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Sailing holidays (11)

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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Filters applied: Private pool (11)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
11 Results  |  
14 Photos

Yacht | 8 Bedrooms | sleeps 16

Short stays welcome

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from £1091 /night

£7632 - £10388 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • May take pets – please enquire
Private Yacht Blue Cruise, gather your loved ones for a once in a lifetime experience. Explore and enjoy some of the most exclusive cruising grounds in Turkey from the comfort of your own yacht. Tailor made yachting holiday,exclusively made for your requirements.  …see more

14 Photos

Yacht | 5 Bedrooms | sleeps 10

Short stays welcome

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from £1272 /night

£8904 - £10388 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Private Yacht Blue Cruise, gather your loved ones for a once in a lifetime experience. Explore and enjoy some of the most exclusive cruising grounds in Turkey from the comfort of your own yacht. Tailor made yachting holiday,exclusively made for your requirements.  …see more

24 Photos

Yacht | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £303 /night

£2120 - £2650 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
For an amazing and unforgettable holiday this year charter the beautiful sailing yacht 'Shanti' and cruise the Ionian islands in style.  …see more

Featured properties

4 Photos

Houseboat | 3 Bedrooms | sleeps 9

1 night min stay

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from £106 /night

£742 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • No pets allowed
  • Private garden
Character cottage. Private pool.  …see more

20 Photos

Yacht | 1 Bedroom | sleeps 5

Excellent 5/5 

1 night min stay

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from £52 /night

£360 - £392 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • No pets allowed
PORTO Yacht Charter Douro River Portugal. BAVARIA IMEXUS 28ft Sail Yacht for hire The Douro Valley water way goes 200km from Porto in the Atlantic coast, to Spain  …see more

15 Photos

Yacht | 4 Bedrooms | sleeps 8

Short stays welcome

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from £667 /night

£4664 - £6360 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Why to rent a villa if you can have your private sailing yacht or share it with new friends! Yes contact us even to book one cabin because we like to organize sailing experiences for like minded people. We will reply to any question.  …see more

10 Photos

Yacht | 3 Bedrooms | sleeps 8

Short stays welcome

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from £158 /night

£1103 - £4198 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • May take pets – please enquire
  • Private garden
Des magnifiques semaines a partager en famille ou entre amis !! CORSICALEMENT . Daniel Nous nous chargerons de vos transfères : aéroport ou férry , compris dans nos tarifs . AUCUNES CAUTIONS ..  …see more

20 Photos

Yacht | 1 Bedroom | sleeps 2

6 Nights min stay

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from £128 /night

£891 - £1781 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for over 5s only
  • Car not necessary
  • No pets allowed
Nous ne faisons pas de remplissage et vous serez le seul couple à bord (ou seul(e) si vous êtes célibataire) Le bateau et ses propriétaires seront à votre entière disposition, nous préférons priviléger la convivialité. pensions complètes, tout est compris hors billet d'avion et transfert du bateau à l'aéroport.  …see more

4 Photos

Yacht | 4 Bedrooms | sleeps 8

Min stay varies

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from £727 /night

£5088 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
voiler, croisière, soleil, vacances, catamaran, plage, Bahamas, sud, voile  …see more

5 Photos

Yacht | 4 Bedrooms | sleeps 8

7 Nights min stay

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from £67 /night

£467 - £509 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
Vacanze in Barca a Vela Eolie, Cabin Charter Eolie, Imbarco Singolo alle Isole Eolie, Flottiglie e Crociere per Single in Sicilia  …see more

18 Photos

Yacht | 4 Bedrooms | sleeps 10

Excellent 5/5 

Min stay varies

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from £93 /night

£645 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
We plan & organize yacht charter by group, couple, or for those wishing to travel alone, creating the most compatible onboard experience & amentities with and a professional, friendly & talented crew. Come join us on IntersailClub!  …see more