Sailing holidays

Sailing holidays (29)

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.

View larger map

Also consider

Luxury Villas
2,684 properties
Coastal Cottages
222 properties
Pet Friendly Cottages
27,095 properties
Romantic Breaks
3,207 properties
Group Holidays
17,143 properties
Log Cabin Holidays
238 properties
Rural Retreats
12,438 properties
City Breaks
8,475 properties
Holiday Cottages
17,239 properties
Villas in Spain
11,248 properties
Villas in Tenerife
707 properties
Gites in France
8,131 properties
Holiday Cottages in Cornwall
2,983 properties
London Holiday Apartments
941 properties
Florida Villas
905 properties
Villas in Ibiza
349 properties
Villas in Portugal
4,126 properties
Villas in Turkey
2,202 properties
Villas in Malta
455 properties
Lake District Cottages
940 properties

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

29 Holiday homes

Filters applied: Shared garden

(18) Excellent 

27

Holiday yacht in Barcelona

Barcelona / Port Forum

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Suitable for children age 5+
“BOAT WAS A FABULOUS AND UNIQUE EXPERIENCE FOR US” I organised the trip for my brothers, in laws and couple of friends, we are all in the 45-55 age category and really just enjoyed renting the whole boat to ourselves. We cooked on board, however, the  …see more

from £257 / night

£1796 / week

Book View

from £257 / night

(21) Excellent 

29

Porto holiday narrowboat rental

Porto District / Porto

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Magnificent sailing through UNESCO world Heritage” Couple and one children, rented a boat for a long weekend, sailed up on river Douro until Spanish border. At the boats base, nice little chalet for the first night. Very good navigation, sightseeing a  …see more

from £166 / night

£566 / week

Book View

from £166 / night

(16) Excellent 

14

Holiday yacht rental

St. George's / Prickly Bay

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Felt like a millionaire on a private yacht in beautiful places with wonderful people.” This was our first private yacht charter and it will not be our last! It was easy to book. The owners are very accommodating and follow up promptly with all inquir  …see more

from £140 / night

£980 - £3920 / week

Book View

from £140 / night

(6) Excellent 

24

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary
  • Ask about pets

from £100 / night

£653 - £696 / week

Book View

from £100 / night

(5) Very Good 

22

Narrowboat rental in Draveil

Essonne / Draveil

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Car not necessary
  • Air conditioning
“A peaceful and comfortable sail along the Marne” We had a great time sailing along the Marne and through the locks between Paris and Epernay. The boat is comfortable and well-equipped and the owner/pilot friendly and welcoming. There was food and win  …see more

from £174 / night

£783 - £1392 / week

Book View

from £174 / night

10

Holiday yacht with golf nearby in Venice

City of Venice / Venice

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £96 / night

£609 - £1835 / week

Book View

from £96 / night

(53) Excellent 

30

Holiday narrowboat rental

Salford / Worsley

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
“fantastic trip” We had an amazing long weekend as usual. The boat (Queenie) was absolutely fab, cosy clean and warm and a real head turner. people stopped and looked and had their photos taken beside it. I would recommend this boating experience to ev  …see more

from £170 / night

£1190 / week

Enquire View

from £170 / night

20

Srinagar holiday houseboat rental

Kashmir / Srinagar

8 16 1 night min

  • 8 bedrooms
  • Sleeps 16
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £32 / night

£241 - £2380 / week

Book View

from £32 / night

7

Vermenton holiday houseboat rental

Yonne / Vermenton

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning

from £249 / night

£1740 - £2783 / week

Book View

from £249 / night

4

Holiday houseboat in Srinagar

Kashmir / Srinagar

20 2 1 night min

  • 20 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £56 / night

£336 / week

Book View

from £56 / night

(16) Excellent 

22

Porto holiday yacht rental

Porto District / Porto

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“A fabulous experience” Seldom do holidays exceed all expectations, but in the case of Dourovou we could not have had a better experience. The Douro is a perfect place to visit for a short sailing holiday, with an almost guaranteed breeze every aftern  …see more

from £166 / night

£653 / week

Book View

from £166 / night

7

Province of Naples / Vico Equense

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly

from £392 / night

£2609 / week

Book View

from £392 / night

(7) Very Good 

24

Holiday houseboat in Amsterdam

Amsterdam / De Pijp

1 2 4 nights min

  • 1 bedroom
  • Sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £105 / night

£696 / week

Book View

from £105 / night

10

Srinagar holiday houseboat rental

Kashmir / Srinagar

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Private garden

from £19 / night

£129 / week

Book View

from £19 / 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

from £96 / night

£720 / week

Book View

from £96 / night

13

Holiday houseboat in Alappuzha

Kerala / Alappuzha

12 6 1 night min

  • 12 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Child friendly

from £320 / night

£2235 / week

Book View

from £320 / night

(6) Very Good 

30

Holiday narrowboat in Tewitfield

Carnforth / Tewitfield

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask owner if suitable for children
  • Ask about pets

from £125 / night

£750 - £800 / week

Book View

from £125 / 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

Pricing unknown

Book View

Pricing unknown

19

Province of Cosenza / Trebisacce

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation

Pricing unknown

Book View

Pricing unknown

(2) Excellent 

7

Srinagar ski houseboat to rent.

Kashmir / Srinagar

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly

Pricing unknown

Book View

Pricing unknown

36

Marmaris ski houseboat to rent.

Mugla Province / Marmaris

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Ski
  • Air conditioning

from £774 / night

£5418 / week

Book View

from £774 / night

10

Samana Province / Santa Barbara de Samana

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 3 km
  • Suitable for children age 5+

from £100 / night

£600 - £960 / week

Book View

from £100 / night

6

Pravia / Somado

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation

from £40 / night

£305 / week

Book View

from £40 / night

(4) Excellent 

17

Primorje-Gorski Kotar County / Lic

6 12 3 nights min

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets

from £80 / night

£544 / week

Book View

from £80 / night

15

Galveston Island / Galveston

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool

from £160 / night

£840 / week

Book View

from £160 / night

18

Key Largo / Tavernier

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach / lakeside relaxation
  • Air conditioning

from £128 / night

£840 - £1064 / week

Book View

from £128 / night

(2) Excellent 

54

North Holland Province / Amsterdam

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 27 km
  • Car not necessary

from £127 / night

£757 / week

Book View

from £127 / night

4

Zadar County / Novigrad

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £622 / night

£4348 / week

Book View

from £622 / night

22

Kashmir / Srinagar

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski

from £20 / night

£20 / week

Book View

from £20 / night

1