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Tobago Luxury Rentals

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358 rentals in Tobago.
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Surfers Paradise Villa. Beach Front, Mt. Irvine, Tobago, vacation rental in Tobago
Surfers Paradise Villa. Beach Front, Mt. Irvine, Tobago, vacation rental in Tobago
Surfers Paradise Villa. Beach Front, Mt. Irvine, Tobago, vacation rental in Tobago

Surfers Paradise Villa. Beach Front, Mt. Irvine, Tobago

Rental Home
6 bedrooms
6 bathrooms
Sleeps 28
Match: Sleeps
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Side one side the, vacation rental in Tobago
Side one side the, vacation rental in Tobago
Side one side the, vacation rental in Tobago

Side one side the

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Ambassadors House, Windy Edge, vacation rental in Tobago
Ambassadors House, Windy Edge, vacation rental in Tobago
Ambassadors House, Windy Edge, vacation rental in Tobago

Ambassadors House, Windy Edge

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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SeaScape -, Beachfront Apartment, vacation rental in Tobago
SeaScape -, Beachfront Apartment, vacation rental in Tobago
SeaScape -, Beachfront Apartment, vacation rental in Tobago

SeaScape -, Beachfront Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Mary's Hill Lodge, Tobago, vacation rental in Tobago
Mary's Hill Lodge, Tobago, vacation rental in Tobago
Mary's Hill Lodge, Tobago, vacation rental in Tobago

Mary's Hill Lodge, Tobago

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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CHACONIA,  Beach front, luxury 3 bedroom apartment, SPECIAL OFFERS AVAILABLE, vacation rental in Tobago
CHACONIA,  Beach front, luxury 3 bedroom apartment, SPECIAL OFFERS AVAILABLE, vacation rental in Tobago
CHACONIA,  Beach front, luxury 3 bedroom apartment, SPECIAL OFFERS AVAILABLE, vacation rental in Tobago

CHACONIA, Beach front, luxury 3 bedroom apartment, SPECIAL OFFERS AVAILABLE

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Mahogany Villa - Luxury Villa in Beautiful Tropical Gardens near Lovely Beaches, vacation rental in Tobago
Mahogany Villa - Luxury Villa in Beautiful Tropical Gardens near Lovely Beaches, vacation rental in Tobago
Mahogany Villa - Luxury Villa in Beautiful Tropical Gardens near Lovely Beaches, vacation rental in Tobago

Mahogany Villa - Luxury Villa in Beautiful Tropical Gardens near Lovely Beaches

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Secluded villa in Englishmans Bay, vacation rental in Tobago
Secluded villa in Englishmans Bay, vacation rental in Tobago
Secluded villa in Englishmans Bay, vacation rental in Tobago

Secluded villa in Englishmans Bay

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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OCEANVIEW APARTMENT Tobago - POOL & BEACH ACCESS, vacation rental in Tobago
OCEANVIEW APARTMENT Tobago - POOL & BEACH ACCESS, vacation rental in Tobago
OCEANVIEW APARTMENT Tobago - POOL & BEACH ACCESS, vacation rental in Tobago

OCEANVIEW APARTMENT Tobago - POOL & BEACH ACCESS

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Castara Roundhouse Tobago - Oceanview apartment 1 br, Paradise awaits you, vacation rental in Tobago
Castara Roundhouse Tobago - Oceanview apartment 1 br, Paradise awaits you, vacation rental in Tobago
Castara Roundhouse Tobago - Oceanview apartment 1 br, Paradise awaits you, vacation rental in Tobago

Castara Roundhouse Tobago - Oceanview apartment 1 br, Paradise awaits you

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning seafront villa with panoramic ocean views, vacation rental in Tobago
Stunning seafront villa with panoramic ocean views, vacation rental in Tobago
Stunning seafront villa with panoramic ocean views, vacation rental in Tobago

Stunning seafront villa with panoramic ocean views

Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Oleander Villa, vacation rental in Tobago
Oleander Villa, vacation rental in Tobago
Oleander Villa, vacation rental in Tobago

Oleander Villa

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chaconia, a luxurious beach front Colonial style apartment, vacation rental in Tobago
Chaconia, a luxurious beach front Colonial style apartment, vacation rental in Tobago
Chaconia, a luxurious beach front Colonial style apartment, vacation rental in Tobago

Chaconia, a luxurious beach front Colonial style apartment

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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It have two one bedrooms & a two bedroom apartment, vacation rental in Tobago
It have two one bedrooms & a two bedroom apartment, vacation rental in Tobago
It have two one bedrooms & a two bedroom apartment, vacation rental in Tobago

It have two one bedrooms & a two bedroom apartment

Condo/Apartment
1 bedroom
4 bathrooms
Sleeps 8
Match: Sleeps
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Robbie's Place Tobago # 2 bedroom, vacation rental in Tobago
Robbie's Place Tobago # 2 bedroom, vacation rental in Tobago
Robbie's Place Tobago # 2 bedroom, vacation rental in Tobago

Robbie's Place Tobago # 2 bedroom

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Caribbean Panoramic Views Birdwatchers Paradise, vacation rental in Tobago
Caribbean Panoramic Views Birdwatchers Paradise, vacation rental in Tobago
Caribbean Panoramic Views Birdwatchers Paradise, vacation rental in Tobago

Caribbean Panoramic Views Birdwatchers Paradise

Rental Home
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Flipkey'sTopVillaRental 4BED villa Nr..QUIET BEACH, vacation rental in Tobago
Flipkey'sTopVillaRental 4BED villa Nr..QUIET BEACH, vacation rental in Tobago
Flipkey'sTopVillaRental 4BED villa Nr..QUIET BEACH, vacation rental in Tobago

Flipkey'sTopVillaRental 4BED villa Nr..QUIET BEACH

Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Robbie's Place Tobago # 1bedroom, vacation rental in Tobago
Robbie's Place Tobago # 1bedroom, vacation rental in Tobago
Robbie's Place Tobago # 1bedroom, vacation rental in Tobago

Robbie's Place Tobago # 1bedroom

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Carpe Diem Villa. Sunset2. Studio with Sea Views even from the Beds! Great Wi-fi, vacation rental in Tobago
Carpe Diem Villa. Sunset2. Studio with Sea Views even from the Beds! Great Wi-fi, vacation rental in Tobago
Carpe Diem Villa. Sunset2. Studio with Sea Views even from the Beds! Great Wi-fi, vacation rental in Tobago

Carpe Diem Villa. Sunset2. Studio with Sea Views even from the Beds! Great Wi-fi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Stunning, idyllic, Caribbean style 3 bedroom villa in one acre of lush gardens., vacation rental in Tobago
Stunning, idyllic, Caribbean style 3 bedroom villa in one acre of lush gardens., vacation rental in Tobago
Stunning, idyllic, Caribbean style 3 bedroom villa in one acre of lush gardens., vacation rental in Tobago

Stunning, idyllic, Caribbean style 3 bedroom villa in one acre of lush gardens.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Eagle’s Base Villa, vacation rental in Tobago
Eagle’s Base Villa, vacation rental in Tobago
Eagle’s Base Villa, vacation rental in Tobago

Eagle’s Base Villa

Rental Home
6 bedrooms
7 bathrooms
Sleeps 26
Match: Sleeps
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2 Double Bed-Room Villa, Own Private Pool, Golf Course and Ocean Views, Sleeps 4, vacation rental in Tobago
2 Double Bed-Room Villa, Own Private Pool, Golf Course and Ocean Views, Sleeps 4, vacation rental in Tobago
2 Double Bed-Room Villa, Own Private Pool, Golf Course and Ocean Views, Sleeps 4, vacation rental in Tobago

2 Double Bed-Room Villa, Own Private Pool, Golf Course and Ocean Views, Sleeps 4

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Villa Kiskadee Tobago, vacation rental in Tobago
Villa Kiskadee Tobago, vacation rental in Tobago
Villa Kiskadee Tobago, vacation rental in Tobago

Villa Kiskadee Tobago

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Mahogany Villa - Luxury Villa Situated In Beautiful Tropical Gardens, vacation rental in Tobago
Mahogany Villa - Luxury Villa Situated In Beautiful Tropical Gardens, vacation rental in Tobago
Mahogany Villa - Luxury Villa Situated In Beautiful Tropical Gardens, vacation rental in Tobago

Mahogany Villa - Luxury Villa Situated In Beautiful Tropical Gardens

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tomas Villa Tobago, vacation rental in Tobago
Tomas Villa Tobago, vacation rental in Tobago
Tomas Villa Tobago, vacation rental in Tobago

Tomas Villa Tobago

Rental Home
8 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps
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Plantation View, vacation rental in Tobago
Plantation View, vacation rental in Tobago
Plantation View, vacation rental in Tobago

Plantation View

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Spacious, Family Friendly, Top Floor, 3 Bedroom Apartment on the Beach, vacation rental in Tobago
Spacious, Family Friendly, Top Floor, 3 Bedroom Apartment on the Beach, vacation rental in Tobago
Spacious, Family Friendly, Top Floor, 3 Bedroom Apartment on the Beach, vacation rental in Tobago

Spacious, Family Friendly, Top Floor, 3 Bedroom Apartment on the Beach

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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PRIDE OF COURLAND - Hummingbird - Unique Beachfront Apartment, vacation rental in Tobago
PRIDE OF COURLAND - Hummingbird - Unique Beachfront Apartment, vacation rental in Tobago
PRIDE OF COURLAND - Hummingbird - Unique Beachfront Apartment, vacation rental in Tobago

PRIDE OF COURLAND - Hummingbird - Unique Beachfront Apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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4BR Luxury Villa in quiet & secure gated development close to airport, beaches, vacation rental in Tobago
4BR Luxury Villa in quiet & secure gated development close to airport, beaches, vacation rental in Tobago
4BR Luxury Villa in quiet & secure gated development close to airport, beaches, vacation rental in Tobago

4BR Luxury Villa in quiet & secure gated development close to airport, beaches

Rental Home
4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Cozy cottage with hill view for bird lovers, vacation rental in Tobago
Cozy cottage with hill view for bird lovers, vacation rental in Tobago
Cozy cottage with hill view for bird lovers, vacation rental in Tobago

Cozy cottage with hill view for bird lovers

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sandy Bay Cottage - beachfront beauty with breathtaking view of Caribbean Sea, vacation rental in Tobago
Sandy Bay Cottage - beachfront beauty with breathtaking view of Caribbean Sea, vacation rental in Tobago
Sandy Bay Cottage - beachfront beauty with breathtaking view of Caribbean Sea, vacation rental in Tobago

Sandy Bay Cottage - beachfront beauty with breathtaking view of Caribbean Sea

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A Beautiful Villa In Englishmans Bay, Tobago, vacation rental in Tobago
A Beautiful Villa In Englishmans Bay, Tobago, vacation rental in Tobago
A Beautiful Villa In Englishmans Bay, Tobago, vacation rental in Tobago

A Beautiful Villa In Englishmans Bay, Tobago

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Being - The Hippest, Happiest Spot in Tobago, vacation rental in Tobago
Being - The Hippest, Happiest Spot in Tobago, vacation rental in Tobago
Being - The Hippest, Happiest Spot in Tobago, vacation rental in Tobago

Being - The Hippest, Happiest Spot in Tobago

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Caribbean Retreat, vacation rental in Tobago
Private Caribbean Retreat, vacation rental in Tobago
Private Caribbean Retreat, vacation rental in Tobago

Private Caribbean Retreat

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Luxury 5 Bedroom Villa, Large Pool and Heated Jacuzzi, Free Wireless Internet, vacation rental in Tobago
Luxury 5 Bedroom Villa, Large Pool and Heated Jacuzzi, Free Wireless Internet, vacation rental in Tobago
Luxury 5 Bedroom Villa, Large Pool and Heated Jacuzzi, Free Wireless Internet, vacation rental in Tobago

Luxury 5 Bedroom Villa, Large Pool and Heated Jacuzzi, Free Wireless Internet

Rental Home
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Villa/Pool by Sea on Championship Golf Course, vacation rental in Tobago
Villa/Pool by Sea on Championship Golf Course, vacation rental in Tobago
Villa/Pool by Sea on Championship Golf Course, vacation rental in Tobago

Villa/Pool by Sea on Championship Golf Course

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Three bedroom with 3 and a half bathrooms, Tobago Villa with panoramic sea view, vacation rental in Tobago
Three bedroom with 3 and a half bathrooms, Tobago Villa with panoramic sea view, vacation rental in Tobago
Three bedroom with 3 and a half bathrooms, Tobago Villa with panoramic sea view, vacation rental in Tobago

Three bedroom with 3 and a half bathrooms, Tobago Villa with panoramic sea view

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Tropical Oasis , Store Bay/ Pigeon Point, vacation rental in Tobago
Tropical Oasis , Store Bay/ Pigeon Point, vacation rental in Tobago
Tropical Oasis , Store Bay/ Pigeon Point, vacation rental in Tobago

Tropical Oasis , Store Bay/ Pigeon Point

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Luxurious Colonial Style  Golf Resort Villa, vacation rental in Tobago
Luxurious Colonial Style  Golf Resort Villa, vacation rental in Tobago
Luxurious Colonial Style  Golf Resort Villa, vacation rental in Tobago

Luxurious Colonial Style Golf Resort Villa

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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VillaBelleFleur - A Home away from Home, vacation rental in Tobago
VillaBelleFleur - A Home away from Home, vacation rental in Tobago
VillaBelleFleur - A Home away from Home, vacation rental in Tobago

VillaBelleFleur - A Home away from Home

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tobago three bedroom Villa with panoramic seaview, close to airport and town., vacation rental in Tobago
Tobago three bedroom Villa with panoramic seaview, close to airport and town., vacation rental in Tobago
Tobago three bedroom Villa with panoramic seaview, close to airport and town., vacation rental in Tobago

Tobago three bedroom Villa with panoramic seaview, close to airport and town.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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SeaScape - Beachfront Accommodation, vacation rental in Tobago
SeaScape - Beachfront Accommodation, vacation rental in Tobago
SeaScape - Beachfront Accommodation, vacation rental in Tobago

SeaScape - Beachfront Accommodation

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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La Jolie..Luxury home with infinity pool, jacuzzi and spectacular ocean view., vacation rental in Tobago
La Jolie..Luxury home with infinity pool, jacuzzi and spectacular ocean view., vacation rental in Tobago
La Jolie..Luxury home with infinity pool, jacuzzi and spectacular ocean view., vacation rental in Tobago

La Jolie..Luxury home with infinity pool, jacuzzi and spectacular ocean view.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Kilgwyn Bay Getaway, vacation rental in Tobago
Kilgwyn Bay Getaway, vacation rental in Tobago
Kilgwyn Bay Getaway, vacation rental in Tobago

Kilgwyn Bay Getaway

Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Bananaquit- Cosy Loft w/ kitchen close to beaches 9, vacation rental in Tobago
Bananaquit- Cosy Loft w/ kitchen close to beaches 9, vacation rental in Tobago
Bananaquit- Cosy Loft w/ kitchen close to beaches 9, vacation rental in Tobago

Bananaquit- Cosy Loft w/ kitchen close to beaches 9

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Villa Kiskadee. Large luxury Tobago villa with pool, vacation rental in Tobago
Villa Kiskadee. Large luxury Tobago villa with pool, vacation rental in Tobago
Villa Kiskadee. Large luxury Tobago villa with pool, vacation rental in Tobago

Villa Kiskadee. Large luxury Tobago villa with pool

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Caribbean Sea View over the beach and infinity pool (Birdie's Nest), vacation rental in Tobago
Caribbean Sea View over the beach and infinity pool (Birdie's Nest), vacation rental in Tobago
Caribbean Sea View over the beach and infinity pool (Birdie's Nest), vacation rental in Tobago

Caribbean Sea View over the beach and infinity pool (Birdie's Nest)

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tropical Treasures Apt5 - Tobago, vacation rental in Tobago
Tropical Treasures Apt5 - Tobago, vacation rental in Tobago
Tropical Treasures Apt5 - Tobago, vacation rental in Tobago

Tropical Treasures Apt5 - Tobago

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Large villa with 50ft pool in Samaan Grove Tobago, vacation rental in Tobago
Large villa with 50ft pool in Samaan Grove Tobago, vacation rental in Tobago
Large villa with 50ft pool in Samaan Grove Tobago, vacation rental in Tobago

Large villa with 50ft pool in Samaan Grove Tobago

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Casa Clara - The Perfect Place For A Family/group Of Friends To Gather & Relax, vacation rental in Tobago
Casa Clara - The Perfect Place For A Family/group Of Friends To Gather & Relax, vacation rental in Tobago
Casa Clara - The Perfect Place For A Family/group Of Friends To Gather & Relax, vacation rental in Tobago

Casa Clara - The Perfect Place For A Family/group Of Friends To Gather & Relax

Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Tobago Vacation Rentals
Let life’s stresses melt away on a breezy island whose rocky coastline is dotted with bays, beaches, and friendly Caribbean fishing villages. Inland is a bird-watching paradise of hillside rainforests punctuated by waterfalls. Horseback ride hills and beaches. Golf, hike, bike, fish, swim, sunbathe, kayak, dive, snorkel, and windsurf. Take the family on a boat tour. Barbecue freshly caught fish on isolated beaches or poolside with your family or new island vacation rental friends. Plus experience Tobago’s smiling, laidback culture by liming (hanging out) with the locals near your money-saving Tobago vacation rental villa, lodge, house, cottage, cabin, apartment, or studio flat.
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Tobago Vacation Rentals
Let life’s stresses melt away on a breezy island whose rocky coastline is dotted with bays, beaches, and friendly Caribbean fishing villages. Inland is a bird-watching paradise of hillside rainforests punctuated by waterfalls. Horseback ride hills and beaches. Golf, hike, bike, fish, swim, sunbathe, kayak, dive, snorkel, and windsurf. Take the family on a boat tour. Barbecue freshly caught fish on isolated beaches or poolside with your family or new island vacation rental friends. Plus experience Tobago’s smiling, laidback culture by liming (hanging out) with the locals near your money-saving Tobago vacation rental villa, lodge, house, cottage, cabin, apartment, or studio flat.
Crown Point
Have a cooling rum punch after landing at Crown Point International Airport (TAB) on Tobago’s southwest tip. Crown Point is minutes from Buccoo Reef’s Nylon Pool, Bon Accord, Pigeon Point, Mt. Irvine Bay, Black Rock, Plymouth, Le Coteaux, and Concordia. Chat with handicraft vendors and sample curry crab and dumplings around the beaches and resort hotels between Pigeon Point, Store Bay, and Canoe Bay. Then be thankful that your money-saving Tobago vacation rental puts you near quiet beaches and friendly fishing villages where you can buy the fresh catch of the day to barbecue.
Scarborough & Boats
Scarborough, Tobago’s capital and largest town, is the dock for the ferry from Port of Spain, Trinidad. When cruise ships dock, vendors come alive selling coconut sugar cakes, sesame benne balls, and handicrafts near Milford Road Esplanade. Tobago has annual boating events and regattas. But protected yacht and sailboat anchorages are over an hour away in the northeast at Charlotteville, near the beautiful beaches of Pirate’s Bay and Man O’ War Bay. Private boat tours, often arranged via vacation rental contacts, are family favorites that can include snorkeling and barbecues on deserted beaches. Besides Scarborough’s shopping and restaurants, visit Fort King George, the Botanical Garden, and the Tobago Museum.
Castara
A money-saving Tobago vacation rental near Castara’s fishing village is midway between Crown Point and Charlotteville’s rocky, frigate bird nesting areas. Lime around Englishman’s Bay and nearby beaches. Watch goats and chickens wander as you chat at the fishing village. Savor the slow pace. Back home on your vacation rental verandah, relax with tropical garden fruits, 50 hummingbird species, and exotic bird songs. Then take the family to waterfalls and rainforests.
Tobago Cocoa, Rainforests & Waterfalls
Legally protected as an essential watershed since 1776, hike and bird-watch with guides in the Tobago Forest Reserve. The cascades and swimmable pools of 175-foot Argyle Waterfall are near Roxborough and the beaches of King’s Bay, an area amenable to sugarcane, fruit trees, cocoa, and coconut plantations. The tiny Tobago Cocoa Estate offers early morning drop-in tours, and rum and chocolate tasting.