Holiday rentals with a kayak in Sussex County

Tiny home in Rehoboth Beach

4.94 out of 5 average rating, 288 reviews

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.

ValueOutdoor spacesAir conditioning

A charming two-story home is featured, showcasing a white exterior with dark shutters. A welcoming front porch is adorned with rocking chairs, inviting relaxation. The landscaped yard enhances the property's curb appeal, while the clear blue sky adds to the overall inviting atmosphere.

4.98 out of 5 average rating, 123 reviews

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.

ValueLocationBarbecue

5.0 out of 5 average rating, 29 reviews

A welcoming entrance is framed by a brick pathway lined with soft green grass and small white lights. Lush trees and vibrant shrubs provide a pleasant contrast to the exterior. Large windows invite natural light into the home, enhancing the overall charm.

Home in Millsboro

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Outdoor spacesLocationAmenities

A spacious dining area features a long wooden table surrounded by green and gray chairs. Large glass sliding doors offer expansive views of the surrounding wetlands, inviting natural light into the room. A modern chandelier hangs above the table, enhancing the dining experience.

4.96 out of 5 average rating, 81 reviews

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!

LocationOutdoor spacesSleep quality

4.94 out of 5 average rating, 18 reviews

Townhouse in Dewey Beach

Bayfront Townhouse - Endless Views & Private Beach

Enjoy coastal living at this bayfront townhouse in Dewey Beach, DE. This 3-bedroom, 2.5-bath rental offers beautiful bay views and an unbeatable walkable location. The open-concept living space includes a fully equipped kitchen, dining area, and comfortable living room—perfect for relaxing after the beach. Step outside for sunsets, kayaking, or paddle boarding right on the bay. The ocean beach, restaurants, bars, and shops are just a short walk away, with Rehoboth Beach minutes nearby.

LocationNearbyCleanliness

4.98 out of 5 average rating, 41 reviews

Home in Milton

Horseshoe Haven-Roof Deck, Beach Views, Game Room

Newly constructed beach house with gorgeous views and lots of space. The roof deck provides amazing views of the marsh and ocean, which is a 3 minute walk. Entire home has Sonos, including under the house, which has a sauna, the 1st and 2nd floor decks. The living room features a see-thru fireplace, which is shared with the deck. The first floor includes a game room featuring a 12' shuffleboard table, foosball, arcade center, and bumper pool/card table combo, as well as a theater room.

LocationOutdoor spacesPets

4.99 out of 5 average rating, 261 reviews

A deck overlooks sandy paths leading to the ocean, framed by lush dune grass and coastal vegetation. The bright blue sky contrasts with the calming sea, creating a serene coastal view. The deck railing offers a defined space for relaxation while enjoying the surrounding nature.

Home in Milton

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

LocationValueIndoor spaces

Superhost

The exterior of the beach house is seen from an angle that highlights large windows and a welcoming entryway. A staircase leads to the elevated porch, which features a railing, while a colorful flag adds a touch of character.

Home in Milton

4.81 out of 5 average rating, 116 reviews

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.

Outdoor spacesValueSleep quality

The kitchen features modern appliances and a spacious island with seating for three. Natural light enters through a skylight and glass door, illuminating the light-colored cabinetry and countertops. A hallway leading to other areas of the house is visible in the background.

4.95 out of 5 average rating, 149 reviews

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.

ValueLocationAccuracy

A modern coastal-style home is pictured, featuring a spacious two-story structure with a covered front porch. Lush green landscaping surrounds the property, and a light-colored facade complements the clear blue sky. Driveway access is visible beneath the elevated home.

5.0 out of 5 average rating, 63 reviews

Cape Shores Luxury - NEW Pool, Beach, Pier, Park!

Welcome to your vacation home in highly desirable Cape Shores community! This renovated, four-bedroom home is only 2 houses (<1 minute walk) away from the brand new (2024) pool (Memorial to Labor Day)! Also, just a short walk (5 houses) to the beach, tennis & pickleball courts, and state park. Cape Shores is the only waterfront community in Lewes with a pool, private fishing pier, & tennis/pickleball courts.

LocationOutdoor spacesLayout

4.84 out of 5 average rating, 101 reviews

A well-lit bedroom features a spacious bed with crisp white linens and decorative pillows. A large window adorned with sheer curtains allows natural light to brighten the room. A wooden dresser and wall art enhance the inviting atmosphere.

Condo in Rehoboth Beach

Cape Suites Room 4 - Free Parking!

Your Place to Stay in Rehoboth Beach, DE! This Second Floor West End Suite has been completely renovated in 2023! It features a brand new bathroom with tub/shower enclosure, new tile and vanity. This suite will have a new layout in the second bedroom featuring a built-in with a small refrigerator, microwave, and wardrobe. Also included is a cafe table with two chairs and all new A/V equipment.

LocationValueKitchen