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Sailing vacations

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1,046 Vacation rentals

Vacation yacht rental

Pont-de-Vaux yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $81 / night

$561 / week

1 / 34

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $201 / night

$1,403 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $134 / night

$938 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $134 / night

$938 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $370 / night

$2,589 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $201 / night

$1,403 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $201 / night

$1,403 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $370 / night

$2,589 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $370 / night

$2,589 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $134 / night

$938 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $201 / night

$1,403 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $370 / night

$2,589 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $134 / night

$938 / week

1 / 25

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $201 / night

$1,403 / week

1 / 20

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $370 / night

$2,589 / week

1 / 20

Penha-de-Franca Vacation houseboat rental

Penha-de-Franca houseboat

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $1,499 / night

$10,492 / week

1 / 6

Houseboat rental in Penha-de-Franca

Penha-de-Franca houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $300 / night

$2,100 / week

1 / 6

Houseboat rental in Penha-de-Franca

Penha-de-Franca houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $300 / night

$2,100 / week

1 / 6

Vacation houseboat in Penha-de-Franca

Penha-de-Franca houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $300 / night

$2,100 / week

1 / 6

Vacation houseboat rental

Penha-de-Franca houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $300 / night

$2,100 / week

1 / 6

Houseboat rental in Penha-de-Franca

Penha-de-Franca houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $300 / night

$2,100 / week

1 / 6

Vacation yacht in St. Petersburg

St. Petersburg yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,374 / night

$9,618 / week

1 / 12

Vacation yacht with shared pool in Key West

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from $1,946 / night

$12,590 / week

1 / 16

Vacation yacht in Phuket Town

Phuket Town yacht

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 16

from $6,409 / night

$44,863 / week

1 / 15

Vacation houseboat in El Porvenir

El Porvenir houseboat

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $686 / night

$4,802 / week

1 / 14

Vacation yacht in Cabo San Lucas

Cabo San Lucas yacht

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $7,443 / night

$52,098 - $55,304 / week

1 / 16

Vacation yacht in El Porvenir

El Porvenir yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $573 / night

$4,008 / week

1 / 23

Vacation yacht in Fethiye

Fethiye yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from $802 / night

$5,608 / week

1 / 14

Yacht rental in Port Klang

Port Klang yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 10

from $2,459 / night

$17,209 / week

1 / 4

Ketchikan Vacation yacht rental

Ketchikan yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $1,718 / night

$10,305 / week

1 / 30

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $161 / night

$1,123 / week

1 / 34

Vacation yacht in La Paz

La Paz yacht

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,718 / night

$12,023 / week

1 / 27

Vacation yacht in Key Biscayne

Key Biscayne yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $4,380 / night

$30,658 / week

1 / 25

Vacation yacht in Key Biscayne

Key Biscayne yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $6,355 / night

$44,484 / week

1 / 19

Vacation yacht in Key Biscayne

Key Biscayne yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $7,729 / night

$54,102 / week

1 / 20

Vacation yacht in Key Biscayne

Key Biscayne yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $4,122 / night

$28,854 / week

1 / 12

Vacation yacht in Key Biscayne

Key Biscayne yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $4,724 / night

$33,062 / week

1 / 27

Vacation yacht in Key Biscayne

Key Biscayne yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $6,785 / night

$47,489 / week

1 / 24

Vacation houseboat in Bai Chay

Bai Chay houseboat

  • 8 bedrooms
  • 1 bathroom
  • sleeps 2

from $331 / night

$2,317 / week

1 / 17

Le Marin Vacation yacht rental

Le Marin yacht

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,184 / night

$8,283 / week

1 / 28

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Sailing vacations (1046)

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.