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Holiday rentals with a pool in Plymouth

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Plymouth

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

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Guest favourite
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
5 out of 5 average rating, 5 reviews

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.

Top Guest favourite
A lush garden is seen with vibrant banana plants and a variety of trees, leading to a serene outdoor area. A calm pathway guides the view down to a swimming pool, while colorful seating options invite relaxation amidst the greenery, with the ocean visible in the background.
Home in Scarborough
5 out of 5 average rating, 61 reviews

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!

Superhost
The villa exterior is showcased under a starry night sky, with a tranquil saltwater pool reflecting the lights of the structure. Surrounding lounge chairs are arranged by the poolside, and vibrant wall art adds character to the setting.
Villa in Tobago
4.79 out of 5 average rating, 99 reviews

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.

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
4.97 out of 5 average rating, 177 reviews

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.

Top 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.
Apartment in Signal Hill
4.95 out of 5 average rating, 42 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.

Top Guest favourite
A spacious bed is dressed with crisp white linens, complemented by colorful decorative pillows featuring floral patterns. A soft lamp with an intricate base sits beside the bed, and gentle light filters through the light-colored curtains.
Apartment in Moriah
4.97 out of 5 average rating, 59 reviews

HOUSE IN THE MOUNTAIN! APARTMENT 2

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
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
4.95 out of 5 average rating, 21 reviews

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.

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
4.9 out of 5 average rating, 123 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.

Superhost
A serene view captures the sun setting over the ocean, with soft golden hues reflecting on the infinity pool. A gentle fountain feature adds a calming element, framed by lush greenery and natural stone decking.
Apartment in Black Rock
4.77 out of 5 average rating, 44 reviews

Condo on the BEACH

This apartment is horizontal with the house as it is frontier towards the beach. The verandah has a top tier view of the ocean and pool. Entering into the living room and kitchen which is more of the garden view. The bed room have a beautiful view over looking the infinity pool and the ocean back drop. The apartment consists of dual colors to create a clam and peaceful ambience as to keep a cool comfort feeling. Please note the pools is shared with two other units.

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
4.97 out of 5 average rating, 35 reviews

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.

Superhost
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
4.87 out of 5 average rating, 54 reviews

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.

Guest favourite
A secluded pool area is framed by a well-maintained deck featuring sun loungers and an umbrella. The wooden lodge is visible in the background, surrounded by lush greenery, enhancing the serene atmosphere. The pool's clear blue water invites relaxation under the sunny sky.
Guesthouse in Arnos Vale
4.82 out of 5 average rating, 17 reviews

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 Plymouth rentals with a pool

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Avg. price$233 NZD$233 NZD$256 NZD$268 NZD$268 NZD$230 NZD$206 NZD$206 NZD$202 NZD$208 NZD$208 NZD$218 NZD
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Quick stats about holiday rentals with a pool in Plymouth

  • Total holiday rentals

    Explore 40 holiday rentals in Plymouth

  • Nightly prices starting at

    Plymouth holiday rentals start at $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 510 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Plymouth holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Plymouth rentals

  • 4.7 Average rating

    Plymouth stays receive an average rating of 4.7 out of 5 from guests