Vacation rentals with a pool in Speightstown

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Top-rated rentals with a pool in Speightstown

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

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Top guest favourite
Condo in Lower Carlton
5 out of 5 average rating, 16 reviews

Alora 7–SkyPool BBQ Sundeck & Ocean View

A beautifully appointed 2-bedroom, 2-bath villa on Barbados’ sought-after West Coast. The standout feature is the Sky Lounge—an elevated shared retreat with a pool, sun deck, and ocean views. It’s the perfect place to soak up the Caribbean sun by day and unwind under the stars by night. Inside, the villa offers elegant modern décor, a fully equipped kitchen, air conditioning throughout, and reliable Wi-Fi. Alora 7 blends relaxed island living with comfort and style for a truly memorable getaway.

Guest favourite
A private pool area features a rectangular pool with crystal-clear water, surrounded by white walls and vibrant greenery. Two sun loungers are positioned nearby, providing a space for relaxation under the sun.
Townhouse in Holetown
4.95 out of 5 average rating, 57 reviews

Newly renovated 3-bedroom holiday home with pool.

Relax at this newly renovated villa, safely tucked away in the gated community of Porters Gate on the west coast. All furnishings and appliances are of the highest standard and the villa is immaculately kept and spotlessly clean. This 3-bedroom retreat features an open plan with fully-equipped kitchen, dining and living area. The air-conditioned bedrooms are on the upper floor with en-suite bathrooms. Outdoors, there is a covered, dining and lounge area with a pool and deck with sun loungers.

Top guest favourite
A crystal-clear swimming pool meanders through the vibrant landscaping, featuring lush palm trees and tropical plants. Poolside loungers and umbrellas provide shaded seating. A charming gazebo sits in the background, surrounded by well-maintained grounds, inviting relaxation in a serene environment.
Apartment in Speightstown
4.97 out of 5 average rating, 62 reviews

Amore Schooner Bay Luxury Villa

Time to relax and unwind in one of the most beautiful, affluent countries in the Caribbean. Amore Barbados has one goal in mind: offering our guests a comfortable, affordable, and all-round exceptional accommodation. Amore covers every aspect of your stay: great location, cosy beds, beautiful beaches, & delicious food at your doorstep. Take a look at our pictures and book your holiday of a lifetime today! Under new ownership, Amore Barbados continues to offer the same great experience!

Top guest favourite
A modern beach complex is featured along a sandy shoreline, surrounded by greenery. The structure consists of three levels, with large glass windows offering views of the beach. Nearby, a wooden deck provides additional outdoor space. Soft waves gently lap against the shore.
Apartment in Clinketts
5 out of 5 average rating, 63 reviews

Dreams(Moontown)( No.3) Beach Apartments. St Lucy.

Dreams (Moontown)Beach Apartments, is a new modern complex located on the beautiful Halfmoon Fort Beach in the parish of St Lucy, Barbados. The area is also called Moontown. It contains 3 fully furnished rental units. ( Apt 3), (Apt 2) and (Apt 1). Each unit sleeps two adults. Stunning views; a nice place to stay. It has a swimming pool, and a roof deck with 360 degree views. There is a free car park for 3 vehicles. Apt 3 on top floor Apt 2 mid floor Apt 1 lower pool floor.

Top guest favourite
A bright living space features a large sectional sofa in soft white upholstery, complemented by a round mirror. Natural light filters through double doors leading to a patio, while a black and white striped rug adds contrast to the tiled floor.
Home in Mullins
4.97 out of 5 average rating, 31 reviews

Cool Runnings: Beach Side Luxury

Experience luxury living at Cool Runnings: a unique ground-floor apartment with 2 bedrooms, a private pool, and tropical garden. This meticulously maintained property offers an unparalleled opportunity for lavish living or smart investment. Enjoy spacious, air-conditioned interiors, a covered terrace with a wet bar, and a fully equipped kitchen with modern appliances. With high-speed internet and cable TV, this turnkey retreat promises indulgent comfort in a tropical paradise.

Guest favourite
An outdoor dining area features a wooden table with four chairs and a vase displaying tropical flowers. Light filters through partially drawn shades, and a view of the marina and lush greenery is visible through the lattice screen.
Condo in Douglas
4.91 out of 5 average rating, 127 reviews

Penthouse in Port St. Charles

Overlooking the Port St. Charles, this exclusive yet vibrant penthouse suite introduces you to the soul of old-world Barbadian life and its boating heritage. Located in a gated community at one of the island's most desired addresses, this 3 bedrooms, 3 bathrooms penthouse gives you access to the shops, restaurants, beaches and goings-on in the island's charming Speightstown without sacrificing beauty and comfort. If the island offers it, we " know a place" to recommend you!

Top guest favourite
A spacious living area is shown, featuring a comfortable seating arrangement and a large glass door leading to the balcony. The view encompasses the turquoise Caribbean Sea and a distant horizon dotted with sailboats. Bright natural light fills the space, complemented by soft, neutral furnishings.
Apartment in St. James
5 out of 5 average rating, 187 reviews

Designer Penthouse - Stunning Views & Location

309 Penthouse Apartment is a gem of a property that is privately owned & professionally managed, located on the West Coast under the umbrella of Beach View Hotel Paynes Bay St. James, Barbados. Even though we are privately owned and managed we still have access to the hotel's amenities, their pools, the restaurant, mini mart and gym. As your super host, I am dedicated to offering impeccable service to assure you get to experience the amazing Barbados dream holiday!

Top guest favourite
Home in Speightstown
5 out of 5 average rating, 12 reviews

Waterfront/Beach/Resort Access/Airport Transfer

Recently refurbished waterfront 3-bedroom townhouse in the exclusive Port St. Charles Resort & Yacht Club. Perfect for families, couples or friends. Features: • 3 king bedrooms with en-suite bathrooms • Fully equipped kitchen • Private plunge pool • Outdoor dining & loungers • Washer & dryer Resort amenities: • Beach with chairs & umbrellas • Gym, restaurants & bars • Complimentary water taxi Bonus: Complimentary airport transfer from airport to the apartment.

Guest favourite
A spacious studio apartment features a wooden bed with soft linens and two patterned armchairs. Natural light floods the room through large windows, illuminating the textured stone walls and exposed wooden beams on the ceiling. A small dining area is visible in the adjacent space.
Apartment in Black Bess
4.83 out of 5 average rating, 106 reviews

The Loft at Ridge View

The Loft at Ridge View is a cosy countryside escape in St. Peter, Barbados—5 minutes from Haymans Market and 10 minutes from Speightstown. This top-floor studio sits on a ridge overlooking the west coast, offering stunning sea views and unforgettable sunsets. Surrounded by nature and local life, it invites slow living, cultural immersion, and relaxation. Amenities such as a pool, garden, A/C and dedicated parking make it the perfect island retreat.

Top guest favourite
A bright living area is showcased, featuring two comfortable sofas positioned around a glass-topped coffee table adorned with decorative items. Natural light filters in through large windows, illuminating a cozy ambiance. A dining set is visible through the adjoining space, along with lush greenery outside.
Townhouse in Gibbes
4.98 out of 5 average rating, 58 reviews

Walk to Beach, Pool, Rooftop Terrace, King Bed(s)

Calm Waters is your casually stylish home away from home! 2 Bdrms, 2 1/2 baths, full kitchen, laundry … Enjoy an ocean swim, relax by the pool, watch sunsets or stargaze on your private rooftop patio! Beautiful Gibbes Bay is a 3 minute walk & Mullins Beach is just a few more minutes up the road & is home to some great restaurants - also a great spot to enjoy a drink & live music while watching the sun go down!

Guest favourite
Home in Gibbes
4.89 out of 5 average rating, 9 reviews

Luxury 3-bedroom Villa with Pool near Gibbes Beach

Enjoy luxury and comfort at Claridges 4, a stylish 3-bedroom villa just a short walk from serene Gibbes Beach. Featuring air-conditioned ensuite bedrooms, elegant living spaces, a fully equipped kitchen, private patio, and access to a stunning lagoon-style pool and gazebo. Fast Wi-Fi, Smart TV, and secure parking included. Perfect for families, friends, or couples seeking a relaxing, upscale Barbados escape.

Guest favourite
A view of the outdoor area reveals a private plunge pool surrounded by lush greenery. A wooden dining table is positioned in front, featuring a white planter with green foliage. The waterfront setting provides a glimpse of boats gently resting in the marina.
Apartment in Speightstown
4.92 out of 5 average rating, 12 reviews

Port St. Charles Luxury 2-Bed w/ Private Pool

Experience effortless Caribbean luxury in this spacious, ground-floor 2-bedroom retreat at the exclusive Port St Charles Marina. Featuring a private plunge pool, elegant interiors, and seamless indoor-outdoor living, this fully furnished home is ideal for couples, families, or friends seeking comfort and privacy in one of Barbados' most prestigious communities.

Popular amenities for Speightstown rentals with a pool

When is the best time to visit Speightstown?

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Quick stats about vacation rentals with a pool in Speightstown

  • Total vacation rentals

    Explore 60 vacation rentals in Speightstown

  • Nightly prices starting at

    Speightstown vacation rentals start at $138 CAD per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Speightstown vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Speightstown rentals

  • 4.8 Average rating

    Speightstown stays are highly rated by guests—averaging 4.8 out of 5!