Vacation rentals in Montego Bay

A light and airy deck features a rectangular dining table surrounded by aqua-colored chairs. A calm water view is visible beyond the railing, with flags gently waving in the breeze. Soft lighting is provided by string lights overhead, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 290 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!

A back deck features a seating area composed of a sofa and ottoman with soft cushions, facing a calm canal. A wooden table is positioned nearby. A red umbrella is closed and stands beside the seating, while a sunset casts gentle hues across the water.

4.93 out of 5 average rating, 152 reviews

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.

5.0 out of 5 average rating, 122 reviews

The living area is spacious, featuring a light blue wall color and a large sectional sofa. Natural light floods through windows, illuminating the decorative rug. The outdoor porch includes dining furniture and offers views of the canal and neighboring buildings.

Condo in Ocean City

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!

A spacious living area features two sofas, one in dark leather and the other in a light fabric, arranged around a low wooden coffee table. A flat-screen TV is mounted on a light wall above a stone fireplace, adding a cozy touch to the room.

4.97 out of 5 average rating, 162 reviews

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.

A spacious living area features comfortable seating arrangements, including a large sectional sofa and recliners. A flat-screen television is positioned on an entertainment unit, and ample natural light is provided by multiple windows and a sliding door leading to the sunroom. Wooden flooring enhances the open atmosphere.

4.95 out of 5 average rating, 108 reviews

Spacious waterfront home & boat access!

Waterfront getaway, easy beach access (0.3 mile walk), pool, restaurants, and more. Linens & towels included! Bring your boat! Pier tie up available. Spacious 3 bedroom + bonus room with sleeping arrangements for 10(8 beds). This well-maintained home is close to dining, shopping, NorthsidePark & all the fun activities Ocean City has to offer. Beach chairs, toys, kayaks & paddleboard available. Fireworks from Northside Park can be viewed every Sunday summer night - right from the driveway!

4.95 out of 5 average rating, 21 reviews

3 BR Home/Beach, Pool, Pickleball, Mini Golf

Relax in the quiet community of Montego Bay while being only minutes away from the beach, restaurants, shopping, entertainment and North Side Park. You will find one of the two community pools, pickleball courts and free miniature golf at the end of the cul de sac. Enjoy a bike ride on one of our bikes or a stroll to the neighborhood boardwalk to watch the sunset over the bay. Northside Park, Ocean City's largest park, has summer fireworks on Sundays, and kayak and paddleboard rentals.

An outdoor deck features a stylish seating area with a sofa and a coffee table, complemented by an umbrella providing shade. A dining table is visible, suitable for gatherings. The view includes a calm canal with houses along the opposite shore.

4.95 out of 5 average rating, 77 reviews

Tranquil Water View! Kayaks & SUP Boards Included!

Welcome to LIVIN ON BEACH TIME! Enjoy this Cozy Peaceful Retreat this year! Our updated home has all you need for a great time! Loaded with all amenities you need to make your stay comfy & fun. Our deck overlooks the gorgeous canal. Enjoy stunning sunsets . We have everything on hand for happy outings at the beach or fun on the water. RELAX... You're at the Beach! BECAUSE THIS IS A SEASONAL LISTING, MAY 23 - SEPT 7 2025, REQUIRE CHECKIN/CHECKOUTS ON SATURDAYS AND SUNDAYS ONLY.

The waterfront home is presented with a two-story gray exterior, accented by a white railing on the deck. Three Adirondack chairs are positioned on the deck, overlooking the water. Neighboring houses are visible on either side, demonstrating the serene community atmosphere.

4.96 out of 5 average rating, 92 reviews

Spacious Waterfront Home; Walk to the Beach & more

Spacious 3 bedroom with two accessory rooms. Sleeps 13 (8 adults maximum). Our waterfront home is one of the best locations in Ocean City and perfect for multi-generational families looking to spend quality time under one roof. Walk to the beach, pools, restaurants and more. Kids love fishing and crabbing off the dock. Bring your own boat or kayak. We have a fully stocked kitchen and amenities to ensure that you feel right at home.

The image shows a spacious ground-level duplex with a deck facing the canal. The building features a light-colored exterior with multiple sets of stairs leading to the upper unit. Sunlight casts a natural glow, enhancing the inviting outdoor area, ideal for relaxation.

4.92 out of 5 average rating, 60 reviews

GALWAY GIRL - WATERFRONT - 3 BLOCKS TO BEACH

This rental is a ground level canal front unit in a duplex located just 2 blocks from the beach in the highly desired Caine Woods Community. There is a separate unit above (not part of this rental). Excellent location directly across the street from Gorman Park, and short walk to beach, Old Pro Golf, Arcade, and Harpoon Hannas. Fish and crab from the large bulkhead. Paddle board or kayak in Assawoman Bay. Super premium location.

The covered porch features a wooden floor and decorative string lights overhead. Two comfortable chairs are positioned for relaxation, offering views of the street and neighborhood. The warm glow of the sunset can be seen in the background, enhancing the inviting space.

4.98 out of 5 average rating, 121 reviews

Coastal Home - Outdoor Shower & 2 Pools

Escape to this relaxing Montego Bay oasis just a short walk to the beach. Perfect for couples or families, the home features 3 bedrooms, 2 baths, a spacious open living area, and a king suite with private bath. Enjoy sunsets on the open-air porch, rinse off in the outdoor shower, and take advantage of 2 community pools, tennis courts, and free mini golf. Walk to Northside Park for trails, kayaking, fishing, and more.

The exterior of a single-story home is shown, featuring a light-colored facade with a welcoming front porch. Lush greenery surrounds the house, and a spacious driveway is visible. A fenced backyard is partially seen, indicating a safe area for children. Clear skies provide a sunny backdrop.

5.0 out of 5 average rating, 30 reviews

Immaculate 3-bedroom house close to beach

Relax with the whole family in this immaculate 3 BR, 2 Bath fully equipped home located in the Caine Woods neighborhood of North Ocean City. Home offers an open floor concept, full kitchen, dining room, spacious bedrooms, full size washer and dryer, and sunporch to sit and enjoy. The house also includes a fenced backyard for the kids to run around in, and a 2 car driveway for off street parking.