Vacation rentals with a kayak in Delaware

Near DE Turf and Dover AFB with Bowers Bay Views!

Gorgeous sunrises and sunsets at Holiday House! Located in the relaxing Bowers Beach and conveniently located near the DE Turf complex, DSU, Dover Airforce base & Speedway. Just a few minute walk to Bowers Beach, JPs Wharf, and local parks. Features beautiful Delaware Bay views from back deck and breathtaking views of the local nature reserve from front. Enjoy what nature has to offer regardless of season. With room for one or multiple families,you’ll feel refreshed after a stay at Holiday House

Location · Value · Indoor spaces

Cutest-Quiet-bk rds-Bikes-Kayaks-Doorstep parking!

Beach Daze is a surprisingly spacious & bright “tiny house” nestled into a quiet zen-like hidden treasure of a neighborhood within the town of Rehoboth Beach, Delaware. It is walking or biking distance (on quiet, quaint streets) to so many delightful natural wonders including the beaches, the canal, the bay, and a nature preserve! Beach Daze is perfect as a couple's retreat or a family vacation! We provide PLENTY of TOYS… 2 kayaks, 2 bikes, 2 beach chairs & random array of games, toys & sporty.

Location · Value · Walkability

Stunning Rustically Modern Downtown Lewes Home

Don’t settle for a hotel! This immaculate three bedroom home in historic downtown Lewes is an ideal blend of classic and modern design. Leave your car in your private space with shops, restaurants, beaches, and the state park a short walk or bike ride away. Enjoy a gourmet kitchen, great room, dining area, & living room space. Lounge in your master bedroom with en-suite bath.The second bedroom (great for families) has double sized bunk beds. The third bedroom has a queen bed and en-suite bath.

Outdoor spaces · Value · Condition

Dog friendly| community pool | gym| kayak| bayside

Welcome to your ultimate family beach escape! Nestled near Fenwick Island this 3 BDR 2 BTH home offers everything you need for a memorable vacation. Unwind with cocktails at the tiki bar, toast marshmallows around the fire pit, or make a splash in the refreshing pool. Stay in shape at the on-site gym, ensuring your fitness routine doesn't miss a beat. With its prime location just moments from the beach and an array of amenities this bayside retreat promises an unforgettable vacation experience.

Location · Value · Laundry

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

Enjoy over 2300 sqft of screened-in porch with 360 views of Rehoboth Bay and a wildlife reserve. Relax in the Hot Tub (all year) or splash with the kids in the Pool (May-Oct). Enjoy our free kayaks, fishing rods, crab traps, and paddle boards in the backyard Bay or in the Ocean at Lewes, Rehoboth or Dewey <20 min away. Reunite your family around the fireplace or host a birthday weekend with friends riding our free bikes across 3 miles of nature paths. Or Launch your jet ski on our boat ramp!

Outdoor spaces · Location · Access

Warm, Cozy, Beach Cottage on the Bay

Relax alone or with the whole family at this peaceful beach cottage. Master bedroom has a queen size bed. The kids bedroom has a twin bunk bed. The walk through bedroom has a full size bed with a pull out twin bed as well as 2 queen size sofa beds. NOTE: THIS IS A BAY BEACH AND IS NOT A SWIMMING BEACH. The beach is great for taking long walks and sunning but not suitable for bathing. House has stairs and is elevated, not suitable for folks who have difficulty with stairs.

Value · Outdoor spaces · Laundry

Coastal Cottage! Walk to Beach!

Welcome to the Cottage at Saltwater Pines, a newly-remodeled 3-bedroom family home, walking distance to the beach and just blocks from downtown Bethany and the boardwalk. With a stylish interior, comfy beds, whole-house state-of-the-art audio system, and a covered pool, your getaway promises a memorable stay. Explore the pristine shores, vibrant boardwalk, and outdoor activities nearby. Book now for a coastal retreat filled with relaxation and fun!

Outdoor spaces · Location · Biking

Beachwalk: ON BEACH. Pet-Friendly. Linens Incl.

For years, we searched for the perfect beach getaway: secluded, tranquil, yet close to attractions. We found it in Beachwalk. Peaceful. Private. Conveniently located at the quiet southern end of Broadkill Beach. Our home offers a more private beach experience with no crowds. If this property is booked or you need multiple homes for a group, we host several nearby beach homes. Click on my host profile to see those other listings

Location · Outdoor spaces · Walkability

Delaware Beach Bliss, steps from the sand & surf!

Our large, comfortable, pet friendly beach house well suited to families and mellow friend groups is 2 lots from a crescent beach that you can walk for miles in either direction, offers some water views from the top of the steps and one bedroom. We have a sandy area under the house with beach chairs, SUP & 4 adult bikes in beach closet that opens with the house key for your stay. Gather together in the great room at days end.

Location · Outdoor spaces · Decor

Bayside Resort Beach Home

Beautifully newly built (2025) modern beach home in Bayside Resort with 6 bedrooms (2 master suites), 3.5 bathrooms, and over 3,000 sq ft of coastal elegance. Enjoy an open-concept layout, high-end finishes, a covered patio, and an outdoor fire pit—perfect for relaxing and unwinding. Just minutes from Fenwick Island and Ocean City, with access to resort-style amenities. Ideal for families, groups, or a luxurious beach retreat.

Location · Laundry · Long stay

Woodsey Beach House - Beach, Lake, Woods!

Beach? Check Cabin? Check Lake? Check Have it all at our home near the beach, in a beautiful wooded setting with a lake view! Quiet neighborhood makes you feel right at home. Newly renovated with new appliances and furnishings. The house has an upside-down layout, so most of the living spaces, including the kitchen, dining, and living rooms are on the second floor. The home is unique, bright and comfortable.

Value · Outdoor spaces · Layout

Beachfront 1BR (1st floor) *FREE Kayaks, Bikes*

No property is closer to the beach! Huge deck with ocean views, Quiet and peaceful getaway. This is a first floor unit of a beachfront house located right next to Prime Hook National Wildlife Refuge. 20 min drive from Lewes, Rehoboth beach & Dewey beaches. Broadkill Beach convenience store nearby, shopping center ~ 10 min away. Kayaks are available free of charge with advance notice.

Outdoor spaces · Location · Cleanliness