Vacation Rentals with Pool in Tobago

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Filtering by: Swimming pool

123 vacation rentals

(19) Excellent 

56

Eagle's Base Villa

Tobago / Prospect

Prospect villa

7 22 3 nights min

  • 7 bedrooms
  • sleeps 22
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$601

Price per night from

$601

(3) Excellent 

18

Flamboyant Suite By The Sea - Resort on the Caribbean side with Shared Pool

Tobago / Black Rock

Black Rock apartment

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$321

Price per night from

$321

(10) Very Good 

25

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

Tobago / Prospect

Prospect villa

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Nearest beach 0.8 mi
  • Swimming pool
  • Child Friendly
“would stay here again!” We very much enjoyed our stay at this villa. The owner was easy to deal with, very pleasant and efficient with communication. The villa itself is in a great location, with good amenities close by. The local bar is a great pla
…see more

Price per night from

$210

Responds fast!
avg. 1 hour 57 minutes

Price per night from

$210

(9) Very Good 

10

Kilgwyn Bay Getaway

Tobago / Bon Accord

Bon Accord townhouse

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

Price per night from

$161

Responds fast!
avg. 3 hours 36 minutes

Price per night from

$161

26

Luxury Villa with Pool, Hot Tub, Steam Room & Steps down to Surf of Mt Irvine

Tobago / Mount Irvine

Mount Irvine villa

4 8 4 nights min

  • 4 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 0.6 mi
  • Swimming pool
  • Child Friendly

Price per night from

$351

Price per night from

$351

(2) Excellent 

7

Atlantis cove: beautiful Cottage above the Ocean

Tobago / Scarborough

Scarborough cottage

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$100

Responds fast!
avg. 2 hours 35 minutes

Price per night from

$100

(1) Excellent 

18

Side one side the

Tobago / Crown Point

Crown Point villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$491

Price per night from

$491

12

Macaw

Tobago / Canaan

Canaan villa

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$449

Price per night from

$449

(23) Excellent 

16

The Marion Villa

Tobago / Bacolet Bay

Bacolet Bay villa

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

Price per night from

$550

Price per night from

$550

(16) Excellent 

14

Villa Colibri: 3BR villa/pool/24 hr guard gated community/Tobago

Tobago / Canaan

Canaan villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
“wonderful vacation retreat” My family stayed at the villa during February and we could not have been happier with our choice in selecting this location. It was immaculately maintained with numerous amenities. The villa has large open common areas with
…see more

Price per night from

$365

Price per night from

$365

(7) Very Good 

18

Large villa with 50ft pool in Samaan Grove Tobago

Tobago / Canaan

Canaan house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“beautiful, well maintained villa with all the comforts” We thoroughly enjoyed our stay here, it had all the amenities promised and even more. We did not feel cramped like some other vacation homes. The Bedrooms were spacious although we spend most of
…see more

Price per night from

$500

Price per night from

$500

(8) Excellent 

12

Romantic Caribbean Get Away.

Tobago / Parlatuvier

Parlatuvier chalet

2 4 4 nights min

  • 2 bedrooms
  • sleeps 4
  • 4 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$136

Price per night from

$136

26

Hibiscus, Holiday Home with the Caribbean Sea on its Doorstep!

Tobago / Black Rock

Black Rock villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$425

Price per night from

$425

18

Sunflower

Tobago / Canaan

Canaan villa

4 12 1 night min

  • 4 bedrooms
  • sleeps 12
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$500

Price per night from

$500

6

Indigo 2 Bedroom Apartment

Tobago / Mount Irvine

Mount Irvine apartment

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$156

Price per night from

$156

(27) Excellent 

33

Sundowner - Beautiful apartment with infinity pool

Tobago / Moriah

Moriah apartment

2 3 7 nights min

  • 2 bedrooms
  • sleeps 3
  • 7 nights min
  • Nearest beach 6 mi
  • Swimming pool
  • Ask about children
“Spectacular setting for a comfortable appartment with very welcoming,friendly hosts on site.” North west Tobago is a very special place if you value natural landscape, magnificent rainforest, blossoming trees,wildlife and few tourists. Beautiful remot
…see more

Price per night from

$126

Price per night from

$126

11

Cool-Breeze-O

Tobago / Lambeau

Lambeau villa

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$325

Price per night from

$325

(1) Excellent 

21

Oceana: Luxurious 4BR/4BA private pool, 24hr guard gated community.

Tobago / Canaan

Canaan house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$360

Price per night from

$360

(2) Very Good 

13

Cisantt

Tobago / Canaan

Canaan villa

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$325

Price per night from

$325

(5) Very Good 

10

Villa Sweet Breeze

Tobago / Prospect, Tobago

Prospect, Tobago villa

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$202

Price per night from

$202

(1) Excellent 

59

Top O' Tobago

Tobago / Plymouth

Plymouth apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$120

Price per night from

$120

(9) Excellent 

16

Coasting Villa - Beautiful, Intimate, Waterfront

Trinidad and Tobago / Tobago

Tobago house

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“A gorgeous escape” Our group stayed at Coasting in March and couldn't have been happier with the accommodation. We were 4 adults and a 13 month old. The house and grounds are breath taking---think tropical flowers, a view to die for, birds galore, pat
…see more

Price per night from

$201

Price per night from

$201

16

Lagoona Villa

Tobago / Bon Accord

Bon Accord villa

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$230

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$230

(1) Very Good 

21

CoCo Chalet in Caribbean - only missing the fireplace!

Tobago / Mount Irvine

Mount Irvine house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$226

Price per night from

$226

14

Atlantic

Tobago / Lowlands

Lowlands villa

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$800

Price per night from

$800

21

Bella Oasis Paradise found

Tobago / Mount Irvine

Mount Irvine apartment

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$201

Price per night from

$201

(2) Excellent 

23

Birdie's Nest Apt#2

Tobago / Black Rock

Black Rock apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Ask about children

Price per night from

$126

Price per night from

$126

(19) Excellent 

17

OCEANVIEW APARTMENT (POOL & BEACH ACCESS) with WIFI - Casa Cassini Tobago

Tobago / Scarborough

Scarborough apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Ask about children
“Totally chilled” We absolutely loved our stay at Casa Cassini. Our last few vacations we stayed at all-inclusive resorts and we were looking for a change from the locked-in environment. I was a bit apprehensive about staying in a guest house situation
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Price per night from

$135

Responds fast!
avg. 2 hours 39 minutes

Price per night from

$135

(5) Very Good 

51

Hummingbird Villa

Tobago / Grafton

Grafton villa

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 1 mi
  • Swimming pool
  • Child Friendly

Price per night from

$331

Price per night from

$331

27

Luciana: Light & Airy 4-Bedroom Home with Windows for Walls

Tobago / Mount Irvine

Mount Irvine villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$300

Price per night from

$300

14

Sunny Daze Villa

Tobago / Lowlands

Lowlands bungalow

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$300

Price per night from

$300

(1) Excellent 

14

Casa La Mancha - close to Mount Irvine Bay Golf Course

Tobago / Mount Irvine

Mount Irvine villa

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$496

Price per night from

$496

20

Mango Tango - A Holiday Home with A truly Authentic and Exotic Heart!

Tobago / Black Rock

Black Rock villa

5 9 min stay varies

  • 5 bedrooms
  • sleeps 9
  • min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$301

Price per night from

$301

10

Villa Colibri

Trinidad and Tobago / Tobago

Tobago villa

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$325

Price per night from

$325

(20) Excellent 

20

Mahogany Ridge, Elegant comfort,Pool, Ocean Views.

Tobago / Black Rock

Black Rock villa

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
“A great place to relax and unwind” I took some of my students here for a yoga retreat and we all enjoyed it very much. Towards the end we just did not want to leave. Even now, back in cold Germany, we are still sitting on the beautiful verandah enjoyi
…see more

Price per night from

$225

Price per night from

$225

(3) Average 

24

VOTED TOP 20 CONDE NAST CARIBBEAN VILLA - 74 STEPS TO BEACH - KIDS TRAVEL FREE

Tobago / Scarborough

Scarborough villa

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$875

Price per night from

$875

(31) Excellent 

29

Mary's Hill Lodge, Tobago

Trinidad and Tobago / Tobago

Tobago house

3 9 2 nights min

  • 3 bedrooms
  • sleeps 9
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
“A place for great family fun.” My sister and I took her six children all under the age of twelve and they had a blast. The pool was safe enough for the children since the deepest point was 5ft, they enjoyed all the board games and the beds were very c
…see more

Price per night from

$126

Price per night from

$126

10

Coral Breeze

Tobago / Crown Point

Crown Point villa

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$375

Price per night from

$375