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Scarborough Rentals with Pools

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    Travelers to Scarborough are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    10 Matching Rentals in ScarboroughView all 18 rentals
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    Moonlight Mountain1 / 23
    (2)Average
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Casa Delamar Ocean Front Villa in Beautiful Tobago1 / 32
    (39)Very good
    4 Bedrooms, 2 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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    VOTED TOP 20 CONDE NAST CARIBBEAN VILLA - 74 STEPS TO BEACH - KIDS TRAVEL FREE1 / 24
    (3)Average
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Children's Pool
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 27, 2015
    The usual superlatives cannot do justice to our experience at Ohana! Our family of six adults and a three-year-old wanted a place to get away, where we could all relax from our...
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    About this property
    Voted amongst the top twenty villas in the Caribbean by Conde Nast Traveler in 2007, Ohana Villa stands apart as one of the most striking places to stay in Tobago and the Caribbean and was designed by one of the Caribbean's foremost architects. Ohana is a Hawaiian word for family rest-house and...
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    Location Information
    Scarborough, Tobago
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    OCEANVIEW APARTMENT (POOL & BEACH ACCESS) with WIFI - Casa Cassini Tobago1 / 17
    (19)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Ocean Views
    • Shared Yard
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 7, 2018
    The breezes were fantastic all day with all the windows and doors open. The huge 2 sided balcony was great for sitting out on, or laying out clothes or dive gear to dry. Steph...
    Reviewed November 16, 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...
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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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    Atlantis cove: beautiful Cottage above the Ocean1 / 7
    (2)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
    Reviewed March 22, 2018
    What a fantastic cottage truly relaxing with all the amenities you could want. Pool superb. Isabelle Jason and family such perfect hosts. It was a pleasure to be their guests...
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    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Ambassadors House, Windy Edge1 / 23
    (21)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Secure Parking
    • Ocean Views
    • Balcony
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 8, 2018
    We stayed over new year 2018 for a week and really enjoyed the house, pool and gardens. Booking was easy and we would recommend this as an excellent place to stay for self...
    Reviewed August 22, 2017
    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...
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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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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
    • Cable/satellite TV
    • Ocean Views
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 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 February 10, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Washer
    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perched upon the verdant hills of Tobago's windward coast, overlooking the vast and stunning Atlantic ocean, a slice of paradise awaits you. Come to our 2+ bedroom escape, and lose yourself amongst 4 acres of awe inspiring views and refreshing ocean breezes. There's a taste of everything natural...
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    Location Information
    Scarborough, Tobago 00000
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    BEACHFRONT VILLA (POOL & BEACH ACCESS) with WIFI - Casa Cassini Tobago1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 18, 2018
    We stayed at Casa Cassini for two weeks and absolutely enjoyed the villa and grounds. The villa’s interior is very spacious, open living and the tropical roof construction...
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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