Holiday Rentals in Cudjoe Head

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Our top choices for Cudjoe Head holiday rentals

Chez Mango Villas

Chez Mango Villas
3.5 star property
Old Towne
7.2 out of 10, Good, (27)
"We enjoyed our stay in Mango vilas"
United Kingdom
Franck
The price is €156
includes taxes & fees
25 Dec - 26 Dec
Chez Mango Villas

RELAX-INN: 2bedroom apartment n JEEP RENTAL

RELAX-INN: 2bedroom apartment n JEEP RENTAL
St.John's
8.8 out of 10, Excellent, (5)
"The property is very nicely kept, very clean and comfortable in the quite location."
Canada
Marek
The price is €114
includes taxes & fees
10 Jan - 11 Jan 2026
RELAX-INN: 2bedroom apartment n JEEP RENTAL

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

Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.
Olveston
10.0 out of 10, Exceptional, (1)
"The overall experience was wonderful, the accommodation offered us everything that we wanted. The situation of the Ville was perferct for our needs, and within easy reach of the whole island.We would definitely want to stay there again."
United Kingdom
Lennox John K.
The price is €323
includes taxes & fees
27 Dec - 28 Dec
Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.

Caribbean Villa with Spectacular Views

Caribbean Villa with Spectacular Views
Garibaldi Hill
10.0 out of 10, Exceptional, (1)
Caribbean Villa with Spectacular Views

Casa Dorada

Casa Dorada
Brades
The price is €69
includes taxes & fees
7 Jan - 8 Jan 2026
Casa Dorada

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

Chic Cottage!Tranquil getaways - 4mins drive from our volcanic black sand beach
Saint Peter Parish, Montserrat
Chic Cottage!Tranquil getaways - 4mins drive from our volcanic black sand beach

Royal 2 - Chez Mango Villa

Royal 2 - Chez Mango Villa
2.5 star property
Salem
The price is €157
includes taxes & fees
5 Jan - 6 Jan 2026
Royal 2 - Chez Mango Villa

Royal 1 - Chez Mango Villa

Royal 1 - Chez Mango Villa
2.0 star property
Salem
The price is €161
includes taxes & fees
24 Jan - 25 Jan 2026
Royal 1 - Chez Mango Villa
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.
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Top Cudjoe Head Hotel Reviews

Find out more about Cudjoe Head

Everything you need to know about Cudjoe Head holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cudjoe Head holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cudjoe Head holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cudjoe Head holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cudjoe Head. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cudjoe Head holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cudjoe Head holiday rentals we have selected for you start as low as €69 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cudjoe Head rentals

At Expedia, we put the best Cudjoe Head holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cudjoe Head rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cudjoe Head holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cudjoe Head. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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, Little Bay and Lime Kiln Beach are a couple of picturesque spots to get outside and enjoy nature. Woodlands Beach and Montserrat Volcano Observatory 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.