Holiday rentals with a kayak in Kent Island

Find and book unique kayak rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for kayak rentals in Kent Island

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 stars4 weeks 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 stars1 week 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 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 Lusby
4.99 out of 5 average rating, 302 reviews

Cove Point Beach Cabin

CassieRating, 5 stars1 week ago
Came back for a third visit and had a lovely time at this peaceful retreat.
Top guest favourite
Home in Woolford
5 out of 5 average rating, 221 reviews

Newly Renovated Modern 3 bed 2 bath Water Front

HilaryRating, 5 stars2 weeks ago
The River House was phenomenal, a beautifully furnished place with large riverfront lawn and private boat launch. Exceptionally clean and well-stocked with everything you could think of for a comfy stay (fluffy towels, extra paper products, cleaning supplies, blankets, tons of pillows). Kitchen is as beautiful as the photos, and amply stocked with everything from ziplocs to pyrex to measuring cups and baking tools. The kayaks and canoe were easy to access and use. Easy place to paddle in a calm and quiet tributary. Highly recommend Lindy’s seafood a mile away. Host has compiled a guidebook with lots of local business recs and info. You will not be disappointed with a stay at this awesome retreat.
Superhost
Home in Annapolis
4.87 out of 5 average rating, 179 reviews

Charming Annapolis Water View Home

ManningRating, 5 stars1 month ago
This house is uncommonly beautiful. There is something in every space worthy of contemplation whether it is coffee table in the living room that has a turn of the century industrial feel to the lacquered kitchen countertop that has sealed in the natural beauty. I spent the weekend in awe of its intricacies. I was in town for a wedding with my family, but noted how the whole house including the outdoor space included everything a beachfront house would have to enjoy an extended summer vacation for the whole family. Outdoor space was well equipped for outdoor activities and entertainment with fire pits, grills, hot tub, a plugin cooler for outdoor use. I only wish we’d been better suited to enjoy every aspect of the amenities provided. My favorite thing about this place was the view of the Chesapeake in all of her glory on full display from the living room window. Delightful.
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!
Top guest favourite
Home in Deale
4.99 out of 5 average rating, 144 reviews

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

MelissaRating, 5 stars1 week ago
This was a beautiful waterfront home! This home was well equipped with everything you may need! The host was available if we needed anything! Would definitely recommend!

Cottage rentals 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 stars2 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, 15 reviews

Sailor's Cottage - Private Waterfront

KathleenRating, 5 stars1 week ago
A peaceful and charming place to stay! It was more than I hoped it would be.
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 stars2 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

MicheleRating, 5 stars1 month ago
It was a great stay. Host was responsive and home was calm and clean. Loved seeing the osprey from bed! Those windows highlighted the beautiful view. The weather was a bit dumpy but the space provided everything we needed.
Guest favourite
Cottage in Lusby
4.89 out of 5 average rating, 44 reviews

Hot Tub Hideaway by Shark Tooth Shores

RebeccaRating, 5 stars3 weeks ago
Surrounded by trees and the sound of waves- perfect place to relax & unwind. Quick but steep hike to the secret beach. Cool spot and more shell than I expected. Kyli was a responsive host, answered all my questions. Also, recommended Island Hideaway for dinner and it was amazing. Homemade pasta and desserts made in house daily. Great views and delicious foods & drinks.

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 stars6 days 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.
Guest favourite
Cabin in Saint Michaels
4.99 out of 5 average rating, 112 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

KateRating, 5 stars1 week ago
WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.
Cabin in Saint Michaels
5 out of 5 average rating, 3 reviews

Serene Waterfront Retreat – Chesapeake Bay Escape

JamesRating, 5 stars5 days 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 stars2 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!
Superhost
Cabin in Lusby
4.75 out of 5 average rating, 20 reviews

Covenant Cove (Cove Point Beach)

NiccoleRating, 5 stars6 days ago
We absolutely loved this place. It was a short drive to the bay and certainly worth it. The cottage was secluded enough from the neighbors and we could hear the waves with the windows open. The beach was a very short walk from the cottage and was also very private. We spent a good chunk of our time finding sharks teeth and relaxing on the porch. Grocery stores and gas stations are also fairly close. We even booked our stay for next year already.
Cabin in Lusby
4.83 out of 5 average rating, 23 reviews

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

GeorgeRating, 5 stars3 weeks ago
We enjoyed our stay . Plenty to due . Easy to find . Closer to stores . Quite great country lake feel.
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.

Destinations to explore