Cudjoe Head Vacation Rentals from $130: Search Short-Term Rentals

Q: What are some of the best vacation home rentals that Cudjoe Head has to offer?

RELAX-INN: 2bedroom apartment n JEEP RENTAL : You might want to consider this vacation home rental near Cudjoe Head, which 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.

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Vacation Rentals in Cudjoe Head

"The stay was pleasant. The hosts were easy to contact and very responsive. "

"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. "

"Everything about this place exceeded all expectations! Never felt more relaxed in my entire life. Can't wait to go back! "

"Staying at adams place was the ultimate Monserrat experience! We enjoyed having the entire villa to ourselves, it was perfect for our romantic getaway but there was plenty of room to bring the whole family next time! The property manager, Kristina, was so kind and attentive to all of our questions and made sure we had everything we needed and having Toni as our private chef for the day was unbeatable! Her food is amazing! We watched the sunset from the saltwater pool every evening and the beach...

"The property is very nicely kept, very clean and comfortable in the quite location."

$130 nightly

Jul 8 - Jul 9

Total includes taxes and fees

"The pool, the view, the stars st night, delightful"

"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...

"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."

$341 nightly

Aug 1 - Aug 2

Total includes taxes and fees

"We had a fantastic 15days in Carpe Diem.The veiw from the veranda was amazing. The villa was comfortable and well situated, with in walking distance of the beautiful Isles bay beach. We hired a car for the duration of our stay which was essential it was through Joe Irish who was very helpful. The pool was lovely and a nice size. The surrounding area was a sun trap but also had plenty of shade. We were however disappointed to find that there were only two sun beds, which were both unusable. For...

"Need upgrades such as screens and ac. Property manager was very rude the home was clean"

"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!"

$160 nightly

Jul 21 - Jul 22

Total includes taxes and fees

"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...

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Find out more about Cudjoe Head

Everything you need to know about Cudjoe Head vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cudjoe Head vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cudjoe Head vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cudjoe Head in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $130 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cudjoe Head rentals

At Expedia, we put the best Cudjoe Head vacation 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 vacation.

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.

Recent reviews of Cudjoe Head properties

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

5/5 Excellent

McAuthurs Ville

"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."

A verified traveler stayed at Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.

Posted 2 months ago

Tranquil island escape with stunning ocean view.

5/5 Excellent

Amazing Seaview Property in Montserrat

"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 had them within 24hrs. They provided great local recommendations and assisted with places to visit as well as arranged tours and hikes. The amenities, such as WiFi, kitchen, parking, and speakers in every room, this allowed us to have some great entertaining evenings, and as the property is set back from all the others, you have complete privacy. You even have the option to play to isolate the music in your own room or an area. ie the pool deck. They even arranged for someone to get us fresh coconuts and mangoes from their trees in the Garden!!!. I highly recommend this place to anyone visiting Montserrat. As well as the tastefully decorated Villa, the scenery is equally breath-taking. waking up to daily sunrise and watching the sunset blows your mind. We would most definitely stay here again!""

A verified traveler stayed at Tranquil island escape with stunning ocean view.

Posted 4 months ago

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

5/5 Excellent

"The villa was even better than the photos- the views are sensational! Marie-Josee was an excellent host, responding quickly to our queries. "

A verified traveler stayed at Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.

Posted 4 months ago

Luxurious Penthouse with Breathtaking Views

5/5 Excellent

Absolutely Wonderful Stay – A Hidden Gem!

"We had the most amazing time here! The space was not only beautiful and spotless, but also incredibly peaceful and well-equipped with everything we needed. From the wraparound balcony with breathtaking views to the refreshing pool, every moment felt like a dream vacation.What made our stay even more special was the kindness and thoughtfulness of the owner and his team. They went above and beyond to make sure we felt at home—from helpful local tips to being super responsive and accommodating throughout our visit. It’s rare to find someone who genuinely cares that your experience is perfect, and that’s exactly how we felt here.Highly recommend to anyone looking for a relaxing, scenic, and well-cared-for place to stay. We’ll definitely be coming back!"

A verified traveler stayed at Luxurious Penthouse with Breathtaking Views

Posted 4 months ago

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

5/5 Excellent

Fantastic property!

"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 wants to experience Montserrat."

A verified traveler stayed at Sonido Del Mar, Island Retreat, 9 minute walk to the beach

Posted 4 months ago

RELAX-INN: 2bedroom apartment n JEEP RENTAL

5/5 Excellent

Very good stay

"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."

A verified traveler stayed at RELAX-INN: 2bedroom apartment n JEEP RENTAL

Posted 8 months ago

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

5/5 Excellent

Gorgeous View!!!!

"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!"

A verified traveler from Sandy Hook, CT stayed at Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

Posted 8 months ago

Frequently asked questions

Can I find vacation rentals in Cudjoe Head?

Yes, you can find vacation rentals near top attractions in Cudjoe Head, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals that Cudjoe Head has to offer?

RELAX-INN: 2bedroom apartment n JEEP RENTAL: You might want to consider this vacation home rental near Cudjoe Head, which 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. Lime Kiln Beach and Foxes Bay Beach are a couple of places you'll find in the larger area.

What are vacation rentals like in Cudjoe Head?

Vacation rentals are private properties you can book for short or long periods in Cudjoe Head. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.

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Cudjoe Head Vacation Rentals

Check prices for these dates

Vacation Rentals in Cudjoe Head

Luxurious Penthouse with Breathtaking Views

Secluded Villa with scenic views of the Atlantic ocean

Seaview Apartment - One bedroom Apartment

Chez Mango Villas

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

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

RELAX-INN: 2bedroom apartment n JEEP RENTAL

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

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

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

Enjoy the lovely Carpe Diem villa in the unspoiled Caribbean isle of Montserrat

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

Tranquil island escape with stunning ocean view.

Caribbean Villa with Spectacular Views

Beautiful modern retreat with stunning views of mountain ranges & Seaview

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

Cozy Fully Equipped Apartment for Ultimate Comfort

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

Modern North Side Hideaway w/Aircon

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

Find out more about Cudjoe Head

Recent reviews of Cudjoe Head properties

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

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

Tranquil island escape with stunning ocean view.

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

Luxurious Penthouse with Breathtaking Views

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

Chez Mango Villas

RELAX-INN: 2bedroom apartment n JEEP RENTAL

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

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