Cudjoe Head Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Cudjoe Head

Luxurious Penthouse with Breathtaking Views

8.4 out of 10, Very good, (10)
"The stay was pleasant. The hosts were easy to contact and very responsive. "
The price is NZ$401
includes taxes & fees
1 Apr - 2 Apr
Luxurious Penthouse with Breathtaking Views

Secluded Villa with scenic views of the Atlantic ocean

Secluded Villa with scenic views of the Atlantic ocean

Seaview Apartment - One bedroom Apartment

Seaview Apartment - One bedroom Apartment

Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated

10.0 out of 10, Exceptional, (9)
"Well-designed ocean-front house with a nice pool, very private landscaped garden, and fiber optic internet. The neighborhood is peaceful, very safe feeling and nice for taking walks. The Attic restaurant in walking distance is excellent. Paul Lewis, the property manager, stepped up like a champion to let us use his office internet when the local internet service provided was down for a little while. Our family was very comfortable. We'd highly recommend staying there if visiting Montserrat. "
Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated

RELAX-INN: 2bedroom apartment n JEEP RENTAL

8.8 out of 10, Excellent, (5)
"The appartment is perfect for a calm stay in Montserrat, and the owner makes it very easy. Beds are good, kitchen pretty well equiped, the terrasse is perfect and everything was very clean and in perfect state. We also rented the car, which was very useful. The location of the appartment is also handful, 50m from a supermarket."
The price is NZ$227
includes taxes & fees
31 Mar - 1 Apr
RELAX-INN: 2bedroom apartment n JEEP RENTAL

Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.

The price is NZ$630
includes taxes & fees
1 Apr - 2 Apr
Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.

Lucy's Sunny Villa apartments, spacious & modern, your ideal tropical retreat.

Lucy's Sunny Villa apartments, spacious & modern, your ideal tropical retreat.

Tranquil island escape with stunning ocean view.

8.8 out of 10, Excellent, (6)
"We had the most amazing stay at Silk Cotton Villa! The Villa was high spec, clean, spacious (needed for our party of 9), it was cosy, well-located, and well equipped with all the amenities needed. The hosts have really given their property a lot of thought to ensure that you have everything to make your stay pleasurable. The check-in process was smooth, and the host was friendly, attentive, they were very responsive to questions and on hand for any support needed. I wanted softer pillows and I...
Tranquil island escape with stunning ocean view.

Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.

9.8 out of 10, Exceptional, (9)
"The villa was even better than the photos- the views are sensational! Marie-Josee was an excellent host, responding quickly to our queries. "
Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.

Chez Mango Villas

3.5 star property
7.6 out of 10, Good, (23)
"A very wooded, island feel with the charm on an old world tropical villa. Perfect accomidations and a very helpfil staff. Lots of wildlife to view, and very comfortable. "
The price is NZ$435
includes taxes & fees
31 Mar - 1 Apr
Chez Mango Villas

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

8.4 out of 10, Very good, (16)
"The view from the villa is amazing and it changes throughout the day. The Villa was the perfect size for my wife and me. It is centrally located and close to everything. Enjoy!"
Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

Caribbean Villa with private pool & ocean view in the heart of Montserrat

10.0 out of 10, Exceptional, (2)
"Adam’s Place is the place to stay in Montserrat. We hated to leave. Ed and Rea were great to communicate with, Kristina and Sunny as property managers were exceptional. The house is superbly furnished, kitchen is amazing, and you cannot beat the sunsets as you lounge on the patio and pool. The grounds are so pretty also. Toni, the private chef, cooked us a fantastic breakfast and two awesome dinners. I wanted to take her home with me. Sunny gave us a tour of the volcano which was spectacular. We...
Caribbean Villa with private pool & ocean view in the heart of Montserrat

Sonido Del Mar, Island Retreat, 9 minute walk to the beach

8.0 out of 10, Very good, (2)
"We had a very relaxing vacation at Sonido Del Mar.Our hosts, David and Valerie, were very responsive to any questions we had. The property was immaculate and the view of the ocean is impressive. We enjoyed evening cocktails watching the sunset from the Estella. It was very beautiful. All the amenities of the house were appreciated especially the dishwasher and washing machine. The house is beautifully decorated and really gives you an island vibe. We highly recommend this property to anyone who...
Sonido Del Mar, Island Retreat, 9 minute walk to the beach

Caribbean Villa with Spectacular Views

Caribbean Villa with Spectacular Views

Breezy, Clean, Comfortable and Peaceful, with a breathtaking view

2.0 out of 10, (1)
Breezy, Clean, Comfortable and Peaceful, with a breathtaking view

5 Minutes Walk to Beach - Ocean & Mountain View Villa with Private Pool

8.0 out of 10, Very good, (2)
"We loved our stay at Grandview. The property manager was quick to try to fix the issues we told him about. I think the VBRO listing needs new pictures and some modifications. There was not a DVD player, grill, dishwasher, children's dinnerware, or spices. The kitchen needs new cookware and more glasses. A baking pan would be nice too. It was just two of us so we were ok but if a family had booked this villa they would have needed much more."
5 Minutes Walk to Beach - Ocean & Mountain View Villa with Private Pool

Modern North Side Hideaway w/Aircon

10.0 out of 10, Exceptional, (2)
"The experience of staying in this place for 5 days was truly remarkable. From the moment we arrived, the host extended a warm and gracious welcome that immediately made us feel at home. Their hospitality and attentiveness surpassed all expectations, as they went above and beyond to ensure that our stay was comfortable and enjoyable. The friendliness of the people at this place is unparalleled. Each day, they looked out for us and made sure we had everything we needed. It's rare to encounter...
Modern North Side Hideaway w/Aircon

Cozy Fully Equipped Apartment for Ultimate Comfort

The price is NZ$280
includes taxes & fees
1 Apr - 2 Apr
Cozy Fully Equipped Apartment for Ultimate Comfort

Chic Cottage!Tranquil getaways - 4mins drive from our volcanic black sand beach

Chic Cottage!Tranquil getaways - 4mins drive from our volcanic black sand beach

Northern Comfort Home w/ Queen Bed, convenient location

Northern Comfort Home w/ Queen Bed, convenient location
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.
Don't see what you're looking for?
See all available properties in Cudjoe Head
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Cudjoe Head you may be interested in

Luxurious Penthouse with Breathtaking Views

8.4 out of 10, Very good, (10)
"The stay was pleasant. The hosts were easy to contact and very responsive. "
The price is NZ$401
includes taxes & fees
1 Apr - 2 Apr
Luxurious Penthouse with Breathtaking Views

Secluded Villa with scenic views of the Atlantic ocean

Secluded Villa with scenic views of the Atlantic ocean

Seaview Apartment - One bedroom Apartment

Seaview Apartment - One bedroom Apartment
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.

Frequently asked questions

Can I find holiday rentals in Cudjoe Head?

Yes, there are holiday rentals close to the most popular sights in Cudjoe Head, 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 Cudjoe Head has to offer?

RELAX-INN: 2bedroom apartment n JEEP RENTAL: This holiday home rental outside of Cudjoe Head has laundry facilities and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What can I see and do in Cudjoe Head?

While you're exploring the area, Woodlands Beach and Montserrat Volcano Observatory are a couple of picturesque spots to get outside and enjoy nature. Montserrat National Trust and Foxes Bay Beach are a couple of places you'll find in the wider area.

What are holiday rentals like in Cudjoe Head?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cudjoe Head. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment 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 a popular option for family trips or small group gatherings.