. Amenities, Galore! Our extended family enjoyed every well thought out detail from the several Kayaks and SUPs with a variety of lifejackets to bikes with safety helmets (even a child sized with child carrier!). The grounds were attractively maintained with a very clean above ground pool, bar and several seating areas under cover or by the channel, with high tops with sun umbrellas to cozy lounge chairs and areas to congregate. They provided child and tween sized picnic tables, lawn games, and fishing equipment, sand cart, many beach chairs, a cooler for our days at the beaches, and beach towels. Inside was just as thoroughly appointed with coffee bar, multiple kitchen appliances, and exquisitely decorated touches. Beds, even bunks and trundle were comfy queens with bedding attractively styled. Our host’s hospitality experience and quality cleaning staff was evident. Clear, timely communications were appreciated!
Waterfront house rentals

Seaside Sunrise. Newly remodeled waterfront
This home was simplistic, clean and a great peaceful location. The hot tub was a nice addition especially because we had cooler weather while we were here. I could make an espresso or regular drip coffee from the appliance provided. The shower was cutting-edge and beds were comfortable. I would recommend this house for anyone that comes to visit the keys.

Dock, Beach Club, January avail., tennis, golf
This house was one of our favorites and would rent again! Huge bedrooms, kitchen was well stocked, everything great!

Paradise in Cudjoe! Perfect Family Home!
Taylor and Kali were friendly and polite. Very accommodating and the location was perfect. Loved having the space to filet fish and easy access to open water. Would def recommend!

Luxury Waterfront Retreat with Dockage & Pool
Last minute booking with Naomi due to problem with another Airbnb on Cudjoe Key. Naomi immediately responded and made arrangements to get us settled. Her place was easy to find, with a lot of amenities provided. Kayaks, hot tub, pool and fishing were easy to access and enjoy.

Waterfront home with direct Atlantic Ocean access
My husband and I stayed for a week for our anniversary and had a fantastic time. House was clean, comfy, and well maintained. We brought our boat down with us and docked it at the house. Dock was perfect for us. Plenty of parking space, and even a spot for our boat trailer. We also loved how well maintained channel the channel was. It was one of the only channels we saw with channel markers. Property owners were so kind and ready to help out or answer any questions we had. Location really could not have been better too, with plenty of amazing restaurants within 10 minutes and just a short boat ride to fuel up at Captain Hooks. We're already talking about planning another trip here!

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK
Looks just like the photo’s. Unfortunately weather was a little chilly the first couple of days. When it warmed up we enjoyed the local cabana club with the heated pool, beach and restaurants. The accommodations were spacious and clean.

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.

Waterfront House with 37 ft Dock & Cabana Club
Great location and squeaky clean throughout. Bikes and water toys. Felt like home, modern furnishings, and fully equipped. Loved being on the water and watching the birds and boat traffic. Key Colony Beach is very friendly, walkable, and has a beach. Marathon has lots of good restaurants and things to do. Outstanding job Jorge! Thank you!
Waterfront condo rentals

Oceanfront 3 bed condo Ocean Edge w/ optional slip
The condo is just like the pictures and the views shown are from the deck. We had an unbelievable time here during our family vacation. We were far enough from the craziness of downtown Key West but close enough for a quick Uber ride when we wanted to see the sites, shop, or enjoy restaurants. The condo had everything we could possibly need, just bring your personal stuff, place a delivery grocery order from Winn Dixie and we were set for the week. The condo is part of a resort so you get all those amenities along with the more private condo only pool and hot tub. We enjoyed walking around the marina and looking at the large boats along with enjoying the tranquility of the views of just water from the deck. Carri was the best host I’ve had the opportunity to deal with. Extremely responsive and helpful at every turn. We will absolutely be back and will base our timing around staying at Carri’s place again.

Oceanfront and Sunrise Views!
The place was amazing! It had everything we needed (and more). Great location and Yolanda was super friendly and quick to respond to our questions. Would definitely stay again!

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.

Henry's Piece of Paradise On The Ocean In Key West
My daughters and I came from 3 different locales to spend a few days together at Henry's condo. We were very comfortable. The condo is stocked with kitchen utensils, beach towels and chairs, tvs, and a sound system. It was a bit chilly for the pool, but we enjoyed the community's hot tub and landscaped community area. Smathers Beach is a short walk away. Higgs Beach is also walkable and has plenty of parking. I wanted to try the snorkeling trail at Higgs, but it was a bit chilly for me. Still, February in Key West was a welcome relief from the 20 degree weather and snow I left behind! There was a lot of paperwork for an Airbnb ahead of arrival, but everything went great. Henry was always available, responsive, and helpful. We had a terrific reunion and enjoyed Key West.

Ocean Front Suite | Beachside Resort
Thoroughly enjoyed our stay! Easy check-in, although from wasn’t ready until an hour after the set check-in time. Clean room. Comfortable bed. Location away from the hustle & bustle of downtown, however downtown was easy to get to with the free shuttle provided by the resort. Both restaurants had delicious food. Tavern-n-Town happen to best the best food on our trip, including Key Lime Pie! The beach was underwhelming with little area to actually swim & no beach chairs set up at the swimming area, however the pool made up for it. The pool was warm, clean & not overly crowded. Nice live music in the afternoons. Fitness center was small, but had the basics & was able to enjoy some beachside yoga during our stay. We would definitely stay again!
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
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