Photo by Michael Lee

Dempsey Hill holiday rentals

We found 129 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Dempsey Hill to find one that's perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the amenities that you expect and more, which might include a garden and pool. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

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Delight in the natural landscape of Dempsey Hill

The gardens and surrounding scenery provide a peaceful ambience to your holiday home in Dempsey Hill. Renowned for its shopping, restaurants and football games, this city welcomes all visitors. Orchard Road and Universal Studios Singapore are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Dempsey Hill

Are you searching for top things to see and do while you're in town? Venture out of your holiday home and experience everything that makes Dempsey Hill a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Universal Studios Singapore (3.6 mi / 5.8 km)
  • Adventure Cove Waterpark (3.3 mi / 5.2 km)
  • Marina Bay Street Circuit (3.8 mi / 6.1 km)
  • Sentosa Golf Club (4.4 mi / 7.1 km)
  • Singapore Sports Hub (4.6 mi / 7.5 km)
  • Night Safari (6.9 mi / 11.2 km)

Exploring the natural landscape of Dempsey Hill

Whether you're an active traveller or just want to appreciate the scenery, Dempsey Hill is a great place to spend some time outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • National Orchid Garden (0.6 mi / 0.9 km)
  • Singapore Botanic Gardens (0.7 mi / 1.2 km)
  • Fort Canning Park (2.6 mi / 4.2 km)
  • Raffles Place (3.2 mi / 5.1 km)
  • West Coast Park (3.3 mi / 5.3 km)
  • Siloso Beach (3.4 mi / 5.5 km)

Travelling to and around Dempsey Hill

Fly into Singapore (XSP-Seletar), the closest airport, located 8.7 mi (14 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Changi Airport (SIN), which is 12.8 mi (20.6 km) away.

Frequently asked questions

What is the best area to stay in Dempsey Hill when booking a holiday rental?
When considering a holiday rental in Dempsey Hill, Singapore, the best area to stay would be within the Dempsey Hill enclave itself. This charming neighbourhood is known for its lush greenery and a relaxed atmosphere, making it an ideal retreat from the hustle and bustle of the city.There are a variety of properties available in this area, ranging from stylish apartments to more expansive villas. Staying in Dempsey Hill allows you to enjoy easy access to some delightful attractions. One standout feature is the nearby Singapore Botanic Gardens, a UNESCO World Heritage site, where you can explore beautiful landscapes and a world-renowned orchid garden. Additionally, the area is home to a selection of trendy eateries and art galleries, providing a vibrant cultural experience right at your doorstep.
What are the top attractions in Dempsey Hill?
Dempsey Hill in Singapore is a vibrant destination known for its unique blend of dining, retail, and cultural experiences. One of the top attractions is the Dempsey Hill enclave itself, which features an array of restaurants and cafes set in a lush, green environment, making it a popular spot for both locals and tourists. The area is also home to the Singapore Botanic Gardens, a UNESCO World Heritage site, which is just a short distance away and offers beautiful landscapes, walking trails, and a stunning collection of orchids.Art enthusiasts can visit the nearby National Orchid Garden, which showcases thousands of orchid species in a picturesque setting. Additionally, the proximity to the Holland Village area provides access to a lively market atmosphere and various boutiques, enhancing the overall experience.
Are all fees included in the Dempsey Hill holiday homes prices shown on Stayz?
Stayz 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 Dempsey Hill holiday homes with parking?
Stayz offers a wide selection of holiday homes in Dempsey Hill 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 Dempsey Hill holiday homes?
You can find great discounts on holiday homes in Dempsey Hill on Stayz, 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 Dempsey Hill holiday home booking on Stayz?
To find Dempsey Hill holiday rentals with free cancellation, just use Stayz'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, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Dempsey Hill?
A long-stay holiday home in Dempsey Hill 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 Stayz?
Stayz'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 Dempsey Hill holiday home?
Book your Dempsey Hill 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Dempsey Hill?
Prices for holiday homes in Dempsey Hill 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. Stayz offers something for every taste and budget, from affordable homes in Dempsey Hill to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz 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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