A beach with a cloudy sky and a distant shoreline.

Westcliff-on-Sea Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Westcliff-on-Sea vacation rentals

1. Pier View Self Catering Apartments

Pier View Self Catering Apartments
3.0 star property
Southend-on-Sea
The price is CA $189
CA $227 total
includes taxes & fees
Sep 27 - Sep 28
Pier View Self Catering Apartments

2. Salvation View 2 Bed Apartment

Salvation View 2 Bed Apartment
2.0 star property
Benfleet
8.0 out of 10, Very good, (1 review)
"Clean spacious flat although it's on a very busy main road. We booked it because of the garden but it was unusable because it was totally overgrown so nowhere to sit or stand. Another point I would like to make is that for safety we think there should be a hand rail on the stairs as they are quite steep and there is nothing to hold on to. Location is central to going places in the area."
United Kingdom
Jennifer
The price is CA $162
CA $240 total
includes taxes & fees
Sep 28 - Sep 29
Salvation View 2 Bed Apartment

3. Hogwarts Bed and Continental Breakfast

Hogwarts Bed and Continental Breakfast
3.0 star property
Sheerness
9.4 out of 10, Exceptional, (127 reviews)
"Lovely stay and great location. Easy check in and no complaints from us. I would stay here again."
United Kingdom
John
The price is CA $103
CA $123 total
includes taxes & fees
Sep 27 - Sep 28
Hogwarts Bed and Continental Breakfast

4. Estuary View

Estuary View
2.0 star property
Rochester
The price is CA $571
CA $686 total
includes taxes & fees
Oct 2 - Oct 3
Estuary View

5. Coastal House Opposite Beach Sleeps 6 Pet Friendly

Coastal House Opposite Beach Sleeps 6 Pet Friendly
3.5 star property
Southend-on-Sea
The price is CA $218
CA $328 total
includes taxes & fees
Oct 8 - Oct 9
Coastal House Opposite Beach Sleeps 6 Pet Friendly

6. Chelmsford Serviced Apartments

Chelmsford Serviced Apartments
5.0 star property
Chelmsford
9.6 out of 10, Exceptional, (58 reviews)
"Immaculate and extremely well appointed apartment. I'll definitely be staying again."
United Kingdom
Geraint
The price is CA $215
CA $257 total
includes taxes & fees
Sep 27 - Sep 28
Chelmsford Serviced Apartments

7. Charming 4-bedroom House Rental in Basildon, UK

Charming 4-bedroom House Rental in Basildon, UK
2.0 star property
Basildon
The price is CA $198
CA $499 total
includes taxes & fees
Sep 27 - Sep 28
Charming 4-bedroom House Rental in Basildon, UK

8. Green Cottages

Green Cottages
2.0 star property
Sittingbourne
10.0 out of 10, Exceptional, (12 reviews)
"A lovely cottage with everything we needed. "
United Kingdom
Nicholas
The price is CA $467
CA $560 total
includes taxes & fees
Oct 5 - Oct 6
Green Cottages

9. 493 Little Wakering Road

493 Little Wakering Road
3.5 star property
Southend-on-Sea
The price is CA $544
CA $653 total
includes taxes & fees
Oct 1 - Oct 2
493 Little Wakering Road

10. Hidden Treasure- 2 Beds Sleeps 3 Gillingham

Hidden Treasure- 2 Beds Sleeps 3 Gillingham
3.0 star property
Gillingham
The price is CA $197
CA $197 total
includes taxes & fees
Sep 26 - Sep 27
Hidden Treasure- 2 Beds Sleeps 3 Gillingham

11. Staycations Maldon Suites

Staycations Maldon Suites
4.0 star property
Maldon
9.2 out of 10, Wonderful, (20 reviews)
"Fantastic suite. Unique. Comfortable. Spacious. Has everything you'll need for short or longer term stays."
United Kingdom
Jonathon
The price is CA $195
CA $233 total
includes taxes & fees
Sep 27 - Sep 28
Staycations Maldon Suites

12. Headland Barn

Headland Barn
3.0 star property
Maldon
The price is CA $2,492
CA $2,990 total
includes taxes & fees
Oct 1 - Oct 2
Headland Barn

13. Modern-luxury 1bedroom-ensuitebathroom-garden-wifi

Modern-luxury 1bedroom-ensuitebathroom-garden-wifi
3.0 star property
Basildon
The price is CA $398
CA $398 total
includes taxes & fees
Sep 26 - Sep 27
Modern-luxury 1bedroom-ensuitebathroom-garden-wifi

14. Luxurious 2 Bedroom Apartment With Free Parking

Luxurious 2 Bedroom Apartment With Free Parking
2.0 star property
Chelmsford
9.8 out of 10, Exceptional, (8 reviews)
"The host made the check in easy and was responsive to all our questions and issues. The apartment, facilities and utensils were spotless and in great condition. For a stay in Chelmsford, the location is an easy walk or drive to any and all destinations."
United States
Paul
The price is CA $216
CA $372 total
includes taxes & fees
Sep 27 - Sep 28
Luxurious 2 Bedroom Apartment With Free Parking

15. Watersmeet - 85 @ Park Avenue Holiday Village

Watersmeet - 85 @ Park Avenue Holiday Village
2.0 star property
Sheerness
The price is CA $543
CA $651 total
includes taxes & fees
Sep 28 - Sep 29
Watersmeet - 85 @ Park Avenue Holiday Village

16. Surridges Studio, Sleeps 4 w/ Parking & Dogs Ok

Surridges Studio, Sleeps 4 w/ Parking & Dogs Ok
3.0 star property
Chelmsford
The price is CA $254
CA $305 total
includes taxes & fees
Sep 28 - Sep 29
Surridges Studio, Sleeps 4 w/ Parking & Dogs Ok

17. The Lower Bell

The Lower Bell
3.0 star property
Aylesford
7.8 out of 10, Good, (154 reviews)
"Small clean well appointed room in outbuilding. Large free car park. Good WiFi. Friendly helpful staff. No food available on sight."
United Kingdom
John
The price is CA $109
CA $131 total
includes taxes & fees
Sep 28 - Sep 29
The Lower Bell

18. Westgate Cottage

Westgate Cottage
3.0 star property
Sittingbourne
The price is CA $625
CA $625 total
includes taxes & fees
Sep 29 - Sep 30
Westgate Cottage

19. House Sleeps 4 With Enclosed Garden

House Sleeps 4 With Enclosed Garden
2.0 star property
Gillingham
House Sleeps 4 With Enclosed Garden

20. Curry Farm

Curry Farm
3.0 star property
Southminster
The price is CA $622
CA $747 total
includes taxes & fees
Oct 17 - Oct 18
Curry Farm
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Westcliff-on-Sea Hotel Reviews

Find out more about Westcliff-on-Sea

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Westcliff-on-Sea. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

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

Yes, we have vacation rentals close to top local attractions in Westcliff-on-Sea, or you can select a secluded option if you want a relaxing place to 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 theater scene and bars during your visit.

What's the top vacation rental in Westcliff-on-Sea?

Luxury Pod-sleeps 2-hot Tub-pets-garden: Visitors like this Westcliff-on-Sea vacation home rental. It is located on the waterfront and has an outdoor pool, a private yard, 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 vacation rentals will I find in Westcliff-on-Sea?

With 12 Expedia vacation rentals, you're sure 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 vacation rentals like in Westcliff-on-Sea?

Vacation rentals are private properties you can reserve for several days or more in Westcliff-on-Sea. Vacation rentals offer amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for families.