
Holiday rentals with a pool in Rehoboth Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Rehoboth Bay
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Luxury Dog Friendly Condo At The Residences
Vacation in this beautiful, professionally decorated, luxury 2 bedroom, 2 bath condo at The Residences at Lighthouse Cove, located in the heart of Dewey Beach, DE, only 1 block from the beach. Workout in the exercise room or swim in the indoor pool Condo guests have exclusive use of our stunning rooftop veranda with fire pits & grills and outdoor pool in the season Enjoy this peaceful "get-away retreat, while having access to all the Dewey/Rehoboth Beach restaurants, beaches, and night life

Newly Renovated Modern 2 Bed/2 Bath Condo w/ Pool
Newly renovated and designer decorated 2 bedroom/2 bath beach condo with the most comfortable beds imaginable. Located in the heart of Dewey Beach with an outdoor pool and only 1 block to beach and bay. One bedroom includes a King sized bed with private bathroom. The 2nd bedroom includes a Queen and a Twin sized beds adjacent to the 2nd bathroom. The fully equipped kitchen features stainless steel appliances, granite countertops, an island w/ seating, and washer/dryer. 2 parking spots included.

Renovated Condo Near Outlets, 3.5 Miles to Beach
Enjoy your stay in this recently renovated and beautifully furnished two-bedroom, two-bathroom 3rd-floor condo conveniently located 3.5 miles from the Rehoboth Beach boardwalk, and 4.5 miles from Lewes Beach. The proximity to the beaches, stores, and restaurants make this condo a great spot to spend a fun-filled vacation at the beach. Our condo amenities include a community pool*( seasonal), free parking, free WiFi, smart TV, washer, and dryer. We supply all the sheets & towels for your stay.

Sunrise Studio - Ocean Front, on Boardwalk, Pool!
Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

Family Friendly Top Floor Condo Near Boardwalk
Located just 2 miles from the Rehoboth Beach boardwalk, yet nestled in a peaceful community. Condo offers a comfortable & well-equipped space Primary Bedroom: King w/ en-suite bathroom Second Bedroom: Queen w/ en-suite bathroom Living Area: Sofa & comfy chairs for relaxing For the Littles: Pack 'n Play, high chair, & many kid-friendly extras—see the last few photos for all the thoughtful touches! Whether you're here to explore Rehoboth’s charm or simply unwind, this is the perfect home base!

Cozy Creekwood Condo - Relaxing Getaway - W/ Pool
Perfect location to enjoy the holiday season in Southern DE for upcoming events, ie. Rehoboth Beach Parade, Rehoboth and Dewey Beach Tree Lighting, NYE Celebrations and Dewey’s Famous Winter Gala! Whether you're planning a beach vacation, a business trip, or a shopping spree at the nearby Outlets, this condo is the ideal retreat. Conveniently located near dining, shopping, scenic trails, and just a short drive to Lewes, Rehoboth, and Dewey by having everything you need for a memorable stay.

Modern 2BR/2BA – Beach Pass + Bikes, 5 Min Drive
This spacious, clean, and modern 2-bedroom, 2-bath condo is the perfect place to unwind after a road trip or a sun-soaked day at the beach. With a King bed, Queen bed, beach parking pass, and bikes included, getting to Rehoboth Beach is as easy as it gets. And when you're back home, parking is a breeze — with hundreds of open spots right outside the condo. We even provide you recommendations to restaurants, fun activities and even what to order! Beach, Outlets, Parks and Good Food.

Cozy Woodland Cottage
Enjoy the sounds of nature when you stay in this unique place. Located less than 5 miles from downtown Lewes and Delaware Beaches. The cottage guest house is nestled in the woods adjacent to a tree house overlooking a tranquil pond with a calming fountain sounds. On the main property guests have access to a in ground swimming pool (seasonal) with a 60 foot lap lane and slide, schedule times with hosts.. The backyard also includes an organic garden, playground and 🐔 chickens.

Direct Oceanfront with a View and Amenities Galore
Note: Must be 25 or older to rent our home. Beautifully renovated 2 bedroom beach front condo with views of both the beach and bay. Enjoy watching the waves roll in or a stunning sunrise through floor to ceiling windows without ever getting out of your king size bed. In the evening, open your front door to witness breathtaking sunsets over the bay. Or just relax with a drink on the beachfront balcony and listen to the waves with full 100% view of the beach and ocean.

Caramar Couples Retreat
This cute little first floor efficiency condo is ocean front for a perfect vacation to the beach. It’s an older building but has been partially renovated and updated. You can get to the beach by a very short walk through a private walkway from the condo building. The view from the private balcony is perfect and relaxing. WiFi provided upon check in- xfinity, Netflix, and internet. Indoor and outdoor dining areas and a full kitchen. Closet and dresser for storage use.

1st Floor Beach-town Condo in Lewes
Come stay at our favorite little beachtown condo in Lewes! This 1st floor 2 bedroom, 2 bath condo has everything you need for an enjoyable and relaxing vacation! You will be just a few miles to the beach and outlet malls, have access to the community pools (May-Sept), park, and sport courts, and will be within walking distance to several great restaurants and shops. While we are "pet friendly" only 1 pet (dog or cat, 40lb maximum) is allowed per the HOA rules.

Condo 2 Bedroom Waterfront Lewes/Rehoboth DE
2 Bedroom Condo Top Floor (3rd Floor) - Waterfront in Lewes/Rehoboth Beach DE Great Scenery Views - The Residence at Rehoboth Bay. *Community Pool available during in-season (8am-8pm) *No cleaning fee Nearby amenities and attractions include: Rehoboth Beach Boardwalk (6 Miles) Cape Henlopen State Park (8 Miles) Dewey Beach, DE (7 Miles) Bethany Beach, DE (18 Miles) Ocean City, MD (32 Miles) Shopping Outlets (4 Miles)
Popular amenities for Rehoboth Bay rentals with a pool
House rentals with a pool

Steps to pool and bakery, baby friendly town home

Artist’s Escape (2-bedrooms/3 beds/3 bathrooms)

Gorgeous Bayfront, Pool, Hot Tub, Linens Included

Beautiful Beach House in Rehoboth

Relaxing Getaway

Luxury Carriage House in Rehoboth Beach

Private pool in BayVista! 4bdrm family beach house

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
Apartment rentals with a pool

Spring Lake Escape-dog friendly, monthly available

Luxury Bay & Oceanview Condo in the Heart of Dewey

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck

Water Views * Balcony * Pool * Fast Wi-Fi

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Clean and Comfy, Close to Schellville and Shopping

Gone Coastal *Pool* Bayside with view* Top Floor

Pines Getaway - Berlin Tree Light & Ice Ice 11/28
Other holiday rentals with a pool

Beautiful 3 Story Town House In Rehoboth Beach

Lakefront condo blocks from the beach

Family & Pet-friendly Beach House with Pool

Forever Young in Rehoboth Beach

Rehoboth-Lewes Beach House by the Bay

Coastal retreat •beaches, trails & historic Lewes•

5 bed 5.5 bath w/ heated pool, 5min walk to beach

Salty Beach Love Family Home
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Outer Banks Holiday rentals
- Pet-friendly rentals Rehoboth Bay
- Beachfront rentals Rehoboth Bay
- Family-friendly rentals Rehoboth Bay
- Rentals with beach access Rehoboth Bay
- Apartment rentals Rehoboth Bay
- Rentals with a patio Rehoboth Bay
- House rentals Rehoboth Bay
- Waterfront rentals Rehoboth Bay
- Rentals with a fireplace Rehoboth Bay
- Rentals with a washing machine and dryer Rehoboth Bay
- Rentals with outdoor seating Rehoboth Bay
- Rentals with pools Sussex County
- Rentals with pools Delaware
- Rentals with pools United States
- Ocean City Beach
- Broadkill Beach
- Fortescue Beach
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Ocean City Boardwalk
- Dewey Beach Access
- Willow Creek Winery & Farm
- Assateague Island National Seashore
- Peninsula Golf & Country Club
- Pearl Beach
- Jolly Roger Amusement Park
- Big Stone Beach
- Cape Henlopen State Park
- Poodle Beach
- Northside Park
- Bear Trap Dunes
- Poverty Beach
- Higbee Beach
- Bayside Resort Golf Club
- Baywood Greens Golf Maintenance
- Stone Harbor Beach
- Towers Beach
- Jolly Roger at the Pier




