Sailing holidays

Sailing holidays (15)

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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15 Holiday homes

Filters applied: Private pool (15)

20

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

 …see more

from £259 / night

£1811 / week

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from £259 / night

11

Palma de Mallorca holiday yacht rental

Majorca / Palma de Mallorca

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Villa exclusive sea view yacht boat sailing  …see more

from £854 / night

£5518 / week

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from £854 / night

(1) Excellent 

10

Communaute d'Agglomeration du Pays Ajaccien / Ajaccio

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Swimming pool

 …see more

Pricing unknown

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Pricing unknown

10

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

 …see more

from £647 / night

£4526 / week

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from £647 / night

(1) Excellent 

10

Holiday yacht with swimming pool in Sliema

Sliema / Tigne Point

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
On-board accommodation, boat accommodation, rent-a-cabin, overnight stay aboard, stay on water. boathouse, botel, sea accommodation,<br />CUTTY JEAN is the most exciting combination of stunning settings, unforgettable adventure and fun.  …see more

from £69 / night

£483 / week

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from £69 / 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
Welcome to Themis IV With our boat we offer you a trip on the calm Greek waters, with the ability to sail between beautiful clusters of islands, to anchor in natural protected rare beauty coves and visit inaccessible beaches and swim in waters with unique purity and cl  …see more

from £819 / night

£5173 - £5604 / week

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from £819 / night

(3) Excellent 

26

Waikato Region / Tuakau

6 12 1 night min

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

 …see more

from £580 / night

£4055 / week

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from £580 / night

44

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

 …see more

from £565 / night

£3952 / week

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from £565 / night

15

Maryland / Baltimore

2 4 2 nights min

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

 …see more

from £202 / night

£1049 / week

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from £202 / night

4

Zadar County / Novigrad

4 8 7 nights min

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

 …see more

from £616 / night

£4311 / week

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from £616 / night

26

Utrecht Province / Vreeland

3 6 Min stay varies

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

 …see more

from £103 / night

£647 - £1216 / week

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from £103 / night

7

Quebec / Montreal

2 8 1 night min

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

 …see more

from £403 / night

£2817 / week

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from £403 / night

22

Kashmir / Srinagar

3 9 1 night min

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

 …see more

from £20 / night

£20 / week

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from £20 / night

4

South Australia / Renmark

5 2 3 nights min

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

 …see more

from £7 / night

£43 / week

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from £7 / night

7

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+

 …see more

from £807 / night

£4839 / week

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from £807 / night