Cudjoe Head Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Cudjoe Head

Luxurious Penthouse with Breathtaking Views
Outdoor pool

Luxurious Penthouse with Breathtaking Views

8.6 out of 10, Excellent, (11)
"The stay was pleasant. The hosts were easy to contact and very responsive. "
$224 nightly
The price is $224
Sep 1 - Sep 2
Total with taxes and fees
Luxurious Penthouse with Breathtaking Views
Secluded Villa with scenic views of the Atlantic ocean
Property grounds

Secluded Villa with scenic views of the Atlantic ocean

Secluded Villa with scenic views of the Atlantic ocean
Seaview Apartment - One bedroom Apartment
Property grounds

Seaview Apartment - One bedroom Apartment

Seaview Apartment - One bedroom Apartment
Chez Mango Villas
Business Suite | Terrace/patio

Chez Mango Villas

3.5 star property
7.4 out of 10, Good, (25)
"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. "
$208 nightly
The price is $219
Aug 27 - Aug 28
Total with taxes and fees
Chez Mango Villas
Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated
Outdoor pool

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

10.0 out of 10, Exceptional, (13)
"Everything about this place exceeded all expectations! Never felt more relaxed in my entire life. Can't wait to go back! "
Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated
RELAX-INN: 2bedroom apartment n JEEP RENTAL
Outdoor dining

RELAX-INN: 2bedroom apartment n JEEP RENTAL

8.8 out of 10, Excellent, (5)
"The property is very nicely kept, very clean and comfortable in the quite location."
$130 nightly
The price is $130
Aug 27 - Aug 28
Total with taxes and fees
RELAX-INN: 2bedroom apartment n JEEP RENTAL
Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.
Outdoor pool

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

9.6 out of 10, Exceptional, (10)
"The pool, the view, the stars st night, delightful"
Oceanfront Luxury. Spectacular Sunsets and Mountain View. HHI Featured. Avalon.
Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.
Fridge, microwave, oven, stovetop

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

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."
$333 nightly
The price is $333
Aug 29 - Aug 30
Total with taxes and fees
Cozy apartment in lovely Olveston with AC, WiFi. Close to Salem and Old town.
Caribbean Villa with private pool & ocean view in the heart of Montserrat
Outdoor pool

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

10.0 out of 10, Exceptional, (2)
"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...
Caribbean Villa with private pool & ocean view in the heart of Montserrat
Lucy's Sunny Villa apartments, spacious & modern, your ideal tropical retreat.
Property grounds

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

Lucy's Sunny Villa apartments, spacious & modern, your ideal tropical retreat.
Sonido Del Mar, Island Retreat, 9 minute walk to the beach
Property grounds

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
Luxury Villa w/Aircon and Pool Table
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Luxury Villa w/Aircon and Pool Table

Luxury Villa w/Aircon and Pool Table
Cozy Fully Equipped Apartment for Ultimate Comfort
Pool

Cozy Fully Equipped Apartment for Ultimate Comfort

$160 nightly
The price is $160
Sep 1 - Sep 2
Total with taxes and fees
Cozy Fully Equipped Apartment for Ultimate Comfort
Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea
Outdoor dining

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
Tranquil island escape with stunning ocean view.
Outdoor pool

Tranquil island escape with stunning ocean view.

8.8 out of 10, Excellent, (8)
"family stayed and we all had our own individual space, the villa was perfect, the view over looking the ocean was superb if there was any criticism it’s just in need of a little upgrade but that doesn’t stop me giving it a 5* rating"
Tranquil island escape with stunning ocean view.
Caribbean Villa with Spectacular Views
Outdoor pool

Caribbean Villa with Spectacular Views

10.0 out of 10, Exceptional, (1)
Caribbean Villa with Spectacular Views
Breezy, Clean, Comfortable and Peaceful, with a breathtaking view
Exterior

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

2.0 out of 10, (1)
Breezy, Clean, Comfortable and Peaceful, with a breathtaking view
Modern North Side Hideaway w/Aircon
Property grounds

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

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

8.0 out of 10, Very Good, (1)
"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...
Enjoy the lovely Carpe Diem villa in the unspoiled Caribbean isle of Montserrat
Chic Cottage!Tranquil getaways - 4mins drive from our volcanic black sand beach
Interior

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

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

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

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

10/10 Excellent
"We booked the villa for us and our adult kids it was so clean and spacious.The kids loved the pool, nieces and nephews used every excuse to come over so they can use it.The fruit trees were a bonus, mangoes, guavas and coconut.The host Dave was easily contactable and made sure we had everything we needed.Would definitely recommend cant wait to visit again."
Denise G. 16-night trip
Posted 2 weeks ago
Oceanfront luxury - 4 beds, AC, 3 bedrooms, king bed, WiFi, gated

Find out more about Cudjoe Head

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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 Montserrat National Trust 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.