
Waterfront vacation rentals in Old Saybrook
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Top-rated waterfront rentals in Old Saybrook
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Popular amenities for Old Saybrook waterfront rentals
Waterfront apartment rentals

Amazing one bdrm flat at the beach!
Jeanette is a wonderful host. She met us on our arrival and gave us a tour of our rental ensuring that she answered any questions. She is very responsive and quick to answer any follow up. questions or concerns. The space is beautifully decorated and comfortable. The location is great, across the street from Long Island Sound and bordering a large nature preserve. All this and easy access to shops, groceries, and restaurants. We highly recommend this rental.

Mystical Ocean View in Historic Stonington Borough
This was possibly the coolest Airbnb I have ever stayed in- the details of this place make you feel like you’re someplace truly special. Sam was amazingly responsive. The descriptions are accurate- that 3rd story spiral staircase is no joke - regardless, I was very comfortable and absolutely loved the setting. Will be back!

Mystic River Getaway - Walk To Downtown & Seaport!
We thoroughly enjoyed our week at this charming home. The location truly is perfect - we walked over to the Seaport one day and took many walks into the downtown area for shopping, meals at amazingly good restaurants, ice cream, and bake shops. Anthony and Kelly were wonderful hosts - the home was just as described and their communication was clear and friendly- just what you want from hosts. We couldn't have asked for more and would be happy to stay here again.

Water View SONO 2 Bedroom Walk to Metro & Dining
Great stay! Thank you Kim!

Bright, private 1,000 sq. ft. 1-Bedroom Apartment
The whole experience was perfect. There were even fresh flowers to greet me. The location is easy, a beautiful neighborhood that is very quiet and safe. I'm ready to return!

Cozy Apartment with Water View of Brook
This was not my first stay at Traci's AirBnB and, much like last time, I would gladly stay again.

Majestic Farmhouse Private & Peaceful Guest Apt.
This was a quick trip to the area to break up the drive to a further destination. Joy's little 18thc apartment was perfect. Joy met and explained everything needed, and was very helpful with local suggestions for dining and activities.Was'nt here long enough to experience any of the hiking trails,.etc but truly seems like a place I'd like to return. if you're lucky, you will meet the inimitable Baloo!

Lakeside apartment 2.5 miles from Wesleyan campus!
Always nice to stay with Mark and Tina. Wonderful people. Very convenient location for us. Beautiful setting. We keep coming back!!
Waterfront house rentals

Direct Waterfront / Riverside
Jim’s place was great, with plenty to see in the area. We ended up spending most of the time enjoying the little beach and kayaks. Very cute house with plenty of room and we’ll stocked kitchen. The grill made for a perfect Labor Day cookout looking out at the water. Would stay again.

True Ocean Front Vacationing - Groton/Mystic
The pictures don't do this place justice! The home itself is gorgeous and the view is stunning. The neighborhood is peaceful and it was perfect for me and four friends to stay the weekend.

Waterfront Secluded Home with Dock
I would highly recommend this property to anyone looking for a comfortable and enjoyable stay.

Waterside retreat! 4BR/3BA with private dock/views
We had the pleasure of staying at Alan's place over Labor Day weekend and it did not disappoint. It was a beautiful setting right across from the water with a dock and walking distance to the town beach , where there are also walking paths along the water. We thoroughly enjoyed sitting out on the expansive front porch watching the birds and fishermen. We rented kayaks from the place around the corner. The house is very charming. There are many nooks and crannies to sit and relax and to enjoy the outdoor scenery. There is plenty of space for everyone to spread out and have their own space. The beds were comfortable with two bedrooms upstairs and 2 bedrooms downstairs. You can access the house from the back where it is only one step in and you are on the main level of the home which is really upstairs. The kitchen is more than adequate with upgraded appliances. Alan was a perfect host/ always available to answer any questions. We will definitely be back!

Home in East Haven directly on Waterfront
Beautiful house beautiful ocean view! We had a wonderful time with our family, we would like to come back again summertime Thank you

Lush Waterview rainforest retreat
The location and views from Phil's place are absolutely beautiful. It was a cozy place to stay and unwind while visiting family in the area. The beach and pathway to it are wonderful. Phil was very responsive to our couple of questions. We would happily go back when in the area again!

Absolutely stunning! New water front house
Ume is a very responsive host! The home was very clean & bright and an easy walk to a nice beach & 2 restaurants. The community was extremely quiet. My husband and kids enjoyed the kayak almost everyday! Nice relaxing vacation!

Waterfront Greenport Boathouse
Very quaint and charming property with a lot of love and history that guests can feel. We really enjoyed all the artifacts and maps collected over the years, much more interesting than your average rental. Very walkable which was particularly handy for a wedding weekend. Really appreciated the proactive outreach just 30 minutes after check out when I forgot some very special jewelry pieces, I was able to get them back quickly!
Waterfront condo rentals

Montauk Sunset at your fingertip!
Picture perfect! Newly updated accommodations with all the comforts of home. Extremely clean and very well managed. The view from this place is incredible. The perfect oasis in Montauk. Khrisna was extremely responsive and accommodating in our needs. Will definitely be back again!

Water front, sunsets, sail boats, Wi-fi, birds
John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

Beautiful condo on Long Islands Northfolk
This was the perfect last-minute getaway for my always on-the-go family in need of some quiet bonding time. The condo was simple and clean, the beach beautiful (even in the winter), and Alice and Gasper were very responsive. Would highly recommend!

Montauk Waterfront Condo w/ Sunset Views
Absolutely wonderful stay and host. I've stayed at dozens of Airbnbs and this is one of my favorites! Doug's place is even better in person than the photos. We were a little nervous taking our first trip away with our baby, but it was extremely clean and comfortable, and Doug was so kind and responsive. The condo complex has a lovely boardwalk for taking walks, and the deck furniture was so comfortable to lounge in and take in the beautiful view. We hope to be back!

Cozy Vacation Villa 5 minutes from Mohegan
My husband and I stayed at Desiree’s place for New Years weekend. The space was beautiful, clean, comfortable and perfect for our getaway. Close to the casino and spa and anything you need. Would definitely recommend!

Beautiful Waterview Condo on the North Fork of LI
Such a beautiful condo by the water! Too bad we stayed in November, we would have enjoyed the terrace way more! Mia was so responsive and helpful with my questions prior to the weekend at her place.

Endless Summer Studio Condo w Balcony Bayview
We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

Beachside Waterview 2Br Condo w/ Pool in Greenport
The place was perfect nice and clean what I like the best is the it was close to the beach to go for a walk.
Quick stats about waterfront rentals in Old Saybrook
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ404 before taxes and fees
Total number of reviews
890 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Beach
- Yale University
- Foxwoods Resort Casino
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Giants Neck Beach
- Shinnecock Hills Golf Club
- Woodmont Beach
- Clinton Town Beach
- Walnut Public Beach
- TPC River Highlands
- Amagansett Beach
- Blue Shutters Beach
- Jennings Beach
- Seaside Beach
- Shennecossett Beach
- Long Island Aquarium
- Attawan Beach
- Groton Long Point Main Beach
- Bushnell Park
- The Connecticut Golf Club
- Burwells Beach
- Fort Trumbull Beach