Cudjoe Head Vacation Rentals from CA $242: Short-Term Rentals for 2026

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 air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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In two weeks

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Our top choices for Cudjoe Head vacation rentals

A pool area with a view of the ocean, a lounge with red chairs, and a white building with a staircase.

1. Chez Mango Villas

Old Towne

Steven

CA $261 total

includes taxes & fees

Oct 3 - Oct 4

A covered outdoor patio with a table and chairs, surrounded by a white wall with square cutouts, and lush greenery in the background.

2. RELAX-INN: 2bedroom apartment n JEEP RENTAL

St.John's

Marek

CA $242 total

includes taxes & fees

Oct 4 - Oct 5

A swimming pool with a view of the ocean, surrounded by a white building with columns.

3. Royal 1 - Chez Mango Villa

Salem

CA $330 total

includes taxes & fees

Oct 3 - Oct 4

A swimming pool with clear blue water, surrounded by white lounge chairs and a red umbrella.

4. Stunning 3-bedroom Villa Suite with Ocean views, AC, & Pool, near the Beach

Salem

CA $565 total

includes taxes & fees

Oct 3 - Oct 4

A swimming pool with a view of the ocean, surrounded by a white building with a balcony.

5. Royal 2 - Chez Mango Villa

Salem

CA $330 total

includes taxes & fees

Oct 5 - Oct 6

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Top Cudjoe Head Hotel Reviews

Chez Mango Villas

10/10 Excellent

"The place was great. Clean,big rooms,nice pool and the hosts were awesome!!! I'll be back"

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

10/10 Excellent

"I really enjoyed having air conditioning and the instant hot shower was wonderful. Host was in the UK so communication was affected by the time difference. The local lady was very helpful when I needed something, though."

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

10/10 Excellent

"It was a wonderful stay. We went about and had a fun time all over the island, seeing places, connecting and reconnecting with people. But coming back to the property every time was beyond beautiful and totally relaxing. The pool and the amazing view washed up my tired day and prepared me for relaxing nights. Thank you Marie for your assistance when was needed. You were great!"

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

8/10 Good

"Great location, close to beach, quiet and private. Nice covered veranda. Great view. Property manager, Yvette, was very helpful and available. Nice cleaning person with service included in rent."

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

10/10 Excellent

"Adams Place was the best appointed VRBO of which I've had the pleasure of staying. The home is expansive with tropical gardens and has all the amenities of your own private home. Nothing is lacking. The owners and managers of the property are extremely attentive and accommodating. Our interactions were always positive and our stay was elevated because of them.Surrounding this wonderful home is the beautiful and unique island of Montserrat. Their marriage is perfect and they must be considered as one. Me and my party did not have any specific preconceptions of Montserrat; we were paralyzed by the beauty of the surroundings, the warmth of the people, and the island's singular history, both recent and more distant.If you need a reset. If you want to be remote ... just enough. This is the address.*Oh, and watching the sunrise over the ridgeline as clouds and mist pour across their apex, well that's just nuts."

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

10/10 Excellent

"Entering the home, you are instantly greeted with a view through the glass doors to the pool and the Caribbean Sea beyond. The family room is bright and spacious, leading either to the master bedroom and bath to the left, the two remaining bedrooms and bath to the right, or the indoor dining and kitchen area. Continuing through the well-appointed kitchen is a second access to the covered patio and large pool area.The entire home is clean and well-maintained. We did not utilize additional housekeeping services during our time here, but the option is there for you if you choose. While air conditioning is not always needed on the island due to constant trade winds, it was a welcome relief, especially during sleep, and the units worked flawlessly.The propane grill situated on the patio got heavy use during our stay and is a great way to keep added heat out of the kitchen during meals.As perfect as the home is, the patio and pool area are where it is all at! From the pool, you get 180 degrees of private Caribbean sea views looking North towards Woodland Beach and South to Old Town. An occasional passing sailboat or yacht only adds to the vibe. The large pool offered much-needed relief from the hours spent staring into the sea.We had zero issues during our 14-day stay and would not hesitate to stay at Villa Kurtena in the future and to recommend it to our family and friends. Thank you, David, for sharing your home with us."

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cudjoe Head vacation rentals we have selected for you start as low as CA $242 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 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.

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 air-conditioning and laundry facilities 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, Montserrat Volcano Observatory and Lime Kiln Beach are a couple of picturesque spots to get outside and enjoy nature. Little Bay and Woodlands 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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Check prices for these dates

Our top choices for Cudjoe Head vacation rentals

1. Chez Mango Villas

2. RELAX-INN: 2bedroom apartment n JEEP RENTAL

3. Royal 1 - Chez Mango Villa

4. Stunning 3-bedroom Villa Suite with Ocean views, AC, & Pool, near the Beach

5. Royal 2 - Chez Mango Villa

Find vacation rentals that suit your style

Top Cudjoe Head Hotel Reviews

Chez Mango Villas

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

Lucy's Sunshine Villa Palm Loop, Spacious 3 Bed 2 Bathroom,

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

Secluded 2 Bedroom Villa With Breathtaking Views Over the Caribbean Sea

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

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

Luxury Spacious Villa with Aircon and Pool Table

Find out more about Cudjoe Head

Frequently asked questions

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