Hip Strip holiday lettings

We found 160 holiday rentals — enter your dates for availability

Discover a selection of 7 flats and other holiday rentals in Hip Strip that are perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as a hot tub and garden. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in Hip Strip?
In Hip Strip, apartments are the most popular type of holiday rental, with about 27 options available throughout the area. These apartments are typically located near the vibrant beachfront, providing easy access to local attractions and the stunning Caribbean Sea. Most rooms come with essential amenities, including fully equipped kitchens, comfortable living areas, and balconies or patios where guests can enjoy the warm tropical breezes.
Are there any beach house rentals in Hip Strip?
In Hip Strip, Saint James, Jamaica, there are approximately 100 beach house holiday rentals available, making it a popular destination for visitors seeking a seaside getaway. These beach houses are typically well-equipped, offering amenities such as fully stocked kitchens, spacious living areas, and often private balconies or patios that provide stunning views of the Caribbean Sea. Many properties also feature easy access to the beach, allowing guests to enjoy sunbathing and water activities right at their doorstep. The Hip Strip is known for its vibrant atmosphere, with a variety of local shops, restaurants, and entertainment options nearby, making it an ideal location for both relaxation and exploration.
How much does it cost to rent a holiday home in Hip Strip?
Prices for holiday rentals in Hip Strip 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Hip Strip to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Hip Strip holiday house rentals?
You can find great discounts on house rentals in Hip Strip on Vrbo, 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.
Are there any Hip Strip holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Hip Strip 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 on Vrbo 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.
Can I find long-stay holiday rentals in Hip Strip?
A long-stay holiday rental in Hip Strip 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Hip Strip for a holiday rental?
April is the most popular time to visit the Hip Strip in Saint James, Jamaica, as it greatly captures the essence of the vibrant Caribbean atmosphere. This month is part of the peak season, which runs from February to April, attracting sun-seeking travellers eager to enjoy the stunning beaches, crystal-clear waters, and lively local culture.

During this peak period, temperatures typically hover around the mid-20s Celsius, creating ideal conditions for outdoor activities such as swimming, snorkelling, and exploring the local markets. The Hip Strip, known for its colourful shops and lively nightlife, offers a plethora of opportunities for sightseeing and relaxation, all within walking distance from your holiday rental.

For those looking for a more budget-friendly experience, consider visiting in October, when the crowds thin out, allowing for a more relaxed atmosphere while still enjoying the island's natural beauty. This month presents a unique opportunity to explore the Hip Strip and its surroundings at a more leisurely pace, with pleasant temperatures and the chance to immerse yourself in authentic Jamaican culture without the hustle and bustle.
Are there any remote work holiday rentals in Hip Strip?
In the Hip Strip area of Saint James, Jamaica, there are numerous remote work holiday rentals available, with around 34 options to choose from. This vibrant neighbourhood is known for its beautiful beaches, lively atmosphere, and proximity to local attractions. Many properties in this area are well-equipped for remote work, featuring amenities such as reliable Wi-Fi, dedicated workspaces including desks and office chairs, and safe environments conducive to productivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Hip Strip holiday rental?
Book your Hip Strip holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Hip Strip?
In the Hip Strip of Saint James, Jamaica, visitors can enjoy a vibrant array of attractions. The area is renowned for its lively atmosphere, with numerous bars, restaurants, and shops lining the streets. One of the highlights is Doctor's Cave Beach, famous for its clear waters and beautiful sandy shores, which is great for swimming and sunbathing. Close by, visitors can explore the vibrant nightlife, with live music and entertainment options available in many of the local venues.
Can I change or cancel my Hip Strip home rental booking on Vrbo?
To find Hip Strip holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Hip Strip holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

More holiday ideas