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Chacachacare Holiday Rentals

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Our top choices for Chacachacare holiday rentals

1. Port of Spain City Escape | Comfortable 1BR on Ariapita Avenue

Port of Spain City Escape | Comfortable 1BR on Ariapita Avenue
Woodbrook
10.0 out of 10, Exceptional, (1 review)
"If using hot water you just turn on a switch, otherwise host in fantastic in communicating with tenants."
United States
QUEENALICIA
The price is AU$166
includes taxes & fees
14 Oct - 15 Oct
Port of Spain City Escape | Comfortable 1BR on Ariapita Avenue

2. Enjoy your stay at our cozy, private and charming Diego Martin apartment.

Enjoy your stay at our cozy, private and charming Diego Martin apartment.
Diego Martin
10.0 out of 10, Exceptional, (6 reviews)
"This was an amazing stay. Our host looked out for our every need, the compound was clean and safe for parking and the apartment was immaculate. The Christmas decor definitely put my partner and I in the holiday spirit, popular food chains and shopping centers are available in near proximity. We felt right at home and we’re desperate to book another stay soon!"
United States
Ryan
The price is AU$170
includes taxes & fees
1 Oct - 2 Oct
Enjoy your stay at our cozy, private and charming Diego Martin apartment.

3. Glencoe Townhome With Loft Jacuzzi and Pool

Glencoe Townhome With Loft Jacuzzi and Pool
3.5 star property
Glencoe
3.0 out of 10, (2 reviews)
"Paid for a service and got no booking or check in information. Zero contact from host and Expedia refuse to refund my money . Do not recommend ! BIG SCAM and I’ll and be reporting fraud."
Canada
Nikio
The price is AU$582
includes taxes & fees
21 Sept - 22 Sept
Glencoe Townhome With Loft Jacuzzi and Pool

4. Cosy 1 B/droom, near Ariapita Avenue, Walk to Dining, Nightlife & Fast WiFi

Cosy 1 B/droom, near Ariapita Avenue, Walk to Dining, Nightlife & Fast WiFi
Downtown Port of Spain
The price is AU$155
includes taxes & fees
1 Oct - 2 Oct
Cosy 1 B/droom, near Ariapita Avenue, Walk to Dining, Nightlife & Fast WiFi

5. Charming 1-bedroom in 5 bedroom 2 baths house with AC in Woodbrook

Charming 1-bedroom in 5 bedroom 2 baths house with AC in Woodbrook
Woodbrook
The price is AU$214
includes taxes & fees
23 Sept - 24 Sept
Charming 1-bedroom in 5 bedroom 2 baths house with AC in Woodbrook

6. Welcome to The Studio Nest — your peaceful perch in paradise.

Welcome to The Studio Nest — your peaceful perch in paradise.
Diego Martin
The price is AU$355
includes taxes & fees
21 Sept - 22 Sept
Welcome to The Studio Nest — your peaceful perch in paradise.

7. Stylish 1-bed Opposite Queens Park Savannah

Stylish 1-bed Opposite Queens Park Savannah
2.0 star property
Downtown Port of Spain
10.0 out of 10, Exceptional, (1 review)
"This property is AMAZING! It is spotless, conveniently located and the owner has used her own travel experiences to anticipate what a traveler may need while staying at her property. The home is beautifully decorated, extremely well maintained. The neighbors are all friendly and helpful & the owner is extremely responsive to any questions you may have. We HIGHLY recommend this property. We are definitely planning to be repeat customers. Top level accommodations and host accountability at a...
United States
Gary
The price is AU$231
includes taxes & fees
21 Sept - 22 Sept
Stylish 1-bed Opposite Queens Park Savannah

8. BUENA VISTA | Views•Pool•Location•Wellness•Nature

BUENA VISTA | Views•Pool•Location•Wellness•Nature
St. Anns
The price is AU$135
includes taxes & fees
19 Sept - 20 Sept
BUENA VISTA | Views•Pool•Location•Wellness•Nature

9. Arlene's & Chris's Guesthouse

Arlene's & Chris's Guesthouse
4.0 star property
Saint James
The price is AU$603
includes taxes & fees
29 Sept - 30 Sept
Arlene's & Chris's Guesthouse

10. Flower Of Joy Wellness Villa

Flower Of Joy Wellness Villa
4.5 star property
St. Anns
2.0 out of 10, (1 review)
"Family of Nine Left Stranded Outside in the Dark An extremely distressing experience. I booked Flowers of Joy Wellness Villa through Hotels.com for nine family members, including my elderly mother and four children aged 7–14. The host called on check-in day and I confirmed arrival between 5–6 pm. Check-in was advertised until 9 pm. At 6:06 pm, I WhatsApped to say we were almost there; the message was delivered. We arrived at 6:20 pm, but repeated calls went unanswered. At 6:24 pm, I messaged...
United States
Bevil
The price is AU$205
includes taxes & fees
21 Sept - 22 Sept
Flower Of Joy Wellness Villa

11. WINDCREST VILLA - Great view near Port of Spain

WINDCREST VILLA - Great view near Port of Spain
St. Anns
The price is AU$166
includes taxes & fees
28 Sept - 29 Sept
WINDCREST VILLA - Great view near Port of Spain

12. This is a Family Friendly property ideal for groups of up to six people.

This is a Family Friendly property ideal for groups of up to six people.
Diego Martin
8.0 out of 10, Very good, (2 reviews)
"Me and my friends had an amazing time being hosted at this property. The owner, Mr Dass was very easy to communicate with, polite and even gifted a birthday cake to one of the guests (since it was her birthday that week). We organized pickup and drop off with the owner and everything was seamless. The home looks even better in person and we felt at home. I would stay here again in the future and I’d also recommend this property to others. "
United States
Woodley A.
The price is AU$389
includes taxes & fees
1 Oct - 2 Oct
This is a Family Friendly property ideal for groups of up to six people.

13. Gulfview Townhouse With Pool and Jacuzzi

Gulfview Townhouse With Pool and Jacuzzi
3.5 star property
Glencoe
4.0 out of 10, (1 review)
The price is AU$658
includes taxes & fees
21 Sept - 22 Sept
Gulfview Townhouse With Pool and Jacuzzi

14. Robert's Guesthouse in Port of Spain. In the Heart of Carnival 2026

Robert's Guesthouse in Port of Spain. In the Heart of Carnival 2026
St Clair
5.0 out of 10, (4 reviews)
"Robert and Joan were very nice and welcoming the place was well kept and I enjoyed my time here! Thanks!"
United States
Rianna B.
The price is AU$89
includes taxes & fees
1 Oct - 2 Oct
Robert's Guesthouse in Port of Spain. In the Heart of Carnival 2026

15. Cozy 2BR studio w/ kitchenette & bath – ideal for couples or small groups

Cozy 2BR studio w/ kitchenette & bath – ideal for couples or small groups
Newtown
The price is AU$120
includes taxes & fees
28 Sept - 29 Sept
Cozy 2BR studio w/ kitchenette & bath – ideal for couples or small groups

16. 2 bedroom Tranquil Retreat

2 bedroom Tranquil Retreat
Port of Spain
The price is AU$183
includes taxes & fees
23 Sept - 24 Sept
2 bedroom Tranquil Retreat

17. Charming Studio in Port of Spain With Pool Access

Charming Studio in Port of Spain With Pool Access
2.0 star property
Belmont
The price is AU$204
includes taxes & fees
22 Sept - 23 Sept
Charming Studio in Port of Spain With Pool Access

18. Cozy 1-bedroom apartment in amazing Port of Spain with AC

Cozy 1-bedroom apartment in amazing Port of Spain with AC
Woodbrook
The price is AU$136
includes taxes & fees
29 Sept - 30 Sept
Cozy 1-bedroom apartment in amazing Port of Spain with AC

19. -20% Queen's Park Court 1 BR Condo in Port-of-Spain

-20% Queen's Park Court 1 BR Condo in Port-of-Spain
Belmont
The price is AU$196
includes taxes & fees
5 Oct - 6 Oct
-20% Queen's Park Court 1 BR Condo in Port-of-Spain

20. Cozy 2-bedroom condo near Savannah Port of Spain with Central AC , free parking

Cozy 2-bedroom condo near Savannah Port of Spain with Central AC , free parking
Newtown
The price is AU$253
includes taxes & fees
20 Sept - 21 Sept
Cozy 2-bedroom condo near Savannah Port of Spain with Central AC , free parking
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 Chacachacare Hotel Reviews

Find out more about Chacachacare

Everything you need to know about Chacachacare 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 Chacachacare holiday rental for you. At Expedia, you can take your pick from private holiday 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 Chacachacare holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chacachacare holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chacachacare. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chacachacare 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 Chacachacare holiday rentals we have selected for you start as low as AU$166 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chacachacare rentals

At Expedia, we put the best Chacachacare 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 Chacachacare 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 Chacachacare 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 Chacachacare. 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 Chacachacare?

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

Gulfview Townhouse With Pool and Jacuzzi: This holiday home rental outside of Chacachacare offers an outdoor pool, a garden and laundry facilities to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

What can I see and do in Chacachacare?

Explore the area and family-friendly sights such as Five Islands Water & Amusement Park, or get out into nature at a spot like Queen's Park Savanah. Hasely Crawford Stadium and Movietowne are a couple of places you'll find in the wider area.

What are holiday rentals like in Chacachacare?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chacachacare. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for small groups.