Vacation rentals with a pool in Maryland Beach

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Top-rated rentals with a pool in Maryland Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite
A balcony is shown featuring two red Adirondack chairs and a small table, positioned to overlook the vast ocean. The horizon is visible in the distance, with a sandy beach below, inviting relaxation and scenic views.
Condo in Ocean City
4.97 out of 5 average rating, 69 reviews

Luxury Oceanfront Getaway!

Welcome to Marigot Beach, one of the most coveted buildings in OC. This newly renovated condo features a spacious one-bedroom with its own private 1/2 bath. Full bathroom located in the hallway. Sleeping arrangements can comfortably accommodate up to 4 guests, 2 can rest in the bedroom while 2 can enjoy the queen-size sofa in the living room. Included: free WiFi, smart TVs, fully equipped kitchen, washer/dryer, elevator. PLUS, a designated parking spot! Pool/hot tub closed until further notice!

Guest favorite
A spacious living area is furnished with a light-colored couch and an armchair, complemented by a ceiling fan above. A flat-screen TV sits on a wooden media console, while a dining table is positioned in the background, leading towards an updated kitchen area.
Condo in Ocean City
4.83 out of 5 average rating, 175 reviews

☀️ Enjoy the Beachlife!! —>2Bed & 2Bath Condo ☀️

Relax with the whole family at this peaceful OCEANFRONT Condo in OCMD! Updated 2 Bedroom & 2 Full Bath on the 1st floor Atlantis High-Rise that sleeps 8. Most Importantly- Only Steps to THE BEACH! Unit is Self-Checkin & is walking distance/short drive to many Restaurants, Shops, Attractions, etc. Large Outdoor Pool is on site (seasonal). Toys, Games, Puzzles & is perfect for families with children. NO Smoking allowed. No Pets or Large groups(8 max) or senior week rentals permitted. Book Today!

Guest favorite
A spacious common area is designed with high-end leather sofas and armchairs, arranged around a central coffee table. Bright natural light enters through large windows, highlighting the tasteful decor. A dining area is visible in the background, creating a warm and inviting environment.
Home in Ocean City
4.88 out of 5 average rating, 132 reviews

Upscale House Steps 2 Ocean 3 Balconies Pool Bikes

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 This spacious 3-level beach home is perfect for family & friends. Relax on 3 balconies, hang out poolside, go for a bike ride or walk to the beach. With 5BD/3.5BA, high-end furniture, high-speed WiFi, 6 flat screens, a Weber grill, and a foosball table, there's room for everyone! Must be 25 or older unless accompanied by adult

Top guest favorite
An open-concept living and dining area features a wooden dining table set for six, complemented by modern chairs. A comfortable seating arrangement with light-colored couches is situated near large windows, offering views of the surrounding area. A mounted TV and decorative elements enhance the space.
Condo in Ocean City
4.96 out of 5 average rating, 124 reviews

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.

Guest favorite
A living area is presented with a light gray couch and loveseat, complemented by a coffee table on a patterned area rug. Large windows offer ocean views, while a mirror reflects natural light. A TV and decorative lamps enhance the space.
Condo in Ocean City
4.87 out of 5 average rating, 211 reviews

🌊Oceanfront studio w/ amazing views & amenities🏖

Efficiency/studio condo oceanfront in Golden Sands. Queen size Murphy bed (has 13 inch thick serta mattress, same as a regular bed), couch, loveseat, full kitchen, bathroom, washer & dryer, ac/heat, parking, awesome amenities. This building is beautiful with amazing views. We clean & stock this condo ourselves so you'll get the owners personal touch without the crazy extra fees that rental companies charge. I love to make everyone's stay as wonderful as possible. Please read entire listing.

Top guest favorite
The exterior of a single-story house is visible, featuring a spacious front porch with white railings. Large windows allow natural light to enter, while a driveway provides parking for two vehicles. A wooded area surrounds the property, enhancing its peaceful setting.
Home in Ocean Pines
4.98 out of 5 average rating, 137 reviews

Camelot

HIGHEST RATED HOUSE IN OCEAN PINES! CHECK OUT OUR AMAZING GUEST REVIEWS :) Jumpstart your ultimate beach getaway at this impressive 3-bedroom, 2-bathroom retreat house! Complete with amenity-packed living spaces with vaulted ceilings and a serene location, you’ll never hunger for entertainment at this family friendly home. Grill out on the patio, roast marshmallows by the fire pit, tee off at a nearby golf course, or enjoy some retail therapy at Outlets Ocean City! A short drive to the beach!

Top guest favorite
A charming bayside home features a covered porch adorned with twinkle lights, creating a welcoming entry. The exterior showcases light-colored siding, large windows, and landscaped greenery, complemented by playful flamingo decorations on the front lawn.
Home in Ocean City
4.97 out of 5 average rating, 106 reviews

Beach Oasis w/ King Suite + Outdoor Shower & Pool

Looking for a romantic weekend away? Planning a family vacation? Enjoy this entire bayside home in the quiet, coveted neighborhood of Montego Bay. This spacious 3 bed/2 bath retreat has it all!! Enjoy sunsets, steamed crabs, or coffee on the large porch picnic table or relax in the gliders with a cocktail under the twinkle lights! There is 2 car off-street parking & the community offers two public pools, tennis courts, trails, mini golf & is just a short walk to the beach & Northside Park!

Guest favorite
Home in Ocean City
4.88 out of 5 average rating, 142 reviews

Beautiful Cottage W/ shared pool & close 2 beach

"Beautifully decorated & completely renovated 3 BR/2 BA/ plus den. The home is 2 blocks from the bay and a 20 min. walk to the beach! Enjoy this entire home in the quiet neighborhood of Montego Bay which boasts 2 pools, tennis courts, a fishing pier, a walking pond, mini golf and Northside Park. The kitchen is fully stocked and the house is kid-friendly. There are 2 parking spaces & off-street parking. Finally, enjoy the sunset on the large deck complete with an area for al fresco dining.

Guest favorite
Condo in Ocean City
4.84 out of 5 average rating, 220 reviews

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.

Guest favorite
A primary bedroom is presented with a spacious bed topped with neutral linens. Floor-to-ceiling windows frame a serene ocean view. Natural light is allowed to fill the room, accentuated by light wood paneling. A bedside table features a lamp, and a comfortable chair is placed nearby.
Condo in Ocean City
4.88 out of 5 average rating, 161 reviews

2 Bdrm Oceanfront-Pool, Xbox, Pickleball, Gym,WiFi

Wake up to panoramic ocean views at Blue Wave, a newly renovated 2BR/1.5BA oceanfront condo in the premier Golden Sands Resort! Sleeps 6 with king bed, queen bed, and queen sleeper sofa. Enjoy your private balcony, indoor & outdoor pools, private beach, fitness center, game rooms, tennis, pickleball, and seasonal tiki bar. Relax with a Smart TV + Xbox Series S with Gamepass! Steps to the beach, close to Northside Park, great restaurants, and the Ocean City Boardwalk!

Guest favorite
An open-plan kitchen and living area feature a light wooden counter with three stools. A fully equipped kitchen is visible, including a refrigerator, while a comfortable seating area with a cream-colored armchair and a coffee table is also present. Natural light enhances the inviting space.
Condo in Ocean City
4.88 out of 5 average rating, 162 reviews

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!

Guest favorite
A comfortable living area features a light-colored table surrounded by ocean-themed upholstered seating. Large glass doors allow natural light to fill the space while offering a view of the balcony and ocean beyond. A flat-screen television is mounted on the wall.
Condo in Ocean City
4.89 out of 5 average rating, 118 reviews

Oceanfront Carousel building, Swimming Pools!

Direct Oceanfront with tons of amenities! Bring the whole family with lots of room for fun... the Carousel building has indoor and outdoor pools, ice skating rink, game room, restaurant, bar, snack shop, gym, sauna & more!!! **Summer Months Check-in/out on Sun & Thurs ONLY** Book Weeks or Mini-weeks. (Weeks: Sun to Sun, OR Thurs to Thurs) (Mini-Weeks: Sun to Thurs, OR Thurs to Sun). *Other months check-in any day of the week*

Popular amenities for Maryland Beach rentals with a pool

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