Houses in South Portland and Apartments – Holiday Lettings - Holiday Rentals South Portland

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175 Holiday homes

(1) Excellent 

    13

    Holiday studio in South Portland

    Maine / South Portland

    Studio 3 7 nights min

    • Studio
    • sleeps 3
    • 7 nights min
    • Beach / lakeside relaxation
    • Child friendly
    • Pet friendly

    from £187 / night

    £1,153 / week

    Book View

    Responds fast!
    avg. 33 minutes

    from £187 / night

      9

      Holiday apartment in South Portland

      Maine / South Portland

      2 4 2 nights min

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

      from £111 / night

      £577 / week

      Book View

      from £111 / night

      (3) Excellent 

        72

        Home letting in South Portland

        Maine / South Portland

        3 9 min stay varies

        • 3 bedrooms
        • sleeps 9
        • min stay varies
        • Child friendly
        • Air conditioning
        • Pet friendly

        from £262 / night

        £1,662 - £4,393 / week

        Book View

        Responds fast!
        avg. 2 hours 12 minutes

        from £262 / night

          22

          Holiday home with golf nearby in South Portland

          Maine / South Portland

          3 4 3 nights min

          • 3 bedrooms
          • sleeps 4
          • 3 nights min
          • Beach / lakeside relaxation

          from £355 / night

          £2,482 / week

          Book View

          Responds fast!
          avg. 3 hours 5 minutes

          from £355 / night

            47

            Holiday home in South Portland

            Maine / South Portland

            3 8 2 nights min

            • 3 bedrooms
            • sleeps 8
            • 2 nights min
            • Child friendly
            • Car not necessary
            • Air conditioning

            from £324 / night

            £2,265 / week

            Book View

            from £324 / night

              63

              Holiday home with golf nearby in South Portland

              Maine / South Portland

              4 13 min stay varies

              • 4 bedrooms
              • sleeps 13
              • min stay varies
              • Child friendly
              • Air conditioning
              • Private garden

              from £528 / night

              £3,081 - £6,627 / week

              Book View

              Responds fast!
              avg. 2 hours 12 minutes

              from £528 / night

              Great rentals within 20 miles that match your search

              Distance approx 16.83 miles from South Portland

                89

                Standish holiday farmhouse rental

                Maine / Standish

                6 22 min stay varies

                • 6 bedrooms
                • sleeps 22
                • min stay varies
                • Beach / lakeside relaxation
                • Nearest beach 8 km
                • Child friendly

                from £404 / night

                £2,478 - £3,475 / week

                Book View

                Responds fast!
                avg. 38 minutes

                from £404 / night

                Distance approx 8.23 miles from South Portland

                (9) Excellent 

                  27

                  Holiday condo in Scarborough

                  Maine / Scarborough

                  1 2 min stay varies

                  • 1 bedroom
                  • sleeps 2
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Ask owner if suitable for children
                  • Car not necessary

                  from £67 / night

                  £399 - £710 / week

                  Book View

                  from £67 / night

                  Distance approx 13.9 miles from South Portland

                    17

                    Holiday home in Biddeford

                    Maine / Biddeford

                    3 6 7 nights min

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

                    from £197 / night

                    £1,374 / week

                    Book View

                    from £197 / night

                    Distance approx 0.1 miles from South Portland Show on Map

                    (6) Very Good 

                      19

                      Holiday condo in Portland

                      Maine / Portland

                      1 4 1 night min

                      • 1 bedroom
                      • sleeps 4
                      • 1 night min
                      • Child friendly
                      • Car not necessary
                      • Air conditioning

                      from £61 / night

                      £488 - £798 / week

                      Book View

                      Responds fast!
                      avg. 3 hours 30 minutes

                      from £61 / night

                      Distance approx 14.01 miles from South Portland

                        12

                        Holiday home in Biddeford Pool

                        Maine / Biddeford Pool

                        3 4 3 nights min

                        • 3 bedrooms
                        • sleeps 4
                        • 3 nights min
                        • Child friendly
                        • Private garden

                        from £178 / night

                        £1,241 / week

                        Book View

                        from £178 / night

                        Distance approx 13.86 miles from South Portland

                          23

                          Holiday home rental

                          Maine / Biddeford Pool

                          3 8 5 nights min

                          • 3 bedrooms
                          • sleeps 8
                          • 5 nights min
                          • Nearest beach 0.2 km
                          • Child friendly
                          • Air conditioning

                          from £311 / night

                          £2,123 / week

                          Book View

                          from £311 / night

                          Distance approx 12.98 miles from South Portland

                          (1) Excellent 

                            12

                            Holiday home in Saco

                            Maine / Saco

                            3 8 1 night min

                            • 3 bedrooms
                            • sleeps 8
                            • 1 night min
                            • Child friendly
                            • Pet friendly
                            • Private garden

                            from £235 / night

                            £1,410 / week

                            Book View

                            from £235 / night

                            Distance approx 12.98 miles from South Portland

                              5

                              Saco holiday bungalow rental

                              Maine / Saco

                              2 4 1 night min

                              • 2 bedrooms
                              • sleeps 4
                              • 1 night min
                              • Child friendly
                              • Pet friendly
                              • Private garden

                              from £107 / night

                              £639 / week

                              Book View

                              from £107 / night

                              Distance approx 10.25 miles from South Portland

                                6

                                Holiday home rental

                                Maine / Old Orchard Beach

                                3 8 7 nights min

                                • 3 bedrooms
                                • sleeps 8
                                • 7 nights min
                                • Child friendly

                                from £211 / night

                                £1,463 / week

                                Book View

                                from £211 / night

                                Distance approx 11.89 miles from South Portland

                                (11) Very Good 

                                  12

                                  Holiday home in Old Orchard Beach

                                  Maine / Old Orchard Beach

                                  2 6 4 nights min

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

                                  from £133 / night

                                  £887 / week

                                  Book View

                                  from £133 / night

                                  Distance approx 16.09 miles from South Portland

                                    16

                                    Holiday guest house in Biddeford

                                    Maine / Biddeford

                                    1 4 2 nights min

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

                                    from £577 / night

                                    £4,034 / week

                                    Book View

                                    Responds fast!
                                    avg. 3 hours 54 minutes

                                    from £577 / night

                                    Distance approx 6.33 miles from South Portland

                                    (3) Very Good 

                                      12

                                      Holiday apartment in Cape Elizabeth

                                      Maine / Cape Elizabeth

                                      2 6 2 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 2 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 0.2 km
                                      • Child friendly

                                      from £169 / night

                                      £1,241 - £2,482 / week

                                      Book View

                                      from £169 / night

                                      Distance approx 11.03 miles from South Portland

                                        16

                                        Holiday apartment with golf nearby in Old Orchard Beach

                                        Maine / Old Orchard Beach

                                        2 6 7 nights min

                                        • 2 bedrooms
                                        • sleeps 6
                                        • 7 nights min
                                        • Beach / lakeside relaxation
                                        • Child friendly
                                        • Air conditioning

                                        from £102 / night

                                        £710 - £1,007 / week

                                        Book View

                                        Responds fast!
                                        avg. 2 hours 24 minutes

                                        from £102 / night

                                        Distance approx 7.02 miles from South Portland

                                          42

                                          Falmouth holiday home rental

                                          Maine / Falmouth

                                          3 6 2 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 2 nights min
                                          • Beach / lakeside relaxation
                                          • Child friendly
                                          • Car not necessary

                                          from £439 / night

                                          £2,372 / week

                                          Book View

                                          Responds fast!
                                          avg. 2 hours 14 minutes

                                          from £439 / night

                                          Distance approx 14.68 miles from South Portland

                                          (3) Excellent 

                                            14

                                            Holiday cottage in Biddeford Pool

                                            Maine / Biddeford Pool

                                            2 6 7 nights min

                                            • 2 bedrooms
                                            • sleeps 6
                                            • 7 nights min
                                            • Beach / lakeside relaxation
                                            • Nearest beach 0 km
                                            • Child friendly

                                            from £279 / night

                                            £1,951 / week

                                            Book View

                                            from £279 / night

                                            Distance approx 3.13 miles from South Portland Show on Map

                                              24

                                              Portland holiday apartment rental

                                              Maine / Portland

                                              5 10 3 nights min

                                              • 5 bedrooms
                                              • sleeps 10
                                              • 3 nights min
                                              • Child friendly
                                              • Air conditioning
                                              • Pet friendly

                                              from £222 / night

                                              £1,552 / week

                                              Book View

                                              from £222 / night

                                              Distance approx 11.65 miles from South Portland

                                                11

                                                Ocean Park holiday cottage rental

                                                Maine / Ocean Park

                                                2 5 7 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Nearest beach 0.1 km
                                                • Child friendly

                                                from £152 / night

                                                £1,064 / week

                                                Book View

                                                from £152 / night

                                                Distance approx 10.3 miles from South Portland

                                                  16

                                                  Apartment accommodation in Old Orchard Beach

                                                  Maine / Old Orchard Beach

                                                  2 6 3 nights min

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

                                                  from £244 / night

                                                  £1,773 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 1 hour 6 minutes

                                                  from £244 / night

                                                  Distance approx 11.68 miles from South Portland

                                                    6

                                                    Holiday home rental

                                                    Maine / Yarmouth

                                                    2 4 2 nights min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 2 nights min
                                                    • Nearest beach 3 km
                                                    • Child friendly
                                                    • Air conditioning

                                                    from £116 / night

                                                    £646 / week

                                                    Book View

                                                    from £116 / night

                                                    Distance approx 13.62 miles from South Portland

                                                      16

                                                      Holiday home in Saco

                                                      Maine / Saco

                                                      2 6 7 nights min

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

                                                      from £127 / night

                                                      £887 - £1,507 / week

                                                      Book View

                                                      from £127 / night

                                                      Distance approx 10.55 miles from South Portland

                                                        24

                                                        Condo rental in Old Orchard Beach with golf nearby

                                                        Maine / Old Orchard Beach

                                                        2 4 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 7 nights min
                                                        • Child friendly
                                                        • Air conditioning
                                                        • Private garden

                                                        from £191 / night

                                                        £1,335 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 1 hour 36 minutes

                                                        from £191 / night

                                                        Distance approx 13.06 miles from South Portland

                                                          8

                                                          Wells holiday apartment rental

                                                          Maine / Wells

                                                          2 5 7 nights min

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

                                                          from £152 / night

                                                          £1,064 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 3 hours 10 minutes

                                                          from £152 / night

                                                          Distance approx 5.66 miles from South Portland

                                                            19

                                                            Holiday home in Cape Elizabeth

                                                            Maine / Cape Elizabeth

                                                            2 6 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 7 nights min
                                                            • Child friendly
                                                            • Air conditioning
                                                            • Ask about pets

                                                            from £355 / night

                                                            £2,482 / week

                                                            Book View

                                                            from £355 / night

                                                            Distance approx 10.34 miles from South Portland

                                                            (1) Excellent 

                                                              27

                                                              Old Orchard Beach holiday cottage rental

                                                              Maine / Old Orchard Beach

                                                              2 6 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • min stay varies
                                                              • Child friendly
                                                              • Air conditioning

                                                              from £157 / night

                                                              £1,530 / week

                                                              Book View

                                                              from £157 / night

                                                              Distance approx 8.33 miles from South Portland

                                                              (1) Excellent 

                                                                34

                                                                Scarborough holiday home rental

                                                                Maine / Scarborough

                                                                6 19 7 nights min

                                                                • 6 bedrooms
                                                                • sleeps 19
                                                                • 7 nights min
                                                                • Child friendly

                                                                from £1,140 / night

                                                                £7,978 / week

                                                                Book View

                                                                from £1,140 / night

                                                                Distance approx 10.04 miles from South Portland

                                                                (2) Average 

                                                                  14

                                                                  Holiday cottage in Old Orchard Beach

                                                                  Maine / Old Orchard Beach

                                                                  3 8 7 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Child friendly

                                                                  from £178 / night

                                                                  £1,241 / week

                                                                  Book View

                                                                  from £178 / night

                                                                  Distance approx 6.68 miles from South Portland

                                                                    24

                                                                    Westbrook ski apartment to rent.

                                                                    Maine / Westbrook

                                                                    1 6 min stay varies

                                                                    • 1 bedroom
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Ski
                                                                    • Child friendly
                                                                    • Air conditioning

                                                                    from £53 / night

                                                                    £367 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 20 minutes

                                                                    from £53 / night

                                                                    Distance approx 16.7 miles from South Portland

                                                                      9

                                                                      Cottage rental in Orrs Island

                                                                      Maine / Orrs Island

                                                                      3 7 3 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 7
                                                                      • 3 nights min
                                                                      • Child friendly

                                                                      from £248 / night

                                                                      £1,732 / week

                                                                      Book View

                                                                      from £248 / night

                                                                      Distance approx 13.47 miles from South Portland

                                                                        24

                                                                        Holiday home in Ocean Park

                                                                        Maine / Ocean Park

                                                                        4 10 7 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 10
                                                                        • 7 nights min
                                                                        • Child friendly

                                                                        from £563 / night

                                                                        £3,941 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 1 hour 36 minutes

                                                                        from £563 / night

                                                                        Distance approx 1.59 miles from South Portland Show on Map

                                                                          30

                                                                          Cape Elizabeth holiday home rental

                                                                          Maine / Cape Elizabeth

                                                                          3 7 7 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 7
                                                                          • 7 nights min
                                                                          • Child friendly

                                                                          from £444 / night

                                                                          £2,638 - £3,258 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 2 hours 38 minutes

                                                                          from £444 / night

                                                                          Distance approx 1.02 miles from South Portland Show on Map

                                                                            71

                                                                            Holiday home in Portland

                                                                            Maine / Portland

                                                                            4 12 min stay varies

                                                                            • 4 bedrooms
                                                                            • sleeps 12
                                                                            • min stay varies
                                                                            • Nearest beach 0 km
                                                                            • Child friendly

                                                                            from £439 / night

                                                                            £2,638 - £6,671 / week

                                                                            Book View

                                                                            Responds fast!
                                                                            avg. 1 hour 51 minutes

                                                                            from £439 / night

                                                                            Distance approx 10.55 miles from South Portland

                                                                              19

                                                                              Holiday condo in Old Orchard Beach

                                                                              Maine / Old Orchard Beach

                                                                              1 4 7 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 7 nights min
                                                                              • Child friendly
                                                                              • Air conditioning

                                                                              from £95 / night

                                                                              £664 - £807 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 1 hour 19 minutes

                                                                              from £95 / night

                                                                              Distance approx 1.21 miles from South Portland Show on Map

                                                                              (1) Excellent 

                                                                                6

                                                                                Home letting in Portland

                                                                                Maine / Portland

                                                                                1 2 3 nights min

                                                                                • 1 bedroom
                                                                                • sleeps 2
                                                                                • 3 nights min
                                                                                • Air conditioning

                                                                                from £157 / night

                                                                                £1,099 / week

                                                                                Book View

                                                                                from £157 / night

                                                                                Distance approx 12.11 miles from South Portland

                                                                                  17

                                                                                  Holiday home in Saco

                                                                                  Maine / Saco

                                                                                  4 10 7 nights min

                                                                                  • 4 bedrooms
                                                                                  • sleeps 10
                                                                                  • 7 nights min
                                                                                  • Child friendly
                                                                                  • Pet friendly

                                                                                  from £672 / night

                                                                                  £4,699 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 2 hours 9 minutes

                                                                                  from £672 / night

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