Sailing holidays

Sailing holidays (682)

Family sailing holidays aren’t just an opportunity for budding skippers to wear silly hats and control the tiller all holiday long – the plus points are rather more numerous than that. Just think about it: you can set sail whenever you like, sailing from one beautiful location to another at the turn of a wheel. Best of all, you don’t have to put up with heaving beaches. Just find your own deserted stretch of sand or an isolated cove, moor up and enjoy the sunshine and quiet. Sailing doesn’t have to be an activity holiday, you know.

The more competent sailors among you might like to take the wheel yourself on one of our yachts in Spain or Greece. Or, for a little added luxury, you can hire your own private skipper.

For families in which there’s an even split between sea legs and landlubbers, there’s the sailing holiday compromise of renting a holiday home that has the use of its own boat and private mooring. Check out these sailing adventures in the Caribbean and along the coast of England.

But if sailing sounds just a little too involving for what’s supposed to be a relaxing holiday, there is the more tranquil option of a houseboat. Either stay put or pootle merrily around the waterways of England and the Netherlands. Whichever appeals more, you should definitely step aboard soon.

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682 Holiday homes

Filters applied: Under 5s

(10) Excellent 

25

Province of Naples / Sorrento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £278 / night

£1740 / week

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from £278 / night

10

Corfu / Gouvia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary

from £298 / night

£2087 - £3044 / week

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from £298 / night

(13) Excellent 

24

Holiday yacht in East Molesey

Surrey / East Molesey

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning

from £105 / night

£735 / week

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from £105 / night

(17) Excellent 

12

Holiday houseboat in Amsterdam

Amsterdam / Eastern Docklands

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets

from £105 / night

£522 / week

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from £105 / night

(12) Excellent 

40

Yacht accommodation in Puerto Calero

Lanzarote / Puerto Calero

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
“Perfect!” I arrived in Puerto Calero by boat, having sailed from Spain via Morocco. I wanted to stay for a longer period in Puerto Calero so booked Vientos Del Sur after a recommendation from a friend. A perfect choice. The boat is comfortable with an  …see more

from £53 / night

£366 - £512 / week

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from £53 / night

(4) Excellent 

13

Narrowboat rental in Henley-on-Thames

Oxfordshire / Henley-on-Thames

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“An amazing family holiday” All information/ communication in the run up to the holiday was very good, we were greeted in a very friendly manner and had a very informative tutorial about the narrowboat and locks which put us at ease and in good sted fo  …see more

from £251 / night

£1245 - £1600 / week

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from £251 / night

23

Holiday houseboat in Jyväskylä

Central Finland / Jyväskylä

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £270 / night

£1561 - £2344 / week

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from £270 / night

(4) Very Good 

7

State of Rio de Janeiro / Angra Dos Reis

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly

from £222 / night

£1553 / week

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from £222 / night

(19) Excellent 

77

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 25 km
  • Child friendly
  • Pet friendly

from £153 / night

£1066 / week

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from £153 / night

(25) Excellent 

20

Holiday houseboat with shared pool in Amsterdam

Amsterdam / Jordaan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £183 / night

£1218 - £1827 / week

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from £183 / night

(3) Excellent 

43

San Diego holiday houseboat rental

California / San Diego

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Child friendly

from £200 / night

£1395 / week

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from £200 / night

(17) Excellent 

23

Yacht rental in San Blas Islands

Guna Yala Region / San Blas Islands

5 8 1 night min

  • 5 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £404 / night

£2823 / week

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from £404 / night

6

Holiday houseboat in Alappuzha

Kerala / Alappuzha

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly

from £158 / night

£1049 / week

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from £158 / night

(9) Very Good 

24

Houseboat accommodation in Henley-on-Thames

Oxfordshire / Henley-on-Thames

3 11 3 nights min

  • 3 bedrooms
  • Sleeps 11
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“An incredibly relaxing holiday in perfect comfort on a beautiful part of the Thames.” From start to finish this turned out to beat many 5 star hotel holidays we had all taken. Firstly the hosts are attentive, lovely and fun. They gave us 2 informed fa  …see more

from £250 / night

£1510 - £2160 / week

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from £250 / night

(13) Excellent 

24

Houseboat rental in Amsterdam

Amsterdam / Eastern Docklands

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Child friendly

from £205 / night

£1431 / week

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from £205 / night

9

Aude / Marseillette

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 35 km
  • Child friendly
  • Pet friendly

from £74 / night

£518 - £609 / week

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from £74 / night

(1) Excellent 

16

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

from £222 / night

£1553 / week

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from £222 / night

16

San Blas Islands / El Porvenir

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £105 / night

£734 / week

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from £105 / night

(21) Excellent 

29

Porto holiday narrowboat rental

Porto District / Porto

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Magnificent sailing through UNESCO world Heritage” Couple and one children, rented a boat for a long weekend, sailed up on river Douro until Spanish border. At the boats base, nice little chalet for the first night. Very good navigation, sightseeing a  …see more

from £166 / night

£566 / week

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from £166 / night

(115) Excellent 

36

Holiday houseboat in Amsterdam

Amsterdam / Central Amsterdam

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
“Ultimate houseboat experience” Me and my partner stayed for 4 days at Houseboat Tante Piet and it was fantastic. Siet, the owner, received us with coffee and 'stroopwafels', and made us feel at home right away. She showed us our cosy bedroom (which wa  …see more

from £122 / night

£766 - £1314 / week

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from £122 / night

(5) Excellent 

15

Pangkalan Bun holiday houseboat rental

Central Kalimantan / Pangkalan Bun

6 10 2 nights min

  • 6 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 10 km
  • Child friendly
  • Air conditioning

from £280 / night

£1750 - £6790 / week

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from £280 / night

(6) Very Good 

32

Holiday houseboat in Alappuzha

Kerala / Alappuzha

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Child friendly

from £138 / night

£960 / week

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from £138 / night

(2) Excellent 

8

Holiday houseboat in Alappuzha

Kerala / Alappuzha

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

from £138 / night

£960 / week

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from £138 / night

(9) Excellent 

17

Holiday houseboat rental

Torridge / Holsworthy

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Child friendly

from £81 / night

£500 - £830 / week

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from £81 / night

(2) Excellent 

11

Olbia / Pittulongu

5 5 5 nights min

  • 5 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £87 / night

£609 / week

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from £87 / night

(23) Excellent 

41

Holiday yacht with shared pool in Playa Blanca

Playa Blanca / Marina Rubicon

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful” We had a fantastic one week holiday,the location was stunning and plenty of restaurants to choose from although we found Lani's the best. Jorge and Raquel are lovely and so friendly.  …see more

from £84 / night

£585 - £974 / week

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from £84 / night

15

North Holland Province / Weesp

7 18 2 nights min

  • 7 bedrooms
  • Sleeps 18
  • 2 nights min
  • Nearest beach 40 km
  • Child friendly
  • Car not necessary

from £435 / night

£3044 / week

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from £435 / night

(10) Excellent 

9

Finistere / Audierne

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly

from £109 / night

£761 - £1096 / week

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from £109 / night

(6) Excellent 

21

Copenhagen holiday houseboat rental

Zealand / Copenhagen

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets

from £479 / night

£3044 / week

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from £479 / night

33

San Blas Islands / El Porvenir

3 2 Min stay varies

  • 3 bedrooms
  • Sleeps 2
  • Min stay varies
  • Child friendly

from £355 / night

£2484 / week

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from £355 / night

23

Holiday yacht rental

Santorini / Fira

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning

from £131 / night

£914 / week

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from £131 / night

(4) Excellent 

29

Amazon River / Manaus

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly

from £22 / night

£170 - £932 / week

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from £22 / night

(1) Excellent 

10

Holiday yacht in Dar es Salaam

Dar es Salaam / Masaki Peninsula

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“Stu Berry yacht trip August 2011” Loved every minute of it. Chilled and superb trip. Great country, and perfect place to travel by yacht. Wonderful crew.  …see more

from £968 / night

£6775 / week

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from £968 / night

9

Lefkada / Vasiliki

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly

from £87 / night

£603 / week

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from £87 / night

(1) Excellent 

14

Italian Riviera / Lavagna

2 6 2 nights min

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

from £216 / night

£1510 / week

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from £216 / night

(3) Excellent 

10

Province of Barletta-Andria-Trani / Trani

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £87 / night

£609 / week

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from £87 / night

(3) Excellent 

6

Yacht rental in Kos Town

Kós / Kos Town

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
“exhilarating and relaxing at the same time” Had a wonderful time visiting many different islands swimming in the sea exhilarating sailing some days with excellent winds whilst on other calmer days we soaked up the sun. Beautiful boat and excellent s  …see more

from £129 / night

£900 - £1700 / week

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from £129 / night

(4) Excellent 

11

Amsterdam holiday houseboat rental

North Holland Province / Amsterdam

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
“Great Stay” We had a wonderful time staying on this beautiful boat, the owners where very helpful without being intrusive. The boat had everything you needed for a self catering break, the bed rooms and bathrooms both matched our expectations based o  …see more

from £244 / night

£1705 / week

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from £244 / night

20

Holiday yacht in Agia Efimia

Cephalonia / Agia Efimia

3 7 7 nights min

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

from £300 / night

£2000 / week

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from £300 / night

(53) Excellent 

30

Holiday narrowboat rental

Salford / Worsley

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
“fantastic trip” We had an amazing long weekend as usual. The boat (Queenie) was absolutely fab, cosy clean and warm and a real head turner. people stopped and looked and had their photos taken beside it. I would recommend this boating experience to ev  …see more

from £170 / night

£1190 / week

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from £170 / night

1