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
Apartment 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.

Top guest favourite
Apartment in Lower Carlton
5 out of 5 average rating, 18 reviews

NEW LUX 2BR, Walk to Beach! Sky Pool Deck

Welcome to Alora Unit 4! ➤ Your Luxury 2BR Condo with Rooftop Pool at Alora! ★ 3-Min Walk to Reeds Bay Beach ★ Rooftop Deck with Amazing Sea Views ★ 10mins to Holetown Dining & Nightlife ★ 7mins to Speightstown’s Laid-Back Charm ➤ Elegance with natural Wooden Elements: • En-suite bedrooms • Modern open-plan layout • Caribbean Luxury • Rooftop with Bar & Bbq station with pergola • Gated community with parking • Easy access to local transport. Ideal for families, couples & friends seeking

Guest favourite
The pool area is illuminated at night, highlighting the tranquil waters. The two-story villa features a balcony on the second floor, surrounded by tropical foliage, with seating areas visible near the pool. The inviting ambiance creates a serene outdoor environment.
Home in Colleton
5 out of 5 average rating, 21 reviews

3Bdrm 3.5 Bath Private Home w Brand New Pool

Located in the friendly estate of Colleton Gardens and new to Airbnb, "Bajan Memories" is on the north west coast of beautiful Barbados. A fully equipped home offering: - 3 bedrooms each w/ full private en-suite & balcony - stunning brand new pool surrounded tropical oasis - full service kitchen including dishwasher 5 min walk to the beach & famous Fish Pot restaurant, 5 mins by car to Speightstown, and 45 mins from Airport, our home offers everything you'd need for an easy tropical vacation!

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.
Flat in Speightstown
4.97 out of 5 average rating, 64 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
The spacious living area features high ceilings and large arched windows that flood the room with natural light. Comfortable seating is arranged around a wooden coffee table, while a dining area is visible in the background. The open layout connects to a terrace with views of the outdoors.
Villa in Westmoreland
4.98 out of 5 average rating, 60 reviews

Royal Villa 4, Luxury 3-Bed Villa w/ Pool & Golf

The 3 bed, 3.5 bath property is located at end of a cul-de-sac in the Royal Westmoreland gated community with 24-hour security. The villa is on a split-level basis with the Queen Bedroom just to the left of the main entrance. The Living Room, Kitchen and Terrace are just a few steps up on entry. The Master Bedroom and Twin Room are downstairs with entry to the private pool accessible from both rooms. All bedrooms are en-suite and include ample walk-in closet space, and air-conditioned.

Top guest favourite
A modern open-concept living space is presented, featuring neutral tones and natural materials. The fully equipped kitchen includes a large island with a sink, complemented by stylish pendant lighting. Floor-to-ceiling glass doors open to a private outdoor seating area, enhancing the airy ambiance.
Home in Lower Carlton
5 out of 5 average rating, 12 reviews

The Carlton Barbados - Luxury Townhouse Rental

The Carlton is a luxury townhouse near Barbados' west coast beaches. Enjoy the 2,063 sq ft space which includes 3 bedrooms, 3 bathrooms, private plunge pool, outdoor soaking tub, and easy access to dining, shopping, and nightlife in Holetown and Speightstown. Enhance your stay with VIP perks like private yacht charters, a Mount Gay Rum tour, and chef-curated dining. Whether relaxing or exploring, The Carlton delivers the best of both worlds. Book your unforgettable Barbadian escape today!

Top guest favourite
A balcony area features two woven chairs overlooking a coastal view. The ocean is visible in the background, with a sailboat gently gliding across the water. Lush greenery and nearby buildings create a serene environment under a partly cloudy sky.
Apartment in Fitts Village
4.96 out of 5 average rating, 112 reviews

SeaRenity Villa - 20 meters from the Sea

SeaRenity Villa is a stunning beachfront retreat just 20 meters from the golden sands of Barbados’ West Coast. Wake up to breathtaking ocean views from the living room, patio, or private pool. This fully air-conditioned villa features 3 spacious bedrooms, a fully equipped kitchen, and high-end amenities. Centrally located, you’re steps from restaurants, a grocery store, and a short ride to Holetown. Enjoy luxury, comfort, and the ultimate beachside escape. Book your stay today!

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.
Flat 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.
Apartment
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.
Flat
5 out of 5 average rating, 188 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.
Flat in Black Bess
4.83 out of 5 average rating, 107 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.

Popular amenities for Speightstown rentals with a pool

When is the best time to visit Speightstown?

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Avg. price€505€454€474€346€334€313€342€349€349€347€433€485
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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 €87 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 & child-friendly amenities

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Speightstown holiday 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!