Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Sailing vacations

All filters

Filters

1,034 Vacation rentals

Houseboat rental in Srinagar with golf nearby

Srinagar houseboat

  • 27 bedrooms
  • 50 bathrooms
  • sleeps 50

from $138 / night

$1,031 / week

1 / 44

Vacation houseboat in Amsterdam

Amsterdam houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $296 / night

$2,070 / week

1 / 15

Manaus Vacation houseboat rental

Manaus houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $35 / night

$241 / week

1 / 26

Yacht rental in Sesto Calende

Sesto Calende yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

from $740 / night

$3,697 / week

1 / 16

Vacation houseboat in Dinan

Dinan houseboat

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from $690 / night

$4,806 / week

1 / 4

Vacation yacht in Termini Imerese

Termini Imerese yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $148 / night

$863 - $5,003 / week

1 / 22

Vacation yacht in New York City

New York City yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $7,443 / night

$34,350 / week

1 / 16

Yacht rental in Anissaras

Anissaras yacht

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from $986 / night

$6,161 / week

1 / 7

Houseboat rental in Srinagar with golf nearby

Srinagar houseboat

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $58 / night

$401 / week

1 / 5

Vacation houseboat in Jyväskylä

Jyväskylä houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

from $643 / night

$4,498 / week

1 / 44

Vacation yacht with shared pool in Geneva

Geneva yacht

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

from $312 / night

$2,179 - $11,982 / week

1 / 24

Vacation houseboat in Jyväskylä

Jyväskylä houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $643 / night

$4,498 / week

1 / 43

Vacation yacht rental

El Porvenir yacht

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $535 / night

$3,720 / week

1 / 28

Vacation houseboat in Alappuzha

Alappuzha houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $210 / night

$1,471 / week

1 / 14

Jyväskylä Vacation houseboat rental

Jyväskylä houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

from $643 / night

$4,498 / week

1 / 44

Vacation narrowboat in Guildford

Guildford narrowboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $561 / night

$2,942 / week

1 / 10

Vacation yacht rental

Panama City yacht

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from $5,725 / night

$36,068 / week

1 / 15

Vacation yacht with shared pool in Port Elizabeth

Port Elizabeth yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $802 / night

$5,691 - $12,103 / week

1 / 4

Vacation yacht rental

Hyeres yacht

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $3,697 / night

$12,322 / week

1 / 11

Vacation yacht in Santiago de Veraguas

Santiago de Veraguas yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 7

from $918 / night

$6,426 / week

1 / 15

Salvador Vacation yacht rental

Salvador yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 9

from $344 / night

$1,661 / week

1 / 47

Chania Town Vacation yacht rental

Chania Town yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $1,109 / night

$7,763 / week

1 / 5

Vacation houseboat in Tuakau

Tuakau houseboat

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

from $723 / night

$5,060 / week

1 / 26

Vacation yacht in Klimno

Klimno yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 10

from $492 / night

$3,442 / week

1 / 11

Vacation yacht in Trogir

Trogir yacht

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $521 / night

$3,646 / week

1 / 10

Vacation yacht in Limay

Limay yacht

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from $222 / night

$1,553 / week

1 / 19

Vacation houseboat in Srinagar

Srinagar houseboat

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

from $172 / night

$1,203 / week

1 / 4

Vacation yacht in Isla de Coiba

Isla de Coiba yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $918 / night

$6,426 / week

1 / 9

Vacation yacht in Chateauguay

Chateauguay yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $155 / night

$1,082 / week

1 / 50

Uturoa Vacation yacht rental

Uturoa yacht

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from $586 / night

$4,097 / week

1 / 9

Vacation yacht in Skiathos Town

Skiathos Town yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $1,171 / night

$8,010 / week

1 / 36

Yacht rental in Gocek

Gocek yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from $678 / night

$4,621 / week

1 / 23

Vacation yacht in Paraty

Paraty yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $436 / night

$3,046 / week

1 / 15

Punta Sabbioni Vacation houseboat rental

Punta Sabbioni houseboat

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $62 / night

$432 / week

1 / 12

Vacation yacht in Kalamata

Kalamata yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $84 / night

$587 / week

1 / 29

East End Vacation yacht rental

East End yacht

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from $1,260 / night

$8,817 / week

1 / 24

Serangan Vacation yacht rental

Serangan yacht

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $573 / night

$4,008 / week

1 / 15

Chania Town Vacation yacht rental

Chania Town yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $358 / night

$2,502 / week

1 / 4

Vacation yacht in Larnaca

Larnaca yacht

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from $1,479 / night

$7,147 / week

1 / 8

Miami Vacation yacht rental

Miami yacht

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $5,153 / night

$30,915 / week

1 / 18

×

Sailing vacations (1034)

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.