Holiday houses in Angola by the Bay

Chalet near DE Beaches Fishing Pier, Pool & Tennis

Make memories at this magical vacation destination. A charming beach retreat located in the bayside amenity-rich, gated Angola-by-the-Bay community in Lewes, DE. Tucked away at the end of a quiet cul-de-sac, its a peaceful getaway just minutes from the coast. A safe neighborhood where kids can go to the playground, swim, play basektball, tennis, ride complimentary bikes to the marina to fish & crab. Backyard has games galore!. Visit historic Lewes Beach & fun, friendly Rehoboth Beach Boardwalk.

Value · Location · Wi-Fi

Bay Pearl House! (grill, screened porch, crabbing)

The Bay Pearl House is spacious, comfortable, sun-filled, colorful and functional home base in a unique water front community -only a block from the water. Tasteful beachy decor with herons, flamingos, seahorses and geckos and 10 original photos of water scenes from 5 of the 7 continents of the world taken by the owner. Sun catchers on windows create rainbow-colored lighting streams around the house from sunrise to sunset, adding dynamic bursts of shape and color to enjoy, surprise and delight!

Location · Family · Laundry

Key West by the Bay Bungalow

Relax with the whole family at this peaceful place to stay. Just steps out the back door are the pool and the community amenities, and a quick bike ride takes you to the community marina and Kayak areas. Come unwind in this well-maintained home that is fully stocked with all the household items to make your trip enjoyable and simple. The community has many miles of trails winding thru the waterfront and woods great for biking and walking. Just a short car ride to Beaches, Boardwalk and Outlets.

Family · Location · Amenities

The Red Chalet

Welcome to our home, the Red Chalet. This house has everything you need to make your stay enjoyable This house features 3 bedrooms, a full bath on the main floor and 1/2 upstairs, and an outdoor shower. Enjoy the wrap around deck with plenty of seating, outdoor grill, fire pit, hammock and evening lighting. There are plenty of community amenities including pool, tennis and pickle ball, basketball and playground. Enjoy the bay access for fishing and crabbing. Just 20 minutes to the beach.

Location · Family · Indoor spaces

Bradley's Bayou

Welcome! Visit our quiet secluded neighborhood 20/25 minutes from Rt. 1 restaurants, beaches & outlets. Our waterfront home has beautiful views & reasonable prices. This is a boating & crabbing community with a community pool, tennis courts, crabbing docks & playground. Fun & easy walking and biking for families! Bring creek boots! NOTE: Linens/towels NOT provided. Bring your own! Or Rental suggestion: Sheets at the Beach, LLC 2026 Pool info: schedule in guest book No smoking/ No pets

Family · Location · Checkout

Rest a Shore | Angola by the Bay - Pool, Amenities

This newly remodeled 4BR home is located in the quiet, gated community of Angola by the Bay. Bring your family, boat, kayaks, and bikes and you won't have to leave the community that includes a pool, tennis courts, bocce courts, basketball court, and walking paths! If you do leave, you are located just a short drive from Rehoboth Beach. *After booking, you will need to sign HOA agreement before you arrive for your stay. This is sent through Docusign. (Boat launch for a fee- please see below)

Family · Location · Parks

'Cottage by the bay', sleeps 8 near Rehoboth beach

This bayside getaway is a beautiful 'A' frame style cottage and is located along the Rehoboth bay with direct access to the water. The cottage is within the gated community of Angola by the Bay. About a block away from the front door is one of the three private crabbing/fishing docks, kayak launch and marina! Enjoy walking or biking along the water and trails throughout the community. The large pool is always a favorite too! Baywood greens golf is nearby also! Enjoy the beautiful sunsets!

Location · Family · View

*NEW * cozy wooded retreat 🌳 near Delaware beaches

Come relax after a busy beach day at the ⚓️Admiral’s hideaway⚓️. A newly renovated 2BR/1bath Villa in Lewes, DE. A perfect getaway for a couple or small family visit to all the beach attractions. The hideaway is close enough for easy access yet far enough for residents to sleep away from the heavy Route 1 traffic noises. The entire home is on a private lot (not a neighborhood) lined with 🌲 leading up to the house with a fenced in yard (perfect for your furry family members).

Value · Location · Wi-Fi

Dock Holiday - Waterfront A-frame Cottage

Kick back and relax with family and friends in this comfy and stylish mid century modern waterfront cottage in Angola by the Bay, a gated community featuring community crab docks, trails, a pool, and tennis and pickleball. House has huge waterfront lawn for outdoor games. Minutes to the action and amenities nearby such as historic Lewes, Cape Henlopen State Park, Dewey Beach and the famous Rehoboth Beach boardwalk. Bring your own boat or kayaks and get out on the water!

Location · Family · Decor

Bay Breeze & Marina Charm

Leave the daily rush behind and embrace the charm of Angola by the Bay in Lewes, Delaware. Relish peaceful walks, bike rides, the community pool, pickleball, crabbing, fishing, boating or kayaking, with a boat launch steps away. Close to pristine beaches, state parks, exceptional restaurants, vibrant breweries, and tax-free outlet shopping. Perfect for romantic retreats, friend getaways, or family vacations. Relax and create lasting memories in this coastal haven!

Location · Family · Beach

Beautiful Waterfront Home-Private, Clean, Relaxing

A beautiful and peaceful get-away all year round! Bright and sunny 3 bed/2 bath waterfront home with wrap-around deck. Fully stocked, community pool, walking trails, kayaks and more! Visit Rehoboth or Lewes Beaches (10 miles away), Cape Henlopen and tax-free outlet shopping (6 miles away)! Great for families, water lovers, and bird lovers! Sunday to Sunday weekly rentals *only* and no pets from June 14 to Labor Day.

Location · Family · Beach

Bay Retreat

Come, relax and stay with the whole family in our resort stye Community located in the beautiful Angola by the Bay. Enjoy a walk in the woods on one of our many beautiful trails , relax on a swing at our waterfront or bring your canoe, for fun day on the water. Angola by the Bay has it all! We are just a few miles from all the area Beaches and fabulous Restuarants, outlets and more for your entertainment.

Family · Value · Kitchen