Westcliff-on-Sea Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Westcliff-on-Sea holiday rentals

Exterior
Hogwarts Bed and Continental Breakfast

Cottage in Sheerness

Hogwarts Bed and Continental Breakfast
3.0 star property
9.4 out of 10, Exceptional, (114)
"This was a lovely place to stay! The breakfast was wonderful also."
Canada
Philip Raymond
The price is S$104
includes taxes & fees
21 Dec - 22 Dec
Hogwarts Bed and Continental Breakfast
Restaurant
The Lower Bell

Apartment in Aylesford

The Lower Bell
3.0 star property
7.8 out of 10, Good, (149)
"Clean comfortable proprty"
United Kingdom
Pete
The price is S$121
includes taxes & fees
22 Dec - 23 Dec
The Lower Bell
Exterior
Staycations Maldon Suites

Aparthotel in Maldon

Staycations Maldon Suites
4.0 star property
9.6 out of 10, Exceptional, (13)
"The place was huge the value wonderful parking right out back great people food, just walk everywhere myself wife and daughter came all the way from the USA and couldn't have ask for better."
United States
Hunter
The price is S$199
includes taxes & fees
6 Jan - 7 Jan, 2026
Staycations Maldon Suites
Miscellaneous
Green Cottages

Cottage in Sittingbourne

Green Cottages
3.0 star property
10.0 out of 10, Exceptional, (11)
"Beautiful cottage in a fantastic, friendly village. It had everything we needed and was located close enough to the places we wanted to visit. Good local walks and a really nice pub over the road. We wouldn't hesitate to stay here again if we are in the area."
United Kingdom
Matthew
The price is S$518
includes taxes & fees
7 Jan - 8 Jan, 2026
Green Cottages
Terrace/patio
The Dairy - Seaside Couples Escape in Whitstable

Cottage in Whitstable

The Dairy - Seaside Couples Escape in Whitstable
3.0 star property
9.2 out of 10, Wonderful, (5)
"Easy check in, clean room, comfortable bed "
United Kingdom
Rachel
The price is S$122
includes taxes & fees
5 Jan - 6 Jan, 2026
The Dairy - Seaside Couples Escape in Whitstable
Fridge, microwave, oven, stovetop
House - Sleeps 7, Private Garden & Parking

Residence in Basildon

House - Sleeps 7, Private Garden & Parking
2.0 star property
The price is S$510
includes taxes & fees
1 Jan - 2 Jan, 2026
House - Sleeps 7, Private Garden & Parking
Exterior
Truly Kentish Holiday Lets

Cabin in Sittingbourne

Truly Kentish Holiday Lets
3.5 star property
10.0 out of 10, Exceptional, (7)
"Lovely peaceful location. Property accurately depicted in the photos. Lovely grounds and great hosts"
United Kingdom
Elizabeth
Truly Kentish Holiday Lets
1 bedroom, iron/ironing board, rollaway beds, free WiFi
Chelmsford Serviced Apartments

Apartment in Chelmsford

Chelmsford Serviced Apartments
5.0 star property
9.6 out of 10, Exceptional, (52)
"Great apartment and facilities. Was very happy. "
United Kingdom
Tara
The price is S$243
includes taxes & fees
23 Dec - 24 Dec
Chelmsford Serviced Apartments
Fridge, dishwasher, electric kettle, toaster
Mabel

Cottage in Whitstable

Mabel
3.0 star property
The price is S$670
includes taxes & fees
4 Jan - 5 Jan, 2026
Mabel
Balcony
Cosy Escape Heated Luxury pod and hot tub

Holiday Home in Sheerness

Cosy Escape Heated Luxury pod and hot tub
3.0 star property
10.0 out of 10, Exceptional, (6)
The price is S$261
includes taxes & fees
22 Dec - 23 Dec
Cosy Escape Heated Luxury pod and hot tub
Lounge
Luxurious ONE Bedroom Apartment IN Bond Street

Apartment in Chelmsford

Luxurious ONE Bedroom Apartment IN Bond Street
3.5 star property
10.0 out of 10, Exceptional, (2)
The price is S$275
includes taxes & fees
28 Dec - 29 Dec
Luxurious ONE Bedroom Apartment IN Bond Street
Living area
House - Sleeps 9 - Garden - Pet Friendly - Parking

Residence in Sittingbourne

House - Sleeps 9 - Garden - Pet Friendly - Parking
2.0 star property
The price is S$421
includes taxes & fees
12 Jan - 13 Jan, 2026
House - Sleeps 9 - Garden - Pet Friendly - Parking
Private kitchen
Charming 2-bed Apartment in Brentwood Free Parking

Apartment in Brentwood Town Centre

Charming 2-bed Apartment in Brentwood Free Parking
3.0 star property
The price is S$324
includes taxes & fees
18 Jan - 19 Jan, 2026
Charming 2-bed Apartment in Brentwood Free Parking
Shared kitchen
Parkway House

Apartment in Chelmsford

Parkway House
3.5 star property
9.6 out of 10, Exceptional, (17)
"The apartment was clean, fresh and very cosy. Its like home away from home. Everything was in place, and in working orders. "
United Kingdom
Miss Sophia P C
The price is S$275
includes taxes & fees
28 Dec - 29 Dec
Parkway House
Fridge, dishwasher, electric kettle, toaster
Sally

Cottage in Whitstable

Sally
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is S$645
includes taxes & fees
28 Dec - 29 Dec
Sally
Pool
Hidden Treasure- 2 Beds Sleeps 3 Gillingham

Apartment in Gillingham

Hidden Treasure- 2 Beds Sleeps 3 Gillingham
3.0 star property
The price is S$219
includes taxes & fees
21 Dec - 22 Dec
Hidden Treasure- 2 Beds Sleeps 3 Gillingham
Outdoor dining
Seaside Bliss Retreat in Heart of Isle of Sheppy

Residence in Sheerness

Seaside Bliss Retreat in Heart of Isle of Sheppy
2.5 star property
The price is S$155
includes taxes & fees
30 Dec - 31 Dec
Seaside Bliss Retreat in Heart of Isle of Sheppy
Private kitchen
Modern-luxury 1bedroom-ensuitebathroom-garden-wifi

Apartment in Basildon

Modern-luxury 1bedroom-ensuitebathroom-garden-wifi
3.0 star property
The price is S$368
includes taxes & fees
20 Dec - 21 Dec
Modern-luxury 1bedroom-ensuitebathroom-garden-wifi
Living area
Cozy Rochester Apartment Retreat

Apartment in Rochester

Cozy Rochester Apartment Retreat
3.0 star property
8.8 out of 10, Excellent, (3)
"We had a lovely weekend stay at this apartment. It was spotlessly clean, modern and very comfortable-perfect for a relaxing getaway. The kitchen was well-equipped, the beds were cosy and the whole place had a fresh, welcoming feel. The only small thing we noticed was that there weren’t many mirrors, which would have been handy-but that didn’t take away from the overall great experience. Would definitely stay again! "
United Kingdom
Sheniz
The price is S$247
includes taxes & fees
29 Dec - 30 Dec
Cozy Rochester Apartment Retreat
Living area
3 Bed Caravan - Sleeps 6 - Pets - Parking - Wifi

Residence in Sheerness

3 Bed Caravan - Sleeps 6 - Pets - Parking - Wifi
2.0 star property
The price is S$160
includes taxes & fees
19 Dec - 20 Dec
3 Bed Caravan - Sleeps 6 - Pets - Parking - Wifi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westcliff-on-Sea Hotel Reviews

King Charles Hotel

King Charles Hotel

10/10 Excellent
"Everything was brilliant "
Raymond 2-night trip
Posted 4 days ago
King Charles Hotel

Frequently asked questions

Can I find holiday rentals in Westcliff-on-Sea?

Yes, there are holiday rentals close to the most popular sights in Westcliff-on-Sea, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Westcliff-on-Sea speak positively about the scenic seaside and top-notch restaurants in this destination. Allow plenty of time to check out the theatre scene and bars during your visit.

What are some of the best holiday rentals that Westcliff-on-Sea has to offer?

Cosy Escape Heated Luxury pod and hot tub: This holiday home rental outside of Westcliff-on-Sea is located on the waterfront, and has an outdoor pool, a private garden and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle.

How many holiday rentals will I find in Westcliff-on-Sea?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Westcliff-on-Sea stay.

What can I see and do in Westcliff-on-Sea?

Cultural attractions include Cliffs Pavilion and Palace Theatre, whereas Chalkwell Beach and Southend Cliff Gardens are a couple of picturesque spots to enjoy the outdoors. While here, Genting Casino and Roots Hall Stadium are other places worth a visit.

What are holiday rentals like in Westcliff-on-Sea?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westcliff-on-Sea. Holiday rentals feature extras like laundry facilities and kitchens so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for families.