
Holiday rentals with a pool in Speightstown
Find and book unique homes with a pool on Airbnb
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 $128 SGD 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!
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.

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.

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!

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.

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.

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.

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

Azure Horizon sea view villa

Stunning villa with amazing view

Amazing Villa in Mullins/ Gibbs

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

Boutique House & Pool Next To The Best Palm Beach
Apartment rentals with a pool

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

"Take It Easy" Loft-Studio, Rockley Resort

Stunning Oceanfront with Beach and Priceless View

"Le Phare" - stylish & charming apt near the beach

Apartment #4, Maple Gardens, Christ Church.
Other holiday rentals with a pool

Luxury Two Bedroom Townhouse in Gibbes

Luxury five star modern 4 bedroom 4 bathroom villa

Modern Sorrento Villa #8- West Coast|Mins to beach

Croton Apartment

Luxury Apt, near Beach with Pool & Sea view

West Coast Villa, Stunning Ocean Views, Sleeps 8

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

3 Bedroom Villa with pool 30 second walk to beach
When is the best time to visit Speightstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $745 SGD | $670 SGD | $699 SGD | $510 SGD | $492 SGD | $461 SGD | $505 SGD | $515 SGD | $515 SGD | $511 SGD | $639 SGD | $716 SGD |
| 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 |
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- Worthing Beach
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- Crane Beach
- Miami Beach Barbados
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- Quayside Centre Shopping Plaza
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