Southend-on-Sea Vacation Rentals

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Check prices for these dates

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Southend-on-Sea vacation rentals

Cottage | Interior
493 Little Wakering Road

493 Little Wakering Road

493 Little Wakering Road
3.5 star property
Southend-on-Sea
The price is ￥59,802
￥71,762 total
includes taxes & fees
Jan 2 - Jan 3, 2026
493 Little Wakering Road
Apartment, Private Bathroom, City View | Dining
Luxurious ONE Bedroom Apartment IN Bond Street

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)
The price is ￥19,134
￥31,176 total
includes taxes & fees
Dec 28 - Dec 29
Luxurious ONE Bedroom Apartment IN Bond Street
42-inch flat-screen TV with satellite channels, plasma TV, DVD player
Chelmsford Serviced Apartments

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
The price is ￥25,221
￥30,265 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Chelmsford Serviced Apartments
Apartment | Property grounds
Countryside Annex- Sleeps 2, Free Parking & Garden

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
The price is ￥22,223
￥26,668 total
includes taxes & fees
Dec 29 - Dec 30
Countryside Annex- Sleeps 2, Free Parking & Garden
Free WiFi
Fantastic Large Room with free parking

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
The price is ￥25,452
￥30,543 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fantastic Large Room with free parking
Exterior
Birds Farm

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
The price is ￥21,656
￥25,988 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Birds Farm
Cottage | Interior
Swallow Cottage

Swallow Cottage

Swallow Cottage
3.5 star property
Herne Bay
The price is ￥65,531
￥78,637 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Swallow Cottage
House, 3 Bedrooms | Interior
Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars

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
The price is ￥31,914
￥38,297 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars
Front of property
Beach Retreat With Parking Near the Sea

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
The price is ￥71,942
￥88,820 total
includes taxes & fees
Dec 30 - Dec 31
Beach Retreat With Parking Near the Sea
Double Room, Ensuite, Park View (Room 2) | 1 bedroom
Hogwarts Bed and Continental Breakfast

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
The price is ￥10,532
￥12,638 total
includes taxes & fees
Dec 28 - Dec 29
Hogwarts Bed and Continental Breakfast
Chalet | Terrace/patio
The Dairy - Seaside Couples Escape in Whitstable

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
The price is ￥8,328
￥15,050 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Dairy - Seaside Couples Escape in Whitstable
1 bedroom
Frinton Escapes

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
The price is ￥22,819
￥27,384 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Frinton Escapes
Apartment | Private kitchen | Fridge, microwave, oven, stovetop
Cozy Rochester Apartment Retreat

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
The price is ￥21,795
￥31,217 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Cozy Rochester Apartment Retreat
Apartment, Accessible, Private Bathroom | Shared kitchen
Parkway House

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
The price is ￥19,134
￥31,176 total
includes taxes & fees
Dec 27 - Dec 28
Parkway House
Interior
Kensington Bliss - 3 Bedroom House in Colchester

Kensington Bliss - 3 Bedroom House in Colchester

Kensington Bliss - 3 Bedroom House in Colchester
2.0 star property
Colchester
The price is ￥25,927
￥31,113 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Kensington Bliss - 3 Bedroom House in Colchester
Superior Apartment, Private Bathroom (D'Arcy Suite) | Interior
Staycations Maldon Suites

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
The price is ￥20,187
￥24,224 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Staycations Maldon Suites
Fridge, dishwasher, electric kettle, toaster
Sally

Sally

Sally
3.0 star property
Whitstable
10.0 out of 10, Exceptional, (1)
The price is ￥66,248
￥79,498 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sally
Deluxe Suite, Ensuite, Courtyard View | 1 bedroom
The Lower Bell

The Lower Bell

The Lower Bell
3.0 star property
Aylesford
7.8 out of 10, Good, (149)
"Clean comfortable proprty"
United Kingdom
Pete
The price is ￥12,287
￥14,745 total
includes taxes & fees
Dec 28 - Dec 29
The Lower Bell
Miscellaneous
Green Cottages

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
The price is ￥52,661
￥63,194 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Green Cottages
Apartment, Private Bathroom | Shared kitchen
Luxurious 2 Bedroom Apartment With Free Parking

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
The price is ￥24,400
￥39,602 total
includes taxes & fees
Dec 30 - Dec 31
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

Cave Hotel & Golf Resort

Cave Hotel & Golf Resort

10/10 Excellent
"Great stay "
Taylor 1-night trip
Posted 2 days ago
Cave Hotel & Golf Resort

Find out more about Southend-on-Sea

Search for holiday rentals in Southend-on-Sea on Expedia! You can easily find your home rentals, villas, holiday apartments in Southend-on-Sea using one of the methods below:

  • View our selection of featured holiday rentals in Southend-on-Sea
  • Use the map to find apartments and other holiday homes in the Southend-on-Sea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Southend-on-Sea while they last

Look no further and take a look at our great range of rental properties in Southend-on-Sea!

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.