Southend-on-Sea Vacation Rentals

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Our top choices for Southend-on-Sea vacation rentals

493 Little Wakering Road

493 Little Wakering Road
3.5 star property
Southend-on-Sea
$380 nightly
The price is $456
Dec 27 - Dec 28
Total with taxes and fees
493 Little Wakering Road

Green Cottages

Green Cottages
3.0 star property
Sittingbourne
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
$334 nightly
The price is $401
Jan 4 - Jan 5, 2026
Total with taxes and fees
Green Cottages

Chelmsford Serviced Apartments

Chelmsford Serviced Apartments
5.0 star property
Chelmsford
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
$152 nightly
The price is $183
Jan 5 - Jan 6, 2026
Total with taxes and fees
Chelmsford Serviced Apartments

Countryside Annex- Sleeps 2, Free Parking & Garden

Countryside Annex- Sleeps 2, Free Parking & Garden
3.0 star property
Canterbury
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
$141 nightly
The price is $169
Dec 29 - Dec 30
Total with taxes and fees
Countryside Annex- Sleeps 2, Free Parking & Garden

Fantastic Large Room with free parking

Fantastic Large Room with free parking
2.0 star property
Chatham
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
$162 nightly
The price is $194
Jan 1 - Jan 2, 2026
Total with taxes and fees
Fantastic Large Room with free parking

Smallcroft

Smallcroft
3.0 star property
Whitstable
10.0 out of 10, Exceptional, (1)
$674 nightly
The price is $809
Dec 29 - Dec 30
Total with taxes and fees
Smallcroft

Beach Retreat With Parking Near the Sea

Beach Retreat With Parking Near the Sea
4.0 star property
Whitstable
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
$605 nightly
The price is $605
Dec 30 - Dec 31
Total with taxes and fees
Beach Retreat With Parking Near the Sea

Birds Farm

Birds Farm
3.0 star property
Colchester
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
$139 nightly
The price is $167
Jan 4 - Jan 5, 2026
Total with taxes and fees
Birds Farm

Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars

Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars
2.0 star property
Tilbury
$195 nightly
The price is $235
Jan 7 - Jan 8, 2026
Total with taxes and fees
Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars

Hogwarts Bed and Continental Breakfast

Hogwarts Bed and Continental Breakfast
3.0 star property
Sheerness
9.2 out of 10, Wonderful, (115)
"This was a lovely place to stay! The breakfast was wonderful also."
Canada
Philip Raymond
$67 nightly
The price is $80
Dec 29 - Dec 30
Total with taxes and fees
Hogwarts Bed and Continental Breakfast

Cozy Rochester Apartment Retreat

Cozy Rochester Apartment Retreat
3.0 star property
Rochester
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
$165 nightly
The price is $198
Jan 11 - Jan 12, 2026
Total with taxes and fees
Cozy Rochester Apartment Retreat

Luxurious ONE Bedroom Apartment IN Bond Street

Luxurious ONE Bedroom Apartment IN Bond Street
3.5 star property
Chelmsford
10.0 out of 10, Exceptional, (2)
$174 nightly
The price is $198
Dec 28 - Dec 29
Total with taxes and fees
Luxurious ONE Bedroom Apartment IN Bond Street

The Dairy - Seaside Couples Escape in Whitstable

The Dairy - Seaside Couples Escape in Whitstable
3.0 star property
Whitstable
9.2 out of 10, Wonderful, (5)
"Easy check in, clean room, comfortable bed "
United Kingdom
Rachel
$79 nightly
The price is $95
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Dairy - Seaside Couples Escape in Whitstable

Parkway House

Parkway House
3.5 star property
Chelmsford
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
$174 nightly
The price is $198
Dec 27 - Dec 28
Total with taxes and fees
Parkway House

Stunning Modern Apartment in Rochester, England

Stunning Modern Apartment in Rochester, England
3.0 star property
Rochester
9.0 out of 10, Wonderful, (9)
"Nice space & location "
United Kingdom
Asim
$225 nightly
The price is $225
Dec 25 - Dec 26
Total with taxes and fees
Stunning Modern Apartment in Rochester, England

Westgate Cottage

Westgate Cottage
3.0 star property
Sittingbourne
$435 nightly
The price is $435
Dec 29 - Dec 30
Total with taxes and fees
Westgate Cottage

Staycations Maldon Suites

Staycations Maldon Suites
4.0 star property
Maldon
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
$129 nightly
The price is $155
Jan 6 - Jan 7, 2026
Total with taxes and fees
Staycations Maldon Suites

Gillingham 4-bed Stay - Wifi, Parking, Ldn Access

Gillingham 4-bed Stay - Wifi, Parking, Ldn Access
2.0 star property
Gillingham
$194 nightly
The price is $233
Jan 3 - Jan 4, 2026
Total with taxes and fees
Gillingham 4-bed Stay - Wifi, Parking, Ldn Access

Frinton Escapes

Frinton Escapes
3.5 star property
Frinton-on-Sea
10.0 out of 10, Exceptional, (16)
"Great place to stay definitely recommend "
United Kingdom
Michele
$145 nightly
The price is $174
Jan 13 - Jan 14, 2026
Total with taxes and fees
Frinton Escapes

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, (6)
"Only stayed for one night but thoroughly enjoyed it and would definitely stay again. "
United Kingdom
Gillian
$221 nightly
The price is $252
Dec 24 - Dec 25
Total with taxes and fees
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southend-on-Sea vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southend-on-Sea vacation 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 low season months. For more hustle and bustle, you may prefer to visit Southend-on-Sea in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $74 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 vacation rentals in Southend-on-Sea?

Yes, there are vacation rentals in Southend-on-Sea close to Southend Pier, or you can go with a more remote 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 vacation home rentals that Southend-on-Sea has to offer?

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

Expedia has 19 vacation rentals for your stay in Southend-on-Sea.

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

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

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

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Southend-on-Sea. Vacation rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for families.