Vacation 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 favorite

Apartment in Plymouth

4.9 out of 5 average rating, 81 reviews

Cabanas 3 with Private Gazebo; Walk to Beach

Cabana 3 at Top O’Tobago is ideal for a couple on a romantic getaway, a young family, or a group of 4 singles on a weekend adventure. It is a studio apartment with a dining gazebo and garden. It is the lowest of our 3 cabanas with level access to parking and steps away from the swimming pool. 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.

Oct 31 – Nov 7

€ 125 per night

Guest favorite

Apartment in Bethel

4.99 out of 5 average rating, 101 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.

Sep 7 – 14

€ 166 per night

Superhost

Villa in Mt.Irvine

4.76 out of 5 average rating, 72 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.

Mar 28 – Apr 4

€ 141 per night

Guest favorite

Villa in Tobago

4.87 out of 5 average rating, 69 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.

Mar 28 – Apr 4

€ 566 per night

Guest favorite

Home in Mt. Irvine

4.93 out of 5 average rating, 68 reviews

Joie de Vivre - a bright and airy holiday retreat

With a large open plan living room, dining room and kitchen area, and folding doors that lead to a spacious pool deck, Joie de Vivre is the perfect villa for a family holiday or as we say in Trinbago 'ah bess lime'. The large, tiled pool is always inviting and poolside BBQs are an absolute must. There are 5 air conditioned bedrooms, three of which lead out to the upstairs verandah which has a view of the famous Buccoo Reef. Grab your morning coffee, sit outside and just take it all in.

Apr 4 – 11

€ 388 per night

Guest favorite

Apartment in Moriah

4.98 out of 5 average rating, 45 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!!!!!!

Apr 23 – 30

€ 59 per night

Guest favorite

Villa in Crown Point

4.95 out of 5 average rating, 21 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

Apr 2 – 9

€ 452 per night

Guest favorite

Condo in Mount Saint George

4.96 out of 5 average rating, 55 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.

Nov 25 – Dec 2

€ 121 per night

Superhost

Bungalow in Tobago

4.9 out of 5 average rating, 41 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.

May 14 – 21

€ 200 per night

Guest favorite

Apartment in Mt Irvine

5.0 out of 5 average rating, 31 reviews

'LITTLE OASIS' Luxury Apartment, Mt Irvine, TOBAGO

LITTLE OASIS, situated on one of the prettiest two-acre private estates at Mt Irvine, Tobago, is just 20 mins. drive from the Airport and 30 mins. from the Ferry Terminal. Neighboring the Mt Irvine beach facilities and Golf Course, you'd love being conveniently positioned to many handy amenities and to some of the best beaches this side of the Caribbean Sea.

Aug 11 – 18

€ 116 per night

Guest favorite

Bungalow in Lowlands

4.91 out of 5 average rating, 55 reviews

Ocean Front Cottage, Petit Point

My place is right on the ocean, and close to a golf course and restaurants. You’ll love it because of the outdoor space, the neighborhood, the ambiance, and the fact that it's on the sea. It's safe and secure, and is next to kayaking, stand up paddling, walking, jogging. My place is good for couples, business travelers, and families (with kids).

Nov 17 – 24

€ 385 per night

Guest favorite

Apartment in Crown Point

4.87 out of 5 average rating, 60 reviews

Beachfront Cabana, Crown Point Beach, Tobago

Relaxing destination for those who love a white sandy beach, expansive grounds to exercise or just enjoy an evening stroll. Witness romantic sunsets and enjoy the clear night skies lit up with stars while sipping on your favourite drink. Ideal for couples. This location is close to all amenities including the airport.

Apr 16 – 23

€ 144 per night