30 Best Vacation Rentals in Sandy Bay - Holiday Lettings - Cabins

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34 Vacation rentals

22

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Knockando Villa at Round Hill is a delightful and luxury villa Jamaica located within the prestigious Round Hill Resort. This property gives a true feeling of relaxing in luxury while in Jamaica, with contemporary comforts and amenities. This is a very family friendly J …see more

from $1280 / night

$8950 - $25350 / week

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from $1280 / night

(1) Excellent 

28

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
6 bedrooms, 6 batrooms, spectacular views - and only 3 minutes golf cart ride to the beach!!! Tryall Resort Membership. The fabulous Wheel House offers picturesque views of the surrounding landscape and ultimate privacy at this six bedroom villa in Jamaica. The spacious …see more

from $1038 / night

$7272 - $16363 / week

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from $1038 / night

20

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
3 deluxe bedrooms, 3 bathroom deluxe villa. Tryall Resort Membership Wonderful fairway and Seaviews! Eureka in Montego Bay is one of the very special deluxe villa rentals in Jamaica, situated in an attractive and private location at the end of a cul-de-sac. The villa pr …see more

from $714 / night

$5000 - $16000 / week

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from $714 / night

28

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Deluxe 4 bedroom, 4 bathroom villa.Tryall Resort Membership. 3 minutes golf cart ride to the beach! Yellowbird Villa in one of the finest and most luxurious villas in Jamaica located within one of the most exclusive gated resorts, the Tryall Club. The privately owned vi …see more

from $785 / night

$5500 - $15950 / week

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from $785 / night

30

Home rental in Sandy Bay

Hanover Parish / Sandy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Deluxe 3 bedroom villa, 3 minutes golf cart ride to the beach! Tryall Resort Membership. Please read for the exclusive resort features for this villa. Linger Longer Villa is one of the most fabulous villas in Jamaica, located within the renowned Tryall Club Resort estat …see more

from $649 / night

$4545 - $15000 / week

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from $649 / night

(1) Excellent 

41

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Wonderful 4 bedroom villa, with lots of gardens and grassy areas - 2 bedrooms in main house + 2 bedroom villa with views to the pool. Great for families sharing! Tryall Resort Membership. Avalon Villa, previously known as Riverlot Gardens, is a newly-renovated Jamaica v …see more

from $785 / night

$5500 - $15950 / week

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from $785 / night

30

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
6 bedrooms, 6 bathrooms - Premier rated villa (the highest rateing within the Tryall Club!Tryall Resort Membership. Exclusive resort features for this villa. Villa Stella is one of the most stunning villas in Jamaica, located on the gorgeous white sand beach and the spa …see more

from $1558 / night

$10909 - $30000 / week

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from $1558 / night

28

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
3 bedroom villa , views to the Caribbean sea. Tryall Resort Membership. Please read for the exclusive resort features for this villa. Island House is a delightfully refurbished villa with lovely crafts and artifacts, each reflecting Jamaican culture. The warm, tropical …see more

from $571 / night

$4000 - $10725 / week

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from $571 / night

25

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Casurina Villa is a divine luxury villa Jamaica that nestles among some of the finest homes in Montego Bay, Jamaica. Situated in the famous Tryall Club estate, the delightful four bedroom villa has been recently refurbished. All guests at Casurina have complimentary mem …see more

from $1298 / night

$9090 - $18181 / week

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from $1298 / night

22

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedroom, 4 bathroom,. spectacular views to the sea and golf course! Tryall Resort Membership. 4 minutes golf cart ride to the white sandy beach! Eve Song in Montego Bay is one of the very enchanting luxury villas in Jamaica that everyone falls in love with the moment …see more

from $642 / night

$4500 - $12155 / week

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from $642 / night

23

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
5 Bedroom Deluxe villa - Infinity pool! Spectacular views! Unique to this villa is the Tryall Resort Membership. No Le Hace Villa in Montego Bay is one of the most fabulous Jamaica villas located within the renowned Tryall Club & Resort. Being situated near the golf cou …see more

from $1000 / night

$7000 - $19250 / week

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from $1000 / night

30

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
5 bedroom, 5 bathroom, deluxe villa 3 minutes golf cart ride to the beach!!! Tryall Resort Membership. Please read for the exclusive resort features for this villa. Windrush Villa is majestically located on a charming hillside within the world renowned Tryall estate. Re …see more

from $2597 / night

$18181 - $27272 / week

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from $2597 / night

31

Vacation home with shared pool in Sandy Bay

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedroom,4 bathroom, elegant and luxurious in everyway. Tryall Resort Membership. Staff of 10 - you will certainly be papmered on this vacation! Little Hill is truly a one of a kind villa located in the Tryall Club Resort. It is located on a little hill, surrounded by …see more

from $1298 / night

$9090 - $20000 / week

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from $1298 / night

31

Sandy Bay Vacation apartment rental

Hanover Parish / Sandy Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Beautiful studio in Jamaica for rent by days or by month for a holiday experience that will allow you to properly discover the real Jamaica. Conveniently located between Montego Bay and Negril. At 2 minutes from the beach. A perfect place for snorkeling / diving. Locate …see more

from $65 / night

$455 / week

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from $65 / night

20

Home rental in Sandy Bay with shared pool

Hanover Parish / Sandy Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
One of Jamaica's most Super Deluxe Villas! Brand new and GLAMOROUS! Tryall Resort Membership. Please read for the exclusive resort features for this villa. Twin Palms in Tryall is possibly the most remarkable achievement in design and architecture in the Caribbean in se …see more

from $3506 / night

$24545 - $36363 / week

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from $3506 / night

(1) Excellent 

23

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
4 bedroom villa - 3 minutes golf cart ride to the beach club! Tryall Resort Membership. Fully staffed, private swimming pool, exclusive gated community! Blue bird at Tryall at Montego Bay is one of the most magnificent villas in Jamaica that overlooks a glorious tropica …see more

from $642 / night

$4500 - $12155 / week

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from $642 / night

(2) Excellent 

21

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Jubilation Villa is the latest reason to enjoy your Jamaican vacation at The Tryall Club. This newly created tropical paradise is elegantly furnished throughout with carefully selected antique treasures, locally built mahogany four poster beds and uniquely crafted local …see more

from $2077 / night

$14545 - $35000 / week

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from $2077 / night

(1) Very Good 

29

Vacation home accommodation

Hanover Parish / Sandy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Walk to the beach in a few minutes!!!Tryall Resort Membership. This villa can be rented as a 4 , 5 or 8 bedroom villa! Retreat Villa in Montego Bay is one of the most charming and gracious Jamaica villas located within the renowned Tryall Club Resort. Being situated nea …see more

from $785 / night

$5500 - $14300 / week

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from $785 / night

17

Vacation home with shared pool in Sandy Bay

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
4 luxury bedroom villa at the famous Tryall Club, expansive Caribbean Seaviews, wonderful and loyal staff! Cielo villa in Jamaica is perched high on Barnes Hill, providing a stunning and breathtaking view of the sloping manicured green lawns, the infinity pool and the v …see more

from $1000 / night

$5500 - $18182 / week

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from $1000 / night

(1) Excellent 

7

Vacation villa in Sandy Bay

Hanover Parish / Sandy Bay

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
  • Car not necessary
Welcome to the Wheel House Villa! The large airy living room features an indoor garden and French doors that open onto the pool deck and swimming pool with views of the golf course and ocean beyond. All the guest bedrooms are newly renovated with beautiful granite and …see more

from $2143 / night

$15000 / week

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from $2143 / night

35

Vacation apartment in Sandy Bay

Hanover Parish / Sandy Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Beautiful place in a very very nice area. The place is well decorated, comfortable and peaceful. It is full equipped apartment and you could not be at a better place to enjoy the real Jamaican culture. Quiet, clean and safe place, the area is amazing. Across the street …see more

from $75 / night

$525 / week

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from $75 / night

39

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Rose Cottage is a fabulous new villa in Tryall, perched dramatically on a plateau, offering extraordinary views of the surrounding mountains and ocean waters. The traditional Jamaican styled luxury villa Jamaica was designed by Nancy D. Maffasanti. The décor is elegant …see more

from $2337 / night

$16363 - $31819 / week

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from $2337 / night

19

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Charming 4 bedroom villa, 5 minutes golf cart ride to the white sandy beach!Tryall Resort Membership. Enjoy this exclusive gated resort - private membership. Ma' Moura Villa in Montego Bay is a fabulous Jamaica villa located within the renowned Tryall Club Resort estate …see more

from $772 / night

$7000 - $18190 / week

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from $772 / night

16

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury 6 bedroom villa, fully staffed villa. Tryall Resort Membership. Fully staffed, 3 minutes golf cart ride to the beach. Exclusive resort features for this villa. The elegantly designed Bumper's Nest nestles on three acres of glorious land, with an imposing view of …see more

from $1948 / night

$13636 - $30000 / week

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from $1948 / night

(14) Excellent 

6

Vacation villa with golf nearby in Sandy Bay

Hanover Parish / Sandy Bay

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxury living is all about the details and Pineapple House has it all. Pineapple House has undergone a multi-million dollar renovation, and it is prepared to please the most discriminating vacationers that appreciate luxury living. Distinctive in its architecture, Pinea …see more

from $2143 / night

$12000 - $35000 / week

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from $2143 / night

(1) Excellent 

17

Sandy Bay Vacation home rental

Hanover Parish / Sandy Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy the first class resort amenities of the Tryall Resort Membership. Please read for the exclusive resort features for this villa. Round House is one of the largest and most spacious villas in Jamaica located within the renowned 2,200 acre Tryall Club Resort. Being s …see more

from $2142 / night

$15000 - $26000 / week

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from $2142 / night

(1) Excellent 

38

Vacation home with shared pool in Sandy Bay

Hanover Parish / Sandy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Newly refurbished and spectacular Premier villa!! 5 bedrooms, 5 bathrooms. Tryall Resort Membership. Spectacular ocean views, 3 minutes golf cart ride to the beach! for this villa. Pineapple House is a premier villa located in the exclusive Tryall Club overlooking the r …see more

from $1948 / night

$13636 - $37500 / week

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from $1948 / night

30

Vacation home with shared pool in Sandy Bay

Hanover Parish / Sandy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
Wonderful 3 bedroom villa, casual villa, fully staffed, 3 minutes ride to the beach!!!Tryall Resort Membership. Please read for the exclusive resort features for this villa. No Problem Villa in Montego Bay is an attractive two-storey Jamaica villa with fantastic views o …see more

from $571 / night

$4000 - $10725 / week

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from $571 / night

54

Home rental in Sandy Bay with shared pool

Hanover Parish / Sandy Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. …see more

from $2857 / night

$20000 - $40000 / week

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from $2857 / night

34

Vacation home rental

Hanover Parish / Sandy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
5 bedroom, 5 bathrooms, 2 swimming pools! 3 minutes golf cart ride to the beach!Tryall Resort Membership. Exclusive resort features for this villa. villa rentals in Jamaica, Mahogany Hill Villa in Montego Bay is one of the most attractive and spacious Jamaica villas loc …see more

from $1785 / night

$12500 - $30000 / week

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from $1785 / night

17

Sandy Bay Vacation apartment rental

Hanover Parish / Sandy Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Property description This spacious, newly decorated two bedroom two bath apartment is situated in Montego Bay in the upscale gated community of The Lagoons, just a few minutes from the Montego Bay airport. The apartment has two bedrooms, both with en suite bathrooms, …see more

from $250 / night

$1575 / week

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from $250 / night

60

Vacation home with shared pool in Sandy Bay

Hanover Parish / Sandy Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
5 bedrooms, Luxury villa! Great staff!Tryall Resort Membership. Please read for the exclusive resort features for this villa. Point of View Villa in Montego Bay is a premier Jamaica villa located on the highest point in the world-class Tryall Club, one of the most fabul …see more

from $3636 / night

$25454 - $45001 / week

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from $3636 / night

28

Vacation home in Sandy Bay

Hanover Parish / Sandy Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
3 bedroom villa, with exclusive Tryall Resort Membership. Only 3 minutes golf cart ride to the white sandy beach of Tryall! Serenity Villa sits on a hillside in the renowned Tryall Club Resort, near the Montego Bay area. The villa offers picturesque views of the surroun …see more

from $681 / night

$4772 - $9772 / week

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from $681 / night

(1) Excellent 

16

Home rental in Sandy Bay with shared pool

Hanover Parish / Sandy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Deluxe 4 bedrooms, 4 bathrooms, spectacular oceansea views! Loyal staff, you will be pampered! Tryall Resort Membership. 5 minutes golf cart ride to the beach! Clive House at Tryall has the most impressive driveway, since it is situated on the Copper Ridge Drives' highe …see more

from $642 / night

$4500 - $12155 / week

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from $642 / night

1