
Holiday rentals with a pool in Scarborough
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Scarborough
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

1st floor private apartment
Welcome to Palm Breeze Villa — ideal for couples and small families. A tropical escape on the edge of Crown Point. Just a short stroll away are two of Tobago’s most stunning beaches: Pigeon Point and Store Bay. Spend your days soaking up the sun, swimming in crystal-clear waters, and your evenings enjoying breathtaking sunsets at Store Bay. We’re also within a 5-minute walk to grocery stores and a strip of restaurants and bars, making it easy to enjoy the best of local flavor and nightlife.

Carlton’s Haven at Robyn’s Nest
Carlton’s Haven at Robyn’s Nest Tucked away in the tranquil village of Union, Tobago, Carlton’s Haven is a modern two bedroom, two bath, condo style duplex designed to make you feel completely at ease. Surrounded by lush greenery, the soothing sounds of birds, and cool island breezes, it’s your perfect escape into nature while still enjoying contemporary comfort and style. A 5-minute drive from Scarborough our capital putting local markets, beaches, and cultural gems right at your fingertips.

BACOLET BLISS
Perfectly nestled amongst the trees, with just a few short steps to reach the warm and inviting Atlantic ocean, a slice of paradise awaits you. Come to our hidden 3+ bedroom escape! Lose yourself within the lush greenery and the cool waves of the ocean. There's a taste of everything natural here, from the sweet sounding birdsong at the first rays of dawn that lingers beyond the last wisps of twilight, to the remarkable sunrises and luminous star studded nights. Welcome to a great vacation!

Firefly Villa - 'Treetop'
Combining luxury and comfort, is any holidaymakers dream, romantic getaway for couples or an ideal space for working away from home. Open-plan floor to ceiling sliding glass doors that open out onto a wrap-around balcony, elevates outdoor living to a whole new level. Admire the stunning views of the Caribbean Sea and Buccoo reef or look down at the treetop canopy and watch the exotic tropical birds fly by. Peaceful, relaxed and inspiring. Contemporary comfort - timeless Caribbean charm.

HOUSE IN THE MOUNTAIN! APARTMENT 1
A home away from home.....that comfortable relaxed feeling. Wake up to fresh air, and the sound of Tobago birds, including the Cocorico. Feel like listening to music......there is a Bluetooth speaker available! Feel like television.......Direct TV is available! Feel like swimming and lounging - check out our pool and our floating breakfast - or - the beaches are not far away. Feel for entertainment....you can book our preferred entertainer!.....SAXOPHONIST......RICARDO SEALES!!!!!!

Apas On The Hill: One Bedroom Apartment 2
Welcome to "Apas On The Hill". Nestled in the quiet Signal Hill area, we are located approx. 4 Kms from the sea port at Scarborough and 11 Kms from the ANR Robinson International Airport. Enjoy peace and tranquility while being in a safe, private and comfortable environment. Our rooms (apartments) are cozy, yet elegant, spacious and comfortable. Each apartment comes with a fully equipped kitchen, outfitted with modern appliances, Wi-Fi, hot and cold water, cable TV, linen and towels.

The House of Serenity, Play & Family
This place is perfect for a small or relatively large group. It is equipped with a fully-functional modern-styled kitchen, a spacious communal area, a family-friendly pool and beautiful garden. The place is situated in a secured gated community in lively Crown Point! We are also located close to the airport (5 mins drive), beaches (e.g. Pigeon Point - the #1 attraction in Tobago!), restaurants, bars, shops, grocery stores and ATMs (bank) for all your needs and amenities.

Island breeze penthouse
Forget your worries in this elegant, beautiful and relaxing space. Our penthouse is located at Building 9, Apartment 4D. Sip your coffee in our balcony while enjoying the morning island breeze and a view of the pool. You will find delicious doubles just in front of the compound and the best chicken sandwich from Block 22. Enjoy both pools, one in the morning and the other in the evening. There is a gym, one minute away, next to to the food court.

Paradise Place Apartments. Close to everything!
Spacious, modern, elegantly decorated apartment close to everything & away from the noise! Surrounded by views of the hillside, the apartment is equipped with queen sized bed, sofa in the living room, smart tv, large bathroom with massage shower, fully equipped kitchen, balcony, hot water, wifi, swimming pool and jacuzzi. Ideal for a couple looking for relaxation. Close access to beaches and night life. Apartment is located in a safe community.

Buccoolito 2B - Modern Condo w/Pool | Near beach
Comfort, convenience, and island charm await at Buccoolito 2B Enjoy this 2-bedroom, 2-bathroom modern condo with a fully equipped kitchen and a perfect view of the pool. Located in a secure, gated development with 24/7 security, Buccoolito 2B is just 15 minutes from both the airport and the ferry terminal. Centrally located, minutes away from the Picturesque Buccoo Beach and 15 minutes drive to the Popular Pigeon Point Beach and Store Bay Beach.

Villa Magnolia
This cozy duplex is located just walking distance from both the airport and the world famous Pigeon Point beach. You can also enjoy several varieties of food just minutes away from this villa. Guests are sure to enjoy a memorable vacation in this fully furnished, cozy 3 bedroom villa, each with its individual bathroom with a powder room located on the main floor. The villa also includes a private pool.

Mary's Hill Guest house
Introduction This beautifully built wooden lodge is situated on a hillside off the quiet Scarborough to Plymouth road. It looks out over mature trees across the valley to the green hills on the other side, and at the rear of the premises there’s a garden laid to lawn with pretty shrubs, at the top of which is a chain link fence and a line of palms giving privacy to the house, its garden and pool.
Popular amenities for Scarborough rentals with a pool
House rentals with a pool

Couple’s hideaway, Castara

Villa Narain, Tobago

Plymouth View Villa: 2br & Pool

Villa Delphinae

Stylish Oceanview Townhouse in Tobago

Beautiful villa nr Castara & beach

Eagle's Base Villa with Spectacular Views-12-22

Villa Escalante TBGO Lower Level
Apartment rentals with a pool

Lovely loft condo with pool access

3 BR-Relaxing Spa Tub+Close to Beaches & Eats

Tobago Plantations penthouse: pool beach and golf

Dream Island Condo Tobago 2 BedR, 2 BathR, 2 Pools

Private Saltwater Pool Lovely 2 bedroom Suite

Hibiscus Suite at Black Rock Dreams

Buccoo Escape - 2 bedroom cozy condo near beach

Romantic One Bedroom Apartment right on the beach
Other holiday rentals with a pool

Welcome to your "Paradise Villa"...come and enjoy

Signal Hill - Upstairs One Bedroom Apartment

Palm Haven - Home away from home

Bay Apartment at Sandy Point

177 Sea Shell Villa, Tobago W.I.

Cozy apartments pool side

TheFairway:6BRFamilyVilla(20-26ppl),Pool,Slide,Spa

Villa Blue Moon
When is the best time to visit Scarborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $288 SGD | $293 SGD | $288 SGD | $289 SGD | $269 SGD | $269 SGD | $264 SGD | $289 SGD | $213 SGD | $263 SGD | $285 SGD | $282 SGD |
| Avg. temp | 27°C | 27°C | 27°C | 28°C | 29°C | 28°C | 28°C | 28°C | 29°C | 28°C | 28°C | 27°C |
Quick stats about holiday rentals with a pool in Scarborough

Total holiday rentals
Explore 40 holiday rentals in Scarborough

Nightly prices starting at
Scarborough holiday rentals start at $65 SGD per night before taxes and fees

Verified guest reviews
Over 410 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 of Scarborough holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Scarborough rentals

4.5 Average rating
Scarborough stays receive an average rating of 4.5 out of 5 from guests
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