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Sailing holidays (20)

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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Filters applied: Private pool (20)

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20 Results   |  

from £1072 / night

£7500 - £8750 / week

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14 Photos

Fethiye / Fethiye Town

Yacht / 5 Bedrooms / sleeps 10

Short stays welcome

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from £1072 / night

£7500 - £8750 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Private Yacht Blue Cruise, gather your loved ones for a once in a lifetime experience. Explore and enjoy some of the most exclusive cruising grounds in Turkey from the comfort of your own yacht. Tailor made yachting holiday,exclusively made for your requirements.  …see more

from £113 / night

£785 / week

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6 Photos

California / Foothill Ranch

Houseboat / 1 Bedroom / sleeps 2

2 Nights min stay

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from £113 / night

£785 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car advised
  • No pets allowed
 …see more

from £62 / night

£429 - £3572 / week

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Excellent 5/5 

18 Photos

Province of Palermo / Palermo

Yacht / 4 Bedrooms / sleeps 10

Excellent 5/5 

1 night min stay

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from £62 / night

£429 - £3572 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
You feel like it is your own boat. Wake up when you want, your favorite breakfast is ready. Jump in the paradisiac water .. no car and traffic to reach a crowd beach.. the water is right there. Sailing, snorkeling, reading, chatting, drinking, relaxing on the hammock!  …see more

Featured properties

from £108 / night

£750 / week

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4 Photos

Anywhere / Far Far Away

Houseboat / 2 Bedrooms / sleeps 4

1 night min stay

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from £108 / night

£750 / week

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Key info:

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

from £215 / night

£1500 / week

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4 Photos

Anywhere / Far Far Away

Houseboat / 5 Bedrooms / sleeps 10

1 night min stay

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from £215 / night

£1500 / week

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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

from £6 / night

£36 - £360 / week

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22 Photos

Anywhere / Far Far Away

Houseboat / 49 Bedrooms / sleeps 5

1 night min stay

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from £6 / night

£36 - £360 / week

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Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
1213234234https://www.holidaylettings.co.uk/content/property_details?mysess=51425999793324751https://www.holidaylettings.co.uk/content/property_details?mysess=51425999793324751https://www.holidaylettings.co.uk/content/property_details?mysess=51425999793324751https://www  …see more

from £47 / night

£325 / week

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Excellent 5/5 

15 Photos

Denpasar / Sanur

Yacht / 2 Bedrooms / sleeps 8

Excellent 5/5 

1 night min stay

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from £47 / night

£325 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Freedom to see the sights, with out having to unpack and back followed by traffic to get to your next point. Come and cruise with us and the dolphins, Make our Yacht your base and mode of transport. We offer safety, activities, great food and unforgettable memories.  …see more

from £608 / night

£4256 / week

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4 Photos

New Providence Island / Nassau

Yacht / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £608 / night

£4256 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • No pets allowed
voiler, croisière, soleil, vacances, catamaran, plage, Bahamas, sud, voile  …see more

from £107 / night

£745 - £1490 / week

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20 Photos

Arrondissement of Le Marin / Le Marin

Yacht / 1 Bedroom / sleeps 2

Min stay varies

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from £107 / night

£745 - £1490 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over 5
  • Car not necessary
  • No pets allowed
Nous ne faisons pas de remplissage et vous serez le seul couple à bord (ou seul(e) si vous êtes célibataire) Le bateau et ses propriétaires seront à votre entière disposition, nous préférons priviléger la convivialité. pensions complètes, tout est compris hor  …see more

from £132 / night

£922 - £3511 / week

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10 Photos

Corse-du-Sud / Ajaccio

Yacht / 3 Bedrooms / sleeps 8

Short stays welcome

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from £132 / night

£922 - £3511 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
Des magnifiques semaines a partager en famille ou entre amis !! CORSICALEMENT . Daniel Nous nous chargerons de vos transfères : aéroport ou férry , compris dans nos tarifs . AUCUNES CAUTIONS ..  …see more

from £123 / night

£860 - £10320 / week

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4 Photos

Cyclades / Antiparos

Yacht / 4 Bedrooms / sleeps 12

1 night min stay

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from £123 / night

£860 - £10320 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Yachts that would otherwise cost several thousands per week (15-50K) are affordable and accessible to all for much less in an all inclusive character. We monitor your kiting and promise, based on up to now testimonials, the best vacation of your life. People come back!  …see more

from £358 / night

£2500 / week

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4 Photos

Malaga Province / Estepona

Yacht / 3 Bedrooms / sleeps 4

1 night min stay

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from £358 / night

£2500 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
Wildlife and Morocco trips  …see more

from £536 / night

£3750 / week

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10 Photos

Arrondissement of Le Marin / Le Marin

Yacht / 4 Bedrooms / sleeps 8

7 Nights min stay

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from £536 / night

£3750 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
croisiere en catamaran départ de Martinique vers st Lucie st Vincent les iles des grenadines leurs plages de sable blanc les coraux poissons multicolores tortues raies dans eaux turquoise etc rencontre avec les habitants promenade dans foret tropicale les cascades no  …see more

from £336 / night

£2347 / week

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6 Photos

Kas / Kas center

Yacht / 3 Bedrooms / sleeps 6

5 Nights min stay

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from £336 / night

£2347 / week

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Key info:

  • Swimming pool
  • Suitable for children over 5
  • No pets allowed
 …see more

from £52 / night

£358 / week

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4 Photos

Anywhere / Far Far Away

Houseboat / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £52 / night

£358 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
AJNAKNHKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH HKDHKVFHKH DH ANDDBADBADN  …see more

from £61 / night

£422 - £708 / week

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15 Photos

Ibiza / Ibiza Town

Yacht / 4 Bedrooms / sleeps 8

4 Nights min stay

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from £61 / night

£422 - £708 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Why to rent a villa if you can have your private sailing yacht or share it with new friends! Yes contact us even to book one cabin because we like to organize sailing experiences for like minded people. We will reply to any question.  …see more

from £113 / night

£785 / week

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15 Photos

Maryland / Baltimore

Houseboat / 2 Bedrooms / sleeps 4

2 Nights min stay

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from £113 / night

£785 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Not suitable for children
  • Car not necessary
  • Air conditioning
  • Pets welcome
 …see more

from £57 / night

£393 / week

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10 Photos

Sliema / Tigne Point

Yacht / 1 Bedroom / sleeps 2

1 night min stay

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from £57 / night

£393 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Some pets are welcome - please contact the owner
  • Private garden
On-board accommodation, boat accommodation, rent-a-cabin, overnight stay aboard, stay on water. boathouse, botel, sea accommodation, CUTTY JEAN is the most exciting combination of stunning settings, unforgettable adventure and fun.  …see more

from £150 / night

£1050 - £1775 / week

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24 Photos

Sintra Municipality / Colares

Yacht / 3 Bedrooms / sleeps 10

4 Nights min stay

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from £150 / night

£1050 - £1775 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa for 10 people w/ private swimming pool , located at 1 km from the beach, inside Sintra natural park, UNESCO World Heritage. The spirit of this house is nature and tranquility close to the beach and the cultural heritage of the region.  …see more

from £673 / night

£4708 - £12746 / week

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17 Photos

Province of Guanacaste / Nosara

Yacht / 7 Bedrooms / sleeps 14

4 Nights min stay

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from £673 / night

£4708 - £12746 / week

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Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
New, luxurious villa just two minutes by foot from Playa Guiones, renowned for its consistent surf break. Jade is a luxury retreat with five master suites, each with a queen sized bed and private, en suite bathroom. Each of these suites is a free standing pavilion; the  …see more

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