Sailing holidays

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Sailing holidays (25)

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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25 Holiday homes

Filters applied: Private pool (25)

1 / 16

Corsaro, our 5* luxury cruiser houseboat, Kariba

Mashonaland West Province / Kariba

3 bedroomsSleeps 81 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Swimming pool; Suitable for children age 5+; Car not necessary;
Corsaro is the Kariba Cruise Company's 5* houseboat on Lake Kariba. There is no better way to explore the shores of this enchanting place than from her decks. Fall asleep to the sounds of Africa from one of two double ensuite rooms, or in one of her two single bunks or  …see more

from £917 / night

£0 / week

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from £917 / night

(4) Excellent 

1 / 30

Sailing Adventure Amalfi Coast and Flegree

Province of Naples / Procida Island

4 bedroomsSleeps 2Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
"CONTACT US FOR ONE PAX AND MORE THAN TWO PAX AVAILABILITIES. PRICES ARE FOR 2 PERSONS GROUPS, PRIVATE QUOTES FOR LARGER GROUPS. Classic Sailing Ketch of 20 meters based in Ibiza & Formentera. Why to rent a villa if you can have your private sailing yacht or share  …see more

from £209 / night

£1434 / week

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from £209 / night

1 / 5

Aeolian Islands / Lipari

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £71 / night

£500 - £584 / week

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from £71 / night

1 / 10

Arrondissement of Le Marin / Le Marin

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £631 / night

£4412 / week

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from £631 / night

1 / 20

Arrondissement of Le Marin / Le Marin

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £250 / night

£0 / week

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from £250 / night

1 / 11

Sailing Yacht Vacation Mallorca Ibiza luxury Villa

Majorca / Palma de Mallorca

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
A unique experience to discover Belaeres (Mallorca, menorca or Ibiza) from the nice side, the bay and cala side We want to offer you the opportunity to live the enriching experience of sailing, (enjoying our sunny Mediterranean weather) learning and improving your navi  …see more

from £832 / night

£5379 / week

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from £832 / night

(1) Excellent 

1 / 10

Corse-du-Sud / Ajaccio

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.05 km; Swimming pool;
 …see more

from £465 / night

£3250 - £4375 / week

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from £465 / night

1 / 4

Martha - Toot Baldon yacht sleeps 50

Oxford / Toot Baldon

50 bedroomsSleeps 501 night min stay

  • 50 bedrooms
  • Sleeps 50
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Ski;
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from £84 / night

£834 - £29417 / week

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from £84 / night

1 / 5

Corse-du-Sud / Ajaccio

6 bedroomsSleeps 107 nights min stay

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
 …see more

from £1003 / night

£7017 / week

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from £1003 / night

1 / 4

New Providence Island / Nassau

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

Pricing unknown

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Pricing unknown

(1) Excellent 

1 / 10

The Historical CUTTY JEAN Cabin 1 - Tigne Point yacht sleeps 2

Sliema / Tigne Point

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Swimming pool;
Cutty Jean offers you the most exciting combination of stunning settings, fantastic on-board atmosphere and fun.Wake up to the most spectacular view directly over the sea. Have a swim before your first morning coffee, sit back and relax or take your summer adventure to  …see more

from £68 / night

£0 / week

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from £68 / night

1 / 14

My Blue Cruise Yachting - Fethiye Town yacht sleeps 10

Fethiye / Fethiye Town

5 bedroomsSleeps 10Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
Private Gulet Yacht Charter in TurkeyThe Turquoise Coast or Turkish Riviera consists of many coastal towns and villages sitting on the Aegean and Mediterranean coastlines of Turkey. Including the centres of Fethiye, Marmaris, Bodrum and Antalya, it is one of the best de  …see more

from £1459 / night

£10209 / week

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from £1459 / night

1 / 5

Sai Gon Cafe Travel - Hanoi yacht sleeps 18

Hanoi

9 bedroomsSleeps 181 night min stay

  • 9 bedrooms
  • Sleeps 18
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
Sai Gon Cafe Travel 09 cabins are divided into three classes Deluxe, Superior and Family, all service provided, with central air-conditioning, en-suite bathroom and private balconies and heavenly-soft bed with wide open view to Halong Bay. Cruise swimming, kayaking an  …see more

from £69 / night

£75 / week

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from £69 / night

1 / 18

Yachts Themis iv - Skiathos Town yacht sleeps 4

Skiathos / Skiathos Town

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; 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 £799 / night

£5463 - £5883 / week

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from £799 / night

1 / 44

Florida Keys / Key West

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 4 km; Swimming pool;
 …see more

from £535 / night

£0 / week

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from £535 / night

(1) Excellent 

1 / 26

Waikato Region / Tuakau

6 bedroomsSleeps 121 night min stay

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £540 / night

£0 / week

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from £540 / night

1 / 15

Maryland / Baltimore

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £191 / night

£993 / week

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from £191 / night

1 / 17

Province of Guanacaste / Nosara

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £786 / night

£5499 - £14886 / week

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from £786 / night

1 / 7

Water Island / Honeymoon Beach

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
 …see more

from £764 / night

£4581 / week

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from £764 / night

1 / 13

Gran Canaria / San Bartolome de Tirajana

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £471 / night

£2900 / week

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from £471 / night

1 / 4

Emirate of Dubai / Dubai

3 bedroomsSleeps 171 night min stay

  • 3 bedrooms
  • Sleeps 17
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £764 / night

£0 / week

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from £764 / night

1 / 4

South Australia / Renmark

5 bedroomsSleeps 23 nights min stay

  • 5 bedrooms
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £6 / night

£0 / week

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from £6 / night

1 / 22

Kashmir / Srinagar

3 bedroomsSleeps 91 night min stay

  • 3 bedrooms
  • Sleeps 9
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Ski;
 …see more

from £20 / night

£20 / week

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from £20 / night

1 / 34

Nassau / Nassau Harbour

3 bedroomsSleeps 87 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £1745 / night

£12214 / week

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from £1745 / night

1 / 7

Quebec / Montreal

2 bedroomsSleeps 81 night min stay

  • 2 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Car advised;
 …see more

from £381 / night

£0 / week

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from £381 / night

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