Vacation rentals in Montego Bay

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Top-rated vacation rentals in Montego Bay

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Guest favorite

Home in Ocean City

4.94 out of 5 average rating, 218 reviews

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!

Feb 25 – Mar 4

G$25,484 GYD per night

Guest favorite

Condo in Ocean City

4.9 out of 5 average rating, 176 reviews

**Beautiful newly renovated OC MD water view home*

Beautiful Bay view ground floor unit steps away from the water, 1 free parking spot available for guests and tons of street parking comfortable for 2 people for a long stay and 4 for a weekend getaway Located in the middle of all Ocean city major attractions Walking distance to the beach and Jolly Roger Amusement water Park and tons of other activities and restaurants. 6 min away from famous Seacrets, Macky’s & Fish Tales 8 min drive to OC famous board walk & downtown 15 min to Shopping Outlets

May 2 – 9

G$22,666 GYD per night

Guest favorite

Condo in Ocean City

4.89 out of 5 average rating, 152 reviews

Prime Condo North OC 2 Blocks to Beach w/ Pool

Pristine condo in North Ocean City with every amenity you can imagine welcomes guests over 21. Rare end unit offers more space than similar units. Two blocks from beach/park makes this the best location in town - fabulous sunset views and pool (Memorial thru Labor Day). 2 bedrooms and 2 stories offers spacious options for 6 guests to spread out. Full kitchen with everything, washer/dryer, central heat/air, Smart TV’s to access your streaming channels High Speed Internet and starter items

Mar 15 – 22

G$14,602 GYD per night

Guest favorite

Condo in Ocean Pines

4.96 out of 5 average rating, 108 reviews

Waterview Retreat

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

Mar 1 – 8

G$28,917 GYD per night

Superhost

Condo in Ocean City

4.85 out of 5 average rating, 100 reviews

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

Stunning newly renovated 2 bedroom oceanfront condo in the premiere Golden Sands! Blue Wave is known for its unique 3-tiered wave wall and incredible ocean views from the living room and primary bedroom. SmartTV w/Xbox! Wake up to the sun rising over the ocean right out your bedroom window, and after a cup of coffee on the balcony (included!) head to the building's sun deck,fitness center, lounge, arcades, tennis court, pickleball court,beach volleyball,or indoor/outdoor pools and tiki bar.

Oct 25 – Nov 1

G$31,268 GYD per night

Guest favorite

Condo in Ocean City

4.91 out of 5 average rating, 239 reviews

Ocean-block 36th St. - Steps to the Beach!

Comfortable and affordable, our 1 bed/1 bath - 1st floor condo is in a prime OC Mid-Town location. Literally just steps from the building to the sand! Walking distance to me of OC's best restaurants, night life, amusements, convention center and more. **Summer Months check-ins on Monday & Friday ONLY from Memorial Day to Labor Day! Book Weeks or Mini-weeks. (Weeks: Fri to Fri, OR Mon to Mon) (Mini-Weeks: Mon to Fri, OR Fri to Mon)** *Other months check-in any night*

Dec 26 – Jan 2

G$21,806 GYD per night

Superhost

Condo in Ocean City

4.88 out of 5 average rating, 106 reviews

Unit 11 on 41 St Ocean Side 50 steps to beach

Dominica Beach is a 2-story condo, close to the ocean on 41st Street Only 50 paces to the sand dunes and you'll have your toes in the sand! There are no streets to cross to get the beach. Complementary linen service based on the number of guests. Within walking distance of the Convention Center, restaurants, amusement parks, mini-golf, & more. You’ll love our place because of the ambiance. It is good for couples, solo adventurers, and families (with kids).

Nov 16 – 23

G$15,812 GYD per night

Guest favorite

Condo in Ocean City

4.92 out of 5 average rating, 87 reviews

The Penthouse Oasis (Bring own linens) Hidden Gem

Relax and enjoy your time in this third-floor, two-story condo in Raffles Condominium complex, located on 127th Street in OCMD. We welcome you into this unique space, 1.5 blocks from the beach (5-minute walk), with plenty of amenities, a spiral staircase, and two queen size beds. Linens NOT provided. **Please be mindful some decor may deviate from the photos due to improvements actively being made**

Jan 10 – 17

G$28,862 GYD per night

Guest favorite

Condo in Ocean City

4.99 out of 5 average rating, 175 reviews

Direct Oceanfront close to Northside Park!

Location, location, location! 2 bed, 2 bath direct oceanfront condo, with incredible ocean sunrise views from your private enclosed patio. Master bedroom features unbelievable views of the ocean, glass slider out to the patio & in suite full bath! Walking distance to Northside Park, restaurants & shopping. 2 assigned parking spaces. Elevator or steps - you pick. Washer/dryer in unit.

Feb 3 – 10

G$25,255 GYD per night

Guest favorite

Guest suite in Berlin

4.97 out of 5 average rating, 530 reviews

Ayers Creek Carriage House

Our beautiful carriage house is located on 5 pristine acres along, scenic Ayers Creek, offering year round beauty. Only minutes from Assateague Island, Berlin, and Ocean City. Serene with abundant wildlife. Ideal oasis for outdoor enthusiasts. Worcester County Maryland Rental License #1324

Oct 12 – 19

G$30,035 GYD per night

Superhost

Apartment in Ocean City

5.0 out of 5 average rating, 3 reviews

Seaside Enchantment Condo

Seaside Enchantment Condo: Nestled within the renowned Sea Witch building, our coastal retreat offers steps to mesmerizing ocean vistas. Immerse yourself in seaside magic, where relaxation and adventure converge. Your enchanting escape by the sea awaits!

Jan 12 – 19

G$24,541 GYD per night

Guest favorite

Condo in Ocean City

5.0 out of 5 average rating, 17 reviews

Relax, Unwind and Enjoy! Steps To The Beach!

Come Relax, Unwind, and Enjoy the beach in our 1 bedroom and 1 bath family friendly condo, with lovely ocean views, located at The Marylander on 127th in North Ocean City. You will be within walking distance to restaurants, Northside Park, and the Beach!

Jan 22 – 29

G$23,643 GYD per night