
Vacation 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.

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.

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.

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!

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.

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.

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!

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!

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.

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.

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!

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.

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
House rentals with a pool

Stunning villa with amazing view

Steps to Beach, Ocean View, Pool & Resort Access!

Stunning 3-Bedroom Villa in tropical garden

Stunning Caribbean sea views & close to Beach

Villa Kameya Mullins Beach 4 Bed • Pool & Hot Tub

the views by DanTopia villa

The Carlton Barbados - Luxury Townhouse Rental

Tranquil, refurbished villa with private pool
Condo rentals with a pool

Deluxe Apartment on idyllic Mullins Beach

Spacious 2 Bedroom Luxury Condo.

Spacious One Bedroom - White Sands Beach Condos

1 bedroom+patio in a luxury gated condo with pool

SeaRenity Villa - 20 meters from the Sea

Stunning Oceanfront with Beach and Priceless View

"Take It Easy" Loft-Studio, Rockley Resort

"Le Phare" - stylish & charming apt near the beach
Other vacation rentals with a pool

Beachside 2BR w/ sky-pool, BBQ & ocean glimpse

Croton Apartment

Fabulous condo, 5 mins from Mullins Beach.

Paradise Townhome on Mullins Beach

✈ NEW! 3Bdrm Family Home-West Coast-Sea View-Pools

Battaleys Mews 24

The Garden Loft with pool and club house access

Interior Designed 2 Bedroom 2 Bathroom Apartment
When is the best time to visit Speightstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $802 CAD | $721 CAD | $753 CAD | $549 CAD | $530 CAD | $497 CAD | $544 CAD | $555 CAD | $555 CAD | $551 CAD | $688 CAD | $771 CAD |
| Avg. temp | 26 °C | 26 °C | 27 °C | 27 °C | 28 °C | 28 °C | 28 °C | 28 °C | 28 °C | 28 °C | 27 °C | 27 °C |
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!
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