
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.

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.

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!

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.

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.

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.

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!!!!!!

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.

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.

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.

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.

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.

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
House rentals with a pool

Villa Delphinae

Miles Away - for lovers of sunsets & sea views

Stylish Oceanview Townhouse in Tobago

Villa Escalante TBGO Lower Level

Suncoast Villa

Bago Beach Vacays: Oceanfront - scale to 38 guests

Infinity - Seafront villa with stunning views

TheNest:5BR Family Villa(16 ppl),Pool,Garden,Swing
Condo rentals with a pool

Lovely loft condo with pool access

Tobago Plantations penthouse: pool beach and golf

Dream Island Condo Tobago 2 BedR, 2 BathR, 2 Pools

Private Saltwater Pool Lovely 2 bedroom Suite

Buccoo Escape - 2 bedroom cozy condo near beach

Hibiscus Suite at Black Rock Dreams

Romantic One Bedroom Apartment right on the beach

Golf View Villa 41A (Lower Level)
Other holiday rentals with a pool

KartHouse Vacation Inn

2 BR steps to the beach, & pool.

Pleasant Cove: Luxe Villa w. Private Beach

Bay Apartment at Sandy Point

Cabanas 3 with Private Gazebo; Walk to Beach

177 Sea Shell Villa, Tobago W.I.

Villa Blue Moon

Buccoo Homes II 9.4C
When is the best time to visit Plymouth?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 27°C | 27°C | 27°C | 28°C | 29°C | 28°C | 28°C | 28°C | 29°C | 28°C | 28°C | 27°C |
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
Destinations to explore
- Isla de Margarita Holiday rentals
- Tobago Holiday rentals
- Lecherías Holiday rentals
- Bridgetown Holiday rentals
- Fort-de-France Holiday rentals
- Les Trois-Îlets Holiday rentals
- Port of Spain Holiday rentals
- Bequia Island Holiday rentals
- Sainte-Anne Holiday rentals
- Sainte-Luce Holiday rentals
- Les Anses-d'Arlet Holiday rentals
- Holetown Holiday rentals