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Sailing holidays (376)

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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376 Results  |  
16 Photos

Yacht | 3 Bedrooms | sleeps 5

Very Good 4/5 

Min stay varies

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from £211 /night

£1474 - £2624 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Neverland is a 47ft luxury Moody Sailing Yacht, in pristine condition built in 2002 available for skippered charter. She can accommodate up to 5 guests. Breakfast light lunch, tea and coffee are included in the price. Cold drinks apart from water are chargeable. Yacht charter from Olbia Free skipper and hostess. Free breakfast, light lunch, tea coffee.  …see more

6 Photos

Yacht | 3 Bedrooms | sleeps 8

Excellent 5/5 

7 Nights min stay

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from £129 /night

£901 - £1219 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
Sailing Yacht Beneteau Oceanis 393 (3 double cabins and 2 heads) based in the Greek Dodecanese islands available direct from English owner. The prices on this website are for bareboat charters. A skipper is available at approx cost of £110 per day.  …see more

6 Photos

Yacht | 2 Bedrooms | sleeps 4

Min stay varies

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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

Featured properties

14 Photos

Yacht | 4 Bedrooms | sleeps 8

Excellent 5/5 

2 Nights min stay

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from £611 /night

£4275 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Suitable for children over
  • Car not necessary
  • Some pets are welcome - please contact the owner
Escursioni e Vacanze in catamarano con equipaggio Escursioni all'Asinara Vacanze in catamarano Noleggio catamarano sardegna Noleggio catamarano corsica Noleggio catamarano stintino Asinara Catamaran è speccializzata nel Charter Nautico, noleggio di catamarani in Sardegna  …see more

14 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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from £92 /night

£642 - £3847 / week

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Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Une façon différente d'apprécier les charmes de l'Ile de Beauté et de profiter pleinement de ses formidables atouts : soleil, eaux cristallines, paysages sauvages et authentiques, plages accessibles par la mer, fonds sous-marins riches et préservés...  …see more

19 Photos

Yacht | 3 Bedrooms | sleeps 8

Min stay varies

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from £294 /night

£2052 / 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

6 Photos

Yacht | 3 Bedrooms | sleeps 4

1 night min stay

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from £110 /night

£770 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • No pets allowed
Blazing Star is a unique experience. The sailing boat has been recently fully restored. It is a racing boat but with superb elegant design with all the modern facilities one would expect.  …see more

12 Photos

Houseboat | 2 Bedrooms | sleeps 4

Min stay varies

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from £46 /night

£318 - £371 / week

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Key info:

  • Great for children of all ages
  • 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

22 Photos

Yacht | 1 Bedroom | sleeps 2

Short stays welcome

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from £55 /night

£385 - £770 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • No pets allowed
Cabin cruises are ideal for single travellers and couples alike. It's the perfect opportunity to get to meet fellow backpackers like yourselves. Whether you're an adventurer or more of a loner type of person, this cruise is the best way to discover the beautiful coast. During the day, you can enjoy all the activities that we have to offer such as paragliding, diving, snorkell  …see more

22 Photos

Yacht | 1 Bedroom | sleeps 2

Short stays welcome

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from £55 /night

£385 - £770 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • No pets allowed
Cabin cruises are ideal for single travellers and couples alike. It's the perfect opportunity to get to meet fellow backpackers like yourselves. Whether you're an adventurer or more of a loner type of person, this cruise is the best way to discover the beautiful coast. During the day, you can enjoy all the activities that we have to offer such as paragliding, diving, snorkell  …see more

22 Photos

Yacht | 1 Bedroom | sleeps 2

3 Nights min stay

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from £55 /night

£385 - £770 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • No pets allowed
Cabin cruises are ideal for single travellers and couples alike. It's the perfect opportunity to get to meet fellow backpackers like yourselves. Whether you're an adventurer or more of a loner type of person, this cruise is the best way to discover the beautiful coast. During the day, you can enjoy all the activities that we have to offer such as paragliding, diving, snorkell  …see more

13 Photos

Yacht | 3 Bedrooms | sleeps 6

Excellent 5/5 

Min stay varies

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from £612 /night

£4280 - £6091 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • 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

15 Photos

Yacht | 2 Bedrooms | sleeps 4

1 night min stay

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from £62 /night

£428 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Not suitable for children
  • Car advised
  • No pets allowed
Sleep on board is just fantastic. As you wake you wake up you can just jump in the fresh Tirrenian Sea...  …see more

5 Photos

Yacht | 5 Bedrooms | sleeps 10

Very Good 4/5 

Short stays welcome

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from £813 /night

£5685 - £8528 / week

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Key info:

  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
PRIVATE YACHT, YACHT CHARTER, GULET, MARMARIS, BODRUM, GOCEK, MOTOR YACHT  …see more

18 Photos

Yacht | 3 Bedrooms | sleeps 2

Min stay varies

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from £43 /night

£300 - £2138 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Vacanza. Charter occasionale. Cene in barca. Alloggio in barca.Escursione in barca. Visita Bari dal mare. Feste e compleanni in barca a vela. Barca a vela.Regate.  …see more

9 Photos

Yacht | 1 Bedroom | sleeps 7

Min stay varies

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from £74 /night

£513 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Ski
  • Great for children of all ages
  • 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

11 Photos

Yacht | 3 Bedrooms | sleeps 6

2 Nights min stay

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from £159 /night

£1112 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Week end with Double G it s not only o stay at the mored we can also arrange and organize around trip as you request. we decide the fares upon your request  …see more

13 Photos

Houseboat | 6 Bedrooms | sleeps 16

Min stay varies

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from £33 /night

£231 - £813 / week

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Key info:

  • Nearest beach 30 km
  • Great for children of all ages
  • 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

14 Photos

Houseboat | 6 Bedrooms | sleeps 18

Min stay varies

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from £31 /night

£214 - £706 / 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

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
  • Car not necessary
  • Some pets are welcome - please contact the owner
B&B ON THE BOAT STINTINO  …see more

4 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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from £110 /night

£770 / week

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Key info:

  • Nearest beach 40 km
  • Great for children of all ages
  • 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

12 Photos

Yacht | 5 Bedrooms | sleeps 2

1 night min stay

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from £165 /night

£1154 - £1242 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Naviguer dans le golfe de Volos découvrir la péninsule de Trikeri sur une goélette traditionnelle en bois de 22 mètres avec un équipage entièrement expérimenté. Vous laissera un souvenir inoubliable de vos vacances en Grèce Le logement c est une belle goélette en bois,  …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

19 Photos

Yacht | 2 Bedrooms | sleeps 4

Short stays welcome

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from £306 /night

£2138 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Car advised
  • No pets allowed
Confortevole barca a vela "High Life", Sun Odyssey 37 con Skipper, 2 ampie camere matrimoniali, spazioso bagno con doccia, cucina, dinette pranzo per sei posti. Randa e Genoa per oltre 60 mq di vele, motore ausiliario 30 hp, tender e tutte le attrezzature nautiche. Marina Porto San Giorgio, Prov. Fermo, Marche. Auto: A14, uscita Fermo-P.S.Giorgio; Treno: P.S.Giorgio  …see more

24 Photos

Yacht | 6 Bedrooms | sleeps 12

7 Nights min stay

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from £1698 /night

£11883 / week

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Key info:

  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
Sailing in the comfort of a world class boutique hotel On gullet Eleganza everything for your comfort is taken care of.You will not only be experiencing a truly enriching cultural exchange with local people, but also an exciting adventure diving in crystal clear waters.  …see more

13 Photos

Yacht | 12 Bedrooms | sleeps 25

Min stay varies

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from £18 /night

£125 / 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

10 Photos

Yacht | 2 Bedrooms | sleeps 4

Excellent 5/5 

Short stays welcome

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from £147 /night

£1026 / week

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Key info:

  • Suitable for children over
  • No pets allowed
Asinara Sail Experience vi porta a visitare uno dei luoghi più suggestivi ed affascinanti dell'intera Sardegna. A bordo delle nostre imbarcazioni a vela, vi porteremo alla scoperta della costa offerta dal Parco Nazionale dell'Asinara per delle crociere indimenticabili.  …see more

4 Photos

Houseboat | 1 Bedroom | sleeps 6

1 night min stay

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from £367 /night

£2565 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Pets welcome
imbarcazione di 11 metri con due comode scalette prendisole ampio comodo per 6 persone possibile fare immersioni sub con la propria attrezzatura fare sci nautico io lo consiglio agli amanti del mare che vogliono trascorrere una o più giornate a contatto della natura  …see more

14 Photos

Houseboat | 20 Bedrooms | sleeps 46

Min stay varies

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from £34 /night

£233 / week

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Key info:

  • Great for children of all ages
  • 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

8 Photos

Yacht | 2 Bedrooms | sleeps 10

1 night min stay

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from £1100 /night

£7694 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
bateau moteur 15mètres, Cranchi Méditerranée 50, yacht type « open », location à la journée ou semaine, toutes options, 10 personnes en journée, 4 personnes en nuitée, 3 cabines, 2 salle de bain, avec équipage. Régions: Var-Corse-Alpes/Maritimes.  …see more

11 Photos

Yacht | 3 Bedrooms | sleeps 7

Min stay varies

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from £428 /night

£2992 - £3420 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
la barca si trova ormeggiata a Forio d' Ischia. Nel prezzo NON e' incluso carburante,porti,e cambusa E' compreso skipper hostess,pulizie  …see more

4 Photos

Houseboat | 3 Bedrooms | sleeps 6

Short stays welcome

Add to shortlist

from £336 /night

£2351 / week

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Key info:

  • Beach / lakeside relaxation
  • Suitable for children over
  • Car not necessary
  • Some pets are welcome - please contact the owner
Il Catamarano è una soluzione ideale per una vacanza sul mare, in completo relax e assoluta sicurezza, adatto sopratutto alle famiglie grazie ad ampi spazi e confort. Una vacanza in Sardegna a bordo del catamarano è sicuramente una esperienza indimenticabile!  …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
  • 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

9 Photos

Narrowboat | 2 Bedrooms | sleeps 6

Min stay varies

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from £130 /night

£910 - £1310 / week

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Key info:

  • Great for children of all ages
  • Pets welcome
Narrowboat  …see more

6 Photos

Narrowboat | 2 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

from £130 /night

£910 - £1765 / week

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Key info:

  • Great for children of all ages
  • 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

6 Photos

Narrowboat | 2 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

from £140 /night

£975 - £1410 / week

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Key info:

  • Great for children of all ages
  • 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

7 Photos

Narrowboat | 2 Bedrooms | sleeps 8

Good 3.5/5 

Min stay varies

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from £133 /night

£930 - £1410 / week

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Key info:

  • Great for children of all ages
  • 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

8 Photos

Narrowboat | 2 Bedrooms | sleeps 5

Min stay varies

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from £118 /night

£825 - £1600 / week

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Key info:

  • Not suitable for children
  • No pets allowed
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

7 Photos

Narrowboat | 1 Bedroom | sleeps 4

Excellent 5/5 

Min stay varies

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from £133 /night

£930 - £1190 / week

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Key info:

  • Great for children of all ages
  • No pets allowed
Narrowboat  …see more

6 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

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from £428 /night

£2996 - £3687 / 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

4 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

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

11 Photos

Yacht | 3 Bedrooms | sleeps 8

Min stay varies

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from £733 /night

£5130 / 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

13 Photos

Yacht | 4 Bedrooms | sleeps 8

Min stay varies

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from £112 /night

£778 / 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

25 Photos

Yacht | 10 Bedrooms | sleeps 24

Min stay varies

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from £121 /night

£847 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Isole Tremiti, Croazia, vacanza in caicco, vacanza in barca a vela, vacanze italia, vacanze puglia, imbarchi individuali, cabin charter, Caicco, caicco freedom , vacanza natura, vacanza mare, vacanza yoga, vacanza per single,Venezia festival del cinema, parco nazionale. Vivere una esperienza unica alle Isole Tremiti nel Parco Nazionale del Gargano  …see more

4 Photos

Yacht | 6 Bedrooms | sleeps 8

1 night min stay

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from £95 /night

£659 - £2633 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Great for children of all ages
  • No pets allowed
Yacht catamaran à voile " pas plus qu'à fond " chambres d'hôtes tout confort sur un emplacement privilégié à flot. 4 Chambres séparés. Prestations ; Parking sécurisé et sous vidéo pour votre véhicule, TV, MP3 , CD, WIFI, électronique marine co  …see more

10 Photos

Houseboat | 3 Bedrooms | sleeps 8

Excellent 5/5 

Min stay varies

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from £65 /night

£452 - £734 / week

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Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Barca a vela di 17 metri con 3 cabine due triple e una doppia tutte con bagno e doccia ,cucina con fornelli a induzione elettrica, forno a gas , microonde macchina del caffè e tante altre comodità per non farvi mancare nulla.  …see more

19 Photos

Narrowboat | 1 Bedroom | sleeps 6

Excellent 5/5 

3 Nights min stay

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from £175 /night

£1219 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
Canal, barge, boat hire, River Thames, Shepperton, Chertsey, Windsor, Thorpe Park, Runnymead, Egham, Marlow, Maidenhead, Clivedon Hall IslandHenley, Day Hire, Holiday Hire, Short Breaks in London, RYA Training Courses for Inland Waterways, Marine VHF Licence, Power 1&2 Great family accommodation on the River Thames Shepperton, Walton, Weybridge, Chertsey, Thorpe Park, Egham  …see more

10 Photos

Yacht | 1 Bedroom | sleeps 4

Min stay varies

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from £123 /night

£855 / week

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Key info:

  • Beach / lakeside relaxation
  • Not suitable for children
  • No pets allowed
Enjoy the beauties of Venice in an amazing wooden sailing boat, docked in a private Island 15' far away from Piazza San Marco. Direct waterbus from/to railway, Piazzale Roma and from airport. Credit card accepted  …see more

15 Photos

Houseboat | 11 Bedrooms | sleeps 33

Min stay varies

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from £4 /night

£27 / 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

23 Photos

Yacht | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £86 /night

£600 / week

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Key info:

  • Suitable for children over
  • No pets allowed
Dartmouth yacht stay, self catering holiday, panoramic harbour view, unique holiday  …see more