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Holiday Rentals with Pools in Scarborough

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    $376 Average
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    Travellers to Scarborough are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    9 Matching Rentals in ScarboroughView all 17 rentals
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    VOTED TOP 20 CONDE NAST CARIBBEAN VILLA - 74 STEPS TO BEACH - KIDS TRAVEL FREE1 / 48
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Villa Sans-Souci1 / 15
    (9)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Casa Delamar Ocean Front Villa in Beautiful Tobago1 / 32
    (33)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cool Breeze Villa - overlooking ocean with pool1 / 9
    (5)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Washer
    • Wi-Fi
    • Satellite TV
    • Ocean Views
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    My stay as titled was peaceful, My family and I enjoyed every moment of it, the garden was beautiful, the back porch was inviting with the cool breeze and the panoramic ocean...
    Reviewed 11 February 2016
    Spent a week at Cool Breeze with my wife and two boys. My boys totally enjoyed the pool, we spent the evenings playing board games on the patio, with a view of the Atlantic...
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    About this property
    3-bedroom, 2-1/2 bath home with pool overlooking the ocean. The open floor plan offers panoramic views of the Atlantic Ocean from the bedrooms, main living areas and even the kitchen. Relax in a hammock on the patio while enjoying the cool tropical breezes. 5 min walk to beach, centrally located....
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    Location Information
    Scarborough, Tobago 00000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    OCEANVIEW APARTMENT (POOL & BEACH ACCESS) with WIFI - Casa Cassini Tobago1 / 17
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Shared Garden
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    • Satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2016
    I had a long weekend and wanted R&R and just chill-out. Well I got a lot more than I asked for. Really great lookout seeing the sun rise over the bay with a three (3) minute...
    Reviewed 1 April 2016
    My husband and I don't do the 'all inclusive holiday' we like to book our own flights, accommodation and make our arrangements for eating. Theses days we don't stay in Hotels...
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    About this property
    We would like to invite you to enjoy a private quiet stay in our fully furnished and self-contained one bedroom apartment offering breathtaking views of the ocean and the old Bacolet coconut plantation. The apartment is separate from the main villa and affords as much privacy as you may need. A...
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    Location Information
    Scarborough, Tobago N A
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Moonlight Mountain1 / 23
    (2)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Satellite TV
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 March 2017
    You're on top of a mountain in Tobago. A beautiful breeze blows constantly - no need for AC. The house is spacious and well laid out with lots of room. Loved it! Being Tobago...
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    About this property
    Moonlight Mountain is built along traditional lines, it is what is called in the Caribbean a gingerbread house - a reference to the decorative fretwork which adorns the outside. Set in what used to be agricultural land and designed to catch the sea breezes, it has its own fruit trees, a nature...
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    Location Information
    Scarborough, Tobago TOBAGO
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Balcony
    • Satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Cassini Villa by the Sea offers stunning ocean views and a pool that is only for guests of the villa and the upstairs apartment. From the property you will have direct access to the 2-mile sand beach (2 min walk through a former coconut plantation). The 3-bedroom villa sleeps 4 to 6 people....
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    Location Information
    Scarborough, Tobago BACOLET
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Atlantis cove: beautiful Cottage above the Ocean1 / 7
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Balcony
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Waterfront
    • Outdoor Dining Area
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Atlantis cove is located approx. 30 min from the International ANR. Robinson Airport and host exhibits of locally made bamboo furniture. Your stay is considered with the greatest interest in mind. We strive to make you as comfortable as if you never left your own home. For the nature loving...
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    Location Information
    Scarborough, Tobago 901854
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Ambassadors House, Windy Edge1 / 23
    (20)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Payment Protection
    Amenities & Details
    • Secure Parking
    • Ocean Views
    • Balcony
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    This is a spectacular spot. Really spectacular. Up in the hills behind Scarborough in its own substantial grounds, this is a house built in the traditional style...
    Reviewed 7 July 2016
    My family and I stayed here during our vacation and it was just a wonderful experience. The time off from the busyness of our daily routines was definitely needed. I took...
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    About this property
    Windy Edge was designed and built by a former US ambassador to Japan and it is still known on the island as the Ambassador's House. Set on the top of Cinnamon Hill, it has sensational views over the Caribbean and Atlantic seas and catches the cooling breezes, unlike many coastal properties. It is a...
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    Location Information
    Scarborough, Tobago TQ139XG
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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