
Holiday rentals with a kayak in Southern Maryland
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Southern Maryland
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

Hideaway on the Bay: Waterfront Vintage A Frame
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Waterfront 4-BR home w/ hot tub & charging station
Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach
Welcome to the Butterfly Effect! Recharge at this tranquil getaway. 2.5 wooded acres with a private dock and cove, a short paddle away from the lake beach with a swimming dock and sandy beach! Fishing, swimming, and floating all on the protected freshwater lake. We have boats for your use, theater space & hot tub to wind down at night after dining on our deck. Picnic at our private Shark Tooth Beach, watch Osprey & Eagles fish the Potomac, and collect 15-million-year-old fossilized shark teeth!

The Little House on Back Creek
Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

Beach Front and 'Perfectly Placed'
Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

The Bird's Nest at Holly Bluff-Riverfront. Beach.
This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Charming Rustic Boathouse right on the Water!
Welcome to the Boathouse!! By offering kayaks, swimming, crabbing/fishing opportunity, a beautiful ambiance for drinks and dinner straight on the water and having almost any water adventure right at your fingertips, this glamping (glamour-camping) bungalow on the water is perfect for just about anyone with an adventurous nature-loving spirit! We encourage you to eat what you catch! And even bring your own boat and stay in one of our boat slips! Minutes from Solomons Island by Boat or Car!

Living on Island Time
Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

Sunset Breezes - quiet waterfront retreat
Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness barn (sauna, golf simulator, free weights, game space and more (completion date of 4/1/2026 or sooner).

Peace Point - Waterfront, Secluded, Home w/hot tub
Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

Historic Rousby Hall, Waterfront, Pool, Beach
Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage
Popular amenities for kayak rentals in Southern Maryland
House rentals with a kayak

Waterfront Getaway with Dock

Rivah View

The River House: A private waterfront oasis…

The River House, a Wicomico Beach Retreat

Spacious Gorgeous Waterfront Home with Sunset View

Cozy & Content River Retreat Beach Hot Tub & Games

Cove Point Cottage with Chesapeake Bay views

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks
Cottage rentals with a kayak

Cottage with a view!

Chesapeake Bay Cottage

Private point on the Bay🌤hammock, hot tub, kayaks❤️

Modern 2 Bdrm Cottage in Historic River Community

Where Eagles Soar *Stunning Waterfront Views*

Levering Creek Cottage with private dock

Bungalow Private Beach & Dock Colonial Beach Water

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
Cabin rentals with a kayak

"Elderberries" Chesapeake Bayfront Cottage

Cozy Historic Cabin on the Water

Pizza Friday

Peaceful Waterfront Retreat on The Bay

Camp Heron : Waterfront Cabin on the Potomac

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Ocean Break

Luxury cabin - Pond - 16 acres
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Outer Banks Holiday rentals
- House rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with a fireplace Southern Maryland
- Motorhome rentals Southern Maryland
- Pet-friendly rentals Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Family-friendly rentals Southern Maryland
- Hotel rooms Southern Maryland
- Cabin rentals Southern Maryland
- Waterfront rentals Southern Maryland
- Private suite rentals Southern Maryland
- Rentals with pools Southern Maryland
- Beachfront rentals Southern Maryland
- Flat rentals Southern Maryland
- Rentals with a cinema Southern Maryland
- Guest house rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Rentals with an accessible-height toilet Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Rentals with breakfast Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a firepit Southern Maryland
- Bed and breakfasts Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Rentals with a hot tub Southern Maryland
- Farm stay rentals Southern Maryland
- Rentals with a patio Southern Maryland
- Rentals with lake access Southern Maryland
- Apartment rentals Southern Maryland
- Rentals with a kayak Maryland
- Rentals with a kayak United States
- Georgetown University
- Walter E Washington Convention Center
- National Mall
- Nationals Park
- The White House
- District Wharf
- Capital One Arena
- National Museum of Natural History
- National Museum of African American History and Culture
- Arlington National Cemetery
- Howard University
- Sandy Point State Park
- Washington Monument
- Georgetown Waterfront Park
- National Harbor
- Smithsonian American Art Museum
- Great Falls Park
- Six Flags America
- The Pentagon
- Lincoln Park
- Library of Congress
- The Anthem
- Smithsonian National Air and Space Museum
- Museum of the Bible




