Vacation 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 favorite

Villa in Arnos Vale

5 out of 5 average rating, 19 reviews

Top O' Tobago Villa & Cabanas: Entire Property

With room to sleep 18, Top O Tobago is ideal for family reunions. It consists of a 3 bedroom house, 3 cabanas (studio apartments), and a large pool on 6 acres of hilly terrain. You can walk to Arnos Vale Beach, one of the island’s best snorkeling beaches, and it is a 25 min. drive to the airport and the many tourist activities on Tobago’s south. Silja, our manager, lives onsite. Since each of the main house and cabanas can be rented separately there is flexibility to accommodate smaller groups.

Guest favorite

Rental unit in Bethel

4.99 out of 5 average rating, 115 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.

Superhost

Villa in Lowlands

5 out of 5 average rating, 8 reviews

Ti Marie - Caribbean luxury with golf course views

Presenting Ti Marie; a bright, spacious villa perfect for your Tobago getaway. Set in the beautiful Tobago Plantations Estate, Ti Marie overlooks the luxurious greens of the Madgalena Golf Course where you can still hear the crashing waves from Little Rockly Bay. The villa offers all the amenities needed for a comfortable stay, including a heated pool and is located a short drive away from many of Tobago's most popular beaches and eateries. Mt Irvine ~ 12mins drive Pigeon Pt ~ 20mins drive

Guest favorite

Villa in Lowlands

4.94 out of 5 average rating, 32 reviews

Villa Yemanjá

Named after the Brazilian goddess of the sea, Yemanjá is a luxurious oceanfront villa located in the prestigious Tobago Plantations Estate. The colonial style architecture of the villa is enhanced by a lush landscaped tropical garden. Balinese inspired decor soothes the senses. The property features four en-suite bedrooms, a double bed loft and a maid’s quarters, comfortably sleeping 11. A spaciously covered patio opens out onto an infinity swimming pool, heated Jacuzzi and pebble beach.

Guest favorite

Rental unit in Western Tobago

4.79 out of 5 average rating, 68 reviews

Pool View Apartment. Close to everything!!!

Be COVID Free! Have a fear of contracting COVID whilst on vacation?Then this is the correct accommodation for you! Spacious, modern, elegantly decorated studio. Close to all major sites and attractions but away from overly crowded spaces. Apartment is equipped with a queen sized bed, sofa, smart tv, large bathroom, fully equipped kitchen, hot water, wifi, swimming pool and much more! Ideal for short or long term stays and for couples looking for time away. Come enjoy relaxation in style.

Superhost

Villa in Mt.Irvine

4.75 out of 5 average rating, 93 reviews

Villa La Hay in Mt Irvine with Stunning Ocean View

This beautiful Tobago Villa is located in the wonderful area of Mount Irvine on a private, secluded cul-de-sac above the Mount Irvine Golf Course. This Mexican-Style Villa boasts stunning panoramic views overlooking the Golf Course and Caribbean Sea. Enjoy the peace and quiet of the Villa while listening to exotic birds and watch the breath taking sunset that follows you where ever you go from your very own panoramic balcony. Be sure to soak in the immense garden filled with tropical life.

Guest favorite

Villa in Tobago

4.88 out of 5 average rating, 80 reviews

Nirvana Luxury Villa Saltwater Pool & Ocean View

Nirvana Tobago is a luxurious Private Villa on the Caribbean coast with Ocean Views. Ample alfresco dining space, poolside cabana bar and saltwater pool. Over 6000+ sq. ft residence is graced with 12-foot ceilings and skylights. Interiors feature a chef kitchen and well-appointed bedrooms with ensuite bathrooms, no better place to restore your sense of bliss! Perfect for weekend getaways, extended stays and remote working. We have fast and reliable wifi and laptop friendly workspaces.

Guest favorite

Villa in Union

4.95 out of 5 average rating, 20 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 favorite

Rental unit in Signal Hill

4.94 out of 5 average rating, 17 reviews

Apas On The Hill: One Bedroom Apartment 1

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 favorite

Villa in Hope estates

5 out of 5 average rating, 7 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 favorite

Villa in Crown Point

4.97 out of 5 average rating, 36 reviews

Villa Blue Moon

Make memories at this unique and family-friendly place. A 4 bedroom 10 person villa located in secured compound close to beaches, bars and restaurants. With fun activities such as pool table, basketball, heated jacuzzi, swimming pool, 3 televisions, modern fully equipped kitchen, laundry room with washer & dryer, comfortable family room and Hi-Fi stereo system. A playful, open and entertaining home to feed your senses, to enjoy and unwind as you will

Guest favorite

Condo in Mount Saint George

4.97 out of 5 average rating, 71 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.