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

Updating

Sailing vacations

All filters

Filters

1,046 Vacation rentals

Vacation yacht in Lefkada Town

Lefkada Town yacht

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $493 / night

$3,082 / week

1 / 13

Salerno Vacation yacht rental

Salerno yacht

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

from $370 / night

$3,069 / week

1 / 15

Vacation yacht in Playa Blanca

Playa Blanca yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $111 / night

$773 / week

1 / 46

Vacation yacht in Lisbon

Lisbon yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $99 / night

$691 / week

1 / 14

Vacation yacht in Lefkada Town

Lefkada Town yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from $493 / night

$3,451 / week

1 / 10

Vacation houseboat rental

Kariba houseboat

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 16

from $687 / night

$4,809 / week

1 / 14

Vacation houseboat in Key Largo

Key Largo houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $98 / night

$682 / week

1 / 21

Vacation houseboat in Ramnaes

Ramnaes houseboat

  • 2 bedrooms
  • sleeps 10

from $233 / night

$835 - $2,018 / week

1 / 5

Yacht rental in Dubrovnik

Dubrovnik yacht

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $5,282 / night

$36,975 / week

1 / 24

Neos Marmaras Vacation yacht rental

Neos Marmaras yacht

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $715 / night

$5,004 / week

1 / 25

Vacation yacht accommodation

Cat Ba yacht

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $68 / night

$473 / week

1 / 25

Yacht rental in Lisbon

Lisbon yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $369 / night

$2,580 / week

1 / 54

Vacation yacht in Sanur

Sanur yacht

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from $2,405 / night

$16,832 / week

1 / 9

Yacht rental in La Manga del Mar Menor

La Manga del Mar Menor yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $140 / night

$814 / week

1 / 10

Vacation yacht rental

Cape Coral yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $573 / night

$2,863 - $3,664 / week

1 / 13

Ranong Vacation yacht rental

Ranong yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $3,607 / night

$25,248 / week

1 / 25

Yacht rental in Split

Split yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $709 / night

$4,961 / week

1 / 14

Vacation yacht in Costa Adeje

Costa Adeje yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $349 / night

$2,442 / week

1 / 43

Vacation yacht in Bodrum City

Bodrum City yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from $493 / night

$3,451 / week

1 / 4

Vacation yacht rental

East End yacht

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $4,008 / night

$25,877 - $37,098 / week

1 / 12

Zagreb Vacation yacht rental

Zagreb yacht

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $5,106 / night

$35,743 / week

1 / 30

Houseboat rental in Earnewald

Earnewald houseboat

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

from $204 / night

$1,233 - $1,664 / week

1 / 19

Vacation yacht in Angra Dos Reis

Angra Dos Reis yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 19

from $4,580 / night

$32,060 / week

1 / 13

Yacht rental in Lakki

Lakki yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $185 / night

$1,295 / week

1 / 12

Yacht rental in Neos Marmaras

Neos Marmaras yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $740 / night

$5,177 / week

1 / 27

Vacation yacht rental

Cat Ba yacht

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $596 / night

$4,168 / week

1 / 42

Vacation houseboat in Cagliari

Cagliari houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $74 / night

$518 / week

1 / 28

Vacation yacht in Charlotte Amalie

Charlotte Amalie yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $3,026 / night

$21,183 / week

1 / 10

Vacation houseboat rental

Kumarakom houseboat

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $344 / night

$2,405 / week

1 / 28

Vacation yacht in Lima

Lima yacht

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $740 / night

$2,465 - $5,916 / week

1 / 16

Vacation yacht in Naxos Town

Naxos Town yacht

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

from $1,603 / night

$11,216 / week

1 / 26

Vacation yacht in Road Town

Road Town yacht

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 9

from $1,636 / night

$11,450 / week

1 / 25

Fethiye Vacation yacht rental

Fethiye yacht

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from $1,356 / night

$9,491 / week

1 / 28

Vacation yacht in Skiathos Town

Skiathos Town yacht

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

from $309 / night

$2,157 / week

1 / 5

Vacation houseboat in Jyväskylä

Jyväskylä houseboat

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $502 / night

$3,513 / week

1 / 11

Vacation houseboat in St. Vincent

St. Vincent houseboat

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $1,088 / night

$7,443 - $9,046 / week

1 / 4

Vacation yacht in Miami

Miami yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $1,603 / night

$11,221 / week

1 / 8

Vila Franca do Campo Vacation yacht rental

Vila Franca do Campo yacht

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $432 / night

$2,712 / week

1 / 10

Vacation yacht in Portonovo

Portonovo yacht

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from $111 / night

$777 / week

1 / 5

Vacation yacht in Portoscuso

Portoscuso yacht

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $222 / night

$1,553 / week

1 / 4

×

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.