Holiday rentals with a pool in Signal Hill

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Top-rated rentals with a pool in Signal Hill

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost

Apartment

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.

LocationFamilyHospitality

4.84 out of 5 average rating, 108 reviews

Top Guest favourite

Condo in Buccoo

Buccoo Luxe Escape|3BR Condo w/Pool & Modern Charm

Welcome to Aurelia - a radiant escape where tropical serenity meets quiet luxury. Featuring warm natural finishes with sleek contemporary lines, Aurelia invites you to slow down and reconnect in refined comfort. This newly furnished 3-bedroom condo is artfully designed for families, friend groups, or long-stay guests seeking a luxurious escape close to beaches and island attractions. Relax in the open-plan living area with comfortable lounge seating and doors that open to your private balcony.

ValueLocationBathroom

5.0 out of 5 average rating, 28 reviews

Superhost

A comfortable living area features two gray sofas adorned with patterned throw pillows, positioned across from a light wooden coffee table. A decorative vase sits on the table, and a subtle area rug completes the space. A door and artwork are visible in the background.

Guesthouse in Scarborough

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.

LocationFamilyAccuracy

4.88 out of 5 average rating, 26 reviews

Superhost

The two-story villa features a warm orange exterior with arched balconies and a tiled roof. A freeform pool is visible in the foreground, accompanied by a spa. Several sun loungers are positioned around the pool, while lush greenery frames the property.

Home in Bon Accord

Casa Bon - a charming Bon Accord home

Casa Bon offers all the comforts you need in a Caribbean holiday home! It is conveniently located in the Bon Accord area and is walking distance to Store Bay and Pigeon Point - two of Tobago's most popular beaches. This charming Spanish-style villa is set in lush, tropical gardens and has four air conditioned bedrooms, three of which have ensuite bathrooms. The open plan living and dining rooms flow right onto the patio and pool deck complete with a free form swimming pool and attached spa.

LocationFamilyIndoor spaces

4.74 out of 5 average rating, 109 reviews

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

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)

LocationValueComfort

4.84 out of 5 average rating, 100 reviews

Top Guest favourite

A wrap-around balcony offers panoramic views of the sunset over lush tropical trees and the Caribbean Sea. Floor-to-ceiling glass doors line one side, inviting natural light and providing easy access to the outdoor space.

Apartment in Bethel

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.

ValueFamilyAmenities

4.97 out of 5 average rating, 183 reviews

Superhost

Villa

Nirvana Tobago 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 4000+ 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.

LocationFamilyNearby

4.8 out of 5 average rating, 111 reviews

Top Guest favourite

An exterior view of the multi-level building is presented, featuring a balcony and a pool in the landscaped yard. Red accents on the fence complement the white walls, while greenery surrounds the property, contributing to the tranquil ambiance of the area.

Apartment in Signal Hill

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.

ValueLocationAccuracy

4.96 out of 5 average rating, 24 reviews

Guest favourite

Home in Lambeau

Rosita with a Waterfall Jacuzzi & Rain Forest feel

Welcome to Rosita, your Caribbean retreat on the tropical island of Tobago. This holiday villa combines comfort, relaxation, and modern amenities, making it perfect for families or groups of friends seeking an unforgettable getaway. Rosita features an open-concept living and dining area designed for seamless indoor-outdoor living. The spacious living area includes comfortable seating and flat-screen TVs for both indoor and outdoor viewing, ensuring entertainment at every turn.

FamilyLocationBathroom

4.9 out of 5 average rating, 10 reviews

Superhost

A spacious kitchen area featuring wooden cabinets and modern appliances is visible, complemented by a dining table with chairs. A comfortable seating area includes a brown sofa, and a ceiling fan is mounted above. Light-colored tiles reflect the ambient lighting from overhead fixtures.

Apartment in Signal Hill

Sampson Suites - One-bedroom Loft Apartment A

Luxury one bedroom suite, with upper loft and private balcony overlooking the beautiful scenic adjacent park and recreational picnic site. Spacious living and a fully equipped kitchen, with one day bed. The master bedroom and full bath are located on the first floor, bedding is queen size. Accommodation that is ideal for a couple and one child. Nested in the hills, the area is quiet, relaxing, comfortable away from all the hustle and bustle, yet easily accessible.

FamilyValueCondition

4.82 out of 5 average rating, 45 reviews

Superhost

Home in Lambeau

Oceanview Townhouse · 4 Ensuites + Plunge Pool

A sophisticated ocean view townhouse with 4 private ensuite bedrooms, a private plunge pool & sweeping ocean balcony views. A property crafted for guests who expect more. Shore Things café steps away. Scarborough's harbour, restaurants & Tobago's best beaches are all within a 15 minute drive. • 4 Private Ensuites • Plunge Pool • Chef's Kitchen • High-Speed WiFi • Panoramic Ocean Views A refined retreat for an elevated Tobago experience. See other notes.

FamilyLocationNearby

4.75 out of 5 average rating, 20 reviews

Top Guest favourite

A bright living and dining area is featured, with large windows allowing natural light to fill the space. A comfortable gray sectional couch and a light-colored coffee table are positioned in front of a television. A dining table with chairs and artwork on the wall add to the inviting ambience.

Apartment in Black Rock

Sunset on the ocean

This apartment is unique in the Tobago short term rental space. Brand new, stylish "island chic" place offers ocean views and is right above one of the most stunning Tobago beaches. You have ample space for your family or as friends to enjoy spacious living and dining space, top of the art kitchen. The two bedrooms and 2.5 bathrooms give you the space to enjoy this calm yet very well located new spot.

ValueFamilyComfort

4.95 out of 5 average rating, 57 reviews