Sailing holidays

Sailing holidays (14)

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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14 Holiday homes

Filters applied: Private pool

20

Holiday yacht with swimming pool in Le Marin

Arrondissement of Le Marin / Le Marin

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £264 / night

£1843 / week

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from £264 / night

10

Le Marin holiday yacht rental

Arrondissement of Le Marin / Le Marin

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £658 / night

£4606 / week

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from £658 / night

(1) Excellent 

10

Ajaccio holiday yacht rental

Communaute d'Agglomeration du Pays Ajaccien / Ajaccio

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Swimming pool

from £608 / night

£4255 / week

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Responds fast!
avg. 2 hours 57 minutes

from £608 / night

31

Holiday yacht in Skiathos Town

Skiathos / Skiathos Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

from £841 / night

£5310 - £7080 / week

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from £841 / night

(3) Excellent 

26

Holiday houseboat in Tuakau

Waikato Region / Tuakau

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £566 / night

£3959 / week

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from £566 / night

7

Yacht rental in Honeymoon Beach with swimming pool

Water Island / Honeymoon Beach

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £788 / night

£4725 / week

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from £788 / night

25

Holiday yacht in Charlotte Amalie

St. Thomas / Charlotte Amalie

3 6 Min stay varies

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

from £512 / night

£3583 / week

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from £512 / night

44

Holiday yacht rental

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool

from £552 / night

£3859 / week

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from £552 / night

26

Vreeland holiday houseboat rental

Utrecht Province / Vreeland

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 40 km
  • Swimming pool

from £119 / night

£746 - £1237 / week

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from £119 / night

4

Novigrad holiday yacht rental

Zadar County / Novigrad

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £627 / night

£4386 / week

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from £627 / night

7

Holiday yacht with swimming pool in Montreal

Quebec / Montreal

2 8 1 night min

  • 2 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £393 / night

£2751 / week

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from £393 / night

25

Holiday yacht with swimming pool in Road Town

Tortola / Road Town

3 6 Min stay varies

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

from £516 / night

£3612 / week

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from £516 / night

22

Srinagar ski houseboat to rent.

Srinagar District / Srinagar

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski

from £21 / night

£21 / week

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from £21 / night

4

Renmark holiday houseboat rental

South Australia / Renmark

5 2 3 nights min

  • 5 bedrooms
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £6 / night

£42 / week

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from £6 / night

1