Sailing holidays

Sailing holidays (20)

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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20 Holiday homes

Filters applied: Heated pool (20)

(5) Excellent 

25

Houseboat rental in Puerto Rico Resort with golf nearby

Gran Canaria / Puerto Rico Resort

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
“Just brilliant!” Everything was fantastic. We were met by Alexis who showed us how everything worked and was just a phone call away if we needed help with anything. The boat is fabulous. Very comfortable, luxurious, clean and it was wonderful to have  …see more

from £130 / night

£906 / week

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from £130 / night

44

Houseboat rental in Srinagar with golf nearby

Kashmir / Srinagar

27 50 1 night min

  • 27 bedrooms
  • Sleeps 50
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children
kashmir ,houseboats ,travel booking ,car rental, bike rental, tour pakages , treaking, camping etc  …see more

from £98 / night

£732 / week

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from £98 / 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

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

24

Holiday yacht in Cogolin

French Riviera - Cote d'Azur / Cogolin

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
Pour profiter de l'ambiance d'un port sur la côte méditerranéenne au coeur même du Golfe de St Tropez !La SARL. "Rêves de Mer et D'Azur" située aux Marines de Cogolin (à 10mn de St Tropez et 15mn  …see more

from £517 / night

£2586 / week

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from £517 / night

20

California / Marina del Rey

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

 …see more

from £82 / night

£570 / week

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from £82 / night

(1) Excellent 

11

Maryland / Baltimore

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £224 / night

£1139 - £15366 / week

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from £224 / night

24

Florida / Ruskin

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

 …see more

from £74 / night

£448 - £561 / week

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from £74 / night

18

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £97 / night

£773 / week

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from £97 / night

(2) Excellent 

9

Massachusetts / Boston

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £407 / night

£2440 / week

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from £407 / night

(2) Excellent 

32

Halong Bay / Tuan Chau Island

20 2 1 night min

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

 …see more

from £219 / night

£1531 / week

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from £219 / 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 £583 / night

£4080 / week

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from £583 / night

13

Southwest Gulf Coast / Cape Coral

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £244 / night

£1220 - £1789 / week

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from £244 / night

24

Florida / Miami Beach

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £159 / night

£976 - £2000 / week

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from £159 / night

9

Florida Keys / Key West

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £265 / night

£1586 - £2155 / week

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from £265 / night

14

Broward County / Pompano Beach

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £159 / night

£1057 / week

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from £159 / 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 £204 / night

£1057 / week

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from £204 / 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

23

Lake of the Ozarks / Lake Ozark

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £425 / night

£1927 - £3533 / week

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from £425 / night