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

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

346 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

    from £105 / night

    (3) 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 £115 / night

      £802 / week

      Book View

      Responds fast!
      avg. 56 minutes

      from £115 / night

        17

        Apartment rental in Southend-on-Sea

        Essex / Southend-on-Sea

        2 4 2 nights min

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

        from £63 / night

        £407 - £727 / week

        Book View

        Responds fast!
        avg. 54 minutes

        from £63 / 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 £75 / night

          £521 / week

          Book View

          from £75 / night

          (5) Excellent 

            15

            Home letting in Shoeburyness

            Southend-on-Sea / Shoeburyness

            3 7 2 nights min

            • 3 bedrooms
            • sleeps 7
            • 2 nights min
            • Beach / lakeside relaxation
            • Child friendly
            • Private garden

            from £126 / night

            £882 / week

            Book View

            from £126 / 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 £144 / night

              £1,002 / week

              Book View

              from £144 / night

              (16) Very Good 

                10

                Holiday apartment rental

                Essex / Southend-on-Sea

                2 5 3 nights min

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

                from £79 / night

                £500 - £520 / week

                Enquire View

                from £79 / night

                (5) 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 £144 / night

                  £808 / week

                  Book View

                  from £144 / 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 £35 / night

                    £241 / week

                    Book View

                    from £35 / 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 £97 / night

                      £642 / week

                      Book View

                      from £97 / 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 £75 / night

                        £458 / week

                        Book View

                        Responds fast!
                        avg. 3 hours 39 minutes

                        from £75 / night

                        (1) Excellent 

                          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 £132 / night

                          £922 / week

                          Book View

                          Responds fast!
                          avg. 2 hours 18 minutes

                          from £132 / 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 £46 / night

                            £321 / week

                            Book View

                            Responds fast!
                            avg. 1 hour 5 minutes

                            from £46 / night

                            (1) Very Good 

                              21

                              Apartment rental in Westcliff-on-Sea

                              Southend-on-Sea / Westcliff-on-Sea

                              2 6 2 nights min

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

                              from £115 / night

                              £802 / week

                              Book View

                              from £115 / 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 £516 / night

                                £3,607 / week

                                Book View

                                from £516 / 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 £287 / night

                                  £1,145 / week

                                  Book View

                                  Responds fast!
                                  avg. 1 hour 2 minutes

                                  from £287 / night

                                    30

                                    Holiday home in Southend-on-Sea

                                    Essex / Southend-on-Sea

                                    3 7 2 nights min

                                    • 3 bedrooms
                                    • sleeps 7
                                    • 2 nights min
                                    • Beach / lakeside relaxation
                                    • Child friendly

                                    from £115 / night

                                    £802 / week

                                    Book View

                                    from £115 / 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 £79 / night

                                      £553 / week

                                      Book View

                                      Responds fast!
                                      avg. 58 minutes

                                      from £79 / night

                                      (1) Excellent 

                                        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

                                        £241 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 5 minutes

                                        from £35 / 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 £109 / night

                                          £762 / week

                                          Book View

                                          from £109 / night

                                            6

                                            Holiday apartment in Southend-on-Sea

                                            Essex / Southend-on-Sea

                                            2 6 2 nights min

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

                                            from £155 / night

                                            £1,082 / week

                                            Book View

                                            from £155 / night

                                            (1) Excellent 

                                              6

                                              Holiday apartment in Thorpe Bay

                                              Southend-on-Sea / Thorpe Bay

                                              1 2 7 nights min

                                              • 1 bedroom
                                              • sleeps 2
                                              • 7 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 1 km
                                              • Child friendly

                                              from £69 / night

                                              £436 / week

                                              Book View

                                              Responds fast!
                                              avg. 2 hours 1 minutes

                                              from £69 / night

                                                68

                                                Apartment rental in Westcliff-on-Sea

                                                Southend-on-Sea / Westcliff-on-Sea

                                                2 6 1 night min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 1 night min
                                                • Nearest beach 2 km
                                                • Child friendly
                                                • Car not necessary

                                                from £144 / night

                                                £762 - £1,339 / week

                                                Book View

                                                from £144 / 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 £115 / night

                                                  £745 / week

                                                  Book View

                                                  from £115 / night

                                                    9

                                                    Holiday apartment in Southend-on-Sea

                                                    Essex / Southend-on-Sea

                                                    1 2 1 night min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 1 night min
                                                    • Child friendly

                                                    from £69 / night

                                                    £401 / week

                                                    Book View

                                                    from £69 / night

                                                      9

                                                      Holiday apartment in Westcliff-on-Sea

                                                      Southend-on-Sea / Westcliff-on-Sea

                                                      1 3 1 night min

                                                      • 1 bedroom
                                                      • sleeps 3
                                                      • 1 night min
                                                      • Nearest beach 1 km
                                                      • Child friendly
                                                      • Car not necessary

                                                      from £69 / night

                                                      £401 / week

                                                      Book View

                                                      from £69 / night

                                                        35

                                                        Holiday apartment in Southend-on-Sea

                                                        Essex / Southend-on-Sea

                                                        2 4 min stay varies

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • min stay varies
                                                        • Child friendly

                                                        from £114 / night

                                                        £687 - £848 / week

                                                        Book View

                                                        from £114 / night

                                                          10

                                                          Holiday apartment rental

                                                          Southend-on-Sea / Westcliff-on-Sea

                                                          1 2 1 night min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 1 night min
                                                          • Nearest beach 1 km
                                                          • Child friendly
                                                          • Car not necessary

                                                          from £69 / night

                                                          £401 / week

                                                          Book View

                                                          from £69 / night

                                                            32

                                                            Holiday apartment in Southend-on-Sea

                                                            Essex / Southend-on-Sea

                                                            1 4 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Child friendly

                                                            from £98 / night

                                                            £573 - £848 / week

                                                            Book View

                                                            from £98 / night

                                                              41

                                                              Holiday apartment in Southend-on-Sea

                                                              Essex / Southend-on-Sea

                                                              1 2 2 nights min

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

                                                              from £92 / night

                                                              £573 - £687 / week

                                                              Book View

                                                              from £92 / night

                                                              Great rentals within 20 miles that match your search

                                                              Distance approx 17.18 miles from Southend-on-Sea

                                                              (1) Excellent 

                                                                10

                                                                Whitstable holiday caravan/mobile home rental

                                                                Kent / Whitstable

                                                                2 6 7 nights min

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • 7 nights min
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Pet friendly

                                                                from £92 / night

                                                                £642 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 1 hour 51 minutes

                                                                from £92 / night

                                                                Distance approx 17.92 miles from Southend-on-Sea

                                                                  11

                                                                  Chelmsford holiday home rental

                                                                  Essex / Chelmsford

                                                                  3 8 2 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 2 nights min
                                                                  • Nearest beach 18 km
                                                                  • Child friendly

                                                                  from £138 / night

                                                                  £962 / week

                                                                  Book View

                                                                  from £138 / night

                                                                  Distance approx 16.54 miles from Southend-on-Sea

                                                                    23

                                                                    Holiday apartment in Tilbury

                                                                    Thurrock / Tilbury

                                                                    1 3 2 nights min

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

                                                                    from £91 / night

                                                                    £602 - £762 / week

                                                                    Book View

                                                                    from £91 / night

                                                                    Distance approx 18.92 miles from Southend-on-Sea

                                                                      15

                                                                      Holiday apartment in Brentwood

                                                                      Borough of Brentwood / Brentwood

                                                                      2 6 2 nights min

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

                                                                      from £155 / night

                                                                      £1,128 - £1,827 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 1 hour 0 minutes

                                                                      from £155 / night

                                                                      Distance approx 17.71 miles from Southend-on-Sea

                                                                      (1) Very Good 

                                                                        13

                                                                        Holiday cottage in Whitstable

                                                                        Kent / Whitstable

                                                                        2 4 2 nights min

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

                                                                        from £138 / night

                                                                        £962 / week

                                                                        Book View

                                                                        from £138 / night

                                                                        Distance approx 17.44 miles from Southend-on-Sea

                                                                        (11) Excellent 

                                                                          12

                                                                          Thurnham holiday apartment rental

                                                                          Maidstone / Thurnham

                                                                          1 2 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • min stay varies
                                                                          • Nearest beach 30 km
                                                                          • Swimming pool
                                                                          • Private garden

                                                                          from £132 / night

                                                                          £687 - £745 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 1 hour 8 minutes

                                                                          from £132 / night

                                                                          Distance approx 17.85 miles from Southend-on-Sea

                                                                          (6) Excellent 

                                                                            18

                                                                            Holiday home rental

                                                                            Kent / Whitstable

                                                                            3 6 min stay varies

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

                                                                            from £138 / night

                                                                            £556 - £985 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 1 hour 23 minutes

                                                                            from £138 / night

                                                                            Distance approx 17.21 miles from Southend-on-Sea

                                                                              12

                                                                              Seasalter holiday boathouse rental

                                                                              Kent / Seasalter

                                                                              1 8 2 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 8
                                                                              • 2 nights min
                                                                              • Nearest beach 0 km
                                                                              • Child friendly
                                                                              • Pet friendly

                                                                              from £155 / night

                                                                              £974 / week

                                                                              Book View

                                                                              from £155 / night

                                                                              Distance approx 15.64 miles from Southend-on-Sea

                                                                              (1) Very Good 

                                                                                11

                                                                                Home rental in Oare

                                                                                Faversham / Oare

                                                                                2 5 2 nights min

                                                                                • 2 bedrooms
                                                                                • sleeps 5
                                                                                • 2 nights min
                                                                                • Suitable for children age 5+
                                                                                • Private garden

                                                                                from £98 / night

                                                                                £602 - £842 / week

                                                                                Book View

                                                                                from £98 / night

                                                                                Distance approx 17.65 miles from Southend-on-Sea

                                                                                  41

                                                                                  Holiday home rental

                                                                                  Kent / Whitstable

                                                                                  4 8 2 nights min

                                                                                  • 4 bedrooms
                                                                                  • sleeps 8
                                                                                  • 2 nights min
                                                                                  • Child friendly

                                                                                  from £193 / night

                                                                                  £771 - £1,254 / week

                                                                                  Enquire View

                                                                                  from £193 / 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 & Car Parking
                                                                                  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
                                                                                  Easy acces to ammenities
                                                                                  very comfortable

                                                                                  very clean warm and user friendly,all amenities very close by.all types of carry out and eateries close by and a couple of pubs with good menus … see more
                                                                                  THE LIGHTHOUSE APARTMENT
                                                                                  Christmas holiday at the lighthouse apartment

                                                                                  We had a lovely stay at the apartment, there was a mini Christmas tree which I thought was thoughtful of the owner for when we arrived. The views from the apartment were lovely as it looked over the beach, we saw the sun setting and rising! There was also a great park very close by with a playground for children which was good. In the apartment was everything we needed, I did take a few extra pans for cooking Christmas dinner but was contacted by Perry offering to bring more round which was kind. All in all it was a lovely week, thank you Perry.see more

                                                                                  Also consider