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Trelawny Parish Rentals with Pools

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98 Houses in Trelawny Parish with pools

Sol Mar Villa

Silver Sands villa

3 bedrooms / 3 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$322

Seadrift Villa w/ private pool, great entertainment space, easy walk to beach.

Duncans villa

3 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 35 minutes

Match: Swimming pool

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Price per night from

$345

Dukes Hideaway - Silver Sands 6 Bedroom

Silver Sands house

6 bedrooms / 6 bathrooms / sleeps 12

Match: Swimming pool

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Price per night from

$1,004

DUKES Hideaway at Silver Sands Resort

Silver Sands villa

6 bedrooms / 6 bathrooms / sleeps 14

“Totally elaxing and worth it!” This was the fourth year that my family has stayed at Duke's Hideaway. We have 2 girls now ages 7 and 10 and we also bring my father who is 78. The location is very convenient to the grill, bar and store. It is also convenient to the beach. We love Judith and Paulina who help at the house and they remember us and the girls each year we have come. They cook delicious food for all of us and it is so nice not to have to eat out every day. One of the best conveniences staying at Duke's is that your laundry is done daily and when you get home, we don't have a bunch of laundry to do. We just come home and unpack our clean clothes! We feel like they are a part of our family when we are staying there. We also love staying there because it is very relaxing and it feels like a true vacation. Each year we have stayed at Duke's there has been some kind of improvement added to the house. There is a hot tub, air conditioning, televisions in each room and Wi-Fi. We have always felt very safe and welcomed at Silver Sands and at Dukes Hideaway.

Responds fast! avg. 1 hour 49 minutes

Match: Swimming pool

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Price per night from

$1,068

Complete Relaxation at OH BOY VILLA at Silver Sands Beach at and affordable rate

Silver Sands villa

4 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$454

Flamingo Beach Villa

Falmouth villa

7 bedrooms / 7 bathrooms / sleeps 14

Match: Swimming pool

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Price per night from

$747

Wind Jammer - Silver Sands 4 Bedrooms

Silver Sands house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$603

Pineapple Cottage The Hidden Gem

Silver Sands cottage

2 bedrooms / 2 bathrooms / sleeps 5

“An incredibly relaxing vacation” This was our 6th visit to Pineapple at Silver Sands. We go instant relaxation mode as soon as we get off the plane. The staff are all incredibly friendly and helpful. The food is great, the place is lovely and clean, and the weather is fabulous.

Responds fast! avg. 1 hour 49 minutes

Match: Swimming pool

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Price per night from

$362

Pineapple Villa

Duncans villa

7 bedrooms / 8 bathrooms / sleeps 14

“Our annual Guilty Pleasure” If you have read my previous reviews, you know that we think that a vacation at Pineapple Villa is perfection. This year we were there for 2 whole weeks and I was worried that it might be a bit too long, well I was sooo wrong, I didn't want to go home. It's very easy to get used to a carefree life with no decisions to make except whether you want to swim in your own pool or go to the beautiful beach where there are very few people. I can sit on the patio and gaze at the ever changing colours of the sea for hours without ever getting tired of it. The Villa itself is cleaned thoroughly inside and out daily, each meal is tastier than the last and the wonderful staff are now like old friends. Every year we return to a new surprise. This year was the addition of flat screen Tv's with satellite in each bedroom. There were already Tv's in each of the 3 living rooms but I must say that it was nice to be able to keep up with our favorite shows . Since our group is getting smaller we are going to have a new experience next year staying in a brand new villa being built by the same owner. It is 31 metres from the beach and will have it's own infinity pool, great views and most importantly familiar staff! Can't wait!

Responds fast! avg. 1 hour 49 minutes

Match: Swimming pool

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Price per night from

$1,067

Mai Tai - Silver Sands 4 Bedrooms beachfront

Silver Sands house

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$717

Beautiful Yellowbird Villa

Silver Sands villa

4 bedrooms / 4 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$483

Quadrille Villa, Silver Sands, Jamaica

Silver Sands villa

4 bedrooms / 4 bathrooms / sleeps 8

“I love the Quadrille!” The Quadrille Villa is an amazing place to vacation. Since discovering this beautiful property, my family and friends have stayed there 3 years in a row and counting! The house is beautiful, the property is amazing, the resort is peacful and alot of fun. The staff are warm, welcomg and accomodating. The meals are excellent. You don't have to leave the property to feel like you are truly on vacation. Oh, and did I mention the view? Stunning!

Match: Swimming pool

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Price per night from

$1,001

Sweet Sunshine Villa

Duncans villa

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$87

Pineapple Cottage - Silver Sands 2 Bedrooms

Silver Sands house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$287

Moonshine Villa, Silver Sands

Silver Sands villa

4 bedrooms / 5 bathrooms / sleeps 8

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Price per night from

$827

Sandpebbles.... 50 Paces to Tranquility

Rio Bueno villa

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 4 minutes

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Price per night from

$904

Azure Cove - Silver Sands 5 Bedroom

Silver Sands house

5 bedrooms / 5 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$5,213

Lord Royale in Duncans Bay is the perfect villa for your long awaited vacation.

Duncans villa

6 bedrooms / 6 bathrooms / sleeps 10

Responds fast! avg. 2 hours 59 minutes

Match: Swimming pool

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Price per night from

$100

Breathless Manor

Falmouth house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 2 hours 0 minutes

Match: Swimming pool

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Price per night from

$115

Mai Tai Villa

Silver Sands villa

4 bedrooms / 5 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$822

Honeycomb Villa, Silver Sands

Silver Sands villa

4 bedrooms / 4 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$615

Pineapple Villa - Silver Sands 7 Bedrooms

Silver Sands house

7 bedrooms / 7 bathrooms / sleeps 14

Match: Swimming pool

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Price per night from

$1,004

Luxury rental with pool

Duncans private room

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$146

Quadrille - Silver Sands 4 Bedroom Beachfront

Silver Sands house

4 bedrooms / 4 bathrooms / sleeps 1

Match: Swimming pool

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Price per night from

$1,004

Oceanview Villa 1 Jamaica

Falmouth villa

1 bedroom / 1 bathroom / sleeps 2

Match: Swimming pool

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Price per night from

$81

Beachfront 3 bed Villa, fully staffed, airport transfers included in Winter

Duncans villa

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

Match: Swimming pool

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Price per night from

$426

Oceanview Villa Jamaica

Falmouth villa

4 bedrooms / 3 bathrooms / sleeps 8

Match: Swimming pool

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Price per night from

$288

Seaview Villa at Stonebrook Manor

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$136

Oceanview Villa 2 Jamaica

Falmouth villa

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$161

Beachfront 4 bed Villa, fully staffed, airport transfers included in Winter

Duncans villa

4 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 56 minutes

Match: Swimming pool

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Price per night from

$541

Silver Sands Villa ~ Hastings Place ~ Sun, Sea, Fun & All the comforts of Home!

Silver Sands villa

3 bedrooms / 3 bathrooms / sleeps 10

Match: Swimming pool

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Price per night from

$573

L&V Paradise Vacation Home with Pool and Gym 2

Falmouth house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Swimming pool

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Price per night from

$104

SEHFEH Luxury Vacation Home

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$155

L&V's Paradise Vacation Home with pool & gym 3

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$138

Great rentals within 20 miles that match your search

Geddes Great House Health and Wellness Farm

St. Ann's Bay house

7 bedrooms / 7 bathrooms / sleeps 20

Match: Swimming pool

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Price per night from

$2,857

Beautiful Luxury 1 BDRM Condo

St James, Montego Bay condo

1 bedroom / 1 bathroom / sleeps 3

Match: Swimming pool

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Price per night from

$161

3BD Villa Including Housekeeper/ Airport Transfers

St. Ann's Bay villa

3 bedrooms / 2 bathrooms / sleeps 6

Match: Swimming pool

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Price per night from

$207

Serendipity Jamaica - You won't want to leave!

Rose Hall villa

6 bedrooms / 8 bathrooms / sleeps 12

“A vacation like no other” We were greeted at the airport by Norman, the most professional driver ever, he made our transition smooth and for a group of 12 adults, that is tough! He had thought of everything - including bringing a second van for our luggage! The staff at the villa greeted us at the door with warm smiles and cool towels, they made sure all our luggage was safely delivered to our rooms and then the fun began! We all stopped and stared at the huge view of the Caribbean Sea spread out in front of us, the breeze, the way the rooms are laid out and the villa itself takes total advantage of that view. We quickly changed, and began the most perfect seven days of nothing but relaxing, laughing and eating punctuated by an occasional sightseeing trip. Derek, the butler completely made the trip, he was attentive, but quiet, helpful but never intrusive - he made us feel so special. Ruby, the cook gave us gormet meals three times a day. We discussed our likes and dislikes the first day and she made it all happen. We did not need to go out to dinner and the one night we went to a lovely restaurant in town, we all agreed that we could have stayed home and eaten at Restaurant Ruby for an even better meal. It is tough to please 12 distinct people, but the staff and managment at Serendipity did just that, from organizing the most incredible massage at the villa, to driving us to out of the way Mayfield Falls, they never stopped working. All the rooms were large and private, we never felt on top of one another, we ate meals in different places, by the pool, in the dining room, on the deck, where ever we felt inspired to eat that day, Derek made it happen. I do not have one bad thing to say - I loved every minute, and would recommend Serendipity to a group like us, a large family, or just a few people that want to get away - It was truly a vacation to remember.

Match: Swimming pool

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Price per night from

$1,035

Viewing 38 of 98
rentals in Trelawny Parish

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