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Sailing holidays (366)

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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366 Results  |  
8 Photos

Yacht | 5 Bedrooms | sleeps 10

1 night min stay

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from £50 /night

£345 - £3859 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Some pets are welcome - please contact the owner
Let yourself be lulled by the lapping of the waves of the sea, between romantic sunsets and starry nights, in unique and evocative contexts in the historical center of one of the most fascinating cities in Italy.  …see more

6 Photos

Yacht | 2 Bedrooms | sleeps 4

Min stay varies

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from £73 /night

£509 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Not suitable for children
  • Car advised
  • No pets allowed
une autre façon de louer qui vous changera d'un appartement Au mouillage sur bouée dans la baie du Marin très bien situé , tous commerces et restaurants avec accès direct en dinghy et les plus belles plages de Martinique à proximité ou navigation à la journée ou plus ou navigation dans les îles voisines à la journee ou + MERCI DE ME DEMANDER VOTRE DEVIS AVANT DE RÉSERVER  …see more

9 Photos

Yacht | 2 Bedrooms | sleeps 4

Min stay varies

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Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
'Mothership' is a mobile yacht/barge from which you can enjoy exciting holidays on the French canals and rivers in 2015. 'Mothership' carries two sit-on kayaks and two mountain bikes for you to use to explore areas away from the main navigable waterways. This is NOT a holiday for the unadventurous. This is a holiday for adventurers regardless of their age!  …see more

Featured properties

5 Photos

Houseboat | 1 Bedroom | sleeps 2

Min stay varies

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Quiet, unusual, exiciting, relaxing, nature, park, sports facilities, unique For an extyra charge, a cruise can be organized.We can spend a night in Paris.  …see more

18 Photos

Yacht | 2 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
Here's to you this beautiful gem! An Amazing Boat, 2 bedroom, 2 bathroom, You can use it as a house on the sea! Or... Get on board with us and decide where to spend an unforgettable holiday!  …see more

12 Photos

Houseboat | 2 Bedrooms | sleeps 4

Min stay varies

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from £46 /night

£318 - £477 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • No pets allowed
  • Private garden
We can offer cruises on Connie at an extra cost depending on amount of days/nights. The skipper would not be on board over night. There is also a dinghy available for rowing on the canal. Excellent cycling on the canal tow path, bikes are available here. We can offer catered dinners on board, also a freezer full of frozen dinners of your choice.  …see more

19 Photos

Yacht | 3 Bedrooms | sleeps 8

Min stay varies

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from £291 /night

£2036 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • No pets allowed
Yacht a vela Dufour 410 Grand' Large 2013, ormeggiato nella darsena di Reggio Calabria, possibilità escursioni alle isole Eolie  …see more

8 Photos

Houseboat | 2 Bedrooms | sleeps 50

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Air conditioning
  • Pets welcome
2 bedroom Houseboat , premium standard and deluxe. at Alapuzha and kumarakom in Kerala  …see more

14 Photos

Houseboat | 6 Bedrooms | sleeps 18

1 night min stay

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from £31 /night

£212 - £700 / week

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Key info:

  • Not suitable for children
  • No pets allowed
sailing trips, sailing vacation, You completely relax during a week or weekend drifting on the IJssel Lake and visiting beautiful old towns.  …see more

13 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Not suitable for children
  • No pets allowed
A romantic & silent accomodatin, Amazing Nature: Sea & The Islands, Best swimming & sailing opportunity in Istanbul  …see more

24 Photos

Yacht | 2 Bedrooms | sleeps 5

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Bateau MONTECARLO 32 HARD TOP 10m50 2010 conception BENETEAU Bateau FLYER SUNDECK 2010 conception BENETEAU L'Esprit de Famille nous anime, nous saurons répondre à vos attentes!  …see more

16 Photos

Key info:

  • Suitable for children over
  • Air conditioning
  • No pets allowed
Have a holiday with a difference by chartering a sailing yacht from Gibraltar; skipper and crew included. Visit Spain, Morocco and Gibraltar on day trips or move around throughout your holiday. Sailing tuition and all safety equipment included.  …see more

4 Photos

Yacht | 2 Bedrooms | sleeps 4

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
B&B ON THE BOAT STINTINO  …see more

5 Photos

Yacht | 1 Bedroom | sleeps 2

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
We specialize in hosting couples for a personalized adventure tailored to your tastes. The yacht is fully equipped for ocean voyages and comfort cruising around the islands. Guests accommodations include a private V-Berth with adjoining private bath. All-Inclusive fee.  …see more

4 Photos

Houseboat | 2 Bedrooms | sleeps 4

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Relaxation.  …see more

7 Photos

Yacht | 4 Bedrooms | sleeps 8

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Air conditioning
  • No pets allowed
Luxury italian yacht for wonderful vacation in the Mediterranean sea  …see more

4 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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from £110 /night

£764 / week

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Key info:

  • Nearest beach 40 km
  • Great for children of all ages 5
  • Car essential
  • Pets welcome
  • Private garden
comfortabele vrijstaande villa met besloten terras aan voorzijde, en vrije achtertuin met groot terras. Geschikt voor 6 personen. 3 slaapkamers, 2 badkamers, 3 toiletten, moderne keuken v.v. apparatuur. Gemeenschap. zwembad, tennisbanen, Half uur per auto van de kust.  …see more

4 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
Location de bateau sur les côtes méditérannée Yacht Hatteras 65' 3 cabines 3 salles de bain Climatisé Cuisine équipé TV Home cinéma Plongée pêche au gros Location au départ de Marina Smir Maroc  …see more

13 Photos

Yacht | 4 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Car not necessary
  • Some pets are welcome - please contact the owner
les san-las sont composés de 350 îles, idéale pour les mouillages tranquilles et soirées conviviales avec musique et ti-punch au rendez-vous. un skipper,une cuisinière et un mousse a votre disposition  …see more

4 Photos

Houseboat | 5 Bedrooms | sleeps 10

Min stay varies

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Beach or lakeside relaxation, Swimming Pool, Great for children of all ages, Air conditioning, No pets allowed, Private garden, Car advised, Nearest beach 5km  …see more

13 Photos

Houseboat | 6 Bedrooms | sleeps 18

Min stay varies

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from £33 /night

£229 - £806 / week

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Key info:

  • Nearest beach 30 km
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Traditional Sailing Clipper houseboat, moored in the centre of the city of Groningen. To be rented as bed and breakfast or to be rented as total ship.  …see more

24 Photos

Houseboat | 1 Bedroom | sleeps 2

Very Good 4.5/5 

Min stay varies

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from £75 /night

£523 - £772 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Studio in former cargo ship located in the Eastern Docklands , close to the city centre. You stay in the wheelhouse and deck-house, the former captain's home. The comfortable, light studio has authentic details. You have your own entrance. Terrace on the waterfront.  …see more

24 Photos

Houseboat | 11 Bedrooms | sleeps 23

Very Good 4.5/5 

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Ski
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
The Dragon's Pearl Junk is ideal for parties for larger groups (up to 23 people) or even incentive groups. Alternatively book a berth and get to meet new friends as you cruise the Halong Bay & Bai Tu Long Bay. Halong Bay & Bai Tu Long Bay cruising – Longer Stay, More Overnights, Night Touring!  …see more

24 Photos

Houseboat | 44 Bedrooms | sleeps 50

Very Good 4/5 

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Ski
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
Visiting Halong Bay & Bai Tu Long Bay Vietnam? Pelican Luxury Vessel's offering amazing low prices, stop searching and start saving - we've got the lowest prices guaranteed. And because all meals, accommodations, a variety of live entertainment and 2 days or 3 days activities are included onboard. Plus let you visit multiple places in Gulf of Tonkin HURRY - SALE ENDS SOON  …see more

24 Photos

Houseboat | 24 Bedrooms | sleeps 48

Min stay varies

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from £178 /night

£1245 - £1467 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Ski
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Rates are Quoted Per Room in U.S Dollars, Rates are Nett and Inclusive of Taxes & Service Charges, Rates are Valid Until December 30th, 2014, Instant Confirmation, 100% Lowest Price Guarantee, Charter Rate applied for 24 Rooms, Free hotel pickup and drop-off included, Confirmation will be received at time of booking, Daily Departure.  …see more

24 Photos

Houseboat | 20 Bedrooms | sleeps 40

Very Good 4.5/5 

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Ski
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Visiting Halong Bay & Bai Tu Long Bay, Vietnam? Bhaya Classic Cruises offering amazing very low prices. Stop searching and start saving and because all meals, accommodations, a variety of live entertainment and 2 days, 3 days or 4 days activities are included onboard HURRY UP - SALE ENDS SOON!  …see more

24 Photos

Narrowboat | 2 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages 5
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Charter Rates are Quoted for Minimum 02 Person & Maximum for 6 Person in U.S Dollars, Charter Rates are Nett and Inclusive of Taxes & Service Charges, Charter Rates are Valid Until December 30th, 2014, 100% Lowest Price Guarantee, Instant Confirmation, Spacious with cozy ambiance, plenty private corners with large window for individual couple  …see more

24 Photos

Houseboat | 17 Bedrooms | sleeps 34

Excellent 5/5 

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Visiting Halong Bay & Bai Tu Long Bay Vietnam? Luxury Syrena Vessel's offering amazing low prices, stop searching and start saving - we've got the lowest prices guaranteed. And because all meals, accommodations, a variety of live entertainment and 2 days or 3 days activities are included onboard. Plus let you visit multiple places in Gulf of Tonkin HURRY - SALE ENDS SOON  …see more

6 Photos

Yacht | 2 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

Key info:

  • Not suitable for children
  • No pets allowed
barca cayman 38 per gite in costa smeralda. bellissima. con marinaio. visibile a golfo aranci. la barca dispone di gps cartografico, ecoscandaglio e radio cd. autopilota. consuma circa 120 litri/ora di carburante e ha due motori da 360 cv caterpillar. ha due cucine e du  …see more

14 Photos

Houseboat | 20 Bedrooms | sleeps 46

Min stay varies

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from £31 /night

£216 / week

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Key info:

  • Great for children of all ages 5
  • Air conditioning
  • No pets allowed
The Paloma is your home while you are in Halong Bay. Good service is key. We always want to hear from our customers so that we can improve our services and we really value their feedback. We built objective for the future is to continue to provide the best service and develop new products.  …see more

9 Photos

Yacht | 1 Bedroom | sleeps 7

Min stay varies

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from £73 /night

£509 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Ski
  • Great for children of all ages 5
  • Car not necessary
  • Pets welcome
With your own boat you can, in all tranquility, visit and explore the world famous archipelago, with its wild and pristine islands, islets and cliffs, more then 150 of them like a pearl necklace on the Adriatic Takeover Ship to 8h in the morning - return afternoon 19h  …see more

6 Photos

Yacht | 2 Bedrooms | sleeps 6

Min stay varies

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from £455 /night

£3180 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
Motor Yacht. 6 berth . Based in the Mediterranean Sea near to Nice. Area has great places to visit, a huge theme and water park and Marine land close by.  …see more

15 Photos

Houseboat | 11 Bedrooms | sleeps 33

Min stay varies

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from £4 /night

£26 / week

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Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
Our houseboats is moored on the west side of Nigeen Lake presenting the breathtaking view of the lake and the mountains. Our houseboats are well furnished with new constructed bathrooms having all the the modern facilities. We also provide exciting offers and discounts.  …see more

13 Photos

Yacht | 12 Bedrooms | sleeps 25

Min stay varies

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from £18 /night

£120 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
The Imperial Cruise, traditional sailboat built of wood with modern facilities and first class service, is perfect for exploring Halong Bay on Imperial Cruise.  …see more

4 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Car not necessary
  • No pets allowed
motor boat / Cruiser Adventure & Leisure Therapy, Trips & Holidays For private charter with Skipper Boats, Beaches and Burgers Sea, Sand and Sausages Guitars, drums and songs Sand Therapy Life Coaching Drummer Boy Boat is a luxury 1982 Storebro Royal Cruiser 34ft with 2x Volvo Penta diesel 135hp engines  …see more

19 Photos

Yacht | 10 Bedrooms | sleeps 20

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Highlights: - Cruise through stunning Halong Bay on traditional Asian junk - Kayak around breathtaking limestone scenery - Vietnamese feast of delicious seafood - Visiting Sung Sot cave and Ti Top island - Cooking Class - Squid fishing at night  …see more

13 Photos

Yacht | 4 Bedrooms | sleeps 8

Min stay varies

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from £111 /night

£772 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Car not necessary
  • No pets allowed
Holidays on a big multi-hulls, in the virgins San Blas Islands, 8 guests maxi in all inclusive, visit of the Indians Kuna villages and snorkelling. Sail, snorkelling , farniente, fishing, Indians villages on the trimaran La Mandragore.  …see more

8 Photos

Yacht | 5 Bedrooms | sleeps 10

Min stay varies

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from £43 /night

£297 - £509 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
abitazione sicura, comoda ed elegante adatta per qualsiasi tipo di visitatore.  …see more

13 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

1 night min stay

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from £590 /night

£4126 - £5872 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages 5
  • Car not necessary
  • No pets allowed
Imagination is a 46 foot catamaran with 3 double en-suite cabins available for charter in St Vincent and the Grenadines. Half board to all-inc is available. We sail the beautiful islands of the Grenadines such as Bequia, Tobago Cays and Mayreau. Come catch your dinner The captain is a PADI Scuba Diving Instructor and Imagination has 10 tanks on board.  …see more

4 Photos

Houseboat | 2 Bedrooms | sleeps 5

Min stay varies

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Key info:

  • Suitable for children over
  • Air conditioning
  • No pets allowed
A beautifully finished boat, SS Maverick has been designed with space, luxury and comfort in mind. A fixed double bed at the back supplemented by a luxurious double sofa bed at the front and spacious wet room, galley and lounge gives you the freedom to unwind and relax.  …see more

22 Photos

Houseboat | 2 Bedrooms | sleeps 6

Min stay varies

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from £143 /night

£1000 / week

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Key info:

  • Great for children of all ages 5
  • Car advised
  • No pets allowed
Short Break Why not try something different and enjoy a short break on a barge fitted out to an exceptionally high standard with bespoke bedroom cabins, a spacious interior and a saloon which opens out on to the front deck, and enjoy the ambience. Moored on the River Thames at Weybridge offering some stunning river views.  …see more

5 Photos

Yacht | 4 Bedrooms | sleeps 8

Min stay varies

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from £67 /night

£467 - £509 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
Vacanze in Barca a Vela Eolie, Cabin Charter Eolie, Imbarco Singolo alle Isole Eolie, Flottiglie e Crociere per Single in Sicilia  …see more

12 Photos

Houseboat | 2 Bedrooms | sleeps 4

1 night min stay

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from £9 /night

£60 - £81 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Great for children of all ages 5
  • Car not necessary
  • Air conditioning
  • No pets allowed
Your houseboat will be a traditional kettuvallam with two en-suite air-conditioned bedrooms. It is built and furnished from local materials, and we provide you with a luxury cruise whilst minimising our impact on the fragile ecosystems of the backwaters  …see more

24 Photos

Houseboat | 10 Bedrooms | sleeps 20

Good 3/5 

Min stay varies

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Key info:

  • Beach / lakeside relaxation
  • Ski
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Rates are Quoted Per Room in U.S Dollars, Rates are Nett and Inclusive of Taxes & Service Charges, Rates are Valid Until December 30th, 2014, Instant Confirmation, 100% Lowest Price Guarantee, Charter Rate applied for 10 cabins, Free hotel pickup and drop-off included Confirmation will be received at time of booking, Daily Departure!  …see more

24 Photos

Yacht | 12 Bedrooms | sleeps 24

Excellent 5/5 

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • No pets allowed
Visiting Halong Bay & Bai Tu Long Bay, Vietnam? Halong Elizabeth Vessel's offering amazing low prices, stop searching and start saving - we've got the lowest prices guaranteed. And because all meals, accommodations, a variety of live entertainment and 2 days or 3 days activities are included onboard. Plus let you visit multiple places in Gulf of Tonkin HURRY - SALE ENDS SOON  …see more

24 Photos

Houseboat | 20 Bedrooms | sleeps 40

Very Good 4.5/5 

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Ski
  • Great for children of all ages 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Visiting Halong Bay & Bai Tu Long Bay, Vietnam? Paloma Vessel's offering amazing low prices ..... Halong Bay & Bai Tu Long Bay Vietnam on Paloma Cruiser - "Longer Stay, More Overnights, Night Touring"  …see more

6 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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from £413 /night

£2889 - £3555 / week

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Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Fantastic 50 ft yacht based in Bequia offering tailor made sailing charters around the grenadines  …see more

11 Photos

Yacht | 3 Bedrooms | sleeps 8

Min stay varies

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from £727 /night

£5088 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
bareboat in Otranto week end in salento in barca settimana in giro isole ioniche Grecia,Corfu',lefkada,Itaca,Zante,Cefalonia,Skorpios,Meganisi,Paxos,Othoni,Merlera giornaliero costa Salentina giornaliero Othoni  …see more

6 Photos

Narrowboat | 3 Bedrooms | sleeps 8

Excellent 5/5 

Min stay varies

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from £140 /night

£975 - £1520 / week

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Key info:

  • Great for children of all ages 5
  • Pets welcome
Relax on a fully equipped narrowboat cruising on the canals of England. We provide all the training you need to enjoy your time aboard. The canals were the motorways of their time, now they are backwaters that take you to the heart of the countryside.  …see more

17 Photos

Narrowboat | 2 Bedrooms | sleeps 5

Excellent 5/5 

Min stay varies

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from £102 /night

£710 - £1020 / week

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Key info:

  • Great for children of all ages 5
  • Pets welcome
Relax on a fully equipped narrowboat cruising on the canals of England. We provide all the training you need to enjoy your time aboard. The canals were the motorways of their time, now they are backwaters that take you to the heart of the countryside.  …see more