A lush garden with a stone tower, diverse plants, and a winding tree sculpture.

Old Road Town Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Old Road Town holiday rentals

1. St. Kitts Castle Premium Suites

St. Kitts Castle Premium Suites
4.0 star property
Basseterre
9.0 out of 10, Wonderful, (2 reviews)
"The property was conveniently located and comfortable. We even received a complementary bottle of wine which was very thoughtful!"
United States
RAKESH
The price is NZ$245
includes taxes & fees
30 Sept - 1 Oct
St. Kitts Castle Premium Suites

2. Panoramic View+Private+Cozy=Affordable

Panoramic View+Private+Cozy=Affordable
Basseterre
9.8 out of 10, Exceptional, (22 reviews)
"Excellent stay, great host"
United States
Wilfried W.
The price is NZ$185
includes taxes & fees
10 Oct - 11 Oct
Panoramic View+Private+Cozy=Affordable

3. Sunset Reef St.Kitts

Sunset Reef St.Kitts
5.0 star property
Basseterre
9.8 out of 10, Exceptional, (12 reviews)
"Beautiful property!"
United States
Nicole Laquis
The price is NZ$1,266
includes taxes & fees
8 Oct - 9 Oct
Sunset Reef St.Kitts

4. Getaway Homes

Getaway Homes
4.0 star property
Basseterre
The price is NZ$214
includes taxes & fees
30 Sept - 1 Oct
Getaway Homes

5. LUX Suites - 2-bedroom apartment in Halfmoon Bay

LUX Suites - 2-bedroom apartment in Halfmoon Bay
Halfmoon Bay
10.0 out of 10, Exceptional, (1 review)
"First time visiting St Kitts and staying here. The place was spacious and clean. Beautiful view of the mountain and the ocean. Checking process with Rigel was simple. Would stay here again"
United States
Bobby P.
The price is NZ$768
includes taxes & fees
2 Oct - 3 Oct
LUX Suites - 2-bedroom apartment in Halfmoon Bay

6. Charming 1-bedroom apartment with AC in Saddlers Village

Charming 1-bedroom apartment with AC in Saddlers Village
Saddlers Village
The price is NZ$270
includes taxes & fees
30 Sept - 1 Oct
Charming 1-bedroom apartment with AC in Saddlers Village

7. Marriott's St. Kitts Beach Club

Marriott's St. Kitts Beach Club
3.5 star property
Basseterre
9.4 out of 10, Exceptional, (123 reviews)
"Loved our stay traveled with my 4 kids and we had a blast"
United States
beverly
The price is NZ$656
includes taxes & fees
22 Oct - 23 Oct
Marriott's St. Kitts Beach Club

8. Modern Minimalist at Haven+

Modern Minimalist at Haven+
St.Kitts
The price is NZ$318
includes taxes & fees
30 Sept - 1 Oct
Modern Minimalist at Haven+

9. Earth at Haven+ | Refined Island Escape

Earth at Haven+ | Refined Island Escape
St.kitts
The price is NZ$318
includes taxes & fees
1 Oct - 2 Oct
Earth at Haven+ | Refined Island Escape

10. Two bedrooms and a large terrace, close to everything

Two bedrooms and a large terrace, close to everything
Trinity
The price is NZ$322
includes taxes & fees
1 Oct - 2 Oct
Two bedrooms and a large terrace, close to everything

11. Coastal at Haven+

Coastal at Haven+
St.kitts
The price is NZ$609
includes taxes & fees
30 Sept - 1 Oct
Coastal at Haven+

12. Paradise Suite

Paradise Suite
4.0 star property
Cotton Ground
9.6 out of 10, Exceptional, (7 reviews)
"Excellent place."
United States
Edgardo
The price is NZ$536
includes taxes & fees
30 Sept - 1 Oct
Paradise Suite

13. Beautiful island getaway, close proximity to popular beaches and historic site A

Beautiful island getaway, close proximity to popular beaches and historic site A
Nevis
9.6 out of 10, Exceptional, (4 reviews)
"Nice property in a quiet area. Nice views and donkeys nearby "
United States
Kelsey R.
The price is NZ$238
includes taxes & fees
30 Sept - 1 Oct
Beautiful island getaway, close proximity to popular beaches and historic site A

14. Beautiful island getaway, close proximity to popular beaches and historic site C

Beautiful island getaway, close proximity to popular beaches and historic site C
Camps
9.6 out of 10, Exceptional, (5 reviews)
"Yes everything was perfect they met us at the condo it was a beautiful inside air condition very modern and very accommodating will probably stay there the next time we go to St Nevis!"
United States
Robert E.
The price is NZ$238
includes taxes & fees
30 Sept - 1 Oct
Beautiful island getaway, close proximity to popular beaches and historic site C

15. Charming 1-bedroom apartment with WiFi, AC in gorgeous St. John's Parish

Charming 1-bedroom apartment with WiFi, AC in gorgeous St. John's Parish
St. John's Parish, Nevis
9.8 out of 10, Exceptional, (7 reviews)
"Very nice apartment and quiet area!!! I would definitely stay there again!"
United States
Shaquilla
The price is NZ$304
includes taxes & fees
30 Sept - 1 Oct
Charming 1-bedroom apartment with WiFi, AC in gorgeous St. John's Parish

16. MONKEY PAW -BLUE CARIBBEAN MEETS MT NEVIS RAIN FORST

MONKEY PAW -BLUE CARIBBEAN MEETS MT NEVIS RAIN FORST
CHARLESTOWN
10.0 out of 10, Exceptional, (2 reviews)
"The house, the pool, the property, and the view are beautiful. The grounds are meticulously maintained. We enjoyed our stay there and had everything we needed to be comfortable. We were concerned before arriving about the lack of air conditioning but it truly is not needed. We were never uncomfortable during the day or at night. The central location is convenient with grocery stores and several great restaurants nearby. You can get to any point on the island within 20 minutes. The host and the...
United States
Heidi S.
The price is NZ$1,901
includes taxes & fees
30 Sept - 1 Oct
MONKEY PAW -BLUE CARIBBEAN MEETS MT NEVIS RAIN FORST

17. A Private Gingerbread Cottage at the Hermitage

A Private Gingerbread Cottage at the Hermitage
Gingerland
The price is NZ$819
includes taxes & fees
30 Sept - 1 Oct
A Private Gingerbread Cottage at the Hermitage

18. Beautiful island getaway, close proximity to popular beaches and historic site B

Beautiful island getaway, close proximity to popular beaches and historic site B
Camps
The price is NZ$238
includes taxes & fees
30 Sept - 1 Oct
Beautiful island getaway, close proximity to popular beaches and historic site B

19. Tamarind Villa, Montpelier Nevis

Tamarind Villa, Montpelier Nevis
Charlestown
The price is NZ$2,631
includes taxes & fees
8 Oct - 9 Oct
Tamarind Villa, Montpelier Nevis

20. Saddle Hill View Villa – Private 2-Bedroom Villa with Pool & Ocean Views

Saddle Hill View Villa – Private 2-Bedroom Villa with Pool & Ocean Views
Charlestown
The price is NZ$3,642
includes taxes & fees
8 Oct - 9 Oct
Saddle Hill View Villa – Private 2-Bedroom Villa with Pool & Ocean Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Old Road Town Hotel Reviews

Find out more about Old Road Town

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Old Road Town holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Old Road Town. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Old Road Town. Seeing all the best attractions is bound to make you fall in love with Old Road Town. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Old Road Town short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Old Road Town?

Yes, there are holiday rentals close to the most popular sights in Old Road Town, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Old Road Town has to offer?

Stunning Caribbean House With Breath-taking Views: This holiday home rental outside of Old Road Town is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Old Road Town?

While you're exploring the area, Frigate Bay Beach and Frigate Bay are a couple of picturesque spots to get outside and enjoy nature. Romney Manor and Warner Park Sporting Complex are a couple of places you'll find in the wider area.

What are holiday rentals like in Old Road Town?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Old Road Town. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.