We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Tobago Rentals with Pools

List your property
Owner log in
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 mi
90 rentals in Tobago.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
Villa Kiskadee & pool
kiskadee at night
Shared batthroom
Villa Kiskadee Tobago
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Surfers Paradise Villa. Beach Front, Mt. Irvine, Tobago
Rental Home
6 bedrooms
6 bathrooms
Sleeps 28
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Oleander Villa
Oleander Villa Pool
Oleander Villa
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Mary's Hill Lodge, Tobago
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

VIEW OF THE POOL AND CARIBBEAN OCEAN FROM THE GROUNDS
LIVING ROOM AREA
CHACONIA, Beach front, luxury 3 bedroom apartment, SPECIAL OFFERS AVAILABLE
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Mahogany Villa - Luxury Villa in Beautiful Tropical Gardens near Lovely Beaches
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Secluded villa in Englishmans Bay
Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

OCEANVIEW APARTMENT Tobago - POOL & BEACH ACCESS
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Ambassadors House, Windy Edge
Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Stunning seafront villa with panoramic ocean views
Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Save time - get the best Tobago rentals sent straight to your email!
Robbie's Place Tobago # 1bedroom
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Flipkey'sTopVillaRental 4BED villa Nr..QUIET BEACH
Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Robbie's Place Tobago # 2 bedroom
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Eagle's Base Villa
Rental Home
6 bedrooms
6 bathrooms
Sleeps 22
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Tomas Villa Tobago
Rental Home
8 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Plantation View
Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

PRIDE OF COURLAND - Hummingbird - Unique Beachfront Apartment
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

4BR Luxury Villa in quiet & secure gated development close to airport, beaches
Rental Home
4 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Being - The Hippest, Happiest Spot in Tobago
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Tobago three bedroom Villa with panoramic seaview, close to airport and town.
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Caribbean Sea View over the beach and infinity pool (Birdie's Nest)
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Romantic Caribbean Get Away.
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Kilgwyn Bay Getaway
Rental Home
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Large villa with 50ft pool in Samaan Grove Tobago
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Beach, Infinity pool and Netflix all have one in common. Birdie's Nest
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

2BR Ocean Front Bungalow with pool, deck and wifi
Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Villa Soleil
Rental Home
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Beautiful Villa, Great Location
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Nirvana Tobago Luxury Villa with Salt water Pool and Ocean Views
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Crown Point 2BR Condo
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Villa Sweet Breeze
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Malindi Villa is located on a cool quiet hill at Bacolet Point
Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

Side one side the
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Crown Point 1BR Condo
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

VOTED TOP 20 CONDE NAST CARIBBEAN VILLA - 74 STEPS TO BEACH - KIDS TRAVEL FREE
Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Atlantis cove: beautiful Cottage above the Ocean
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Cool Breeze Villa - overlooking ocean with pool
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Tropical Apartment Tobago
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Villa Escalante
Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Kapinjala Villa
Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

VILLA Tobago - POOL & BEACH ACCESS
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Stunning Views from Luxury 3 Bedroom Villa Bimiti with Pool - Sleeps 7
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, All pools
More info
Vrbo.com logo
Check in
Check out

The Coterie Villa
Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Top O' Tobago
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Moonlight Mountain
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Welcome to Villa Emunah - Where every detail counts.
Rental Home
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Jacaranda House
Rental Home
4 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Peninsula
Rental Home
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

Lagoona Villa
Rental Home
5 bedrooms
4 bathrooms
Sleeps 2
Match: Sleeps, All pools
More info
Check in
Check out
Payment Protection

PreviousNext
12
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.
More
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.