Sailing holidays

Sailing holidays (674)

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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674 Holiday homes

Filters applied: Under 5s (674)

(37) Very Good 

18

Kumarakom holiday houseboat rental

Kerala / Kumarakom

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Child friendly
“Really great houseboat experience, succeeding our expectations” We are a couple from Germany in our mid-thirties and spent 2 days/1 night at the Jumbo Houseboat early January. We booked from Germany by contacting the owner Akhil directly. Was a bit of  …see more

from £159 / night

£1397 - £2329 / week

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from £159 / night

(15) 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

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from £140 / night

(11) Excellent 

77

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 25 km
  • Child friendly
  • Pet friendly
A lovely old cargo ship in the nautic centre of Amsterdam port. Nearby the old city with a beautiful view on the famous canals. The National Maritime Museum and the Mill of Brewery 't IJ in sight. The Artis Zoo, the Nieuwmarkt area with its charming cafés, bohemien res  …see more

from £149 / night

£1039 / week

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from £149 / night

(15) Excellent 

12

Holiday houseboat in Amsterdam

Amsterdam / Eastern Docklands

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
Annie's Boat is suitable for 2 people and maximum 2 children.Children up to 12 years stay for free. For children up to the age of 3 years there is a cot present. For children from 3 up to 12 years is a thick luxury air mattress (2x 1pers. mattress) of very good  …see more

from £101 / night

£505 / week

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from £101 / night

(6) Very Good 

32

Holiday houseboat in Alappuzha

Kerala / Alappuzha

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 6 km
  • Child friendly
ITINERARY» Guests can check in at 12:00 hrs, we will welcome you with welcome drink and start cruise after a short briefing introduction, relax and enjoy the canals, rivers and backwater, at 13:00 hrs houseboat will stop for lunch, with lavish menu of traditional Keral  …see more

from £159 / night

£1112 / week

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from £159 / night

(29) Very Good 

16

Leiden holiday houseboat rental

South Holland Province / Leiden

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 27 km
  • Child friendly
Houseboat Pride of Leyden is fully equipped with every comfort, from a well stocked kitchen, to central heating and air conditioning, a TV and Wifi internet, and a veranda with a spectacular view. The main bedroom sleeps two in a king-size bed, the study sleeps one on a  …see more

from £100 / night

£674 - £781 / week

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from £100 / 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
Houseboat are easy to navigate. They are the comfort of a first class summer cottage. Wide range of different activities available for children and other family members. You will explore many unique cultural and natural attractions along your route. Pets are allowed.If  …see more

from £263 / night

£1522 - £2284 / week

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from £263 / night

(2) Excellent 

19

Yacht accommodation in El Porvenir

San Blas Islands / El Porvenir

1 6 1 night min

  • 1 bedroom
  • Sleeps 6
  • 1 night min
  • Child friendly
Enjoy a luxurious yacht trip with me & my small family through San Blas! I have 3 room for 6 guests in 3 beds. This price is including food and drink. Please contact us for an accurate quote. With me you can: - Have 3 Italian cooked meals a day - Snorkel - Fish - Mee  …see more

from £286 / night

£874 - £5874 / week

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from £286 / night

(1) Average 

24

Holiday yacht in Amsterdam

North Holland Province / Amsterdam

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
The accommodation makes the perfect choice for a family or a group of friends desiring the chance to enjoy a traditional old houseboat experience. Blending authentic elements with a wooden finish and only basic amenities, the lodging offers a simple space after a busy d  …see more

from £145 / night

£1009 / week

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from £145 / night

(24) 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
Pantheos Romantic Houseboat Prinsengracht AmsterdamA public swimmingpool "Het Marnixbad" is located just around the corner.  …see more

from £153 / night

£1187 - £1780 / week

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from £153 / night

23

Yacht accommodation in Karfas

Chios / Karfas

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
What's Included?GENERALRental of yachtYacht equipmentAll taxesEnd cleaningYACHT EQUIPMENTDinghy, outboard engine & gasoline.GPS & nautical chartsSheets, blankets & towelsStereo & cockpit speakersExtra Costs:In addition you will also have to pay for  …see more

from £221 / night

£1543 - £2670 / week

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from £221 / night

(1) Excellent 

5

Worsley holiday narrowboat rental

Salford / Worsley

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 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

£795 / week

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from £150 / night

34

San Blas Islands / El Porvenir

3 2 2 nights min

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

 …see more

from £477 / night

£3000 / week

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from £477 / night

(13) Excellent 

24

Houseboat rental in Amsterdam

Amsterdam / Eastern Docklands

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Child friendly
Two luxury, 100% smoke-free rooms on a boat, and en suite bathrooms, free WiFI. After a busy day in the center you can enjoy the grand view of the eastern docklands on the deck terrace on a nice summer day.  …see more

from £178 / night

£1246 / week

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from £178 / night

(9) Very Good 

24

Houseboat accommodation in Henley-on-Thames

Oxfordshire / Henley-on-Thames

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
“An incredibly relaxing holiday in perfect comfort on a beautiful part of the Thames.” From start to finish this turned out to beat many 5 star hotel holidays we had all taken. Firstly the hosts are attentive, lovely and fun. They gave us 2 informed fa  …see more

from £250 / night

£1510 - £2160 / week

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from £250 / night

(22) 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 £82 / night

£570 - £3323 / week

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from £82 / night

22

Holiday houseboat in Mannum

South Australia / Mannum

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
River Breez Is a 6-8 berth luxury houseboat moored at Mannum Waters Marina. Just over 1hr from Adelaide & I can arrange transfers for you. Embracing an open design concept with a contemporary interior, our elegance and sophistication will suit the most discerning guest  …see more

from £589 / night

£2353 - £3177 / week

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from £589 / night

35

Holiday houseboat in Halong Bay

Quang Ninh Province / Halong Bay

20 46 1 night min

  • 20 bedrooms
  • Sleeps 46
  • 1 night min
  • Child friendly
  • Air conditioning
Housed in a traditional wooden boat, Halong Paloma Cruise offers luxurious cabins with stunning views of the well-known Ha Long Bay, a UNESCO World Heritage Site, as well as a New World Wonder 2011. It has a rooftop sun terrace and provides free Tai Chi lesson on board  …see more

from £223 / night

£1556 / week

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from £223 / night

24

Holiday houseboat rental

North Holland Province / Amsterdam

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden
A beautiful quiet location, only 10 min. to center by bike; free car parking in weekend! Basic houseboat, for up to 8 guests, only 10minutes from the Center and situated upon the scenic Nieuwe Meer and large forest. The accommodation makes the perfect choice for a famil  …see more

from £272 / night

£1899 / week

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from £272 / night

(4) Excellent 

11

Amsterdam holiday houseboat rental

North Holland Province / Amsterdam

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
“Great Stay” We had a wonderful time staying on this beautiful boat, the owners where very helpful without being intrusive. The boat had everything you needed for a self catering break, the bed rooms and bathrooms both matched our expectations based o  …see more

from £238 / night

£1662 / week

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from £238 / night

(6) 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
Houseboat, roof terrace, brand new, centre amsterdam, museum square  …see more

from £102 / night

£678 / week

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from £102 / night

(1) Excellent 

11

Olbia / Pittulongu

5 5 5 nights min

  • 5 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £85 / night

£594 / week

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from £85 / night

(2) Very Good 

11

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
The Manta is a beautiful 120 years old Dutch sailing ship, It is still in very good condition, centrally heated, 100m2, With thge atmosphere of the old ships, but modern and comfortable as well. It has a well equiped kitchen, a large living room, central heating, plen  …see more

from £140 / night

£763 - £1060 / week

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from £140 / night

(17) Excellent 

23

Yacht rental in Central and South America

Guna Yala Region / San Blas Islands

5 8 1 night min

  • 5 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Looking for a lifetime holiday experience, with friends, kids, or just the two of you ? Check us out :) Cinco is a lovely 47 feet monohull with 5 double cabins, and large comfortable areas to relax, enjoy the tropical waters.Your crew, Jaad and Lourdes would be happy to  …see more

from £397 / night

£2778 / week

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from £397 / night

6

Alappuzha holiday narrowboat rental

Kerala / Alappuzha

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
The main attractions of a shikara Boat alleppey ride are the shallow and narrow canals, Paddy , village in Kuttanad, mouthwatering lunch on the outskirts of the lake with fresh lake fish and variety of other dishes.Riding on a shikara in the evening is a tranquilising  …see more

from £8 / night

£56 / week

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from £8 / 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 £212 / night

£848 - £933 / week

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from £212 / night

(2) Excellent 

21

USA East Coast holiday houseboat rental

Florida Keys / Key West

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and fre  …see more

from £322 / night

£1985 - £3473 / week

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from £322 / night

(3) Excellent 

62

Holiday houseboat in Srinagar

Kashmir / Srinagar

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
( The taste of Home, where we treat you like Family)  …see more

from £9 / night

£60 / week

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from £9 / night

(9) Excellent 

24

Holiday yacht in East Molesey

Surrey / East Molesey

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
EXCLUSIVE USE, and available all year round, this perfectly appointed liveaboard moored in the most idyllic palm fronted Hampton Court marina. “Eucala” is a very beautiful and cleverly laid out classic French motor yacht with a really rich heritage. We have rece  …see more

from £95 / night

£665 / week

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from £95 / night

10

Amsterdam holiday houseboat rental

North Holland Province / Amsterdam

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
The accommodation makes the perfect choice for a family or a group of friends desiring the chance to enjoy a traditional old houseboat experience. Blending authentic elements with a wooden finish and only basic amenities, the lodging offers a simple space after a busy d  …see more

from £128 / night

£890 / week

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from £128 / night

(1) Very Good 

10

Chester / Broxton

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from £144 / night

£1008 - £1591 / week

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from £144 / night

13

Monaco-Ville

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from £178 / night

£1246 / week

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from £178 / night

(1) Excellent 

9

Holiday yacht in Ta' Xbiex

Island of Malta / Ta' Xbiex

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Berthed on a pontoon berth with spectacular views of Valletta and Msida Creek  …see more

from £84 / night

£588 / week

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from £84 / night

21

Holiday yacht in Amsterdam

North Holland Province / Amsterdam

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
The accommodation makes the perfect choice for a family or a group of friends desiring the chance to enjoy a traditional old houseboat experience. Blending authentic elements with a wooden finish and only basic amenities, the lodging offers a simple space after a busy d  …see more

from £136 / night

£950 / week

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from £136 / night

5

Arrondissement of Le Marin / Le Marin

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly

 …see more

from £327 / night

£2289 - £4068 / week

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from £327 / 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
Looking for a different type of Holiday? Try our Turkish Gullet Accommodation Only. We offer a registered skipper day cruise to one of the beautiful local bays around kaş. on bookings of 3 or more nights. At extra charge, weather permitting. Our beautiful 5 year old  …see more

from £60 / night

£400 - £505 / week

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from £60 / night

(2) Excellent 

7

Holiday houseboat in Mallacoota

Gippsland / Mallacoota

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
Mallacoota wilderness houseboats offers customers a unique experience on Mallacoota Inlet. Wake up on the water at one of many Parks Victoria jetties located at varios locations around the lake. Listen to the Koalas at night and witness the beauty of far east Gippsland  …see more

from £153 / night

£736 - £1353 / week

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from £153 / 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
Welcome to our houseboat named: “Saturnus”. This houseboat is located in front of the Rembrandt house in the old city centre of Amsterdam. Staying on a houseboat is a unique experience, it will allow you to see life from a different perspective: as an inhabitant of  …see more

from £215 / night

£1501 / week

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from £215 / night

15

Tortola / Road Town

4 8 Min stay varies

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

 …see more

from £1588 / night

£11112 / week

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from £1588 / night

(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  …see more

from £129 / night

£900 - £1700 / week

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from £129 / night