Montego Bay holiday homes
We found 1,321 holiday rentals — enter your dates for availability
Discover a selection of 32 homes and other holiday rentals in Montego Bay that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts – Montego Bay
Showing deals for:18 Dec - 25 Dec

Exceptional
(18 reviews)
MADISON BAY BEACH GETAWAY-PRIVATE POOL-HOT TUB- FIRE PIT- WEEKLY STAY DISCOUNT
Ocean City
NZ$16,795
for 7 nights, 1 home
NZ$2,399 per night
includes taxes & fees

Exceptional
(99 reviews)
Water front, open bay views from both decks!!
Ocean City
NZ$5,485
for 7 nights, 1 home
NZ$784 per night
includes taxes & fees

Exceptional
(52 reviews)
Book now for 2025! Perfect for large family. Ocean block. Steps to Beach & Pool!
Ocean City
NZ$5,264
for 7 nights, 1 apartment
NZ$752 per night
includes taxes & fees

Exceptional
(14 reviews)
GORGEOUS NEW Fenwick Island Duplex with views of LIGHTHOUSE COVE
Fenwick Island
NZ$6,781
for 7 nights, 1 home
NZ$969 per night
includes taxes & fees

Exceptional
(71 reviews)
3 Bedroom, 2 Bath, Ocean Block Condo in North OC, Sleeps 6
Ocean City
NZ$5,471
for 7 nights, 1 apartment
NZ$782 per night
includes taxes & fees

Exceptional
(39 reviews)
Coastal chic waterfront townhouse w/bayside sunsets.
Ocean City
NZ$3,238
for 7 nights, 1 home
NZ$463 per night
includes taxes & fees

Exceptional
(11 reviews)
Wave Watcher's Condo - Steps to the beach!
Ocean City
NZ$2,949
for 7 nights, 1 home
NZ$421 per night
includes taxes & fees

Exceptional
(11 reviews)
⛱️⛱️ Ocean City Bayside 🦀
Ocean City
NZ$4,430
for 7 nights, 1 home
NZ$633 per night
includes taxes & fees

Exceptional
(55 reviews)
10 minute walk to the beach! Family- size condo
Ocean City
NZ$2,611
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees

Exceptional
(17 reviews)
Direct Oceanfront at 129th St--2 BR--2 BA--Huge Deck--Recently Renovated
Ocean City
NZ$4,925
for 7 nights, 1 apartment
NZ$704 per night
includes taxes & fees

Exceptional
(25 reviews)
Relax Here in this quiet Beach house!
Ocean City
NZ$4,035
for 7 nights, 1 home
NZ$576 per night
includes taxes & fees

Exceptional
(30 reviews)
SERENE WATER VIEWS-Relaxing family beach house
Ocean City
NZ$6,460
for 7 nights, 1 home
NZ$923 per night
includes taxes & fees

Exceptional
(150 reviews)
BEAUTIFUL & CLEAN! Waterfront condo with epic sunsets and a POOL!
Ocean City
NZ$2,496
for 7 nights, 1 apartment
NZ$357 per night
includes taxes & fees

Exceptional
(105 reviews)
Direct Oceanfront Condo on 11th Floor with Amazing views of Ocean and Bay
Ocean City
NZ$2,220
for 7 nights, 1 apartment
NZ$317 per night
includes taxes & fees

Exceptional
(28 reviews)
Stunning Ocean Front Renovated 2BR, 1 Bonus Rm , 2BA , Pool/Pickleball-North OCM
Ocean City
NZ$5,973
for 7 nights, 1 apartment
NZ$853 per night
includes taxes & fees

Exceptional
(41 reviews)
OCEAN VIEW 2bed 2 bath 'Clean' sleeps 9 in beds
Ocean City
NZ$1,572
for 7 nights, 1 apartment
NZ$225 per night
includes taxes & fees

Exceptional
(6 reviews)
2BR Condo,Pools & Walk to Beach
Ocean City
NZ$3,463
for 7 nights, 1 apartment
NZ$495 per night
includes taxes & fees

Exceptional
(17 reviews)
Easy Access to Sand, Sun + Surf
Ocean City
NZ$3,833
for 7 nights, 1 apartment
NZ$548 per night
includes taxes & fees

Exceptional
(71 reviews)
Beautiful Bayside Condo with canal front views and boat slips
Ocean City
NZ$3,610
for 7 nights, 1 apartment
NZ$516 per night
includes taxes & fees

Excellent
(6 reviews)
Harbour Bay 34-Baywater 116th St, Pool, W/D, AC, Free WIFI.
Ocean City
NZ$2,843
for 7 nights, 1 home
NZ$406 per night
includes taxes & fees

Exceptional
(47 reviews)
V73 - Beautiful 3BR/2BA Ocean View! Pet-Friendly! Just one bldg from the beach!
Ocean City
NZ$3,035
for 7 nights, 1 apartment
NZ$434 per night
includes taxes & fees

Very good
(6 reviews)
Wake Up to Ocean Views & Watch the Sunset from Your Private Balconies!
Ocean City
NZ$3,248
for 7 nights, 1 apartment
NZ$464 per night
includes taxes & fees

Exceptional
(13 reviews)
Best Oceanfront - North Ocean - 134th Street
Ocean City
NZ$5,266
for 7 nights, 1 apartment
NZ$752 per night
includes taxes & fees

Exceptional
(9 reviews)
Cozy Beachside Condo a short walk to the sand
Ocean City
NZ$4,737
for 7 nights, 1 apartment
NZ$677 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Montego Bay

Beautiful 3 BR 2 BA Home in Montego Bay - Community Pool
Sleeps 8 · 3 bedrooms · 2 bathrooms

3 BR/ 2 BA Mobile, North OCMD, Desirable Montego Bay Community, Linens incld
Sleeps 8 · 3 bedrooms · 2 bathrooms

Ocean City - Montego Bay - Beautiful comfort. Summer and off season rentals
Sleeps 6 · 3 bedrooms · 1+ bathroom

Quiet Montego Bay. Walking distance to beach, pool, restaurants, & activities.
Sleeps 11 · 4 bedrooms · 2 bathrooms

3 BR 2 BA located in the Montego Bay Community, 2 Pools Tennis. Pets welcome
Sleeps 8 · 3 bedrooms · 2 bathrooms

Bayfront House W Decks Dock Boatslip 2 Pools + Tennis Court in Montego Bay
Sleeps 10 · 3 bedrooms · 2 bathrooms
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday rental in Montego Bay?
In Montego Bay, condos are the most popular type of holiday rental, with about 124 available throughout the area. These condos are often situated in vibrant neighbourhoods close to the beach, offering easy access to local attractions like the Hip Strip and Doctor's Cave Beach. Most units come equipped with modern amenities, including fully fitted kitchens, spacious living areas, and balconies or terraces that provide stunning ocean views.In addition to condos, there are several apartments and holiday houses available for those seeking alternative accommodations. These properties typically offer a homely atmosphere, with many featuring multiple bedrooms, outdoor spaces, and amenities such as swimming pools or BBQ areas, suiting families or groups.
Are there any beach house rentals in Montego Bay?
In Montego Bay, there are about 35 beach house holiday rentals available, offering a variety of options for travellers. These properties are typically situated near the stunning waterfront, providing easy access to local attractions such as Doctor's Cave Beach and the vibrant Hip Strip. Holiday homes often feature spacious living areas, fully equipped kitchens, and multiple bedrooms, making them ideal for families or larger groups. Many also come with outdoor spaces, such as decks or patios, where guests can relax and enjoy the beautiful coastal views.
What are popular rental amenities in Montego Bay?
In Montego Bay, popular holiday rental amenities include fully equipped kitchens, which allow travellers to prepare their own meals, and balconies that provide a lovely space to enjoy the views and fresh air. Many rentals also feature onsite parking, making it convenient for those who wish to explore the area by car. For additional comfort, some properties come with sofa beds, ideal for accommodating extra guests. Coffee and tea makers are also commonly found, ensuring that guests can enjoy a warm beverage at their leisure.
Can I find family house rentals in Montego Bay?
In Montego Bay, there are 28 family-friendly house rentals available, making it a wonderful destination for groups looking to enjoy a memorable holiday. These homes often come equipped with spacious living areas, full kitchens ideal for preparing family meals, and outdoor spaces where children can play and adults can relax. Many properties also feature amenities such as air conditioning and Wi-Fi to ensure a comfortable stay.The area boasts proximity to various attractions, including the stunning beaches of Doctor's Cave and the vibrant Hip Strip, where visitors can explore local shops and restaurants. Additionally, families can enjoy activities like water sports and excursions to nearby attractions, ensuring there's something for everyone.
Can I rent a holiday home with a pool or hot tub in Montego Bay?
In Montego Bay, there are plenty of holiday homes available for rent that come with either pools or hot tubs, with around 26 options featuring pools and several properties equipped with hot tubs. This vibrant coastal town offers a range of neighbourhoods, including the popular Ironshore area, known for its beautiful beaches and proximity to local attractions.Travellers can expect a wide variety of amenities in these rentals, including private swimming pools superb for relaxing under the sun, hot tubs ideal for unwinding in the evenings, and spacious outdoor areas for entertaining. Many properties also feature fully equipped kitchens, allowing guests to prepare their own meals, and comfortable living spaces designed for family gatherings or socialising with friends.
Can I book pet-friendly holiday rentals in Montego Bay?
In Montego Bay, there are several pet-friendly holiday rentals available, suiting travellers seeking accommodations that welcome their furry companions. The area offers a variety of properties, including charming cottages and spacious homes, many of which come equipped with modern amenities such as fully stocked kitchens, outdoor spaces, and comfortable living areas.While enjoying your stay, you can take advantage of the nearby parks and open spaces that are superb for walks with pets. The local environment is quite friendly towards pets, enhancing the overall experience for those travelling with animals.
When is the best time to visit Montego Bay for a holiday rental?
The best time to visit Montego Bay for a holiday rental is during the peak season from June to August, with July being the most popular month. This period attracts sun-seekers and families looking to enjoy the beautiful beaches, vibrant culture, and lively option. The warm temperatures, typically ranging from 24 to 32 degrees Celsius, create great conditions for outdoor activities, including swimming, snorkelling, and exploring the stunning coastal scenery.While July is bustling with tourists, it also offers a range of exciting events and festivals that highlight the local culture. Visitors can immerse themselves in the rhythm of Jamaican life, enjoying music, dance, and delicious cuisine right by the sea.For those seeking a more budget-friendly experience, November is a fantastic month to visit Montego Bay. This low season presents an opportunity to enjoy the stunning landscapes and attractions with fewer crowds, allowing for a more relaxed exploration of the area. The weather remains pleasant, making it an ideal time for sightseeing and enjoying the natural beauty of the coastline without the hustle and bustle of peak tourist season.Ultimately, the choice of when to visit Montego Bay will depend on your preference for vibrant summer experiences or a quieter getaway in November.
Are there any remote work holiday rentals in Montego Bay?
In Montego Bay, Maryland, there are a substantial number of remote work-friendly holiday rentals available, with around 132 options to choose from. Many of these properties offer essential amenities for those looking to work remotely, such as free Wi-Fi in the rooms, ensuring that you can stay connected while enjoying your getaway.These rentals often feature comfortable workspaces within the living areas, and some may even include dedicated office setups. Guests can expect additional conveniences like fully equipped kitchens for preparing meals, spacious living rooms for relaxation, and outdoor spaces that provide a pleasant environment for breaks or informal meetings.Moreover, Montego Bay's picturesque surroundings and access to local attractions create a friendly space for balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are the top attractions in Montego Bay, Maryland, United States of America?
In Montego Bay, Maryland, visitors can enjoy a range of attractions that highlight the area's natural beauty and recreational opportunities. The nearby Sandy Point State Park is a popular destination, offering scenic views of the Chesapeake Bay, sandy beaches, and picnic areas, great for a day of relaxation or outdoor activities.The historic downtown area features charming shops and eateries, and visitors can explore the local culture at the Montego Bay Museum. For those interested in boating or fishing, the waters around the town provide ample opportunities, with marinas offering various services.Additionally, the nearby Chesapeake Bay Bridge offers stunning views and serves as a gateway to explore further attractions on the eastern shore.
Are all fees included in the Montego Bay holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Montego Bay holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Montego Bay with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Montego Bay holiday homes?
You can find great discounts on holiday homes in Montego Bay on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Montego Bay holiday home booking on Bookabach?
To find Montego Bay holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Montego Bay?
A long-stay holiday home in Montego Bay is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Montego Bay holiday home?
Book your Montego Bay holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Montego Bay?
Prices for holiday homes in Montego Bay vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Montego Bay to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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