Holiday rentals with a pool in Plymouth

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.

Family · Location · Walkability

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.

Location · Value · Amenities

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.

Location · Family · Wi-Fi

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)

Family · Value · Quiet

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.

Value · Family · View

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.

Value · Family · Accuracy

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.

Family · Value · Beach

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

Family · Value · Condition

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.

Family · Location · Checkout

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.

Family · Location · Pool

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.

Location · Family · Pool

177 Sea Shell Villa, Tobago W.I.

Private home with three bedrooms with AC and in rooms toilet and bath. All amenities for cooking, washing, Wi-Fi. Large outdoor pool and located five minutes from airport. Easy walk to beaches, shopping, banking, eating. Property recently painted and renovated February 2025

Value · Location · Getting around