Sailing holidays

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Sailing holidays (52)

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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52 Holiday homes

Filters applied: Fireplace (52)

(4) Excellent 

1 / 78

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

3 bedroomsSleeps 52 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min stay

from $166 / night

$0 / week

Book Book View

from $166 / night

(3) Excellent 

1 / 23

Holiday houseboat in Portland

Oregon / Portland

2 bedroomsSleeps 45 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min stay

from $275 / night

$1925 / week

Book Book View

from $275 / night

(1) Excellent 

1 / 21

Holiday houseboat rental

Florida / Clearwater

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from $80 / night

$501 / week

Book Book View

from $80 / night

1 / 11

Bathampton holiday houseboat rental

Bath / Bathampton

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $364 / night

$1459 - $2189 / week

Book Book View

from $364 / night

(24) Excellent 

1 / 20

Holiday narrowboat rental

Warwickshire / Rugby

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $687 / night

$2920 - $4351 / week

Book Book View

from $687 / night

(2) Excellent 

1 / 21

Holiday narrowboat in Guildford

Surrey / Guildford

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $365 / night

$2190 / week

Book Book View

from $365 / night

(34) Excellent 

1 / 15

Holiday narrowboat in Newbridge, Bath

Bath / Newbridge, Bath

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $438 / night

$1468 - $3373 / week

Book Book View

from $438 / night

(1) Excellent 

1 / 24

Clearwater holiday houseboat rental

Florida / Clearwater

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay

from $120 / night

$751 / week

Book Book View

from $120 / night

(92) Excellent 

1 / 47

Holiday houseboat in Amsterdam

Amsterdam / Central Amsterdam

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $150 / night

$1107 - $1991 / week

Book Book View

from $150 / night

1 / 11

Holiday houseboat in Seattle

Washington / Seattle

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from $196 / night

$1201 - $1780 / week

Book Book View

from $196 / night

(5) Excellent 

1 / 14

Amsterdam holiday houseboat rental

North Holland Province / Amsterdam

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from $299 / night

$2987 - $3204 / week

Book Book View

from $299 / night

(12) Very Good 

1 / 26

Holiday houseboat rental

Western Cape / Knysna

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $92 / night

$637 - $1015 / week

Book Book View

from $92 / night

1 / 19

Seattle holiday houseboat rental

Washington / Seattle

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay

from $175 / night

$1150 - $2140 / week

Book Book View

from $175 / night

(5) Excellent 

1 / 23

Great Billing holiday narrowboat rental

Northamptonshire / Great Billing

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from $117 / night

$760 - $789 / week

Book Book View

from $117 / night

1 / 24

Yacht rental in Miami Beach

Florida / Miami Beach

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $196 / night

$1201 - $2461 / week

Book Book View

from $196 / night

(13) Excellent 

1 / 28

Halong Bay holiday houseboat rental

Quang Ninh Province / Halong Bay

14 bedroomsSleeps 281 night min stay

  • 14 bedrooms
  • Sleeps 28
  • 1 night min stay

from $300 / night

$0 / week

Book Book View

from $300 / night

(1) Excellent 

1 / 12

Holiday houseboat in Kumarakom

Kerala / Kumarakom

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay

from $100 / night

$0 / week

Book Book View

from $100 / night

1 / 22

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

7 bedroomsSleeps 142 nights min stay

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min stay

from $775 / night

$4314 / week

Book Book View

from $775 / night

(4) Excellent 

1 / 17

Lic holiday houseboat rental

Primorje-Gorski Kotar County / Lic

6 bedroomsSleeps 123 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min stay

from $100 / night

$680 / week

Book Book View

from $100 / night

1 / 33

Holiday houseboat in Levallois-Perret

Hauts-de-Seine / Levallois-Perret

4 bedroomsSleeps 55 nights min stay

  • 4 bedrooms
  • Sleeps 5
  • 5 nights min stay

from $354 / night

$0 / week

Book Book View

from $354 / night

(45) Excellent 

1 / 28

Holiday narrowboat rental

Salford / Worsley

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from $249 / night

$1738 / week

Enquire Enquire View

from $249 / night

(11) Very Good 

1 / 19

Narrowboat rental in Nantwich

Cheshire / Nantwich

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $117 / night

$1167 - $2627 / week

Book Book View

from $117 / night

(2) Very Good 

1 / 20

Holiday narrowboat with golf nearby in Lancaster

Lancashire / Lancaster

1 bedroomSleeps 43 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from $183 / night

$1198 / week

Book Book View

from $183 / night

1 / 17

Holiday yacht in Vero Beach

Florida / Vero Beach

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $76 / night

$475 / week

Book Book View

from $76 / night

(4) Excellent 

1 / 15

Pangkalan Bun holiday houseboat rental

Central Kalimantan / Pangkalan Bun

6 bedroomsSleeps 102 nights min stay

  • 6 bedrooms
  • Sleeps 10
  • 2 nights min stay

from $409 / night

$2555 - $9914 / week

Book Book View

from $409 / night

1 / 72

Holiday houseboat in Cornwall

England / Cornwall

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from $110 / night

$767 / week

Book Book View

from $110 / night

(1) Excellent 

1 / 15

Henley-on-Thames holiday narrowboat rental

Oxfordshire / Henley-on-Thames

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $443 / night

$2030 - $2649 / week

Book Book View

from $443 / night

(8) Excellent 

1 / 17

Holiday houseboat rental

Devon / Holsworthy

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $146 / night

$694 - $1212 / week

Book Book View

from $146 / night

(12) Excellent 

1 / 17

Holiday houseboat rental

Hauts-de-Seine / Meudon

4 bedroomsSleeps 85 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min stay

from $365 / night

$2190 - $2701 / week

Book Book View

from $365 / night

(1) Excellent 

1 / 12

Houseboat accommodation in Corbie

Somme / Corbie

1 bedroomSleeps 22 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay

from $117 / night

$813 / week

Book Book View

from $117 / night

1 / 13

Ski yacht to rent in Halong Bay

Quang Ninh Province / Halong Bay

14 bedroomsSleeps 321 night min stay

  • 14 bedrooms
  • Sleeps 32
  • 1 night min stay

from $330 / night

$0 / week

Book Book View

from $330 / night

1 / 14

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay

from $161 / night

$0 / week

Book Book View

from $161 / night

1 / 22

Holiday houseboat accommodation

Florida / Clearwater

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from $50 / night

$401 / week

Book Book View

from $50 / night

(1) Excellent 

1 / 16

Holiday houseboat in Holsworthy

Devon / Holsworthy

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $146 / night

$657 - $1212 / week

Book Book View

from $146 / night

1 / 7

Holiday houseboat in Labuan Bajo

Flores / Labuan Bajo

4 bedroomsSleeps 81 night min stay

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from $3001 / night

$20021 / week

Book Book View

from $3001 / night

(1) Excellent 

1 / 15

Houseboat rental in Puteaux

La Defense / Puteaux

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $443 / night

$2766 / week

Book Book View

from $443 / night

(1) Excellent 

1 / 20

Holiday houseboat in Chevaigne

Ille-et-Vilaine / Chevaigne

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $216 / night

$725 - $896 / week

Book Book View

from $216 / night

1 / 11

Seattle holiday houseboat rental

Washington / Seattle

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay

from $196 / night

$1201 - $1850 / week

Book Book View

from $196 / night

1 / 10

Holiday narrowboat in West Row

Mildenhall / West Row

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from $219 / night

$0 / week

Book Book View

from $219 / night

(8) Excellent 

1 / 24

Houseboat accommodation in Henley-on-Thames

Oxfordshire / Henley-on-Thames

3 bedroomsSleeps 113 nights min stay

  • 3 bedrooms
  • Sleeps 11
  • 3 nights min stay

from $365 / night

$2059 - $5183 / week

Book Book View

from $365 / night

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