Holiday rentals with a kayak in Anne Arundel County

Find and book unique kayak rentals on Airbnb

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Popular amenities for Anne Arundel County kayak rentals

Holiday House Rentals with a Kayak

Guest favourite
Home in Annapolis
5 out of 5 average rating, 18 reviews

Annapolis waterfront, private pier with kayaks

MeghanRating, 5 stars1 month ago
The place was great! Amazing spot located right on the water. Beautiful open space that was perfect for a large group wanting to spend time together. Calling ubers into town was a little tricky and came with some long wait times, but we were always able to connect with a ride and get where we needed to go.
Top Guest favourite
Home in Edgewater
5 out of 5 average rating, 11 reviews

Stunning waterfront views with dock near Annapolis

CynthiaRating, 5 stars1 month ago
Absolutely beautiful lakefront home. Bob’s place boasted a fantastic chefs kitchen including everything needed to catch your own crabs! The master suite featured a spa like bathroom and stunning sunset views from the private balcony. The location was quiet and very private and located within driving distance of DC and Baltimore. Bob and his wife were lovely hosts and had several recommendations for beautiful day trips and restaurants. We truly felt on vacation in luxury.
Superhost
Home in Edgewater
4.81 out of 5 average rating, 21 reviews

South River Beach Front House

TammyRating, 5 stars7 months ago
Great location, beautiful home that was very comfortable.
Guest favourite
Home in Shady Side
4.93 out of 5 average rating, 45 reviews

Cozy Bay home w/180 degree view

DeanaRating, 5 stars2 months ago
Madeline place was great to watch cruise ships and other boats come and go into Baltimore. Beautiful sunrises and sunsets right off the balcony. Quiet and peaceful. Madeline was very helpful and responded quickly. We would highly recommend staying here.
Guest favourite
Home in Pasadena
5 out of 5 average rating, 52 reviews

Waterfront CHeerful 2 with Private home

DavidRating, 5 stars3 weeks ago
The cottage /house was peaceful on the edge of an inlet from the Bay. The patio was lovely. It was chilly so we couldn’t use the kayaks. The kitchen was very well equipped. The dishes, utensils, cookware were quality. The extra cozy blankets were nice. He responded to a request very timely. We enjoyed the stay very much.
Superhost
Home in Shady Side
4.83 out of 5 average rating, 12 reviews

Chesapeake Bay - West River Home

JenniferRating, 5 stars8 months ago
Fabulous house in a terrific location. The house was very clean and Rick was a great host.
Guest favourite
Home in Edgewater
4.98 out of 5 average rating, 123 reviews

Luxury Modern Home on Water+Hotub- Annapolis 25min

SamirahRating, 5 stars1 month ago
An Unforgettable Couples Getaway Thank you so much for allowing us to host our couples gathering at your beautiful property. The home was not only stunning and well-appointed, but it also created the perfect atmosphere for a weekend filled with connection, laughter, and unforgettable memories. The care and attention to detail in preparing the space did not go unnoticed. From the beach towels by the hot tub to the extra bedding that came in handy (especially since I forgot to mention my feather allergy!), everything was thoughtfully stocked and readily accessible. Our group felt immediately at home. Finding a property that can comfortably and effortlessly accommodate a group like ours is rare—but yours exceeded every expectation. We’re incredibly grateful for your warm hospitality and would gladly recommend your home to anyone looking for a cozy, welcoming place to stay. We hope to return again in the future!
Top Guest favourite
Home in Shady Side
4.98 out of 5 average rating, 48 reviews

Sunset Cottage

NicoleRating, 5 stars1 week ago
The house was so beautiful and was even bigger than the pictures make it look. The beds were comfy, the host had great communication, and the outdoor area was as so gorgeous. Highly recommend!

Cottages with a kayak

Guest favourite
Cottage in Edgewater
4.99 out of 5 average rating, 155 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

MattRating, 5 stars2 weeks ago
Great place. Spotless with tons of amenities. Beautiful sunrise over the water in the morning. Nice sized newer dock to walk out on to feel closer to water and nature. Stylish and comfortable furnishings. Can’t wait to come back!
Guest favourite
Cottage in Edgewater
4.92 out of 5 average rating, 48 reviews

Waterfront Cottage with Private Pier

SarahRating, 5 stars1 week ago
This is a gem of a cottage. The host was lovely , the decor was wonderfully curated, and the house was fully stocked with anything we needed! Coffee, travel soaps, full kitchen, even a dog dish! We had such a relaxing time enjoying the perfect views. Felt like we were in another time!
Superhost
Cottage in Annapolis
4.87 out of 5 average rating, 83 reviews

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

ChelseaRating, 5 stars3 days ago
The host was very kind, accommodating, and had a quick response time to all messages. The house is adorable and was a great fit for 5 friends wanting to get away for a night! I would highly recommend this house and encourage you to use the outdoor space!
Guest favourite
Cottage in Deale
4.96 out of 5 average rating, 159 reviews

Chesapeake Bay Cottage

AndyRating, 5 stars3 weeks ago
fantastic stay. clean and very quiet right on the bay. highly recommended. would definitely revisit again.
Top Guest favourite
Cottage in Annapolis
4.98 out of 5 average rating, 112 reviews

Weems Creek Cottage, Annapolis Waterfront

BenjaminRating, 5 stars1 month ago
What a beautiful off the beaten path place to stay. You are within walking distance of restaurants, coffee, and grocery. But feel like you’re miles away. That’s the effect the cabin has on you. There is a beautiful waterfront that you can enjoy from just about every area of the home. Jim was more than helpful. He really went above and beyond over most host. We would definitely Stay again. It’s the perfect spot if you need to relax.
Superhost
Cottage in Annapolis
4.93 out of 5 average rating, 14 reviews

Beachfront & dog-friendly home just mins to DTA

JaimieRating, 5 stars2 weeks ago
My family really enjoyed our stay! The most amazing part of the home is the private beach right outside your back door! Absolutely beautiful to wake up to the sunrise each morning. The location was great, quick drive into town (under 10 minutes) where you have access to incredible restaurants, pubs, shopping and the Naval Academy rich with history. Also easy access to supermarkets, pharmacies…etc. this was our first trip to Annapolis and the house and location did not disappoint. The hosts were very kind and responsive and the house felt very cozy with lots of natural light and amenities.
Guest favourite
Cottage in Pasadena
4.97 out of 5 average rating, 173 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

JulieRating, 5 stars5 months ago
The place is wonderful. We were down for Thanksgiving with my family and were travelling with our 2 dogs, Wally & Dolly. The location was perfect, close to Riviera Beach where our Family Thanksgiving Dinner was, very private, no noise or distractions for the dogs (that was great). The property was surrounded by water on three sides, great views! It is right next to Ft. Smallwood Park where we took the dogs for walks every day, they loved it. As for the house it was perfect for us, just about the size of our home, so that made it very comfortable for us. All one level, which made it great for us older people. It was furnished with very comfortable furniture. Lots of information about the local surroundings, things to do, and restaurants. Keith was wonderful to work with, very easy to communicate with which made the whole process very easy for us. We even had a conversation over the phone once we were in the house to make sure everything was to our liking, and we were happy !

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