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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.

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Guest favourite
A sparkling blue swimming pool is complemented by a relaxing jacuzzi. The pool area is surrounded by well-maintained landscaping and features elegant arch-shaped windows of a nearby building, creating a serene and inviting outdoor space.
Flat in Western Tobago
4.86 out of 5 average rating, 98 reviews

Stylish Getaway Near Beaches. Quiet. Pool. Jacuzzi

Enjoy comfort and privacy in this spacious, modern apartment set in a quiet, safe community close to beaches, dining and nightlife. Perfect for professionals or couples, the space features a queen-size bed, cozy living area with Smart TV, fast Wi-Fi, fully equipped kitchen, large bathroom with massage shower, hot water, and private balcony. Guests also enjoy access to a swimming pool and jacuzzi—ideal for relaxing after work or a day out. We look forward to helping you make your visit memorable.

Top guest favourite
An infinity pool glistens under a bright blue sky, with clouds casting soft shadows. Comfortable lounge chairs with umbrellas line the poolside, surrounded by lush greenery. The structure of the villa features large windows and a wooden overhang, blending seamlessly with the natural environment.
Flat in Bethel
4.99 out of 5 average rating, 140 reviews

Firefly Villa - 'Roots'

A spacious, modern, beautifully decorated home with a zen vibe and an inspiring location for working away from home. ‘Roots’ has two cozy double bedrooms, comfortable work spaces and fully-equipped kitchen with kitchen island, and deluxe double fronted fridge, en-suite bathrooms and wooden floors. Lie by the infinity pool and watch as a bright blue-grey tanager flies right over your head from one tree to the next. The perfect blend of treehouse and charming, stylish Caribbean poolside villa.

Guest favourite
The exterior of a modern villa is displayed, featuring a spacious upper balcony with white railings above large glass doors. Lush greenery surrounds the property, and a private pool is visible on the lower level, creating a serene outdoor atmosphere.
Villa in Lowlands
4.83 out of 5 average rating, 89 reviews

Sea View Villa Cluster 63A(2BR,Pool,Wifi,Golf)

Sea front villa with scenic entrance near the Magdalena Hotel with an international Golf Course. Minutes away from iconic beaches and shopping malls. Furnished, 2 bedrooms with upgraded ensuite bathrooms, open concept, and a private pool with sundeck on the ground floor of the duplex. Gated community(manned 24 hours) Fully air-conditioned along with ceiling fans & Netflix. Contains outside bathroom and utility room. * Maid service available at an additional charge.(Mandatory after 3nights)

Superhost
A comfortable sleeping area features a spacious bed with neatly arranged linens. Two bar stools are positioned at a small kitchenette in the background, enhancing the functional layout. Neutral and warm tones are present in the decor, complemented by a wall art piece.
Villa in Union
4.87 out of 5 average rating, 47 reviews

The Forest View at Robyn’s Nest

This stylish studio is designed for the utmost comfort of two guests, featuring contemporary furnishings and amenities. The highlight of the space is undoubtedly the view that seamlessly merges the indoors with the beauty of nature. Inside, you'll find a fully equipped kitchenette and a sleek bathroom for your convenience. Step into the shared pool or outside onto the open deck to bask in the gentle breeze and panoramic vistas, accompanied by the melodic tunes of the local birdsong.

Guest favourite
The pool area features a vibrant blue-tiled surface, illuminated by soft lights at night. A spacious deck surrounds the water, with a gazebo visible above, providing a cozy atmosphere. Lush plants are positioned near the water's edge, adding greenery to the scene.
Flat in Moriah
4.98 out of 5 average rating, 60 reviews

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!!!!!!

Guest favourite
An aerial view captures a spacious two-story building surrounded by greenery. The exterior features multiple windows and a simple design. A pool is visible in the yard, along with outdoor seating arranged on the patio. A low fence encloses the property.
Flat in Signal Hill
4.93 out of 5 average rating, 43 reviews

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.

Guest favourite
A modern villa is positioned along the coastline, featuring a saltwater pool adjacent to a spacious open area. The ocean can be seen in the background, while lounge chairs are arranged around the pool, creating an inviting outdoor space. Lush greenery surrounds the property.
Villa in Hope estates
4.93 out of 5 average rating, 28 reviews

"Malibu" in Tobago at the Ocean's Edge!

Think 'Malibu in Tobago' and you will know what it feels like to be welcomed into this luxurious penthouse villa at the ocean's edge. This stunning 3-bdrm villa located in Hope Estate, about a 10-min drive from the port in Scarborough, offers an unparalleled oceanfront experience with breathtaking views of the Atlantic and a salt water pool to make Malibu an even more enticing choice. All rooms are air-conditioned and minimally, yet beautifully, appointed with an ocean view.

Guest favourite
A communal living area features a spacious sectional sofa arranged around a central ottoman. Natural light fills the room through large windows, showcasing the modern kitchen in the background with wood cabinetry and high chairs at the island.
Home in Bon Accord
4.89 out of 5 average rating, 131 reviews

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.

Top guest favourite
An open-concept living area features a comfortable sectional sofa and a dining table set for six. Large windows with modern shades allow natural light to fill the space. A kitchen area with sleek cabinetry is visible in the background, providing a modern and functional environment.
Flat in Buccoo
4.9 out of 5 average rating, 58 reviews

Beachy Buccoo Bay Apartment

Welcome to your modern slice of island life. We’re pleased to host you and your group in our spacious apartment just 10 minutes driving from the airport. Beachy Buccoo is located on Level 1 in the building. Those of you who are non-hikers will know that level 1 is pretty much “a walk in the park” and that’s exactly what we are! Our easy access, ground floor location, assigned parking, makes offloading and escaping to the beach a breeze. Building 5, Apt 1B

Top guest favourite
Flat in Buccoo
5 out of 5 average rating, 25 reviews

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.

Guest favourite
A lush hillside is depicted, featuring tropical vegetation and palm trees along the coastline. The vibrant orange building sits atop the hill, overlooking the clear blue water. A wooden walkway meanders along the shore, providing access to the rocky edge of the ocean.
Apartment in Mount Saint George
4.95 out of 5 average rating, 81 reviews

The Oasis w/ private beach & great view #432211004

The Oasis is as the name suggests; an escape from the hustle and bustle in a space designed to replenish and renew your spirit and your senses. See the beauty of nature, feel the warmth of cooling breezes, taste excitement in our natural salt water pool and touch the heart of your loved one with whom you will share this sanctuary. The Oasis is located on a hillside and steps are provided to allow you to experience all that we have to offer.

Top guest favourite
A private pool is surrounded by well-maintained greenery and decorative planters. The pool features a smooth edge with stairs leading into the water, and the bright blue surface reflects the sky above. A storage tank is positioned discreetly in the background.
Home in Bon Accord
4.98 out of 5 average rating, 125 reviews

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.

Popular amenities for Scarborough rentals with a pool

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Avg. price$280 SGD$285 SGD$280 SGD$281 SGD$262 SGD$262 SGD$257 SGD$281 SGD$207 SGD$207 SGD$220 SGD$244 SGD
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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 $76 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