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

2BRCapri: Indoor Pool, Game Room, Massage Chair
ALL THE COMFORTS OF HOME AT THE BEACH! BRAND NEW RENOVATED BATHROOMS! -ALL LINENS INCLUDED -Comfortable electric-reclining sofas -65-in smart Roku TV with soundbar. -Massage chair in master bedroom -Balcony & Dining Area w/ Ocean +Bay Views -In-unit W/D -Many conventional & USB Outlets -Arcade level features b-ball hoop, pool tables, ping-pong, shuffleboard, air-hockey -Outdoor tennis court -Large heated indoor pools -can swim full laps -Sauna and Gym -Board games in unit -Fast Wifi

Bayfront Family Friendly Beach Condo w/BoatSlip
Come enjoy our Cozy Bay/Canal Water Front Beach Condo. 1 bedroom, 1 bath condo with a Boat Slip & Pool and just a few blocks from the Beach and Northside Park, in the desired Hidden Harbor Community. Also just a short walk to the Beach Bus Stop. ** For July and August we try to rent Saturday to Saturday, 7 night stays! ** Contact me if you're interested in shorter stays. Pool Open Memorial Day to Labor Day Xfinity WiFi and Smart TV for your streaming needs. New Mattress and TV added 2024!

OCEAN FRONT Gem w/Pools, Movie Theater, Gameroom
Launch your fabulous beach getaway at amenity-rich Sunset Cove at Sea Watch, part of an oceanfront condo complex offering 3 pools, complimentary movie theater, game room, gym, and much more. Enjoy spectacular ocean and bay views from 2 balconies, smart TVs in every bedroom and living room with provided satellite programming, fully equipped kitchen, comfortable living and bedroom spaces–and that’s just the beginning as your group has a blast at the beach and all of Ocean City’s fun attractions.

Stay Salty OC Beach House
Welcome to your ultimate getaway near Assateague State Park & Ocean City! Our spacious retreat sleeps 14 guests and boasts resort-style amenities including pools, a gym, kayaks, and tennis courts. Located just moments from beaches, charming towns, and exciting attractions, you'll have everything you need for an unforgettable vacation. With a fully stocked kitchen, game rooms, cozy reading nooks, puzzles, and a balcony, there's something for everyone. Book now and let the relaxation begin!

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines
Beautifully updated and recently renovated, rancher on a great street in Ocean Pines perfect for families and adults looking for a relaxing stay. We offer 3 bedrooms and 2 bathrooms on one level, with new large flat screen TV's, stainless appliances, and everything you'll need for your stay. We have a large driveway and a screened patio. Ocean Pines boasts over a dozen parks and walking trails, a public Yacht Club, 5 pools, 2 marinas, and a championship golf course - 10 min to the beach!

Bayside community, near OCMD, great rates
Welcome to MERMAID DREAMS where you can have FUN or just RELAX! We are ONLY 5 miles from OC, MD beaches & Assateague National Park/beaches. Our gated, beautiful community, is bayside, has 2 awesome pools, big splash pool, rec center, a fishing/crabbing pier, pond with paddle boats, 2 playgrounds+ more For kiddos of all ages, we are located right next door to Frontier Town, which has awesome water slides , western shows, mini golf, a rope course, ice cream shop.. short term stay

Newly built bright and airy guest suite!!!!
FREE oceanfront parking pass with bookings. 2nd floor private suite with parking, patio/firepit, and self check-in private entry. We are located just minutes from the Ocean City beaches, quaint small town of Berlin, Ocean Downs Casino, Assateague, Windmill Creek Winery, restaurants, and outlets. Enjoy neighborhood amenities such as a waterfront Yacht Club with restaurant and live music (seasonal), golf, farm market, playgrounds, 5 pools/fee, (no pool on property) racquet club.

Farmhouse located on a horse farm
Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

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.

Mosaic Life Escapes -Bayfront Million Dollar Views
At Mosaic Life Escapes the BAYFRONT is our back yard! Safe gated community home. Water access for paddle boards & kayaks. Community fishing/crabbing pier 2 pools 3 ponds arcade room, playgrounds, paddle boats. 2 bd home w/a million dollar view. Minutes from Ocean City, Assateague Island & Casino. WiFi + 3 smart TVs We have implemented additional sanitizing procedures between guest stays to ensure a clean house! Perfect for a family or romantic get away!

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
Book 3 nights, get 1 night FREE stays thru March 10. inquire before booking This is a Ocbeachfrontrentals .com premier property 24/7 SUPPORT LINEN & TOWELS PROVIDED 8TH FLOOR PENTHOUSE! This stunning top floor 3 b 2.5 ba unit is the ULTIMATE friends & family beach trip, located in a premier building in Ocean City. Enjoy the ocean breeze and stunning views from over 150 square ft of private balcony. Wake up to ocean views from every room!

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+
Welcome to Salty Shark - direct oceanfront studio! This remodeled studio sleeps 4 and is in North Ocean City near great restaurants, bars, and 58 acre North Side Park. The park has sports fields, a recreation center, a walking/biking path, crabbing pier, playground, and outdoor fitness area. Building has outdoor pool in summer too! The unit features a King Murphy bed, and a Queen sofa bed. There's also an outdoor pool open in summer months!
Popular amenities for Worcester County rentals with a pool
House rentals with a pool

Salty Serenity

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB

Amazing Sunsets at Ponte Vista

Little house in Berlin, Md.

Oceanfront | Beachfront | Elevator | eFireplace

Beautiful Cottage W/ shared pool & close 2 beach

Beachy Sunset Island Townhouse!

Whimsical Willow w/ Beach Club Pass and No Pet Fee
Condo rentals with a pool

Oceanfront Family Oasis: Pool, Beach & Parking!

Ocean Block - Clean, cozy 1 Bedroom. Pool, Wifi

BeachParadise203-DOWNTOWN•WATERFRONT•Luxury Condo

Beautiful Ocean Front Condo 2b/2ba with pool

Ocean Pines Winter Retreat

Direct Oceanfront with a View and Amenities Galore

🌊Carousel Oceanfront 2 Bedroom Amazing Amenities

Nice 2 BR Oceanfront, Year Round Fun & Amenities!
Other vacation rentals with a pool

Stunning Home w/Private Pool, Garden & Firepit

Amazing Bayside Views @Sunset309

Luxury Retreat By The Sea!

52 lookout Point

The Coastal Condo

Tranquil Waters, OceanPines, 3 br, Dog Friendly

New Coastal Style Vacation Home

Fenwick Island Sunset Retreat
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- Ocean City Beach
- Broadkill Beach
- Ocean City Boardwalk
- Assateague Island National Seashore
- Dewey Beach Access
- Assateague Beach
- Peninsula Golf & Country Club
- Jolly Roger Amusement Park
- Cape Henlopen State Park
- Northside Park
- Poodle Beach
- Bear Trap Dunes
- Bayside Resort Golf Club
- Baywood Greens Golf Maintenance
- Towers Beach
- Jolly Roger at the Pier
- Whiskey Beach
- North Shores Beach
- Assateague State Park
- Plantation Lakes Golf and Country Club
- Delaware Seashore State Park
- Fenwick Island State Park Beach
- Lewes Public Beach
- Coin Beach




