Holiday rentals with a pool in Speightstown

Find and book unique homes with a pool on Airbnb

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
Home in Colleton
5 out of 5 average rating, 6 reviews

Lovely Villa, Stunning Sea Views

A beautiful open plan villa enjoying breezes, amazing sea views and sunsets. The spacious pool deck has a large pool, sun loungers, BBQ, bar and outdoor living. There is a secluded gazebo with hammock in the garden and a back gate opens to a path leading to the beach. You can walk to the fishing village Six Mens where fresh fish is for sale, local rum shops, bars and food spots as well as Fish Pot restaurant. In Speightstown, are supermarkets, bars and restaurants. Holetown is 20 minutes away.

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, 129 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!

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.

Guest favourite
Home in Gibbes
4.9 out of 5 average rating, 10 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 bright dining area features a wooden table surrounded by several chairs, with large glass doors providing a view of the outdoor space. Sunlight fills the room, highlighting the modern décor and the serene pool area visible through the opened doors.
Home in Westmoreland Hills
5 out of 5 average rating, 17 reviews

Villa Seaview

A stunning three- bedroom Villa accommodating up to 6 guests situated in the 5-star gated community of Westmoreland Hills with breathtaking views of the Caribbean Sea. The exclusive development comprises of 45 villas with 24 hour security. Villa Seaview is modern consists of 3 bedrooms, 4 bathrooms, private 26ft pool, wifi and air conditioning throughout. Kick back and relax in this calm, stylish space.

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 2 Bed~Private Pool + Beach Access

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.

Top Guest favourite
A private pool is surrounded by sun loungers and shaded seating areas. Umbrellas provide shade for relaxation. Lush greenery frames the serene outdoor space, with views of the Caribbean Sea in the background and partly cloudy skies above.
Home in Six Mens
4.95 out of 5 average rating, 44 reviews

Sweetwater House

A brand new 4-bedroom holiday home just across the road from the beach, with a beautiful pool and garden and with terrific patio views of the West Coast of Barbados. Perfect for a large family or a few couples. Relax on the breezy patio or lounge in the pool while watching the sun glisten on the Caribbean sea.

Popular amenities for Speightstown rentals with a pool

When is the best time to visit Speightstown?

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Avg. price$995 NZD$894 NZD$933 NZD$681 NZD$657 NZD$616 NZD$674 NZD$688 NZD$688 NZD$682 NZD$853 NZD$955 NZD
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Quick stats about holiday rentals with a pool in Speightstown

  • Total holiday rentals

    Explore 60 holiday rentals in Speightstown

  • Nightly prices starting at

    Speightstown holiday rentals start at $171 NZD per night before taxes and fees

  • Verified guest reviews

    Over 700 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Speightstown holiday rentals include Wi-Fi 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!