Sailing holidays

Sailing holidays (1056)

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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1,056 Holiday homes

(7) Excellent 

21

Holiday narrowboat in Guildford

Surrey / Guildford

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
“A novices weekend” Four complete novice guys aged 41, 58, 65 and 71 took on a weekend on Box of Delights. We worked out a route north to Addlestone with 3 nightime stopovers. We were given a comprehensive instruction including accompaniment to the fir
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from £300 / night

£1500 / week

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from £300 / night

(4) Excellent 

22

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 35 km
  • Suitable for children age 5+
“Stayed and Partied like a King” So this was our second stay on De Cornelia, we previously stayed in a group back in May 2014. Sometimes when you rebook the same place you have that fear of it not being as good or a bit more tired than before but I
…see more

from £604 / night

£3363 / week

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from £604 / night

(2) Excellent 

20

Holiday yacht letting

Hampshire / Southampton

1 2 2 nights min

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

from £59 / night

£413 / week

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from £59 / night

(14) Very Good 

18

Holiday yacht in Argostolion

Cephalonia / Argostolion

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
“The best way to see the Greek Islands” We spent the most amazing 3 days with Ray and Stuart on Mala. Cruising around Zante and Kefalonia. They made us feel instantly at ease and Tom absolutley loved sailing on the boat and helping Stuart. The places w
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from £350 / night

£1850 - £2100 / week

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from £350 / night

4

Holiday yacht in Portoscuso

Province of Carbonia-Iglesias / Portoscuso

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly

from £156 / night

£1087 / week

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from £156 / 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 £200 / night

£18017 / week

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from £200 / night

(2) Excellent 

12

Holiday narrowboat in Worcester

Worcestershire / Worcester

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £250 / night

£999 / week

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from £250 / night

(41) Excellent 

31

Holiday houseboat in Cagliari

Province of Cagliari / Cagliari

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning

from £52 / night

£345 / week

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from £52 / night

9

Vasiliki holiday yacht rental

Lefkada / Vasiliki

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly

from £86 / night

£598 / week

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from £86 / night

4

Holiday yacht rental

Faial Island / Horta

3 8 3 nights min

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

from £130 / night

£819 / week

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from £130 / night

(1) Excellent 

14

Holiday yacht rental

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

5

Holiday houseboat in Lampedusa

Islands of Sicily / Lampedusa

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Child friendly

from £69 / night

£733 / week

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from £69 / night

24

Holiday yacht in Ilhabela

State of Sao Paulo / Ilhabela

3 14 1 night min

  • 3 bedrooms
  • Sleeps 14
  • 1 night min
  • Child friendly

from £1300 / night

£9100 / week

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from £1300 / night

6

Holiday yacht in Port Elizabeth

Bequia / Port Elizabeth

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Car not necessary

from £462 / night

£3231 / week

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from £462 / night

7

Holiday yacht in Bodrum City

Bodrum / Bodrum City

1 15 1 night min

  • 1 bedroom
  • Sleeps 15
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Car not necessary

from £344 / night

£1811 / week

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from £344 / night

23

Cagliari holiday houseboat rental

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

(10) Excellent 

83

Falmouth holiday yacht let

Cornwall / Falmouth

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 2 km
  • Child friendly
  • Car not necessary
“Excellent stay” We stayed on Yemaya for two days and did a day sail with Cyprian and Maddie. We had a great time. Yemaya is the real deal, capable of transatlantic journeys, though we didn't quite go that far on our day sail :-) Cyprian couldn't h
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from £100 / night

£700 / week

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from £100 / night

19

Porto Ercole holiday yacht rental

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

(7) Very Good 

37

San Blas Islands holiday yacht rental

Guna Yala Region / San Blas Islands

3 2 1 night min

  • 3 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly

from £385 / night

£2693 / week

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from £385 / night

(6) Excellent 

18

Houseboat rental in Chertsey with golf nearby

Surrey / Chertsey

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden

from £90 / night

£600 - £810 / week

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from £90 / night

(21) 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 £731 / night

£3231 - £10508 / week

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from £731 / night

(12) Excellent 

17

Holiday houseboat rental

Hauts-de-Seine / Meudon

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Suitable for children age 5+
  • Car not necessary
  • Air conditioning
“Excellent accomodation , Spacious, Comfortable & Clean” My Children 13,16,17 plus Grandparent 78 all had an excellent time in Paris . The boat made an excellent base for seeing the sights as public transport is minutes walk away.The boat is spacious,
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from £250 / night

£1500 - £1850 / week

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from £250 / night

(1) Excellent 

53

Nettuno holiday houseboat rental

Province of Rome / Nettuno

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Suitable for children age 5+

from £207 / night

£1449 / week

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from £207 / night

7

Yacht rental in Vila Nova de Gaia

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 £104 / night

£725 / week

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from £104 / night

21

Holiday yacht rental

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

(1)  

19

Amsterdam holiday houseboat rental

North Holland Province / Amsterdam

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Private garden

from £138 / night

£966 / week

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from £138 / 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 £75 / night

£525 / week

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from £75 / night

20

Roses holiday yacht rental

Costa Brava / Roses

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly

from £130 / night

£725 / week

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from £130 / night

(2) Very Good 

38

Holiday houseboat in Amsterdam

Amsterdam / New West

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min

from £192 / night

£1340 / week

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from £192 / night

14

Holiday yacht in Casamicciola Terme

Isola d'Ischia / Casamicciola Terme

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Car not necessary

from £87 / night

£863 / week

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from £87 / night

(1) Excellent 

16

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

from £222 / night

£1553 / week

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from £222 / night

9

Holiday yacht in Brindisi

Province of Brindisi / Brindisi

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Air conditioning

Pricing unknown

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Pricing unknown

(2) Excellent 

4

Narrowboat rental in Peterborough

Cambridgeshire / Peterborough

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Ask about pets

from £200 / night

£1285 / week

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from £200 / night

(1)  

24

Holiday houseboat rental

North Holland Province / Amsterdam

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden

from £276 / night

£1932 / week

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from £276 / night

19

Yacht letting in Porto San Giorgio

Province of Fermo / Porto San Giorgio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Suitable for children age 5+

Pricing unknown

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Pricing unknown

(3) Excellent 

6

Yacht rental in Kos Town

Kós / Kos Town

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
“exhilarating and relaxing at the same time” Had a wonderful time visiting many different islands swimming in the sea exhilarating sailing some days with excellent winds whilst on other calmer days we soaked up the sun. Beautiful boat and excellent s
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from £136 / night

£950 - £1700 / week

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from £136 / night

39

Belem holiday yacht rental

Lisbon District / Belem

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Child friendly
  • Car not necessary

from £518 / night

£3018 / week

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from £518 / night

(1) Very Good 

20

Houseboat rental in Alappuzha

Alappuzha District / Alappuzha

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Suitable for children age 5+

from £70 / night

£700 - £805 / week

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from £70 / night

(1) Excellent 

14

Holiday yacht in Labuan Bajo

Flores / Labuan Bajo

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Air conditioning

from £1770 / night

£12385 / week

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from £1770 / night

6

Holiday yacht rental

Magnesia Region / Volos

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £48 / night

£332 / week

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from £48 / night

1