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Southend-on-Sea Holiday Rentals

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Our top choices for Southend-on-Sea holiday rentals

Cottage in Southend-on-Sea

493 Little Wakering Road
3.5 star property
The price is NZ$789
includes taxes & fees
30 Dec - 31 Dec
493 Little Wakering Road
3.5 star property
10.0 out of 10, Exceptional, (2)
The price is NZ$342
includes taxes & fees
28 Dec - 29 Dec
Luxurious ONE Bedroom Apartment IN Bond Street

Apartment in Chelmsford

Chelmsford Serviced Apartments
5.0 star property
9.6 out of 10, Exceptional, (53)
"Nothing negative to say - location & cleanliness all superb. Code system for doors worked well & parking useful "
United Kingdom
stephen
The price is NZ$332
includes taxes & fees
29 Dec - 30 Dec
Chelmsford Serviced Apartments
3.0 star property
10.0 out of 10, Exceptional, (5)
"The flat is very clean and well equipped, the hosts are friendly and helpful, and the area is lovely. I would definitely recommend."
United Kingdom
Dan
The price is NZ$293
includes taxes & fees
4 Jan - 5 Jan 2026
Countryside Annex- Sleeps 2, Free Parking & Garden
2.0 star property
8.0 out of 10, Very good, (1)
"House is good comfortable stay, however parking is difficult and is located in a less desired area."
United Kingdom
Scott
The price is NZ$335
includes taxes & fees
1 Jan - 2 Jan 2026
Fantastic Large Room with free parking

Aparthotel in Colchester

Birds Farm
3.0 star property
9.2 out of 10, Wonderful, (10)
"We loved it here, had a a good couple of nights with friends. Beautiful apartment, amazing mattresses and pillows, very quiet environment. The pool wasn’t open and some work was happening but you can tell it’s going to look amazing once they put it all together and summer prep work is expected at this time of year. Kara was fab and we met a super helpful housekeeper who is doing a degree who was a literal walking tourist information centre. Great atmosphere all round ."
United Kingdom
Karen
The price is NZ$282
includes taxes & fees
18 Jan - 19 Jan 2026
Birds Farm

Cottage in Herne Bay

Swallow Cottage
3.5 star property
The price is NZ$887
includes taxes & fees
6 Jan - 7 Jan 2026
Swallow Cottage
The price is NZ$416
includes taxes & fees
2 Jan - 3 Jan 2026
Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars

Holiday Home in Whitstable

Beach Retreat With Parking Near the Sea
4.0 star property
6.0 out of 10, (1)
"Unable to use hob. Hot water supply to bath poor Shower okay The description "near the sea" a bit misleading. Insufficient instructions and labelling with regard to bins and TV. Overall standard of property good and comfortable"
United Kingdom
Tom
The price is NZ$919
includes taxes & fees
30 Dec - 31 Dec
Beach Retreat With Parking Near the Sea
3.0 star property
9.2 out of 10, Wonderful, (115)
"This was a lovely place to stay! The breakfast was wonderful also."
Canada
Philip Raymond
The price is NZ$139
includes taxes & fees
28 Dec - 29 Dec
Hogwarts Bed and Continental Breakfast
3.0 star property
8.8 out of 10, Excellent, (6)
"Easy check in, clean room, comfortable bed "
United Kingdom
Rachel
The price is NZ$165
includes taxes & fees
6 Jan - 7 Jan 2026
The Dairy - Seaside Couples Escape in Whitstable

Apartment in Frinton-on-Sea

Frinton Escapes
3.5 star property
10.0 out of 10, Exceptional, (16)
"Great place to stay definitely recommend "
United Kingdom
Michele
The price is NZ$301
includes taxes & fees
14 Jan - 15 Jan 2026
Frinton Escapes

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 NZ$348
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Rochester Apartment Retreat

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 NZ$342
includes taxes & fees
28 Dec - 29 Dec
Parkway House
2.0 star property
The price is NZ$342
includes taxes & fees
10 Jan - 11 Jan 2026
Kensington Bliss - 3 Bedroom House in Colchester

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 NZ$266
includes taxes & fees
12 Jan - 13 Jan 2026
Staycations Maldon Suites

Cottage in Whitstable

Sally
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is NZ$873
includes taxes & fees
2 Jan - 3 Jan 2026
Sally

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 NZ$162
includes taxes & fees
29 Dec - 30 Dec
The Lower Bell

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 NZ$694
includes taxes & fees
10 Jan - 11 Jan 2026
Green Cottages
2.0 star property
9.8 out of 10, Exceptional, (6)
"Only stayed for one night but thoroughly enjoyed it and would definitely stay again. "
United Kingdom
Gillian
The price is NZ$435
includes taxes & fees
6 Jan - 7 Jan 2026
Luxurious 2 Bedroom Apartment With Free Parking
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 Southend-on-Sea Hotel Reviews

Find out more about Southend-on-Sea

Everything you need to know about Southend-on-Sea holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southend-on-Sea holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southend-on-Sea holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Southend-on-Sea holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southend-on-Sea. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southend-on-Sea holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southend-on-Sea holiday rentals we have selected for you start as low as NZ$128 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southend-on-Sea rentals

At Expedia, we put the best Southend-on-Sea holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southend-on-Sea rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southend-on-Sea holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southend-on-Sea. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Southend-on-Sea?

Yes, there are holiday rentals in Southend-on-Sea close to Adventure Island, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Southend-on-Sea speak positively about the scenic seaside and lively bars in this destination. Make sure you have time to check out the gardens and golf courses during your trip.

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

Cosy Escape Heated Luxury pod and hot tub: This holiday home rental outside of Southend-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 are there in Southend-on-Sea?

Expedia has 18 holiday rentals for your stay in Southend-on-Sea.

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

Cultural attractions include Leigh Heritage Centre and Southend-On-Sea Pier Museum, whereas Southend Beach and Thorpe Bay Beach are a couple of picturesque spots to enjoy the outdoors. While here, Adventure Island and Sealife Adventure are other places worth a visit.

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

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Southend-on-Sea. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of security away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.