Guest houses in Southend-on-Sea and Cottages - Holiday Lettings - Holiday Rentals Southend-on-Sea

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337 Holiday homes

(7) Excellent 

21

Apartment accommodation in Westcliff-on-Sea

Southend-on-Sea / Westcliff-on-Sea

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Child friendly

from £105 / night

£735 - £1,015 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from £105 / night

(3) Very Good 

Certificate of Excellence

7

Home rental in Southend-on-Sea

Essex / Southend-on-Sea

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 2 km
  • Car not necessary
  • Private garden

Certificate of Excellence

from £40 / night

£280 / week

Book View

Responds fast!
avg. 25 minutes

from £40 / night

(4) Very Good 

19

Westcliff-on-Sea holiday apartment rental

Southend-on-Sea / Westcliff-on-Sea

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £145 / night

£850 / week

Book View

from £145 / night

39

Holiday home in Shoeburyness

Southend-on-Sea / Shoeburyness

3 4 7 nights min

  • 3 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

from £120 / night

£680 - £800 / week

Book View

Responds fast!
avg. 41 minutes

from £120 / night

(15) Very Good 

10

Holiday apartment rental

Essex / Southend-on-Sea

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £75 / night

£525 / week

Enquire View

from £75 / night

17

Holiday home rental

Essex / Southend-on-Sea

4 6 3 nights min

  • 4 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary

from £115 / night

£805 / week

Book View

from £115 / night

(1) Very Good 

21

Apartment rental in Westcliff-on-Sea

Southend-on-Sea / Westcliff-on-Sea

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 1 km
  • Child friendly

from £77 / night

£496 - £1,193 / week

Book View

from £77 / night

50

Apartment rental in Westcliff-on-Sea

Southend-on-Sea / Westcliff-on-Sea

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Child friendly

from £65 / night

£455 / week

Book View

from £65 / night

(1) Excellent 

12

Holiday private room in Leigh-on Sea

Southend-on-Sea / Leigh-on Sea

3 2 1 night min

  • 3 bedrooms
  • sleeps 2
  • 1 night min

from £30 / night

£210 / week

Book View

from £30 / night

(5) Excellent 

15

Home letting in Shoeburyness

Southend-on-Sea / Shoeburyness

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £85 / night

£580 - £1,234 / week

Book View

from £85 / night

(4) Excellent 

17

Southend-on-Sea holiday apartment rental

Essex / Southend-on-Sea

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly

from £450 / night

£3,150 / week

Book View

from £450 / night

(2) Excellent 

22

Holiday home in Southend-on-Sea

Essex / Southend-on-Sea

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly

from £250 / night

£1,000 / week

Book View

Responds fast!
avg. 59 minutes

from £250 / night

(2) Excellent 

38

Holiday apartment in Westcliff-on-Sea

Southend-on-Sea / Westcliff-on-Sea

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary

from £80 / night

£560 / week

Book View

from £80 / night

(3) Very Good 

26

Holiday apartment in Southend-on-Sea

Essex / Southend-on-Sea

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min

from £65 / night

£400 / week

Book View

Responds fast!
avg. 3 hours 40 minutes

from £65 / night

37

Holiday apartment in Southend-on-Sea

Essex / Southend-on-Sea

2 2 2 nights min

  • 2 bedrooms
  • sleeps 2
  • 2 nights min
  • Child friendly

from £84 / night

£560 / week

Book View

from £84 / night

23

Southend-on-Sea holiday apartment rental

Essex / Southend-on-Sea

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

from £125 / night

£875 / week

Book View

from £125 / night

7

Holiday home in Southend-on-Sea

Essex / Southend-on-Sea

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Car not necessary
  • Private garden

from £35 / night

£245 / week

Book View

Responds fast!
avg. 25 minutes

from £35 / night

(1) Very Good 

10

Apartment letting in Southend-on-Sea

Essex / Southend-on-Sea

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary

from £69 / night

£483 / week

Book View

Responds fast!
avg. 48 minutes

from £69 / night

13

Apartment rental in Southend-on-Sea

Essex / Southend-on-Sea

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Ask owner if suitable for children

from £79 / night

£497 - £1,650 / week

Book View

from £79 / night

30

Holiday home in Southend-on-Sea

Essex / Southend-on-Sea

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Child friendly

from £85 / night

£548 - £1,073 / week

Book View

from £85 / night

12

Holiday apartment in Southend-on-Sea

Essex / Southend-on-Sea

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly

from £100 / night

£650 / week

Book View

from £100 / night

13

Holiday home in Westcliff-on-Sea

Southend-on-Sea / Westcliff-on-Sea

9 18 5 nights min

  • 9 bedrooms
  • sleeps 18
  • 5 nights min
  • Child friendly

from £600 / night

£4,200 / week

Book View

Responds fast!
avg. 41 minutes

from £600 / night

(1) Excellent 

18

Holiday home in Southend-on-Sea

Essex / Southend-on-Sea

4 5 4 nights min

  • 4 bedrooms
  • sleeps 5
  • 4 nights min
  • Nearest beach 0.3 km
  • Child friendly
  • Car not necessary

from £95 / night

£665 / week

Book View

from £95 / night

Great rentals within 20 miles that match your search

Distance approx 17.77 miles from Southend-on-Sea

(2) Excellent 

11

Holiday apartment in Whitstable

Kent / Whitstable

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Child friendly

from £80 / night

£560 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from £80 / night

Distance approx 18.99 miles from Southend-on-Sea

(6) Very Good 

Certificate of Excellence

13

West Mersea holiday home rental

Mersea Island / West Mersea

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 1 km
  • Private garden

Certificate of Excellence

from £56 / night

£370 / week

Book View

Responds fast!
avg. 36 minutes

from £56 / night

Distance approx 18.58 miles from Southend-on-Sea

14

Cottage rental in West Mersea

Mersea Island / West Mersea

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Nearest beach 1 km
  • Private garden

from £80 / night

£560 / week

Book View

Responds fast!
avg. 56 minutes

from £80 / night

Distance approx 17.78 miles from Southend-on-Sea

(1) Excellent 

16

Holiday home in Whitstable

Kent / Whitstable

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £110 / night

£350 - £685 / week

Book View

Responds fast!
avg. 3 hours 53 minutes

from £110 / night

Distance approx 12.26 miles from Southend-on-Sea

(13) Very Good 

9

Holiday chalet in Leysdown-on-Sea

Isle of Sheppey / Leysdown-on-Sea

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £50 / night

£350 / week

Book View

from £50 / night

Distance approx 16.89 miles from Southend-on-Sea

(19) Very Good 

15

Holiday cottage in Canterbury

Kent / Canterbury

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 8 km
  • Child friendly
  • Car not necessary

from £50 / night

£250 - £360 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £50 / night

Distance approx 17.7 miles from Southend-on-Sea

49

Holiday apartment in Chelmsford

Essex / Chelmsford

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary

from £103 / night

£600 - £810 / week

Book View

from £103 / night

Distance approx 17.7 miles from Southend-on-Sea

(2) Very Good 

20

Holiday home rental

Kent / Whitstable

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £150 / night

£1,050 - £1,250 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £150 / night

Distance approx 16 miles from Southend-on-Sea

(7) Very Good 

23

Holiday barn in Maldon

Essex / Maldon

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

from £220 / night

£1,300 - £1,760 / week

Enquire View

from £220 / night

Distance approx 12.63 miles from Southend-on-Sea

(1) Excellent 

20

Holiday home in Leysdown-on-Sea

Isle of Sheppey / Leysdown-on-Sea

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 1 km
  • Child friendly

from £50 / night

£320 / week

Book View

Responds fast!
avg. 10 minutes

from £50 / night

Distance approx 18.25 miles from Southend-on-Sea

(12) Very Good 

24

Holiday apartment in Whitstable

Whitstable / Tankerton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £75 / night

£525 - £690 / week

Book View

Responds fast!
avg. 3 hours 6 minutes

from £75 / night

Distance approx 12.53 miles from Southend-on-Sea

(3) Very Good 

12

Leysdown-on-Sea holiday caravan/mobile home rental

Isle of Sheppey / Leysdown-on-Sea

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool

from £35 / night

£320 - £500 / week

Book View

Responds fast!
avg. 30 minutes

from £35 / night

Distance approx 19.2 miles from Southend-on-Sea

9

Holiday apartment in Brentwood

Borough of Brentwood / Brentwood

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £120 / night

£820 - £1,240 / week

Book View

from £120 / night

Distance approx 6.91 miles from Southend-on-Sea

7

Holiday private room in Sheerness

Isle of Sheppey / Sheerness

1 1 4 nights min

  • 1 bedroom
  • sleeps 1
  • 4 nights min
  • Car not necessary

from £35 / night

£175 / week

Book View

Responds fast!
avg. 1 hour 37 minutes

from £35 / night

Distance approx 17.43 miles from Southend-on-Sea

13

Holiday apartment accommodation

Essex / Chelmsford

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child friendly

from £105 / night

£735 / week

Book View

from £105 / night

Distance approx 12.93 miles from Southend-on-Sea

11

Holiday chalet with shared pool, golf nearby in Leysdown-on-Sea

Isle of Sheppey / Leysdown-on-Sea

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0.3 km
  • Swimming pool
  • Child friendly

from £60 / night

£420 / week

Book View

from £60 / night

Distance approx 17.8 miles from Southend-on-Sea

10

Holiday home in Chelmsford

Essex / Chelmsford

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 18 km
  • Child friendly

from £120 / night

£840 / week

Book View

from £120 / night

Why Southend-on-Sea?

This fabulous seaside resort in the east of England is one of the most exciting traditional British beach destinations around. With the longest Victorian pleasure pier in the world, and more entertainment than you could ever ask for, it'll be an unforgettable family vacation. Be sure to book your next holiday rental in Southend on Sea!

About Southend on Sea

40 miles east of London, Southend on Sea has historically been a popular destination of Londoners looking to enjoy the beach and all the seaside amusements that come with it. As a result, it’s become a fantastic beach resort.

With the longest Victorian pier in the world housing only a small fraction of the seaside entertainments on offer, and several gorgeous sandy beaches, Southend on Sea is a true delight for the whole family.

What to Do

Get a glimpse of local history at the Central Museum.

Golfers will be spoilt for choice with two excellent 18-hole courses in town.

Top Southend on Sea Travel Tips

For an unforgettably exciting traditional British beach getaway, be sure to book your next holiday rental in Southend on Sea.

Top Destination reviews

Close to ammenities
Great Stay.

Had a lovely weekend in Southend. The accommodation was perfect for my needs. It was very clean, modern and comfortable. I slept well and enjoyed my morning coffee in the beautiful garden. Angela was very welcoming, friendly and helpful. My weekend was very relaxed and I felt right at home. … see more
Apartment Thorpe Bay near Sea
Lived up to our expectations of a tasteful modern apartment

Nice space and some good features - really useful washing machine helped in our situation. Sharon was welcoming and helpful. Would come back again. … see more
York House
York house

Great location. Full instructions from landlord really helped, particularly as the weather was freezing for us visiting from Dubai so finding the boiler and heating was critical! With other family visiting, the flat was big enough for 10 of us to squeeze around the dining table and the kitchen managed to cope with roast dinners and the like. The flat itself is nice and cosy, some lovely features and well furnished and stocked. The balcony would be great for a summer evening aperitif as the sun sets. All very comfortable with some great highlights. We will definitely book again in future.see more
Shoebury Nest - 3 Bedroom Property
Perfect location

This house is in the perfect location, a 5 minute walk to the train station with access not just to London but also more local attractions. The beach is just around the corner and a welcome day out. Very comfortable and well equipped. The kitchen area was the focus for all of our interactions with friends and family and we managed to pull off lunch for 11 people without a hitch. On the down side, the washer/dryer didn't dry well. An outside clothesline would be a great addition. The bathrooms lack counter space and the sinks are quite small. Saying this, I would happily stay at this property again.see more
Everhome Self Catering Apartment in Southend-on-Sea
Fantastic

Lovely place to stay great value for money,clean, comfortable, quiet and homely. Malcolm is a lovely approachable man and we'll definitely be booking through him again. Sheila, Graham , Tiff and Izzy … see more