Cheapside Holiday Rentals
Villa
- Bridgetown
- ·
- Brighton
- 0.23 mi to center
10.0Exceptional
(63 Reviews)
5 Bedrooms
4 Baths
14 Guests
5000 ft²
Private Pool
Oceanfront
Parking
Pool
US $2,234/Night
7 Nights - US $15,637
Apartment
- Bridgetown
- ·
- Bayville
- 0.13 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
2 Baths
5 Guests
1550 ft²
- Oceanfront
Breakfast- Parking
Ocean View
US $160/Night
7 Nights - US $1,122
Apartment
10.0Exceptional
(21 Reviews)
1 Bedroom
1 Bath
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $136/Night
7 Nights - US $952
Villa
- Hastings
- ·
- Saint Matthias
- 0.26 mi to center
10.0Exceptional
(61 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Pool
- Ocean View
Balcony/Terrace
View
US $353/Night
7 Nights - US $2,470
House
- Bridgetown
- ·
- Bayville
- 0.18 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
2 Baths
6 Guests
2421.88 ft²
- Breakfast
- Parking
- Balcony/Terrace
- View
US $249/Night
7 Nights - US $1,740
Condo
- Christ Church
- ·
- Hastings
- 0.28 mi to center
10.0Exceptional
(49 Reviews)
2 Bedrooms
2 Baths
4 Guests
1300 ft²
- Oceanfront
Hot Tub- Parking
- Pool
US $393/Night
7 Nights - US $2,750
Condo
- Christ Church
- ·
- Hastings
- 0.28 mi to center
10.0Exceptional
(43 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $360/Night
7 Nights - US $2,521
House
- Christ Church
- ·
- Rockley
- 0.09 mi to center
10.0Exceptional
(26 Reviews)
3 Bedrooms
2 Baths
6 Guests
1500 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $231/Night
7 Nights - US $1,616
New
Apartment
- Bridgetown
- ·
- Black Rock
- 0.41 mi to center
10.0Exceptional
(25 Reviews)
1 Bedroom
2 Baths
2 Guests
264 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $79/Night
7 Nights - US $550
Luxury Holiday Rentals in Cheapside
Over 839+ Luxury Holiday Rentals in or Near Cheapside
Villa
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $4,287/Night
7 Nights - US $30,010
House
6 Bedrooms
6 Baths
12 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $3,824/Night
7 Nights - US $26,765
New
Villa
- St. Michael
- ·
- Bridgetown
- 1.49 mi to center
8 Bedrooms
6 Baths
20 Guests
Air Conditioner
Internet
Child Friendly
Laundry
US $3,018/Night
7 Nights - US $21,123
Villa
10.0Exceptional
(3 Reviews)
5 Bedrooms
5 Baths
9 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $2,338/Night
7 Nights - US $16,368
New
House
- Bridgetown
- ·
- Spring Garden
- 0.21 mi to center
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $2,313/Night
7 Nights - US $16,191
House
- St. Michael
- ·
- Bridgetown
- 0.81 mi to center
9 Bedrooms
10 Baths
37 Guests
- Air Conditioner
- Internet
Pet Friendly- Child Friendly
US $2,220/Night
7 Nights - US $15,538
House
5 Bedrooms
5 Baths
10 Guests
- Child Friendly
US $1,913/Night
7 Nights - US $13,393
Villa
10.0Exceptional
(2 Reviews)
7 Bedrooms
5 Baths
12 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,823/Night
7 Nights - US $12,761
Apartment
- Bridgetown
- ·
- Spring Garden
- 0.25 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
6 Guests
3000 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $1,616/Night
7 Nights - US $11,309
Top-Rated Holiday Rentals with a Pool in Cheapside
Over 314+ The Best Private Villas and Holiday Rentals in Cheapside with a Pool
Apartment
- Christ Church
- ·
- Hastings
- 0.12 mi to center
10.0Exceptional
(23 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Pool
- Ocean View
- View
- Air Conditioner
US $412/Night
7 Nights - US $2,887
Cottage
- Rockley
- ·
- Marine Gardens
- 0.09 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $212/Night
7 Nights - US $1,481
Apartment
- Rockley
- ·
- Marine Gardens
- 0.10 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $210/Night
7 Nights - US $1,473
House
- Rockley
- ·
- Marine Gardens
- 0.07 mi to center
10.0Exceptional
(22 Reviews)
5 Bedrooms
5 Baths
10 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $720/Night
7 Nights - US $5,040
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(18 Reviews)
2 Bedrooms
2 Baths
4 Guests
1227 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $737/Night
7 Nights - US $5,162
Condo
- Hastings
- ·
- Saint Matthias
- 0.13 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
2000 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $556/Night
7 Nights - US $3,895
Apartment
- Rockley
- ·
- Navy Gardens
- 0.07 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $180/Night
7 Nights - US $1,259
Condo
- Christ Church
- ·
- Hastings
- 0.26 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $219/Night
7 Nights - US $1,534
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
1666 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,100/Night
7 Nights - US $7,701
Pet-Friendly Holiday Rentals in Cheapside
Over 31+ Pet-Friendly Holiday Rentals in or Near Cheapside
House
- St. Michael
- ·
- Bridgetown
- 1.24 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
11 Guests
1350 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $310/Night
7 Nights - US $2,170
Apartment
10.0Exceptional
(3 Reviews)
8 Bedrooms
7 Baths
17 Guests
- Oceanfront
- Breakfast
- Parking
- Ocean View
US $338/Night
7 Nights - US $2,369
Apartment
- Christ Church
- ·
- Rockley
- 0.15 mi to center
8.0Excellent
(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
Kitchen- Air Conditioner
US $97/Night
7 Nights - US $680
Villa
- Christ Church
- ·
- Hastings
- 0.14 mi to center
9.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Ocean View
- View
- Kitchen
US $477/Night
7 Nights - US $3,336
Apartment
- Bridgetown
- ·
- Brighton
- 0.05 mi to center
9.1Exceptional
(7 Reviews)
10 Bedrooms
4 Baths
18 Guests
1001.04 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $191/Night
7 Nights - US $1,339
House
- Bridgetown
- ·
- Spring Garden
- 0.17 mi to center
8.6Fabulous
(9 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $294/Night
7 Nights - US $2,060
Apartment
- Christ Church
- ·
- Hastings
- 0.27 mi to center
8.4Excellent
(12 Reviews)
2 Bedrooms
1 Bath
4 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $119/Night
7 Nights - US $831
Apartment
6.0Good
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $126/Night
7 Nights - US $880
House
- Bridgetown
- ·
- Eagle Hall
- 0.19 mi to center
4.0Average
(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Internet
- Pet Friendly
- Child Friendly
- Laundry
US $129/Night
7 Nights - US $903
Large Holiday Rentals and Private Villas in Cheapside
Over 104+ Large Holiday Rentals and Private Villas in or Near Cheapside
Villa
- Bridgetown
- ·
- Bayville
- 0.03 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $586/Night
7 Nights - US $4,105
House
- Bridgetown
- ·
- Brighton
- 0.28 mi to center
10.0Exceptional
(3 Reviews)
8 Bedrooms
9 Baths
16 Guests
3751.22 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,300/Night
7 Nights - US $9,100
House
- Christ Church
- ·
- Hastings
- 0.23 mi to center
6 Bedrooms
5 Baths
8 Guests
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $528/Night
7 Nights - US $3,696
Villa
- Bridgetown
- ·
- Garrison Historic Area
- 0.22 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $419/Night
7 Nights - US $2,936
House
- Bridgetown
- ·
- Brighton
- 0.11 mi to center
9.2Exceptional
(74 Reviews)
5 Bedrooms
5 Baths
10 Guests
584.84 ft²
- Oceanfront
- Breakfast
- Parking
- Ocean View
US $154/Night
7 Nights - US $1,079
Villa
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $981/Night
7 Nights - US $6,865
Villa
- Christ Church
- ·
- Hastings
- 0.22 mi to center
9.8Exceptional
(68 Reviews)
2 Bedrooms
2 Baths
6 Guests
1201 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $368/Night
7 Nights - US $2,578
Villa
- Bridgetown
- ·
- Brighton
- 0.27 mi to center
9.8Exceptional
(55 Reviews)
1 Bedroom
1 Bath
3 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $257/Night
7 Nights - US $1,802
Apartment
- Christ Church
- ·
- Rockley
- 0.11 mi to center
9.8Exceptional
(9 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $399/Night
7 Nights - US $2,792
Wheelchair Accessible Holiday Homes in Cheapside
Over 153+ Wheelchair Accessible Holiday Homes in or Near Cheapside
Condo
- Rockley
- ·
- Marine Gardens
- 0.04 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1304 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $354/Night
7 Nights - US $2,475
Apartment
- Bridgetown
- ·
- Blue Waters
- 0.23 mi to center
8.9Fabulous
(298 Reviews)
13 Bedrooms
4 Baths
10 Guests
430.56 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $127/Night
7 Nights - US $889
Resort
- Hastings
- ·
- Saint Matthias
- 0.10 mi to center
9.0Exceptional
(1008 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
Spa
US $833/Night
7 Nights - US $5,829
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
3 Baths
6 Guests
1666 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $1,114/Night
7 Nights - US $7,799
Apartment
- St. Michael
- ·
- Bridgetown
- 1.15 mi to center
8.4Excellent
(38 Reviews)
3 Bedrooms
2 Baths
6 Guests
457.47 ft²
- Breakfast
- Parking
- Ocean View
- Balcony/Terrace
US $78/Night
7 Nights - US $546
Condo
- Bridgetown
- ·
- Brighton
- 0.07 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1277 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $423/Night
7 Nights - US $2,958
Apartment
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
1654 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $970/Night
7 Nights - US $6,787
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
3 Baths
6 Guests
1720 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $905/Night
7 Nights - US $6,333
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1666 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $834/Night
7 Nights - US $5,837
Cheapside Private Villas and Holiday Homes Under $200
Over 332+ Cheapside Private Villas and Holiday Homes Under $200
Cottage
- Rockley
- ·
- Marine Gardens
- 0.10 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
400 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $175/Night
7 Nights - US $1,225
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
5 Guests
8503.49 ft²
Private Beach- Oceanfront
- Parking
- Ocean View
US $197/Night
7 Nights - US $1,377
Apartment
- Bridgetown
- ·
- Howells
- 0.35 mi to center
9.0Exceptional
(95 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $92/Night
7 Nights - US $647
House
- St. Michael
- ·
- Bridgetown
- 1.59 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $105/Night
7 Nights - US $737
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
602.78 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $157/Night
7 Nights - US $1,097
Apartment
- Christ Church
- ·
- Rockley
- 0.24 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
615 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $161/Night
7 Nights - US $1,129
House
- Rockley
- ·
- Navy Gardens
- 0.18 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $120/Night
7 Nights - US $837
Apartment
- Bridgetown
- ·
- Pine Gardens
- 0.18 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $76/Night
7 Nights - US $530
House
- Rockley
- ·
- Marine Gardens
- 0.14 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $189/Night
7 Nights - US $1,322
Instantly Bookable Holiday Homes in Cheapside
Over 416+ Instantly Bookable Holiday Homes in or Near Cheapside
Condo
- Christ Church
- ·
- Hastings
- 0.41 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $272/Night
7 Nights - US $1,907
Condo
- Bridgetown
- ·
- Brighton
- 0.26 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1720 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $770/Night
7 Nights - US $5,389
Condo
- Bridgetown
- ·
- Brighton
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
1247 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $655/Night
7 Nights - US $4,582
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
2400 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $359/Night
7 Nights - US $2,513
House
- St. Michael
- ·
- Bridgetown
- 1.39 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $250/Night
7 Nights - US $1,752
House
- Rockley
- ·
- Marine Gardens
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1600 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $233/Night
7 Nights - US $1,631
Apartment
- Hastings
- ·
- Saint Matthias
- 0.12 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $133/Night
7 Nights - US $929
Cottage
- St. Michael
- ·
- Bridgetown
- 1.78 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
4 Guests
820 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $109/Night
7 Nights - US $760
Apartment
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $497/Night
7 Nights - US $3,479
Book a Last Minute Place to Stay in Cheapside
About Casai's Private Villas and Holiday Rentals in Cheapside
Discover more than 848 vacation rentals available in Cheapside. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Cheapside.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Cheapside, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Cheapside. On average, places to stay near Cheapside offer 754.74 ft², with nightly prices averaging US $479.
With Casai, finding and comparing holiday rentals in Cheapside is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Cheapside
| Type | Count |
|---|---|
| Holiday Apartments | 376 |
| Vacation Homes | 179 |
| Villas | 79 |
| Cottages | 23 |
Use these Quick Filters to Find a Holiday Rental in Cheapside
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Cheapside.
Top Attractions Around Cheapside, BB
Casai offers a large selection of top attractions around Cheapside . Research things to do on your vacation before you visit Cheapside.
Other Places to Stay in Cheapside, BB
Frequently Asked Questions About Cheapside?
What are the top holiday rentals in Cheapside?
With numerous options available in Cheapside, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Cheapside:
- Luxury Stunning 5 Bedroom Beach-House on the Best Beach in Barbados
- Centrally located villa with spectacular sunsets and ocean views
- South Ocean Villas 201 - With Breathtaking Panoramic Beach and Ocean Views
- South Ocean Villas 203 with breathtaking views
- Blue Haven House (LOCATION, LOCATION, LOCATION), ‘A Home Away From Home’
- Almond Palm Apartment
- Private steps down to the beach with stunning ocean views
- Upper Beachgate - On the Beach.
- Cherry Garden Villa Cottage pool in the desirable Rockley Beach location
- Cherry Garden Villa Apartment - private pool in desirable Rockley Beach location
How many holiday rentals have private pools in Cheapside?
Discover a selection of holiday rentals with private pools near Cheapside with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Crotona Garden Upper Cottage 1 Bed Apt, Pool, Lush, Tropical, 2 Min Walk to Sea
- Portico 1
- Luxury West Coast 3 Bed Apartment with Private Pool and Path to Beach
- Exclusive Townhouse with Luxury Upgrades and private Pool and amazing Views
Which holiday homes in Cheapside are best for families?
If you're searching for a family-friendly holiday home in Cheapside, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Cheapside:
- Private steps down to the beach with stunning ocean views
- Embassy Villa
- Believe Caribbean Apartments
How many Casai.com holiday rentals are available in Cheapside?
As of 2026, Casai boasts over 848 properties listed in the Cheapside area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Cheapside.
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