Holiday rentals with a pool in Tobago

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Top-rated rentals with a pool in Tobago

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

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Guest favourite

Apartment in Tobago

4.9 out of 5 average rating, 31 reviews

Premium Condo Accommodation at Tobago Plantations

Located in the prestigious gated community of Tobago Plantations. This location is great with 10 minutes drive to Pigeon Point, Store Bay, restaurants, shops and nightlife in Crown Point. Condo is fully furnished with great amenities. Two large bedrooms with two queen size beds in each room. To accommodate 8 guests. Access to three (3) shared pools, twenty four hour security, view of ocean and golf course, dedicated parking, high speed internet and Netflix on (3) 65" flat screen televisions.

Guest favourite

Villa in Tobago

4.9 out of 5 average rating, 21 reviews

Fair View Villa-A rustic home in tropical gardens

If you're booking your trip to Tobago for a much needed getaway, you can find refuge at Fair View! This 4-bedroom home is on very private and peaceful grounds where you're surrounded by mature fruit trees and tropical foliage, giving you that true Caribbean relaxed vibe. When you're all rejuvenated after your morning coffee/evening cocktail by the pool overlooking the Mt. Irvine golf course, take a gentle stroll to one of the stunning, nearby beaches- Buccoo Bay, Grange Bay, or Mt. Irvine Beach.

Guest favourite

Flat in Plymouth

4.91 out of 5 average rating, 86 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.

Guest favourite

Villa in Canaan

4.93 out of 5 average rating, 29 reviews

Heart Villa:5BR FamilyRetreat,Sleeps15,Pool,Garden

The Heart Villa in Samaan Grove, a tropical paradise with a unique heart-shaped pool ideal for groups and family gatherings. Located near all the beautiful beaches. This 5 Bedroom villa combines luxury with tropical elegance, featuring an open-plan indoor and outdoor living areas that open to a stunning pool, offering Caribbean views and breeze. Equipt rooms with en-suite baths and air conditioning. Enjoy a large gazebo with outdoor TV & BBQ area, and full amenities for a comfortable stay.

Superhost

Apartment in Lowlands

4.7 out of 5 average rating, 120 reviews

Tobago Plantations penthouse: pool beach and golf

17B Penthouse overlooks the Atlantic Ocean and golf course of Tobago Plantations Golf and Beach Resort — the island’s top resort with acres of pristine land and lakes, and an amazing boardwalk through the mangrove. Our airy condo features a bedroom, bathroom, living space, full kitchen and two scenic patios - the perfect cozy setting for your Caribbean getaway. The condo is ideally located for golfing, exploring the island, relaxing and taking in the gorgeous views of Tobago.

Superhost

Villa in Canaan

4.85 out of 5 average rating, 27 reviews

Sea Sea Zeb Villa #113

Sea Sea Zeb is a beautiful family vacation villa, with 4 gorgeous bedrooms all conveniently designed with ensuite bathrooms. The villa has a spacious layout and design, where guests can enjoy their own room and private bathroom when relaxing in their personal space. When the team gets together to lime, you'll enjoy the open-plan kitchen and living room, which leads out onto the pool deck and private swimming pool. Swim in the 12'x 28' pool. It has 3 depths 18", 32" and 54"

Superhost

Home in Plymouth

4.94 out of 5 average rating, 16 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

Home in Bon Accord

4.92 out of 5 average rating, 106 reviews

La Casa de Serenidad, Juego & Familia

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

Flat in Black Rock

4.77 out of 5 average rating, 39 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

Home in Canaan

4.9 out of 5 average rating, 20 reviews

Flamingo Villa Tobago-sleeps 14

Experience the epitome of elegance and luxury in this stunning 4-bedroom villa, nestled within a serene and secure gated community. Ideally located just moments from the airport and pristine, sun-kissed beaches, this exquisite retreat offers the perfect blend of sophistication, comfort, and convenience. For larger groups, the adjacent Sea Glass Villa—accessible via a private gated entrance—offers an exceptional opportunity to expand your accommodations.

Guest favourite

Apartment in Mount Saint George

4.95 out of 5 average rating, 79 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.

Guest favourite

Flat in Crown Point

4.87 out of 5 average rating, 45 reviews

Modern studio on Crown Point strip- Suite

Enjoy a stylish experience at this central location. This 1 bedroom can accommodate 4 persons, with 2 double beds , 1 bathroom and 1 kitchenette. Each room has a private hot tub with resort pool access. Our units are located in the heart of Crown Point next to all of the major bars, restaurants and beaches. Walk to Jade Monkey bar or simply walk around Crown Point. Does get loud on weekends. Guests cannot be sensitive to noise.