Holiday rentals with a kayak in Kent Island

Find and book unique kayak rentals on Airbnb

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Popular amenities for Kent Island kayak rentals

Holiday House Rentals with a Kayak

Guest favourite
Home in Riviera Beach
4.95 out of 5 average rating, 141 reviews

Waterfront Cheerful 5 home

LeslieRating, 5 stars1 month ago
We were in town for a wedding and this home was as described and was perfect for our family of 8 that stayed here. The neighborhood was quiet and peaceful. I wish we had time to enjoy the views from the lake. John was a great host and communicated with us throughout our stay. I would recommend this home to anyone who is looking to stay in the Riviera Beach or Pasadena area. It was close to everything we needed during our stay including the airport.
Top Guest favourite
Home in Woolford
4.93 out of 5 average rating, 151 reviews

Waterfront Getaway with Dock

SarahRating, 5 stars2 weeks ago
We loved the experience from booking to check-out. The setting exceeded our expectations. Peaceful and beautiful landscape. Easy to launch kayaks. Chickens were an added bonus. Appreciated the close proximity of Blackwater. Would love to return.
Guest favourite
Home in North Beach
4.93 out of 5 average rating, 67 reviews

A Little Piece of Paradise - Waterfront Home

LisaRating, 5 stars1 week ago
It was a great stay and a perfect location for our quick family back east. It was very comfortable, clean and a the right size for our family of 4. It was nice to have our own place to stay and not to far from our family. We didn’t spend much time in the town but it looked cute with shops, cafes and restaurants. We had great communication with Maria, she was very quick to respond. Thanks for a great and comfortable stay!!
Guest favourite
Home in Shady Side
4.96 out of 5 average rating, 106 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

NicholasRating, 5 stars7 months ago
We had 6 people for a weekend retreat and this was a fantastic house and location for us. the host was super communacitive and easy/friendly to work with. We'll go back for sure next time we need a retreat space that is quiet, private and affordable.
Top Guest favourite
Home in Rock Hall
5 out of 5 average rating, 31 reviews

1-Particular Harbor: A Coastal Oasis!

FrannieRating, 5 stars1 week ago
We had an amazing weekend and Gregory’s home was perfect. So clean and well equipped. Gregory thought of everything!! Highly recommend ⭐️⭐️⭐️⭐️⭐️
Guest favourite
Home in Cambridge
4.97 out of 5 average rating, 115 reviews

Gorgeous, waterfront home - Perfect for Families.

DavidRating, 5 stars2 weeks ago
Clare and Chris could not be nicer and easier to work with. My family/friends have been getting together since 1994 and have been to many great Airbnb's and VRBO's. My group could not stop telling me how great of a week we had. The primary features that were import to us which the house scored big are as follows: It has a dock (we arrived via boat), The kitchen is big, laid out for many "Cooks", The kitchen was open to the dining room table, The dining room table is open to the sitting areas, The pool was clean and inviting, The fire pit with seasoned firewood was a big hit for our group, All the beds were comfortable, The bedrooms were large and comfortable, The baths were clean, modern & large and The location to "What to do in Cambridge" is only 7-10 miles away. We made prearrangements: Richardson Maritime Museum to have a guided tour with David Williams on Friday and Spocott Windmill with George Radcliff. Both of these tours were fascinating. Our weekend was 5-Stars.
Guest favourite
Home in Crownsville
4.93 out of 5 average rating, 14 reviews

Welcome to Heron House! Annapolis Waterfront Oasis

JenniferRating, 5 stars2 weeks ago
Very peaceful surroundings, you are out on a point overlooking the bay, with lots of outside space to relax in the mornings to enjoy your morning tea/coffee. I loved having the real fireplace and enjoyed an evening fire on the more chillier evenings. Felt at home and comfy.
Superhost
Home in Shady Side
4.88 out of 5 average rating, 181 reviews

Cattail Landing- Photographer's Waterfront Retreat

AshleyRating, 5 stars8 months ago
We had a wonderful time during our visit. The peaceful environment on the water was just what our group needed. Thank you!

Cottages with a kayak

Superhost
Cottage in Annapolis
4.85 out of 5 average rating, 86 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

MichaelRating, 5 stars3 weeks ago
Nice house, very secluded, lots of entertaining space, hot tub was great, back patio, fire pit, everything was great. Isaac was very communicative with all aspects of our stay. An excellent getaway.
Top Guest favourite
Cottage in Oxford
5 out of 5 average rating, 17 reviews

Sailor's Cottage - Private Waterfront

ChristopherRating, 5 stars1 day ago
We recently stayed at this beautiful Airbnb tucked away on a secluded property in Oxford, and it was exactly the reset our family needed. The house was spotless, cozy, and surrounded by nature—offering the kind of quiet you don’t realize you’ve been craving until you hear it. What truly made this stay exceptional were the hosts. We arrived by boat at a nearby marina, and due to our boat’s deep draft, they picked us up to bring us to the house. That extra effort made all the difference, especially with a group that included kids and family coming in from different ends. The home felt like a retreat—private, peaceful, and welcoming. It gave us a much-needed chance to reconnect, recharge, and create some lasting memories. We’d absolutely stay again and recommend this home to anyone looking for an escape from the hustle without sacrificing comfort or kindness.
Guest favourite
Cottage in Deale
4.96 out of 5 average rating, 160 reviews

Chesapeake Bay Cottage

MargaretRating, 5 stars1 month ago
Lovely stay on the water! Mini beach is an added bonus. Great restaurants nearby!
Guest favourite
Cottage in Cambridge
4.98 out of 5 average rating, 49 reviews

Cozy Cottage on the Bay

SarahRating, 5 stars6 months ago
My husband, dog, and I enjoyed a wonderful Thanksgiving break at this very nice and beautifully situated cottage! The views from the back deck and kitchen are as gorgeous as the listing photos suggest and, while the house is right next door to another one, we heard not a peep from the neighbors during our 5 days there. Everything was very attractive and well thought out - the kitchen was well appointed with everything we needed; the chairs, sofa, and bed were super comfy, the bathroom was clean and cheerful. Maxine was great host, answering all our questions quickly and helpfully. It's a 15-20 minute drive to downtown Cambridge, where we had nice dinners out in town at Blue Ruin and Bombay Social. We also took good day trips to Easton, St. Michaels, the Blackwater National Wildlife Refuge, and the impressive Harriet Tubman Underground Railroad Park and Visitor Center. The whole area is full of beauty and history, and this cottage was a great home base!
Top Guest favourite
Cottage in Annapolis
4.98 out of 5 average rating, 115 reviews

Weems Creek Cottage, Annapolis Waterfront

AmyRating, 5 stars4 days ago
Cottage is very cute and the perfect size for a couple. Beautiful view and has all the necessary amenities. Jim was very responsive and communicative!
Guest favourite
Cottage in Pasadena
4.97 out of 5 average rating, 175 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

EmilyRating, 5 stars3 weeks ago
Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !
Top Guest favourite
Cottage in East New Market
4.95 out of 5 average rating, 64 reviews

Cottage on Cabin Creek

MattRating, 5 stars1 week ago
Beautiful private hidden gem on the water, perfect place to escape for a weekend.
Top Guest favourite
Cottage in Essex
5 out of 5 average rating, 43 reviews

The Little House of Rockaway Beach, Maryland

CasandraRating, 5 stars3 months ago
There are no words to express our gratitude 🙏 !! We absolutely loved “the little house” on rockaway beach…It was truly a healing home…we went to Baltimore for my husband’s ankle replacement surgery..this home could not be any more perfect for us…we can’t wait to come back….thank you again and again Brent & Jennifer!! ❤️❤️❤️❤️❤️❤️Casandra Amazing sunrises on the Potomac, close to Baltimore/Washington DC/Annapolis &more, nestled in the charming Rockaway Beach in Essex… The Little House is a comfortable & welcoming retreat. Me on my knee scooter, rolling into the kitchen, bedroom, bathroom and shower. Brent & Jennifer are Super Hosts for good reason, their warm hospitality and impeccable curated beach cottage make for the perfect Maryland getaway, no matter the season. We’ll be back! Scott 😍😍

Cabin rentals with a kayak

Guest favourite
Cabin in Lusby
4.9 out of 5 average rating, 266 reviews

Peaceful Waterfront Retreat on The Bay

SarahRating, 5 stars1 week ago
It’s our second stay at Camp Maier and we are already planning to come back. As soon as we step in, we feel calmed by the view and the comfortable space. The place has had a fresh coat of paint since we were here last, and we appreciated the kitchen upgrades too. We loved pizza at Cryptic Pizza in Solomons Island and a walk with dogs at Flag Ponds nature park. Even found a small fossilized shark tooth! A magical time. Thank you.
Cabin in Saint Michaels
5 out of 5 average rating, 3 reviews

Serene Waterfront Retreat – Chesapeake Bay Escape

JamesRating, 5 stars1 week ago
Elizabeth's house was perfect for our weekend stay in St. Michael's. The house sits right on the water about a 5 minute drive from the center of town. It was the perfect home base for the Ironman event we were attending in Cambridge. Elizabeth was incredibly responsive and provided thoughtful recommendations for our stay. If we are in the area again we will certainly stay again.
Guest favourite
Cabin in Worton
4.93 out of 5 average rating, 92 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

RachelRating, 5 stars3 weeks ago
We loved being in the woods and right by the river. Access to kayaks was a big draw. The home was comfortable and had everything we needed. We also loved being just a quick drive to Chestertown.
Superhost
Cabin in Queenstown
4.9 out of 5 average rating, 21 reviews

Cozy Historic Cabin on the Water

KrystalRating, 5 stars2 weeks ago
Staying at Shawna and Keith's cabin was a wonderful experience. Peaceful and serene, it was relaxing just to wake up in this private oasis. Shawna and Keith were very friendly and easy to get in touch with if we had any questions. They even provided items for some of the activities we decided to try while staying there. The cabin was clean, quaint, quiet, well-equipped; and looked exactly as described. We would definitely return for another weekend getaway! Thanks again!
Guest favourite
Cabin in Saint Michaels
4.75 out of 5 average rating, 80 reviews

Cottage #4 Chesapeake Blue down the drive way.

DavidRating, 5 stars10 months ago
I recently had the pleasure of staying at Alexander and his wife's charming cottage, and we couldn't be happier with the experience. From the moment we arrived, Alex and his wife were incredibly accommodating and helpful, ensuring we had everything needed for a comfortable stay. The cottage itself was cozy and well-maintained, offering everything we required for a relaxing getaway. One of the highlights of our stay was the breathtaking sunset views. Watching the sun dip below the horizon from the dock was simply mesmerizing. The location is also ideal—just a short 10-minute drive to downtown St. Michaels, where we enjoyed exploring the local shops and restaurants. The hosts truly go above and beyond to make their guests feel welcome, and it shows in every aspect of their hospitality. I highly recommend this place for anyone looking for a peaceful and memorable retreat.

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