Bayside

Voted Delaware's Community of the Year, and one of America's 100 Best Places to Live, you'll enjoy an array of amenities that support wellness and relaxation. During your vacation you'll have access to a Jack Nicklaus Signature golf course (extra fees apply), beach shuttle, outdoor pools with a kid's splash zone, a heated 5-lane indoor pool, hot tub, fitness center, saunas, tennis courts, basketball courts, sand volleyball courts, pier fishing and crabbing, stocked-pond fishing, kayaking & standup paddleboarding, and nature trails. And that's not even all of it!

The Bayside Community is also a proud neighbor of the award-winning Freeman Arts Pavilion, an outdoor entertainment venue known 'round the coast for its premier concerts and family events. Just down the road you'll enjoy some of the Eastern Shore's most famous dining establishments, whether you're looking for a "crab bloody" from the Crabcake Factory, Harpoon Hannah's popular happy hour, or to enjoy the fine dining at Catch 54.

Located only 5 miles from the Fenwick Island Beach and less than 10 miles from the Bethany Beach Boardwalk, and with Ocean City, MD right around the corner, Bayside provides a level of luxury, peace, convenience, and comfort that cannot be found anywhere else.

Properties Available 8 properties available
PET-FRIENDLY! Bring your furry family members on vacation with you. - - - - - - - - - - - - - - - - - - - - - - - - - - - - INTRODUCTION Welcome to Heron Hideaway, located in the Heron's Ridge neighborhood in Delaware's finest golf resort community: Bayside. Located in a peaceful nook backing to trees - a rarity in this popular, bustling co
Hot HOT 10
Heron Hideaway
Heron Hideaway
HOUSE
$235 - $330 / per night
Bedrooms 4 bedrooms
Bathrooms 2.5 baths
Guests 10 guests
Welcome to the Tower on 10, located in the Harbor Crest neighborhood in Delaware's finest golf resort community: Bayside. The Tower on 10 is a luxury home so large you'll actually forget it's a townhouse - as you, your friends, and family enjoy the peaceful golf course view situated on the 10th Hole. There is so much to love about this home, from
Hot HOT 12
The Tower on 10
The Tower on 10
TOWNHOME
$350 - $580 / per night
Bedrooms 5 bedrooms
Bathrooms 4.5 baths
Guests 14 guests
Rating 5 (7)
5-STAR REVIEWS COMING SOON! This home is brand new to rentals and will soon have plenty of top-notch reviews, as all properties rented through Win-Le Vacation Rentals do. Book now and be among the first to stay in this beautiful home! - - - - - - - - - - - - - - - - - - - - - - - - - - - - INTRODUCTION Welcome to Cook's Cove Retreat, located in
Cook's Cove Retreat
Cook's Cove Retreat
HOUSE
$245 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 3.5 baths
Guests 9 guests
Rating 5 (3)
5-STAR REVIEWS COMING SOON! This home is brand new to rentals and will soon have plenty of top-notch reviews, as all properties rented through Win-Le Vacation Rentals do. Book now and be among the first to stay in this beautiful home! - - - - - - - - - - - - - - - - - - - - - - - - - - - - INTRODUCTION Welcome to Sunflower Shores, located in th
Sunflower Shores
Sunflower Shores
HOUSE
$265 - $410 / per night
Bedrooms 5 bedrooms
Bathrooms 3.5 baths
Guests 12 guests
Welcome to the Bayside Community of Fenwick Island, DE. This spacious home features 4 bedrooms and 2.5 baths, comfortably accommodating up to 13 people. There is a full kitchen, a first floor ensuite primary bedroom, a laundry room with a full-size washer & dryer, a loft-style lounging & gaming area, and a 1-car garage with beach equipment for your
Indigo Sands Getaway
Indigo Sands Getaway
HOUSE
$245 - $350 / per night
Bedrooms 4 bedrooms
Bathrooms 2.5 baths
Guests 13 guests
Rating 4.9 (10)
INTRODUCTION Welcome to the Bayside Community of Fenwick Island, DE! This modern home features 4 bedrooms and 3.5 baths, comfortably accommodating up to 8 people. There is a full kitchen, dining area, living area, a first floor primary bedroom, and a laundry room with a full-size washer & dryer. The second floor has another primary bedroom, 2 addit
Sunchase Sunset Villa
Sunchase Sunset Villa
HOUSE
$235 - $330 / per night
Bedrooms 4 bedrooms
Bathrooms 3.5 baths
Guests 8 guests
Rating 4.8 (6)
INTRODUCTION Welcome to the Bayside Community of Fenwick Island, DE. This spacious home features 5 bedrooms and 4.5 baths, comfortably accommodating up to 13 people. There is a full kitchen, a first floor ensuite primary bedroom, a laundry room with a full-size washer & dryer, a loft-style lounging area, and a 2-car garage with a foosball table,
Hot HOT 10
Sunchase Coastal Retreat
Sunchase Coastal Retreat
HOUSE
$205 - $345 / per night
Bedrooms 5 bedrooms
Bathrooms 4.5 baths
Guests 13 guests
Rating 4.8 (6)
5-STAR REVIEWS COMING SOON! This home has been lovingly enjoyed as a vacation rental in the past with all 5-start reviews. This is the owner's first year renting with Win-Le and will soon have plenty of top-notch reviews, as all properties rented through Win-Le Vacation Rentals do. Book now and be among the first to stay in this beautiful home!
Lily by the Shore
Lily by the Shore
TOWNHOME
$190 - $265 / per night
Bedrooms 3 bedrooms
Bathrooms 2.5 baths
Guests 10 guests
Rating 5 (1)

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