
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!

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

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.
Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

Gone Coastal *Pool* Bayside with view* Top Floor
Welcome to Gone Coastal! Relax in this beautiful 2BR/2BA getaway featuring: đ 1 King (Master) | 1 Twin-over-Full Bunk | 1 Sleeper Sofa đââď¸ Outdoor Community Pools â Lap & Family Pool (Directly Across!) đ Keyless, Contactless Check-in đ Spacious Deck â Outdoor Dining + Bay & Pool Views đş Smart TVs + YouTube TV đ 1-Minute to Grocery Store đ˝ Fully Equipped Kitchen đ Prime Location â 120th St, Heron Harbor đ Ample Free Onsite Parking A perfect retreat for families & beach lovers! đâď¸

Cozy oceanfront condo with stunning ocean views
Fully updated 1 bed/1 bath oceanfront condo in a quiet, mid-rise building with a beachfront pool in uptown OC. The perfect unit for a quick romantic getaway, long weekend, or family vacation. We are happy to accommodate the dates and timeframes that meet the needs of our guests. If possible, please consider these recommended timeframes for your booking: Memorial Day - Labor Day -7 Nights, Fri-Fri or Mon-Mon -3 Nights, Fri-Mon -4 Nights, Mon-Fri Labor Day - Memorial Day -Any 2 Nights

Oceanfront 1 Bedroom, Balcony, Sitting Room, Pool
Opal Osprey: This OVERSIZE one-bedroom condo has been completely remodeled... giant oceanfront balcony PLUS a large patio room on the bayside! Expansive ocean views from every angle, super easy beach access, wonderful atmosphere in the quiet north end of OC. Linens included! Property Amenities - King size bed & queen sleeper - Large outdoor pool - Elevators - Dedicated high-speed WiFi and router w/ ethernet (Xfinity 100Mbps) - 2 Smart TVS with Xfinity, Roku - Keyless check-in 24/7

Love Above the Waves-Best Ocean View & Heated Pool
đĽ Complimentary champagne, endless ocean views, private balcony, breathtaking sunrises, warm swimming pool and beach strolls await you at this romantic retreat. Love Above the Waves is more than a stayâitâs an unforgettable celebration of love and romance, perfect for birthdays, anniversaries, engagements, or quiet escapes for two. Let the ocean be your witness, the champagne your spark, and the sunrise your reminder that some moments are meant to stay with you forever.

Beachfront 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 a breathtaking 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. Itâs 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.

PENTHOUSE 8th Floor- Boardwalk, Pool, Sundeck
Book 2 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!

Water Front Condo w/Pool Short Walk to Beach
FIRST FLOOR UNIT Bayside Condominium Sleeps 4 - 6 max Walking Distance to Northside Park Walk to the Ocean , don't worry about beach parking NON SMOKING 1 Bedroom 1 Bath condo, First floor unit with an outside deck This Air Conditioned, One Bedroom Condo has a fully equipped kitchen, washer/dryer, full refrigerator. There is a Queen bed and a full bed along with 1 Queen Sleep sofa in the living room *MUST BE 21 OR OVER* No Pets!

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.
Popular amenities for Maryland Beach rentals with a pool
House rentals with a pool

2 BR Ocean Front Condo w/Pool, Expansive Views

Beach Paradise 2101-Downtown Luxury Condo Bay View

Bayside Townhome with Ample Parking

Low Tide Hideaway

Ocean View Paradise w/Hot Tub & Free Massages!

Bayside community near OCMD great rates

Updated 3 Bedroom 2 Bathroom Home - Ocean Pines

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

đđŞđđ¨đŠ đđđŤđ¤đ§đđŠđ Lovely 2lvl Condo Steps 2Beach+Pool

Spacious Direct Oceanfront 1BR Condo w/Balconies

2BR Waterfront | 1st Floor | Patio | Pool | W/D

BeachParadise203-DOWNTOWNâ˘WATERFRONTâ˘Luxury Condo

Freshly renovated ! Steps to outdoor pool & beach

Oceanfront Bldg.| 2 pools | Tennis | Game Room

BaysideGetaway | 2 Blk to Beach & Boardwalk | Pool

Dazzling Views Ocean Front one bedroom
Other holiday rentals with a pool

DBTB6-3BR Steps to Beach & Boardwalk+Pool/Parking

*New*- North OC Oceanfront 1+BR with Pool

Let's go to the Beach!

Little Paradise

Spacious Ocean View Condo

Upscale New Home | Pool | 2600 sq.ft|Baby Friendly

OceanViewBeachClub-minutes from Bethany Beach/Golf

My Happy Place! Beach Side Condo with Ocean Sounds
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Flat rentals Maryland Beach
- Rentals with a hot tub Maryland Beach
- Rentals with an accessible-height toilet Maryland Beach
- Townhouse rentals Maryland Beach
- Rentals with a patio Maryland Beach
- Beach house rentals Maryland Beach
- Rentals with a washing machine and dryer Maryland Beach
- Beachfront rentals Maryland Beach
- Waterfront rentals Maryland Beach
- Pet-friendly rentals Maryland Beach
- Fitness-friendly rentals Maryland Beach
- Rentals with a fireplace Maryland Beach
- House rentals Maryland Beach
- Apartment rentals Maryland Beach
- Rentals with outdoor seating Maryland Beach
- Family-friendly rentals Maryland Beach
- Rentals with beach access Maryland Beach
- Rentals with pools Ocean City
- Rentals with pools Worcester County
- Rentals with pools Maryland
- Rentals with pools United States
- Ocean City Beach
- Broadkill Beach
- Ocean City Boardwalk
- Wildwood Crest Beach New Jersey
- Cape May Beach NJ
- Chincoteague Island
- Assateague Island National Seashore
- Willow Creek Winery & Farm
- Jolly Roger Amusement Park
- Bayside Resort Golf Club
- Northside Park
- Bear Trap Dunes
- Cape Henlopen State Park
- Assateague State Park
- Killens Pond State Park
- Fenwick Island State Park Beach
- Delaware Seashore State Park
- Lewes Public Beach
- Gordons Pond State Park Area
- Mariner's Arcade
- Trimper Rides of Ocean City
- Funland
- Hawk Haven Vineyard & Winery
- Roland E Powell Convention Center




