Vacation rentals with a pool in Plymouth

4.84 out of 5 average rating, 108 reviews

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.

5.0 out of 5 average rating, 28 reviews

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.

4.74 out of 5 average rating, 109 reviews

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.

4.84 out of 5 average rating, 100 reviews

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)

4.97 out of 5 average rating, 183 reviews

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.

4.8 out of 5 average rating, 111 reviews

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.

5.0 out of 5 average rating, 6 reviews

Villa in Mt. Irvine

TheCasaVilla 7Bdrm, 27ppl, Sunsets, Pool, Theatre

Sunsets hit perfectly from the hilltop. The Casa Villa is our newest flagship, a 7-bedroom luxury villa perched above Mt. Irvine with sweeping Caribbean views, an infinity pool that spills toward the sea, and a private theatre & games room. Sleeps up to 27 across seven beautifully appointed bedrooms, built for family reunions, milestone birthdays, destination weddings & corporate retreats. Minutes from Mt. Irvine Beach, Stonehaven Bay & Pigeon Point. With a focus on large groups.

4.92 out of 5 average rating, 25 reviews

A vibrant sunset paints the sky with shades of orange and purple above a lush green landscape. The view encompasses the distant ocean and various trees, with a spacious villa and neighboring structures positioned in the foreground.

Home in Plymouth

Plymouth View Villa: 2br & Pool

Bring the whole family to this great place with lots of room for fun. Our lovely villa in the serene paradise of Tobago is the perfect retreat! It offers a peaceful location where you can relax and unwind with your loved ones. One of the highlights of our villa is the wrap balcony, offering glimpses of the ocean in the distance. It's the perfect spot to savor your morning coffee or enjoy an evening cocktail while witnessing breathtaking sunsets that will leave you in awe.

4.87 out of 5 average rating, 62 reviews

The inviting pool area features a circular pool surrounded by a stone patio, with lounge chairs and umbrellas providing shade. Lush greenery and tall trees create a natural backdrop, enhancing the serene outdoor space. A gazebo adds to the charm, offering a shaded seating area.

Villa in Tobago

Mock Turtle is an Enchanting & Affordable Escape!

This delightfully charming one-level holiday home is graced with high ceilings and tastefully furnished in island style. Mock Turtle has three (3) en-suite bedrooms, a well-equipped full kitchen, and a well-maintained landscaped garden. The open plan living and dining area lead out to the pool and sun terrace - perfect place for relaxing and watching the sunset. Perfect for families and small groups.

4.95 out of 5 average rating, 57 reviews

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.

4.94 out of 5 average rating, 130 reviews

The covered porch area features wooden lounge chairs, inviting relaxation. A backdrop of lush greenery and the tranquil bay is visible beyond the railing, where palm trees sway gently. The patio flooring is wooden, enhancing the natural ambiance.

Cabin in Parlatuvier

Tamarind House Villa Parlatuvier

Tamarind House Villa is situated on the leeward coast of Tobago in the beautiful fishing village of Parlatuvier. It is suitable for small groups, couples and families who enjoy a relaxed lifestyle away from commercial tourist areas. The villa overlooks the bay on one side and pristine tropical rainforest on the other. Guests will have sole occupancy of the house, pool and gardens.

4.82 out of 5 average rating, 99 reviews

A tranquil pool area is set against a colorful sunset sky, highlighting the serene water surface. Lush greenery and scenic trees frame the space, while blue railings and a small spa are visible nearby, creating a peaceful outdoor setting.

Villa in Mt. Irvine

Expansive deck! Luxurious super king beds!

Windance is a Spanish style villa set in the hills of Mt Irvine. Relax and enjoy the pool and extensive deck area, lush gardens and permaculture farm. We are very close to the beach and other activities, should you be looking for some laid back beach time or an adventure filled day out on the water.

Popular amenities for Plymouth rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 136 reviews

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

Villa Magnolia

4.81 out of 5 average rating, 43 reviews

A shaded pool area features a spacious in-ground pool with calm blue waters, accented by a rock feature. Two lounge chairs are positioned beside the pool, while panoramic sea views and lush greenery surround the space, creating a serene outdoor environment.

Home in Castara

The Wood House

4.62 out of 5 average rating, 21 reviews

An infinity pool extends towards the horizon, appearing to merge with the Atlantic Ocean. The clear blue water reflects the bright sky, while palm trees are visible along the edges. Soft waves are gently lapping at the distant water surface.

Home in Bacolet

Infinity - Seafront villa with stunning views

4.75 out of 5 average rating, 20 reviews

Home in Lambeau

Oceanview Townhouse · 4 Ensuites + Plunge Pool

5.0 out of 5 average rating, 18 reviews

Two comfortable chairs are positioned on a tile patio, overlooking a scenic ocean view. Lush greenery surrounds the area, and a vibrant blue sky with scattered clouds enhances the relaxing atmosphere. The infinity pool is visible, seamlessly blending with the horizon.

Home in Golden Grove

Oceanview Villa w/ Infinity Pool

4.94 out of 5 average rating, 31 reviews

A serene swimming pool is framed by a smooth patio, where several loungers invite relaxation. Lush greenery surrounds the area, enhancing the peaceful atmosphere of the outdoor space.

Home in Canaan

Sea Glass Villa Tobago-sleeps 12

5.0 out of 5 average rating, 16 reviews

Home in Lowlands

New 5-BR Villa Pool • Cine • Gym • Beach • Private

4.9 out of 5 average rating, 50 reviews

A large outdoor pool is surrounded by sun loungers positioned on a tiled patio. Lush vegetation and palm trees frame the scene, with a partially shaded area provided by the villa's roof. A clear blue sky is visible overhead.

Home in Castara

Beautiful villa nr Castara & beach

Condo rentals with a pool

4.85 out of 5 average rating, 89 reviews

A shared pool is framed by a stone patio, reflecting the nearby condominium. Lush greenery and ornamental plants enhance the surroundings. The modern two-level building in the background features multiple balconies and large windows, allowing for natural light to illuminate the interior spaces.

Condo in Buccoo

Island Getaway - Buccoo. 3 bedroom condo, sleeps 6

5.0 out of 5 average rating, 23 reviews

Condo in Golden Grove

Pearl | Pool · Beaches · Buccoo· 8 Mins to Airport

4.78 out of 5 average rating, 92 reviews

The two-story villa features a spacious terrace with a private plunge pool surrounded by tropical greenery. A dining table and chairs are positioned on the terrace, offering a place for outdoor relaxation. The well-maintained exterior includes large windows and a barbecue area.

Condo in Lowlands

Austin Tobago Retreat - Villa 41A (Lower Level)

Condo in Mount Saint George

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.

The Oasis w/ private beach & great view #432211004

4.94 out of 5 average rating, 84 reviews

5.0 out of 5 average rating, 5 reviews

The exterior of the property features a modern triangular roofline with a mix of light-colored stone and painted walls. Large windows are situated symmetrically along the front, showcasing a balanced architectural design. A spacious entrance is highlighted by a stone accent wall.

Condo in Lowlands

Lovely 6 Bedroom Villa Saltwater Pool 24 Guests

4.91 out of 5 average rating, 11 reviews

The inviting swimming pool reflects the colors of the sunset, surrounded by a spacious patio. A covered seating area is visible in the background, with palm trees framing the scene. The calm water enhances the tranquil ambiance of the hotel grounds.

Condo in Crown Point

Romantic One Bedroom Apartment right on the beach

5.0 out of 5 average rating, 25 reviews

Condo in Buccoo

Buccoo Escape - 2 bedroom cozy condo near beach

4.36 out of 5 average rating, 11 reviews

A refreshing swimming pool is surrounded by a landscaped area and features lounge chairs for relaxation. Nearby, a gazebo with a white frame provides a shaded seating area. Two-story yellow buildings are visible in the background, under a clear blue sky.

Condo

TPL Condo Tropicana 26A

Other vacation rentals with a pool

Guesthouse in Scarborough

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.

Carlton’s Haven at Robyn’s Nest

4.88 out of 5 average rating, 26 reviews

4.89 out of 5 average rating, 72 reviews

A two-story yellow house is set on a lush landscape, featuring palm trees and vibrant flora. A curved driveway leads to the entrance, framed by a decorative gate. Balconies are visible on the upper level, surrounded by greenery.

Apartment in Black Rock

2 BR steps to the beach, & pool.

5.0 out of 5 average rating, 39 reviews

A modern dining area features a wooden table surrounded by six light-colored chairs. A decorative plant sits at the center of the table. A large framed image of a turtle swimming above coral decorates the wall, adding a coastal touch to the space.

Apartment in Buccoo

Buccoolito 2B - Modern Condo w/Pool | Near beach

5.0 out of 5 average rating, 21 reviews

An inviting infinity pool is centered in the image, with a circular jacuzzi adjacent to it. Palm trees sway gently in the background, while a grassy area extends towards the ocean beyond. A gazebo is positioned to the side, enhancing the outdoor relaxation space.

Villa in Lowlands

Pristine Villa Tobago

4.8 out of 5 average rating, 51 reviews

Apartment in Black Rock

Condo on the BEACH

4.94 out of 5 average rating, 48 reviews

The exterior of the villa is presented, featuring a sloped roof and vibrant orange window frames. A green wooden fence encloses the property, complemented by neatly trimmed hedges and a manicured lawn, which adds to the welcoming ambiance of the gated community.

Villa in Canaan, Tobago

Cardinal Villas Tobago-Bram Villa, Samaan Grove

4.98 out of 5 average rating, 86 reviews

A spacious living area is characterized by modern furnishings, featuring a navy blue sectional sofa with decorative pillows. A coffee table sits atop a woven area rug, and natural light floods the space through ceiling windows, illuminating the open layout that connects to the kitchen.

Villa in Crown Point

Villa Blue Moon