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

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Beautiful waterview 2B condo w/Dock&Close to Beach
Welcome to the Canal Bungalow! A stylish 1000 sq. foot retreat to enjoy all the fun & relaxation of the coastal lifestyle in North Oc. Bring your boat with you and dock alongside your back porch, enjoy pool access in a private gated community, or bring your sports gear for Northside Park. We are tucked away on the quiet bayside of OC & only a few minutes walk to the beach. Unwind on our beautiful balcony while watching the boats go by & finally understand the true meaning of a coastal lifestyle!

3 BR Waterfront Home, Minutes to the Beach
Recently updated waterfront house located in the family-friendly Montego Bay community. Enjoy beautiful sunsets on the back deck or hop in one of the kayaks for a paddle around the wide-open canal. Try your hand at crabbing or fishing off the dock to catch your dinner. Within easy walking distance of the beach and Northside Park (about 10 minutes walk to both). Beach chairs, toys, boogie boards, and umbrellas are yours to use for fun in the sand and surf. The dock is available for boat tie-ups.

SeaGate Serenity | Oceanfront Condo with Balcony
Wake up to the sound of the waves crashing outside your window and finish your days relaxing on the private balcony as you watch the pastel skies over the ocean at sunset. Come find your serenity by the sea in our newly renovated oceanfront condo. Located in midtown, you can keep your car parked in our reserved spot and walk to many of the towns best restaurants, bars, and entertainment as well as the World Famous Ocean City Boardwalk. Morning beach strolls, pool days, and evening sips await :)

Luxe Oceanfront 1BR | Pool, Hot Tub, Sun Deck
Wake up to breathtaking beach and ocean views from this beautifully renovated 3rd-floor oceanfront 1BR condo in North Ocean City. Enjoy direct beach access, one reserved parking space, elevators, linens and towels, a heated indoor pool and hot tub, and a stunning new 4,000 SF ocean-view sun deck completed for 2026. Inside, this stylish coastal retreat sleeps 4 with a king bedroom, queen sleeper sofa, 1.5 bathrooms, a renovated kitchen, private oceanfront balcony, and comfortable lounge space.

1st Floor Canal Front POOL 2 Blocks 2 Beach/Park
Sit along the canal-front deck, watch boats, birds, and walk to beach, restaurants, shopping, Northside Park Fully equipped kitchen, washer/dryer, comfy queen bed and queen sleeper, plenty of blankets and pillows are provided. PLEASE PACK BED LINENS, BEACH and BATH TOWELS We enjoy hosting families and singles 25 years + NON SMOKING Provided: Hand/Dish/laundry detergents Starter Toilet Paper / Paper towel Hair dryer FREE parking Hi speed Wifi Pool OPEN Memorial-Labor Day 9:15am-8pm

Upscale Family Home in OC, Community Pool, Grill
Unwind in North OC at the Nautical Vibes House! • A new, stylish single-family home designed to make your stay comfortable and memorable • Equipped with EV Charger, full kitchen, 2 Smart TVs with Youtube TV, washer/dryer, and outdoor shower • In a quiet neighborhood, but still close to restaurants, bars & shopping. Just under a mile to the beach & Northside Park • Has 2 community pools, tennis courts & putt-putt course (between Memorial Day/Labor Day only, keycard provided)

Oceanfront Condo w/ Resort Amenities 3BDR &3pools
Sea Watch Condo's is an ideal family location with tons of amenities. The until is a recently updated 3 bedroom 2 bathroom condo that sleeps 6 people in 2 queen beds, 2 twin beds . The unit is ocean front with a large oceanfront balcony. The amenities Include, basketball court, tennis courts, playground, arcade, movie theater, billiard room, indoor pool and outdoor pool as well as a restaurant. The condo has 24 hour security and plenty of parking. Pools closed in off season

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.

Beautiful 2BR 2BA oceanfront condo at the Atlantis
Beautiful ocean views from this 2BR, 2BA oceanfront condo. One of the few units in the Atlantis with an OPEN BALCONY. Located on the 14th floor in the Atlantis Building within midtown Ocean City. Equipped with elevator, wifi, outdoor pool, Direct TV streaming, washer/dryer, onsite Security, and much more. 1 parking spot for $60 registration fee paid at check-in. Food shopping, coffee shop, and restaurants are located across the street (walking distance).

Oceanfront Family Oasis: Pool, Beach & Parking!
Escape to your dream family vacation in this amazing 2-bedroom condo on the 8th floor! Enjoy incredible ocean views, direct beach access, and proximity to Ocean City's top attractions like the vibrant OC Boardwalk and thrilling amusement parks. This condo offers modern amenities, a refreshing seasonal outdoor pool, and the convenience of free parking. Perfect for families seeking fun and relaxation near the ocean.

21st Floor Carousel - 2 BR Oceanfront & Bay View
NEW!! Welcome to our direct oceanfront 2 bedroom & 2 bath unit at the Carousel! Bringing the comfort of your home to the beach! Bring the whole family for lots of fun memories! We strive to take care of this condo to ensure you have a relaxing, comfortable, and clean stay! Our condo includes 2 DOUBLE SIZED balconies! An oceanfront balcony and a bay view balcony! You can enjoy both the sunrise and sunset!
Popular amenities for Maryland Beach rentals with a pool
House rentals with a pool

House 1 Block from the ocean

Cozy Beach Escape Mallard Lakes Resort Amenities

Low Tide Hideaway

North OC 3BR + Loft Sleeps 12 Walk to Pool & Beach

Mi Casa at Bay Knolls

High Tide @ Lighthouse Bay

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Beautiful Waterfront Home-Private, Clean, Relaxing
Condo rentals with a pool

Cozy Waterview Stay with Balcony & Rooftop Pool

Oceanfront•Pool•Private Balcony w/Sunrise Views

Serene Bayfront Bliss 3 Bedroom Condo

Luxury 3BR/4BA Condo: Indoor Pool, Walk to Beach

Oceanfront Bldg.| 2 pools | Tennis | Game Room

Direct Ocean Front/Gorgeous Views/Indoor Pool

Modern Coastal Calm 2 BR Retreat + Pool

Water Front Condo w/Pool Short Walk to Beach
Other holiday rentals with a pool

143rd St. Large upscale Townhouse -Sleeps 8 / Pool

2 BR 2BA North Ocean City Condo

1 Block from Beach! New OCMD Townhome!

Ocean Front Condo

Let's go to the Beach!

NEW: Oceanfront End-Unit Condo w/ 100ft Balcony

Very clean, cozy, safe, four blocks to the beach

Little Paradise
Destinations to explore
- New York Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Ocean City Holiday rentals
- Pittsburgh Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Jersey City Holiday rentals
- Baltimore Holiday rentals
- Newark Holiday rentals
- Richmond Holiday rentals
- Outer Banks Holiday rentals
- Condo rentals Maryland Beach
- Rentals with a hot tub Maryland Beach
- Apartment rentals Maryland Beach
- Townhouse rentals Maryland Beach
- Pet-friendly rentals Maryland Beach
- Beach house rentals Maryland Beach
- Family-friendly rentals Maryland Beach
- House rentals Maryland Beach
- Beachfront rentals Maryland Beach
- Waterfront rentals Maryland Beach
- Rentals with beach access Maryland Beach
- Rentals with an accessible height toilet Maryland Beach
- Rentals with pools Ocean City
- Rentals with pools Worcester County
- Rentals with pools Maryland
- Rentals with pools United States
- Chincoteague Island
- Cape May Beach NJ
- Assateague Island National Seashore
- Wildwood Crest Beach New Jersey
- Ocean City Beach
- Broadkill Beach
- Ocean City Boardwalk
- Rehoboth Beach
- Cape Henlopen State Park
- Bethany Beach Boardwalk
- Assateague State Park
- Willow Creek Winery & Farm
- Northside Park
- Ocean City Boardwalk
- Wildwood Boardwalk
- Stone Harbor Beach
- Delaware Seashore State Park
- Jolly Roger Amusement Park
- Fenwick Island State Park Beach
- Roland E Powell Convention Center
- Wildwoods Convention Center
- Ocean Pines Golf Club
- Mariner's Arcade
- Funland





