Sailing holidays

Sailing holidays (169)

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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169 Holiday homes

Filters applied: Walking holidays

(10) Excellent 

25

Province of Naples / Sorrento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

from £275 / night

£1725 / week

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from £275 / night

(39) Very Good 

24

Holiday houseboat in Halong Bay

Quang Ninh Province / Halong Bay

50 50 1 night min

  • 50 bedrooms
  • Sleeps 50
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly

from £143 / night

£2112 / week

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from £143 / night

(5) Excellent 

11

Holiday yacht in Lymington

New Forest / Lymington

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Suitable for children age 5+
“Luxury living on a yacht” Myself and 3 friends stayed on this beautiful boat, moored ideally with no boats in front of us, giving us a perfect view across to the Isle of Wight. The yacht was clean, had 2 bathrooms and showers, and a well equipped kit  …see more

from £200 / night

£1400 / week

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from £200 / night

23

Holiday houseboat in Jyväskylä

Central Finland / Jyväskylä

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £268 / night

£1548 - £2324 / week

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from £268 / night

(17) Very Good 

19

Narrowboat rental in Nantwich

Cheshire / Nantwich

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Ask about pets
“Lovely short break on Adele Marie” Martin couldn't have been more helpful with sending us on our way up the Shropshire canal, his wife even went to the trouble of baking scones (on the day!) with jam and cream for us, plus there was tea coffee milk .  …see more

from £80 / night

£800 - £1835 / week

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from £80 / night

(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 £255 / night

£1781 / week

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from £255 / 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 £164 / night

£561 / week

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from £164 / night

(1) Excellent 

5

Worsley holiday narrowboat rental

Salford / Worsley

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“What a lovely family weekend!” We arrived and it was thundering, lightning and raining like there was no tomorrow but the central heating on the boat kept us all snug, warm and dried us out quickly. With the freedom to stop and start where and when yo  …see more

from £150 / night

£1050 / week

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from £150 / night

(9) Very Good 

9

Holiday yacht with shared pool in Halong Bay

Quang Ninh Province / Halong Bay

12 18 1 night min

  • 12 bedrooms
  • Sleeps 18
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £128 / night

£10080 / week

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from £128 / night

(7) Excellent 

28

Yacht rental in San Sebastián de la Gomera

La Gomera / San Sebastián de la Gomera

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Suitable for children age 5+

from £49 / night

£343 / week

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from £49 / night

(1) Excellent 

3

Houseboat rental in Chioggia

Province of Venice / Chioggia

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly

from £155 / night

£1081 - £1666 / week

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from £155 / night

(13) Excellent 

24

Houseboat rental in Amsterdam

Amsterdam / Eastern Docklands

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Child friendly

from £203 / night

£1419 / week

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from £203 / 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

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from £170 / night

(24) Very Good 

28

Halong Bay ski yacht to rent.

Quang Ninh Province / Halong Bay

18 2 1 night min

  • 18 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

from £207 / night

£18589 / week

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from £207 / night

9

Aude / Marseillette

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 35 km
  • Child friendly
  • Pet friendly

from £74 / night

£513 - £604 / week

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from £74 / night

21

Arrondissement of Le Marin / Le Marin

6 8 7 nights min

  • 6 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £419 / night

£2932 - £3621 / week

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from £419 / night

(33) Excellent 

14

Holiday houseboat in Srinagar

Kashmir / Srinagar

6 15 1 night min

  • 6 bedrooms
  • Sleeps 15
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £48 / night

£334 / week

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from £48 / night

(21) Excellent 

30

Yacht rental in Dubrovnik

Dubrovnik / Gruz

12 24 7 nights min

  • 12 bedrooms
  • Sleeps 24
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Feeling of constant care and joy” Marin and his crew have demonstrated the ability to include us in their love for the Adriatic and Dalmatia. They showed us the most beautiful of the entire area of the islands. We did not feel like casual tourists, bu  …see more

from £110 / night

£768 - £14656 / week

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from £110 / night

(2) Excellent 

30

Holiday houseboat in Marigot Bay

Castries Quarter / Marigot Bay

3 2 4 nights min

  • 3 bedrooms
  • Sleeps 2
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool

from £68 / night

£476 / week

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from £68 / night

(16) Excellent 

14

Holiday yacht rental

Bequia / Port Elizabeth

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £953 / night

£4921 - £9731 / week

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from £953 / night

(9) Excellent 

17

Holiday houseboat rental

Torridge / Holsworthy

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Child friendly

from £81 / night

£500 - £830 / week

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from £81 / night

11

Holiday houseboat in Montauban

Tarn-et-Garonne / Montauban

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £1478 / night

£10345 / week

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from £1478 / night

32

Province of Syracuse / Marzamemi

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Child friendly

from £57 / night

£388 - £776 / week

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from £57 / night

(4) Excellent 

23

Oost-knollendam holiday houseboat rental

North Holland Province / Oost-knollendam

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“Houseboat for relaxation and with exellent view.” We spend 6 days on Humpy Dumpy. It was a great place to arrive home to after exploriating northern Holland during the day. I would have liked to have more time on the boat. using the bikes and renting  …see more

from £216 / night

£863 - £949 / week

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from £216 / night

(5) Excellent 

42

Holiday yacht in Unterterzen

Canton of St. Gallen / Unterterzen

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £52 / night

£363 / week

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from £52 / night

(1) Excellent 

14

Kas holiday yacht rental

Antalya Province / Kas

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £60 / night

£400 - £505 / week

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from £60 / night

(29) Very Good 

16

Holiday houseboat letting

Amsterdam / Central Amsterdam

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
“Great accommodation and location to explore Amsterdam” I travelled to Amsterdam to visit friends and was very fortunate to stay on this fabulous houseboat. It was very well equipped, homely, warm and comfortable. I was surprised to find how spacious t  …see more

from £173 / night

£1272 - £1634 / week

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from £173 / night

(1) Excellent 

14

Italian Riviera / Lavagna

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £214 / night

£1497 / week

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from £214 / 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 £95 / night

£604 - £1819 / week

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from £95 / night

(26) Excellent 

21

Holiday houseboat in Amsterdam

Amsterdam / Central Amsterdam

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 15 km
  • Car not necessary
  • Private garden

from £125 / night

£725 / week

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from £125 / 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

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from £19 / night

(2) Excellent 

25

Province of Massa Carrara / Marina di Carrara

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km

from £518 / night

£3449 - £6164 / week

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from £518 / 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 £164 / night

£647 / week

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from £164 / night

19

Monte Argentario / Porto Ercole

2 2 1 night min

  • 2 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

from £311 / night

£1638 / week

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from £311 / night

(2) Excellent 

11

Holiday yacht in Alimos

Athens / Alimos

10 10 1 night min

  • 10 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
“Excellent sailing trip” The condition of the boat was great. George from the charter company did a great job and organized everything what we needed, including help for our big shooping at the supermarket, petrol refillling after the return etc. When  …see more

from £388 / night

£2716 / week

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from £388 / night

23

Province of Cagliari / Cagliari

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary

from £51 / night

£363 - £996 / week

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from £51 / night

(2) Excellent 

29

Holiday yacht in Bacvice

Split-Dalmatia County / Bacvice

12 24 7 nights min

  • 12 bedrooms
  • Sleeps 24
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly

from £110 / night

£768 - £14656 / week

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from £110 / night

18

Castries Quarter / Castries

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Car not necessary

from £285 / night

£1811 / week

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from £285 / night

7

Porto District / Vila Nova de Gaia

4 6 1 night min

  • 4 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary

from £65 / night

£453 / week

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from £65 / night

9

Konakli holiday yacht rental

Alanya / Konakli

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation

from £345 / night

£2328 / week

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from £345 / night

1