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Vacation rentals in Jolly Harbour

Vacation rentals in Jolly Harbour

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Jolly Harbour

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Sugar Fields Hoilday Home with Private Pool.
    SUPERHOSTEntire house · 4 guests · 3 beds · 2.5 bathrooms
    Sugar Fields Hoilday Home with Private Pool.

    On route to your temporary home you will glimpse authentic Caribbean living. Traveling through small villages you will notice colorful chattel homes before arriving at your relaxing retreat. Perfect for chilling. Perfect for a staycation. We are confident that you will enjoy your air-conditioned bedrooms, each with a private balcony and your cozy, open plan indoor, outdoor living space.

    What guests are saying:

    “The home is just as pictured in the listing, and then some. The private balconies outside both bedrooms were a perfect space for morning tea and meditation and the pool deck was the the preferred space for dinner. We spent a week at Tony and Alyson's home and although they were not on island, they were prompt in responding to any questions or concerns we had, and had people in place to help us with whatever we needed. I rate our stay A+ across the board and look forward to staying here again.”

  • LUX, BEST VIEW-REVIEWED, INFINITY POOL, CLEAN-SAFE
    Entire villa · 6 guests · 3 beds · 3.5 bathrooms
    LUX, BEST VIEW-REVIEWED, INFINITY POOL, CLEAN-SAFE

    Villa Sunset is a 4000+ foot private villa located in the gated and secure and exclusive Sugar Ridge community located across the street from Jolly Harbour. We have every amenity as it is our home we rent.

    What guests are saying:

    “Honestly, I couldn’t wait to write a review about this beautiful place. THE. PICTURES. DONT. DO. IT. JUSTICE. I booked it based on the pictures posted but when I arrived, I was blown awaaay. It is more beautiful than you could ever imagine. It says “Caribbean home” from top to bottom. The kitchen has everything you could possibly need and then some. My husband and I cooked some wonderful meals during the days we spent there. The best part was that the supermarket was no more than 3 minutes away by car and it is very well stocked with everything. The rooms are beautifully decorated and so cozy. In the mornings you just can’t seem to drag yourself out from under the covers but you just have to because there’s so much to do and so much to see. The view in the morning from the balcony is great but the best view is at dusk when the sun just settled behind the hills and there’s slightly purple, pink and red rays shooting over the skies. The lights down at Jolly Harbour come on and it’s almost surreal. The house is so windy and you’ll find yourself stopping in the middle of a task and just taking a breath because you won’t believe that you’re actually is this amazing place. There are some very brave little birds that swoop in every once in a while when you’re eating breakfast or just minding your business in the kitchen. They mean no harm. Just shoo them away or they leave on their own accord. I didn’t mind their little visits at all. I enjoyed it very much while I sat on the balcony drinking my morning coffee and watching them bounce about and sing. Take a drive to English Harbour and down to Nelson’s Dockyard. Have a swim over at Half Moon Bay, and then end your day with a delicious dinner at Sheer Rocks or Basilico (both very close to the villa). We truly had a wonderful stay at the villa and the management team is so helpful and kind. They made it even harder to say goodbye. I do hope I get to visit again in the near future. It was like a dream. I have to pinch myself to be sure that it was all real. Thank you for having us! And I am more than happy to suggest this to any and everyone who is looking for a quiet place to enjoy beautiful views.”

  • Secluded Woodland Cabin
    SUPERHOSTEntire cabin · 2 guests · 1 bed · 1 bathroom
    Secluded Woodland Cabin

    The wooden shingled cabin is totally off the grid. To reach the cabin is a short walk up through a small wood on a narrow winding path from the parking area. Built on stilts the cabin over looks farmland and woods with a long view down the valley to the hills of English Harbour. The cabin has a large bedroom with wooden four poster bed with mosquito net. Barn doors open onto a side balcony, an open air bathroom with rain water shower heated by solar and a full kitchen. Wonderful night skies.

    What guests are saying:

    “We arrived at Tranquil Farm late on a Saturday afternoon (after a seamless experience picking up our rental car from Bigs Car Rental at the airport and a mildly harrowing drive for a couple of folks used to driving on the other side of the road, though Louise's directions were perfect!) Louise, Martin, and the dogs greeted us warmly, and Flossie was all decked out and ready for her task of transporting our luggage up the path to the cabin. It's just a short walk, charmingly lit by string lights with beer-bottle bulbs...don't let it deter you; it takes two minutes or less and the reward is worth it! At the end of the walk we came upon the cottage, just as lovely as it is in the photos, and even more intriguing in person. I love a tiny house, and discovering the touches that make it work are part of the fun. The cottage is basically two separate rooms that open onto the verandah. The kitchen is small but well-equipped. We did a lot of meal-prep there (restaurants are so expensive, and we weren't super-keen on driving after dark the first few days), and the kitchen had everything we needed. There were even a few staples provided, so if we hadn't stopped at the grocery on our way from the airport, we would not have starved! The bedroom is large and lovely, painted all white with shuttered windows and doors. My favorite part was the one door in the long wall of closets that was actually the pass-through to the outdoor bathroom (which sounds like it will be strange, but is actually lovely). We loved our week at the cottage...the quiet seclusion, the feeling of being somewhere entirely different from home, and the low-key adventure of being off-grid. Wi-fi kept us connected and gave us access to island info. The mid-island location was remote, but if your goal is to experience as many beaches as possible, it's just a matter of deciding whether to go north, south, east, or west that day...a 30-minute drive will get you to any coast! We made it to 7 beaches in 6 days (Deep Bay and Half-Moon Bay were our favorites). We hope to come back next year and see 7 more, and we would not hesitate to stay here again!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Jolly Harbour holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Jolly Harbour

Anne’s Home
SUPERHOSTPrivate room
Anne’s Home
Price:$ 139 SGD / night
Palm cottage....cozy, relaxing, private space
SUPERHOSTEntire flat
Palm cottage....cozy, relaxing, private space
Price:$ 67 SGD / night
3 Bedroom Villa with own pool near Jolly Harbour
SUPERHOSTEntire house
3 Bedroom Villa with own pool near Jolly Harbour
Price:$ 288 SGD / night
A tasteful 2 bedroom retreat
SUPERHOSTEntire house
A tasteful 2 bedroom retreat
Price:$ 383 SGD / night
Jumby House, 
The Caribbean Suite
Antigua.
SUPERHOSTPrivate room
Jumby House, The Caribbean Suite Antigua.
Price:$ 209 SGD / night
Aloe Villa in Galley Bay, Pool & Stunning Views
SUPERHOSTEntire house
Aloe Villa in Galley Bay, Pool & Stunning Views
Price:$ 296 SGD / night
Villa Inah - 2 Bedroom Waterfront Luxury Villa
SUPERHOSTEntire villa
Villa Inah - 2 Bedroom Waterfront Luxury Villa
Price:$ 417 SGD / night
Sweet HouSe
SUPERHOSTEntire house
Sweet HouSe
Price:$ 252 SGD / night
Jolly Harbour North Villa E
Entire flat
Jolly Harbour North Villa E
Price:$ 209 SGD / night
Serene Waterfront Villa Jolly Harbour South Finger
SUPERHOSTEntire villa
Serene Waterfront Villa Jolly Harbour South Finger
Price:$ 117 SGD / night
A True Caribbean Escape - Starfish Suite
SUPERHOSTEntire flat
A True Caribbean Escape - Starfish Suite
Price:$ 111 SGD / night
Valley View Villas
SUPERHOSTEntire villa
Valley View Villas
Price:$ 139 SGD / night
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