Southend-on-Sea Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Southend-on-Sea vacation rentals

Interior
493 Little Wakering Road

Cottage in Southend-on-Sea

493 Little Wakering Road
3.5 star property
The price is P22,306
P26,767 total
includes taxes & fees
Dec 27 - Dec 28
493 Little Wakering Road
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 P19,642
P23,571 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Green Cottages
42-inch flat-screen TV with satellite channels, plasma TV, DVD player
Chelmsford Serviced Apartments

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 P9,502
P11,402 total
includes taxes & fees
Dec 29 - Dec 30
Chelmsford Serviced Apartments
Property grounds
Countryside Annex- Sleeps 2, Free Parking & Garden

Apartment in Canterbury

Countryside Annex- Sleeps 2, Free Parking & Garden
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 P8,289
P9,947 total
includes taxes & fees
Dec 29 - Dec 30
Countryside Annex- Sleeps 2, Free Parking & Garden
Free WiFi
Fantastic Large Room with free parking

Apartment in Chatham

Fantastic Large Room with free parking
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 P9,493
P11,392 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Fantastic Large Room with free parking
Exterior
Smallcroft

Cottage in Whitstable

Smallcroft
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is P39,602
P47,523 total
includes taxes & fees
Dec 29 - Dec 30
Smallcroft
Front of property
Beach Retreat With Parking Near the Sea

Vacation 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 P29,187
P35,515 total
includes taxes & fees
Dec 30 - Dec 31
Beach Retreat With Parking Near the Sea
Exterior
Birds Farm

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 P8,780
P10,536 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Birds Farm
Interior
Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars

Vacation Home in Tilbury

Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars
2.0 star property
The price is P12,068
P14,481 total
includes taxes & fees
Dec 24 - Dec 25
Peaceful Family Home in Tilbury With Garden & Parking for 3 Cars
1 bedroom
Hogwarts Bed and Continental Breakfast

Cottage in Sheerness

Hogwarts Bed and Continental Breakfast
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 P3,928
P4,714 total
includes taxes & fees
Dec 30 - Dec 31
Hogwarts Bed and Continental Breakfast
Private kitchen
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 P8,368
P11,927 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy Rochester Apartment Retreat
Dining
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 P7,137
P11,628 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Luxurious ONE Bedroom Apartment IN Bond Street
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 P3,138
P5,651 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Dairy - Seaside Couples Escape in Whitstable
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 P7,137
P11,628 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Parkway House
Living area
Stunning Modern Apartment in Rochester, England

Apartment in Rochester

Stunning Modern Apartment in Rochester, England
3.0 star property
9.0 out of 10, Wonderful, (9)
"Nice space & location "
United Kingdom
Asim
Stunning Modern Apartment in Rochester, England
Private kitchen
Westgate Cottage

Cottage in Sittingbourne

Westgate Cottage
3.0 star property
Westgate Cottage
Interior
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 P7,529
P9,035 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Staycations Maldon Suites
Private kitchen
Gillingham 4-bed Stay - Wifi, Parking, Ldn Access

Residence in Gillingham

Gillingham 4-bed Stay - Wifi, Parking, Ldn Access
2.0 star property
The price is P11,854
P14,225 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Gillingham 4-bed Stay - Wifi, Parking, Ldn Access
1 bedroom
Frinton Escapes

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 P8,511
P10,214 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Frinton Escapes
Shared kitchen
Luxurious 2 Bedroom Apartment With Free Parking

Apartment in Chelmsford

Luxurious 2 Bedroom Apartment With Free Parking
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 P9,101
P14,771 total
includes taxes & fees
Jan 5 - Jan 6, 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

ORIDA Maidstone Hotel

ORIDA Maidstone Hotel

10/10 Excellent
"Amenities are good - pool - gym - bar - food Good location to or from London/ports "
Ian 1-night trip
Posted 18 hours ago
ORIDA Maidstone Hotel

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:

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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.