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

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372 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

    (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 £92 / night

      £642 / week

      Book View

      Responds fast!
      avg. 1 hour 21 minutes

      from £92 / 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 £98 / night

        £682 / week

        Book View

        from £98 / 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

            13

            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 £91 / night

            £569 - £850 / week

            Book View

            from £91 / night

            (16) 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

                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

                (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

                  from £132 / 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 £166 / night

                    £974 / week

                    Book View

                    from £166 / 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 

                      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. 40 minutes

                        from £46 / 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 25 minutes

                          from £75 / 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

                            (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 £89 / night

                              £568 - £889 / week

                              Book View

                              from £89 / 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

                                (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

                                  (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. 48 minutes

                                    from £79 / 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 £98 / night

                                      £628 - £1,029 / week

                                      Book View

                                      from £98 / 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. 40 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

                                            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

                                              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. 1 hour 38 minutes

                                                from £69 / 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

                                                  Great rentals within 20 miles that match your search

                                                  Distance approx 13.23 miles from Southend-on-Sea

                                                  (5) Very Good 

                                                    20

                                                    Sittingbourne holiday home rental

                                                    Kent / Sittingbourne

                                                    3 5 5 nights min

                                                    • 3 bedrooms
                                                    • sleeps 5
                                                    • 5 nights min
                                                    • Nearest beach 10 km
                                                    • Child friendly
                                                    • Car not necessary

                                                    from £115 / night

                                                    £802 / week

                                                    Book View

                                                    Responds fast!
                                                    avg. 3 hours 2 minutes

                                                    from £115 / night

                                                    Distance approx 19.82 miles from Southend-on-Sea

                                                    (5) Very Good 

                                                    Certificate of Excellence

                                                      18

                                                      Holiday shepherds hut rental

                                                      Faversham / Stalisfield

                                                      1 2 2 nights min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 2 nights min

                                                      Certificate of Excellence

                                                      from £81 / night

                                                      £481 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 3 hours 11 minutes

                                                      from £81 / night

                                                      Distance approx 17.66 miles from Southend-on-Sea

                                                        15

                                                        Holiday apartment rental

                                                        Kent / Whitstable

                                                        2 6 2 nights min

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

                                                        from £120 / night

                                                        £598 - £900 / week

                                                        Enquire View

                                                        from £120 / night

                                                        Distance approx 19.77 miles from Southend-on-Sea

                                                        (2) Excellent 

                                                          21

                                                          Holiday apartment in Greenhithe

                                                          Kent / Greenhithe

                                                          2 4 3 nights min

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

                                                          from £86 / night

                                                          £602 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 44 minutes

                                                          from £86 / night

                                                          Distance approx 9.59 miles from Southend-on-Sea

                                                          (6) Average 

                                                            11

                                                            Holiday caravan/mobile home with shared pool in Minster on Sea

                                                            Isle of Sheppey / Minster on Sea

                                                            3 6 3 nights min

                                                            • 3 bedrooms
                                                            • sleeps 6
                                                            • 3 nights min
                                                            • Swimming pool
                                                            • Child friendly
                                                            • Private garden

                                                            from £69 / night

                                                            £458 / week

                                                            Book View

                                                            Responds fast!
                                                            avg. 58 minutes

                                                            from £69 / night

                                                            Distance approx 17.86 miles from Southend-on-Sea

                                                              38

                                                              Holiday home rental

                                                              Kent / Whitstable

                                                              2 4 2 nights min

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

                                                              from £157 / night

                                                              £784 - £983 / week

                                                              Book View

                                                              from £157 / night

                                                              Distance approx 18.25 miles from Southend-on-Sea

                                                              (13) Very Good 

                                                                24

                                                                Holiday apartment in Whitstable

                                                                Whitstable / Tankerton

                                                                2 4 4 nights min

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

                                                                from £94 / night

                                                                £642 - £796 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 2 hours 45 minutes

                                                                from £94 / night

                                                                Distance approx 17.78 miles from Southend-on-Sea

                                                                (2) Excellent 

                                                                  17

                                                                  Holiday home in Whitstable

                                                                  Kent / Whitstable

                                                                  2 4 min stay varies

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

                                                                  from £58 / night

                                                                  £401 - £785 / week

                                                                  Book View

                                                                  Responds fast!
                                                                  avg. 3 hours 25 minutes

                                                                  from £58 / night

                                                                  Distance approx 19.26 miles from Southend-on-Sea

                                                                  (2)  

                                                                    8

                                                                    Apartment rental in Brentwood

                                                                    Borough of Brentwood / Brentwood

                                                                    2 6 3 nights min

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

                                                                    from £125 / night

                                                                    £874 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 38 minutes

                                                                    from £125 / night

                                                                    Distance approx 17.79 miles from Southend-on-Sea

                                                                    (42) Very Good 

                                                                      55

                                                                      Holiday cottage rental

                                                                      Kent / Whitstable

                                                                      4 12 3 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 12
                                                                      • 3 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0.1 km
                                                                      • Child friendly

                                                                      from £344 / night

                                                                      £1,718 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 2 hours 18 minutes

                                                                      from £344 / night

                                                                      Distance approx 13 miles from Southend-on-Sea

                                                                        15

                                                                        Gillingham holiday apartment rental

                                                                        Kent / Gillingham

                                                                        1 2 5 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 5 nights min
                                                                        • Private garden

                                                                        from £904 / night

                                                                        £6,324 / week

                                                                        Book View

                                                                        from £904 / night

                                                                        Distance approx 17.76 miles from Southend-on-Sea

                                                                          16

                                                                          Home rental in Whitstable

                                                                          Kent / Whitstable

                                                                          4 8 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Child friendly
                                                                          • Pet friendly

                                                                          from £273 / night

                                                                          £1,093 - £1,553 / week

                                                                          Enquire View

                                                                          from £273 / night

                                                                          Distance approx 13 miles from Southend-on-Sea

                                                                            4

                                                                            Holiday chalet in Leysdown-on-Sea

                                                                            Isle of Sheppey / Leysdown-on-Sea

                                                                            1 4 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 2 nights min
                                                                            • Child friendly
                                                                            • Pet friendly

                                                                            from £58 / night

                                                                            £401 / week

                                                                            Book View

                                                                            from £58 / night

                                                                            Distance approx 12.96 miles from Southend-on-Sea

                                                                            (1) Very Good 

                                                                              19

                                                                              Caravan/mobile home rental in Leysdown-on-Sea with golf nearby

                                                                              Isle of Sheppey / Leysdown-on-Sea

                                                                              2 6 3 nights min

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

                                                                              from £69 / night

                                                                              £447 / week

                                                                              Book View

                                                                              from £69 / night

                                                                              Distance approx 19.06 miles from Southend-on-Sea

                                                                                14

                                                                                Holiday apartment rental

                                                                                Kent / Swalecliffe

                                                                                1 2 2 nights min

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

                                                                                from £100 / night

                                                                                £462 - £642 / week

                                                                                Book View

                                                                                from £100 / night

                                                                                Distance approx 18.54 miles from Southend-on-Sea

                                                                                (110) Excellent 

                                                                                Certificate of Excellence

                                                                                  141

                                                                                  Holiday guest house in Whitstable

                                                                                  Kent / Whitstable

                                                                                  5 23 2 nights min

                                                                                  • 5 bedrooms
                                                                                  • sleeps 23
                                                                                  • 2 nights min
                                                                                  • Beach / lakeside relaxation
                                                                                  • Nearest beach 1 km
                                                                                  • Child friendly

                                                                                  Certificate of Excellence

                                                                                  from £653 / night

                                                                                  £2,462 - £10,300 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 14 minutes

                                                                                  from £653 / 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
                                                                                  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

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