Wiltshire Holiday Rentals: Short-Term Accommodations for Rent

Q: What are some of the best holiday rentals that Wiltshire has to offer?

Sunshine Lodge- Your Home Away From Home : This holiday home rental outside Wiltshire is located by the ocean, and has a private balcony, a private garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

Check prices for these dates

In two weeks

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Our top choices for Wiltshire holiday rentals

An outdoor dining area with a view of the sea, featuring a thatched-roof structure and wicker furniture.

1. Sky Beach Rooms

Montego Bay

Clayton

HK$846 total

includes taxes & fees

31 Aug - 1 Sept

A swimming pool with a hot tub, surrounded by palm trees and a white building.

2. Turquoise Sea Villa

Montego Bay

HK$1,492 total

includes taxes & fees

31 Aug - 1 Sept

A spacious kitchen with wooden cabinets, a refrigerator, and a dining area with a table and chairs.

3. Claudeville Condo

Montego Bay

Devine

HK$870 total

includes taxes & fees

31 Aug - 1 Sept

A yellow villa with a swimming pool, surrounded by lush greenery and a clear view of the sea.

4. Montego Bay Ironshore Luxury Studios

Ironshore

Dapea

HK$860 total

includes taxes & fees

4 Sept - 5 Sept

A cozy room with wooden walls and a high ceiling, featuring a seating area with cushioned benches and a small table.

5. Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

Mount Salem

"I stayed at Topaz Dream Guesthouse in Montego Bay during Sumfest 2025, and it was such a beautiful and unforgettable experience. The space is cozy, artistic, and full of character, but what truly makes it special is Cherri, the host.Cherri is warm, wise, and simply amazing. She carries the spirit of Jamaica in her heart and has the most incredible stories of life, love, triumph, and resilience. Connecting with her was the true highlight of my trip—our conversations left me feeling inspired and...

English C.

HK$627 total

includes taxes & fees

6 Sept - 7 Sept

A balcony with two black metal chairs, a window with a diamond-patterned metal screen, and a view of greenery and hills.

6. Charming & Comfortable 1-Bedroom Suite in Montego Bay

Montego Bay

HK$619 total

includes taxes & fees

2 Sept - 3 Sept

A thatched-roof hut with a concrete pathway leading to it, surrounded by greenery and a low wall.

7. Unity Villa

Montego Bay

Susan

HK$1,017 total

includes taxes & fees

31 Aug - 1 Sept

A beach with lounge chairs and a clear view of the ocean.

8. Seawind F104

Montego Bay

"Let me start with the property was very nice including the apartment we stayed in. Very modern and tastefully decorated. Location of this property was perfect as we were visiting family and it was close by. To pay for the cleaning fee prior to check in was a little challenging; when traveling with a cell phone you are unable to pay using the link they provide. We were able to pay cash onsite which helped. I would like to focus on the false advertising of guest laundry, there is no guest laundry...

Rachel

HK$1,972 total

includes taxes & fees

1 Sept - 2 Sept

A beach with clear turquoise water, a sandy shore, and a view of the ocean.

9. Montego Bay Club Apartments

Hip Strip

Neema

HK$1,662 total

includes taxes & fees

11 Sept - 12 Sept

A modern kitchen with white cabinetry, a large island, and a flat-screen TV mounted on the wall.

10. Charming 1-bedroom apartment in Montego Bay near beaches andrestaurants

Montego Bay

Varnetta S.

HK$1,334 total

includes taxes & fees

31 Aug - 1 Sept

A swimming pool with a waterfall feature, surrounded by a brick patio and a white fence.

11. Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

Hopewell

Roberta M.

HK$1,215 total

includes taxes & fees

1 Sept - 2 Sept

A beach with clear turquoise water, a sandy shore, and wooden lounge chairs.

12. Hospitality Expert SWF104 - Pool, Beach, Chef

Montego Bay

Xavier

HK$1,655 total

includes taxes & fees

31 Aug - 1 Sept

A two-story building with a large balcony, a swimming pool, and white outdoor furniture.

13. Lawrence Pool House

Ironshore

Vincent

HK$708 total

includes taxes & fees

31 Aug - 1 Sept

A beach resort with a clear blue sea, palm trees, and a small hut on a pier.

14. Hospitality Expert CB1

Montego Bay

"Unfortunately, I would not stay at this property again. The listing and pricing were misleading, and there seemed to be unexpected charges and restrictions that were not clearly communicated upfront. This is a two-bedroom, two-bathroom property advertised for up to four people, yet I was charged for three “extra” people, including my 7-year-old child. I was also surprised to learn that guests were apparently not allowed. The most uncomfortable part of the stay happened around 9:45 PM when the...

Beneita

HK$1,365 total

includes taxes & fees

8 Sept - 9 Sept

A bedroom with a bed, a desk, two chairs, a wardrobe, and a bathroom with a mirror and sink.

15. YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

Montego Bay

HK$1,530 total

includes taxes & fees

1 Sept - 2 Sept

A residential property with a gated entrance, a well-maintained lawn, and a house with a red-tiled roof.

16. La Rose Apartment Jamaica

Montego Bay

Earl

HK$1,171 total

includes taxes & fees

31 Aug - 1 Sept

A covered outdoor seating area with a table and chairs, columns, and a view of the surrounding landscape.

17. Come on Home to Paradise, Your Montego Bay Escape.

Paradise Acres

Lina S.

HK$1,419 total

includes taxes & fees

28 Sept - 29 Sept

18. 2 Bedroom 2 Bathroom Modern Ocean View Hip Strip Apartment with Wi-Fi

Hip Strip

Sheena C.

HK$2,234 total

includes taxes & fees

1 Sept - 2 Sept

A balcony with a table and chairs overlooking a marina with boats and a mountainous backdrop.

19. Bayview Apartment Montego Bay Montego Freeport

Montego Bay

Rebekah S.

HK$2,105 total

includes taxes & fees

1 Sept - 2 Sept

A residential area with multiple houses, a well-maintained lawn, and a clear view of the ocean.

20. Comfy Villa With Ocean View

Ironshore

HK$1,882 total

includes taxes & fees

31 Aug - 1 Sept

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Top Wiltshire Hotel Reviews

Hotel Riu Reggae - Adults Only - All Inclusive

10/10 Excellent

"This place was just what me N the wife needed. He loved the sun/room/water. EVERYTHING ‼️‼️ going back every 2 years"

Toby's Resort

10/10 Excellent

"⭐⭐⭐⭐⭐ **Come With the Right Expectations and You’ll Really Enjoy Toby’s** We genuinely enjoyed Toby’s Resort and would absolutely recommend it. The key is knowing what to expect: this is a comfortable, casual, laid-back Jamaican resort—not a polished luxury property. We loved that you really don’t need to leave the resort. The food was delicious and reasonably priced, the drinks were well mixed, and the bartender was amazing. Drivers are available on-site, and there’s even a floral shop. The pool area is a whole vibe! The pool is open all night, so you can relax, have drinks, socialize, or create your own little party atmosphere instead of heading to the nearby bars and clubs. Our bed was unusually comfortable—we got some of the best sleep we’ve ever had while traveling! Toby’s is also minutes from the airport, yet we heard virtually no airplane noise, and the Hip Strip and Doctor’s Cave are nearby. For realistic expectations: we had ants in our room, the property’s presentation was a little more modest than I expected from the pictures online, and service moves at a noticeably relaxed pace. It was never frustratingly slow, but should be noted if speed is a deal breaker for you. What Toby’s may lack in polish, it makes up for in character, convenience, value, great food and drinks, and a relaxed Jamaican feel. If that’s what you’re looking for, I absolutely recommend it. **We would happily stay again!**"

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

10/10 Excellent

"We absolutely loved our stay here for our anniversary! ❤️ It was our first time at S Hotel Montego Bay, and we definitely had an amazing time! The location is super convenient and so close to the airport. We also took advantage of their taxi service, which made getting around so easy and convenient. All of the restaurants and bars are definitely worth checking out! We really enjoyed the amazing food, beautiful views, and overall experience. 🌴✨ If you’re considering staying here, I definitely recommend taking advantage of the all-inclusive option—you won’t regret it! 😊 Thank you, S Hotel Montego Bay, for making our anniversary so special! ❤️"

Round Hill Hotel And Villas

10/10 Excellent

"I travelled solo to Roundhill. The hotel was perfect in every way. I have travelled extensively and I would rate the hotel as one of the best that I have ever stayed in. The Managing Director/General Manager is outstanding. The hotel employs over 300 staff who have been impeccably trained. It is very high end and I cannot find fault with anything that it does."

Find out more about Wiltshire

Search for holiday rentals in Wiltshire on Expedia! You can easily find your home rentals, villas, holiday apartments in Wiltshire using one of the methods below:

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Frequently asked questions

Can I find holiday rentals in Wiltshire?

Yes, there are holiday rentals close to the most popular sights in Wiltshire, or you can select a more secluded option if you're looking for a relaxing stay. Wiltshire is known for its beaches and sporting events. Make sure you have time to check out the shopping and restaurants during your trip.

What are some of the best holiday rentals that Wiltshire has to offer?

Sunshine Lodge- Your Home Away From Home: This holiday home rental outside Wiltshire is located by the ocean, and has a private balcony, a private garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Wiltshire?

While exploring the area, visit family-friendly sights like Montego Bay Marine Park, or get outside and enjoy nature at Doctor's Cave Beach. In the wider area, you’ll find Montego Bay Cruise Ship Terminal and Saint James Parish Church.

What’s a holiday rental in Wiltshire like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wiltshire. Holiday rentals feature extras like laundry facilities and kitchens 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 shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.

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Check prices for these dates

Our top choices for Wiltshire holiday rentals

1. Sky Beach Rooms

2. Turquoise Sea Villa

3. Claudeville Condo

4. Montego Bay Ironshore Luxury Studios

5. Hummingbird Room in Guest Home: WiFi, Hot Water AC Montego Bay Live-in Hosts

6. Charming & Comfortable 1-Bedroom Suite in Montego Bay

7. Unity Villa

8. Seawind F104

9. Montego Bay Club Apartments

10. Charming 1-bedroom apartment in Montego Bay near beaches andrestaurants

11. Charming Seaview Studio with Private Pool & Complimentary Airport Transfer!

12. Hospitality Expert SWF104 - Pool, Beach, Chef

13. Lawrence Pool House

14. Hospitality Expert CB1

15. YanceyLargo Estate - Newly Built Modern 1 Bedroom Suite 1 Villa by RedAwning

16. La Rose Apartment Jamaica

17. Come on Home to Paradise, Your Montego Bay Escape.

18. 2 Bedroom 2 Bathroom Modern Ocean View Hip Strip Apartment with Wi-Fi

19. Bayview Apartment Montego Bay Montego Freeport

20. Comfy Villa With Ocean View

Find holiday rentals that suit your style

Top Wiltshire Hotel Reviews

Hotel Riu Reggae - Adults Only - All Inclusive

Deja Resort All Inclusive

Toby's Resort

Iberostar Waves Rose Hall Beach - All Inclusive

S Hotel Montego Bay - Luxury Boutique All Inclusive Hotel

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

Round Hill Hotel And Villas

SeaGarden Beach Resort - All Inclusive

Find out more about Wiltshire

Frequently asked questions

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