Sailing holidays

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Sailing holidays (45)

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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45 Holiday homes

(5) Very Good 

1 / 41

San Diego holiday yacht rental

California / San Diego

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £189 / night

£1165 - £1856 / week

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from £189 / night

(13) Excellent 

1 / 12

Holiday yacht with golf nearby in Manilva

Manilva / Puerto de la Duquesa

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £125 / night

£800 - £1220 / week

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from £125 / night

(1) Excellent 

1 / 26

San Diego holiday houseboat rental

California / San Diego

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from £171 / night

£1194 / week

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from £171 / night

1 / 12

Holiday yacht with golf nearby in San Diego

California / San Diego

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £168 / night

£1028 - £1548 / week

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from £168 / night

1 / 27

Holiday yacht rental

Florida / Miami Beach

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from £206 / night

£1233 - £1713 / week

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from £206 / night

1 / 23

Holiday yacht with golf nearby in Glyfada

Athens / Glyfada

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay

from £388 / night

£2714 / week

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from £388 / night

(16) Excellent 

1 / 7

Holiday houseboat with golf nearby in Loch Ness

Scottish Highlands / Loch Ness

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from £167 / night

£770 - £1362 / week

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from £167 / night

1 / 44

Holiday yacht rental

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from £480 / night

£3357 / week

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from £480 / night

1 / 24

Holiday yacht rental

Tenerife / Las Galletas

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £388 / night

£2714 / week

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from £388 / night

1 / 42

Yacht rental in Freeport with golf nearby

Grand Bahama Island / Freeport

  • 2 bedrooms
  • Sleeps 8
  • 5 nights min stay

from £69 / night

£480 / week

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from £69 / night

1 / 20

Yacht rental in Urbanitzacio Rat Penat, Sitges with golf nearby

Barcelona Province / Urbanitzacio Rat Penat, Sitges

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from £1551 / night

£10853 / week

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from £1551 / night

(2) Very Good 

1 / 20

Holiday narrowboat with golf nearby in Lancaster

Lancashire / Lancaster

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from £125 / night

£820 / week

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from £125 / night

(1) Excellent 

1 / 12

Holiday yacht rental

New Providence Island / Nassau

  • 4 bedrooms
  • Sleeps 6
  • 1 night min stay

from £265 / night

£1850 / week

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from £265 / night

1 / 18

Holiday yacht with golf nearby in Punta Ala

Castiglione Della Pescaia / Punta Ala

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from £272 / night

£1396 / week

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from £272 / night

1 / 10

Holiday yacht with golf nearby in Venice

City of Venice / Venice

  • 1 bedroom
  • Sleeps 6
  • 1 night min stay

from £109 / night

£760 / week

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from £109 / night

1 / 18

Punta Ala holiday yacht rental

Castiglione Della Pescaia / Punta Ala

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay

from £1551 / night

£9303 / week

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from £1551 / night

(5) Excellent 

1 / 25

Houseboat rental in Puerto Rico Resort with golf nearby

Gran Canaria / Puerto Rico Resort

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min stay

from £117 / night

£814 / week

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from £117 / night

1 / 13

Ski yacht to rent in Halong Bay

Quang Ninh Province / Halong Bay

  • 14 bedrooms
  • Sleeps 32
  • 1 night min stay

from £227 / night

£1583 / week

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from £227 / night

1 / 14

Buford holiday houseboat rental

Georgia / Buford

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from £343 / night

£1850 / week

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from £343 / night

(23) Excellent 

1 / 14

Holiday houseboat in Srinagar

Kashmir / Srinagar

  • 6 bedrooms
  • Sleeps 15
  • 1 night min stay

from £36 / night

£250 / week

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from £36 / night

1 / 37

Holiday houseboat with golf nearby in Sentosa Island

Singapore / Sentosa Island

  • 4 bedrooms
  • Sleeps 9
  • 1 night min stay

from £617 / night

£4316 / week

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from £617 / night

1 / 13

Holiday yacht with golf nearby in Turtle Cove

Providenciales / Turtle Cove

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from £1370 / night

£9590 / week

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from £1370 / night

(1) Excellent 

1 / 19

Narrowboat rental in Chertsey with golf nearby

Surrey / Chertsey

  • 1 bedroom
  • Sleeps 6
  • 1 night min stay

from £250 / night

£950 / week

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from £250 / night

1 / 13

Yacht rental in San Diego with golf nearby

California / San Diego

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £168 / night

£1028 - £1548 / week

Book Book View

from £168 / night

1 / 34

Holiday yacht with golf nearby in Kalives, Chalkidiki

Halkidiki Region / Kalives, Chalkidiki

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay

from £582 / night

£3721 - £4652 / week

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from £582 / night

1 / 7

Holiday yacht with golf nearby in Muscat

Muscat Governorate / Muscat

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay

from £1781 / night

£12466 / week

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from £1781 / night

(3) Good 

1 / 11

Holiday yacht in Torcy

Marne-la-Vallee / Torcy

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from £63 / night

£388 - £605 / week

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from £63 / night

1 / 44

Houseboat rental in Srinagar with golf nearby

Kashmir / Srinagar

  • 27 bedrooms
  • Sleeps 50
  • 1 night min stay

from £83 / night

£617 / week

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from £83 / night

1 / 4

Houseboat rental in Srinagar with golf nearby

Kashmir / Srinagar

  • 8 bedrooms
  • Sleeps 21
  • 1 night min stay

from £10 / night

£68 / week

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from £10 / night

1 / 5

Houseboat rental in Srinagar with golf nearby

Kashmir / Srinagar

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay

from £35 / night

£240 / week

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from £35 / night

1 / 4

Holiday yacht in Nans les Pins

Nans-les-Pins / Nans les Pins

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £698 / night

£698 / week

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from £698 / night

1 / 24

Yacht rental in Sausset-les-Pins with golf nearby

Bouches-du-Rhone / Sausset-les-Pins

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £66 / night

£404 / week

Book Book View

from £66 / night

1 / 10

Holiday houseboat rental

Kashmir / Srinagar

  • 10 bedrooms
  • Sleeps 20
  • 1 night min stay

from £35 / night

£35 - £39 / week

Book Book View

from £35 / night

1 / 8

Holiday yacht with golf nearby in Alicante

Alicante province / Alicante

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min stay

from £1908 / night

£13357 / week

Book Book View

from £1908 / night

1 / 12

Yacht rental in Bodrum City with golf nearby

Bodrum / Bodrum City

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay

from £2325 / night

£16279 / week

Book Book View

from £2325 / night

(6) Excellent 

1 / 22

Ski houseboat to rent in Srinagar

Kashmir / Srinagar

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies

from £35 / night

£274 / week

Book Book View

from £35 / night

1 / 22

Srinagar ski houseboat to rent.

Kashmir / Srinagar

  • 3 bedrooms
  • Sleeps 9
  • 1 night min stay

from £18 / night

£18 / week

Book Book View

from £18 / night

(2) Excellent 

1 / 7

Srinagar ski houseboat to rent.

Kashmir / Srinagar

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies

from £154 / night

£1007 / week

Book Book View

from £154 / night

1 / 10

Ajaccio holiday yacht rental

Corse-du-Sud / Ajaccio

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £277 / night

£1938 - £4070 / week

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from £277 / night

1 / 30

Holiday houseboat with golf nearby in Srinagar

Kashmir / Srinagar

  • 8 bedrooms
  • Sleeps 18
  • 1 night min stay

from £15 / night

£106 / week

Book Book View

from £15 / night

1 / 4

Holiday yacht with golf nearby in Richelieu Beach

Herault / Richelieu Beach

  • 6 bedrooms
  • Sleeps 8
  • Min stay varies

from £342 / night

£2388 / week

Book Book View

from £342 / night

1 / 15

San Diego holiday yacht rental

California / San Diego

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £141 / night

£857 - £2068 / week

Book Book View

from £141 / night

1 / 15

Holiday yacht rental

California / San Diego

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £141 / night

£857 - £2068 / week

Book Book View

from £141 / night

1 / 18

Holiday yacht with golf nearby in Punta Ala

Castiglione Della Pescaia / Punta Ala

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay

from £194 / night

£1163 / week

Book Book View

from £194 / night

1 / 18

Holiday yacht with golf nearby in Punta Ala

Castiglione Della Pescaia / Punta Ala

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay

from £233 / night

£1318 - £2404 / week

Book Book View

from £233 / night

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