
Holiday houses in Old Town
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Old Town
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Old Town holiday rentals
Other great holiday rentals in Old Town
Guest favourite

Home in Jolly Harbour
5 out of 5 average rating, 7 reviewsSpectacular Caribbean-Sunset-Ocean-view home!
RebeccaRating, 5 stars2 months ago
Wonderful villa, beautiful views, gorgeous pool, lots of space, nicely furnished, beautifully clean, very well kitted out. Had a few issues at beginning but hosts v responsive and keen to sort quickly. Would have been great to have an information booklet / folder with practical info about the villa but also recommendations / opinions about restaurants, beaches, excursions etc. The hosts were very helpful - but just useful to have this kind of thing in any accommodation you stay in. It was a shame about the construction noise - beyond their control I know. Mainly it was in the distance but sometimes it was enough to send us to the beach rather than relaxing at the villa. In the main though a wonderful villa which we all enjoyed being in and particularly the beautiful views during the day and at sunset 🌅 - thank you Patrick and the team for all your help.

Home in Woodlands
4.82 out of 5 average rating, 22 reviewsCrows Nest Villa...2 bed with pool
RussRating, 5 stars10 months ago
Unfortunately, I can’t honestly review Tom & Chrystal’s place. Tom had reached out a couple of weeks prior to inform me that due to scheduling issue, he had made arrangements for us stay at another villa, which was absolutely amazing! By chance we ran into Tom and family at the local dive shop, and we ended up eating lunch together. Everything I had come to learn online was met in person: kind, friendly, funny, generous… Good people, and we count ourselves lucky to have gotten to spend time with them. So, even though I can’t speak about Crow’s Nest in Woodlands, I can say my interactions with Tom and Chrystal were 100% positive, and I would happily stay at their place at the next opportunity.
Top Guest favourite

Cottage in Sawcolts
5 out of 5 average rating, 5 reviewsPeaceful nature escape
AndreasRating, 5 stars3 months ago
We had a wonderful time in Andrews Sugar Cottage. It is very nice cottage in a calm setting surrounded by a green garden and jungle sounds. We didnt meet him or his assistant in person but the communication and service was flawless - we were even greeted with a fruit basket and a starter pack, thanks! We enjoyed the big terrace a lot and are already looking back to evenings just waiting for the sun to go down and listening to the island sounds. There is also the lovely house dog Mango - very friendly and attentive. There are also other dogs in this area so there is some barking going on during the day. Be aware of the mosquitos and get used to carry the provided mosquito bats along. You will also need a car to get to all the beaches, restaurants and sights. We highly recommend the cottage for people who want to stay away from the big resorts and feel more like a local. We loved it and would definitely book again. Thanks Andrew and Mowava for this unique stay!

Condo in Woodlands
4.8 out of 5 average rating, 10 reviewsMin-y-Don, Montserrat Caribbean hideaway
CatherineRating, 5 stars4 months ago
Our stay at Min Y Don was wonderful. The house is in an incredibly beautiful and convenient spot. Hearing the waves crashing below, the warm breeze in the palms, birds in the day and a chorus of tree frogs at night was bliss. The view over the ocean is amazing. The accommodation is so comfortable and spacious, everything you could possibly need for a luxurious stay. Well equipped kitchen, wonderful pool (with pool toys!) and such comfy beds. Sian and Peter have been so kind, generous, and friendly throughout. They've thought of everything, suncream abd shampoo, baked bread on arrival, and chilled water in the fridge. Lots of information on Montserrat too. To say we enjoyed our stay is an understatement. I was working part of the time, exploring the rest; and having such a beautiful and welcoming home to return to was the icing on the cake. Thankyou Sian and Peter.
Guest favourite

Apartment in Urlings
4.83 out of 5 average rating, 6 reviewsDream View Apartment
RalitsaRating, 5 stars5 months ago
This place is a hidden gem. Darryl and Daff are extremely kind and interesting hosts. Their stories about the island, the people and the culture are very insightful and make the exploration of the island much more interesting. The location is the best possible one on the island : we had access to all the best beaches , just in close distance. Watching the blue water and the sunset from the balcony was our favorite part. We were having coffee in the morning while watching the humming birds flying around the blooming flowers in front of the balcony. The house has everything that we needed and even more: the beach beds, the snorkeling gears.. they have thought of every detail to make our stay easy and enjoyable. It was one of the best places that we have stayed so far. Thank you, guys. We will be back.
Guest favourite

Villa in Saint Peter's
4.9 out of 5 average rating, 10 reviewsVilla Isotica: Scenic and Breathtaking Views
KarenRating, 5 stars2 months ago
Montserrat is a beautiful and quiet island but there isn’t a whole lot in terms of infrastructure or options — so it’s worth knowing what to expect. This Airbnb was incredibly expensive for what it is, but given the context, that’s not entirely surprising. Choices on the island are limited and basic so this was luxurious comparatively. The space was clean, thoughtfully decorated, and clearly well taken care of. It doesn’t have AC but based on location in the hills it has an awesome breeze and sleeping at night was comfortable. Beautiful orchestra of tree frogs! Daphne and Norman were extremely friendly and helpful - clearly care for their guests and want them to have a good time. They helped organize a car from Jerret (tip top enterprise) and we highly recommend him. He met us at the airport and was super easy to deal with. The car was brilliant - without it you would be unable to move around. The roads are difficult to navigate so important to important to have a good.
Guest favourite

Apartment in Davy Hill
5 out of 5 average rating, 24 reviewsRELAX-IN: 2-bedroom apartment w/ Jeep rental svcs
Mike And KerryRating, 5 stars3 weeks ago
Great stay here.
Top Guest favourite

Villa in Bolands
4.97 out of 5 average rating, 32 reviewsUnique Caribbean Secluded Open Air Villa 1 Bedroom
RobertRating, 5 stars3 weeks ago
This was our second visit to this home - it was as magical as the first. The house and view are stunning, proximity to Jolly Beach and Jolly Harbor mean everything you need is nearby. Susan took care of everything we needed prior to arrival and we had an amazing several days. Drinking coffee each morning we'd get fly-bys of tarpon, barracuda, eagle rays, sting rays, and a zillion other things in the crystal clear water. Could watch that all day long. Note: the listing is pretty clear on this, but it is a pretty good hike up and down the path to get from the road to and from the house - make sure you're good with that. But if you're on the fence, just book and have as much fun as we did.
Destinations to explore
- Sainte-Anne Holiday rentals
- Le Gosier Holiday rentals
- Basse-Terre Island Holiday rentals
- Deshaies Holiday rentals
- Marie-Galante Holiday rentals
- Îles des Saintes Holiday rentals
- Sainte-Rose Holiday rentals
- Pointe-à-Pitre Holiday rentals
- Jolly Harbour Holiday rentals
- Bouillante Holiday rentals
- Le Moule Holiday rentals
- San Juan Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom