Sailing holidays

Sailing holidays (79)

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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79 Holiday homes

Filters applied: Swimming pool

(25) Excellent 

20

Holiday houseboat with shared pool in Amsterdam

Amsterdam / Jordaan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £182 / night

£1207 - £1811 / week

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from £182 / 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

29

Yacht rental in Brewers Bay with shared pool

Tortola / Brewers Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £1600 / night

£6395 / week

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from £1600 / night

16

San Blas Islands / El Porvenir

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £104 / night

£728 / week

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from £104 / night

(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

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Pricing unknown

(23) Excellent 

41

Holiday yacht with shared pool in Playa Blanca

Playa Blanca / Marina Rubicon

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful” We had a fantastic one week holiday,the location was stunning and plenty of restaurants to choose from although we found Lani's the best. Jorge and Raquel are lovely and so friendly.  …see more

from £83 / night

£580 - £966 / week

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from £83 / 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 £208 / night

£18738 / week

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from £208 / 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

(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

7

Magnesia Region / Volos

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £156 / night

£953 / week

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from £156 / night

(9) Excellent 

14

Isla Chiloe holiday yacht rental

Los Lagos Region / Isla Chiloe

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
“Toby 2014” Excellent experience. We had typical March Chiloe weather with a mix of sunny and rainy days. The food and service at the boat were great. In fact the sea food was outstanding, Kayaking and using the small motor boats were pluses. Visit to  …see more

from £2240 / night

£15680 - £22400 / week

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from £2240 / night

(1) Excellent 

40

Kas holiday yacht rental

Kas / Kas center

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

from £300 / night

£2000 - £3500 / week

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from £300 / night

20

Arrondissement of Le Marin / Le Marin

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £259 / night

£1811 / week

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from £259 / night

(5) Excellent 

22

Santa Ponsa / Santa Ponsa Marina

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £164 / night

£1147 - £3440 / week

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from £164 / 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

(4) Excellent 

21

Key West holiday houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £324 / night

£2000 - £5320 / week

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from £324 / night

22

Naxos / Naxos Town

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary

from £863 / night

£6035 / week

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from £863 / night

20

Chioggia / Sottomarina

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly

from £57 / night

£371 - £1421 / week

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from £57 / night

8

Holiday yacht with shared pool in Gouvia

Corfu / Gouvia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool

Pricing unknown

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Pricing unknown

(1) Very Good 

32

Port d'Andratx holiday yacht rental

Port d'Andratx / Cala Llamp

3 4 1 night min

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

from £50 / night

£350 / week

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from £50 / night

48

Holiday yacht with shared pool in Lisbon

Lisbon / Santos

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

from £647 / night

£4526 / week

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from £647 / night

10

Arrondissement of Le Marin / Le Marin

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £647 / night

£4526 / week

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from £647 / 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

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Pricing unknown

5

Yacht accommodation in French Harbour with shared pool

Roatan / French Harbour

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £1100 / night

£4400 / week

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from £1100 / night

11

State of Bahia / Salvador

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly

from £160 / night

£800 / week

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from £160 / 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

(2) Excellent 

5

Tenerife / Amarilla Golf

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £164 / night

£1026 - £3319 / week

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from £164 / night

13

Ski yacht to rent in Halong Bay

Quang Ninh Province / Halong Bay

14 32 1 night min

  • 14 bedrooms
  • Sleeps 32
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski

from £304 / night

£2128 / week

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from £304 / 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

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from £96 / night

8

Magnesia Region / Volos

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool

from £190 / night

£1457 / week

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from £190 / night

7

Magnesia Region / Volos

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £44 / night

£302 / week

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from £44 / night

6

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

14

Road Town holiday yacht rental

Tortola / Road Town

2 4 1 night min

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

from £130 / night

£906 / week

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from £130 / night

(10) Very Good 

36

Bodrum / Bodrum City

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Nearest beach 0.1 km
  • Swimming pool
  • Child friendly

from £99 / night

£686 - £8253 / week

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from £99 / night

7

Magnesia Region / Volos

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £52 / night

£363 / week

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from £52 / night

31

Holiday yacht in Skiathos Town

Skiathos / Skiathos Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

from £819 / night

£5173 - £5604 / week

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from £819 / night

4

State of Rio de Janeiro / Rio de Janeiro

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £400 / night

£2800 / week

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from £400 / night

11

State of Rio de Janeiro / Angra Dos Reis

4 10 1 night min

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

from £480 / night

£3360 / week

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from £480 / night

24

Holiday yacht in Cogolin

French Riviera - Cote d'Azur / Cogolin

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £517 / night

£2586 / week

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from £517 / night

(4) Excellent 

9

Roanoke Island / Manteo

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

from £200 / night

£1200 / week

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from £200 / night

1