List your home
Apply filters
£ to

Sailing holidays (7)

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.

Show results on map

Also consider

Luxury Villas
2,684 properties
Coastal Cottages
222 properties
Pet Friendly Cottages
27,095 properties
Romantic Breaks
3,207 properties
Group Holidays
17,143 properties
Log Cabin Holidays
238 properties
Rural Retreats
12,438 properties
City Breaks
8,475 properties
Holiday Cottages
17,239 properties
Villas in Spain
11,248 properties
Villas in Tenerife
707 properties
Gites in France
8,131 properties
Holiday Cottages in Cornwall
2,983 properties
London Holiday Apartments
941 properties
Florida Villas
905 properties
Villas in Ibiza
349 properties
Villas in Portugal
4,126 properties
Villas in Turkey
2,202 properties
Villas in Malta
455 properties
Lake District Cottages
940 properties

Filters applied: Heated pool (7)

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
7 Results  |  
24 Photos

Houseboat | 2 Bedrooms | sleeps 3

Excellent 5/5 

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over
  • Car advised
  • No pets allowed
  • Private garden
Luxury holidays in Gran Canaria in this wonderful houseboat with all the necessary to have a perfect holidays.  …see more

23 Photos

Yacht | 1 Bedroom | sleeps 4

2 Nights min stay

Add to shortlist

from £197 /night

£1377 - £1607 / week

View

Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children over
  • Air conditioning
  • No pets allowed
Miami Beach Marina is steps away from the best nightlife, amazing beaches and fabulous restaurants. Stay aboard this comfortable stylish yacht, enjoy a glass of wine as the sun goes down or charter her and explore. There are great bars, clubs and restaurants all in walking distance from the marina.  …see more

24 Photos

Yacht | 2 Bedrooms | sleeps 5

Min stay varies

Add to shortlist

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • 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

Featured properties

10 Photos

Yacht | 3 Bedrooms | sleeps 8

Short stays welcome

Add to shortlist

from £159 /night

£1112 - £3847 / week

View

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

14 Photos

Yacht | 3 Bedrooms | sleeps 6

Min stay varies

Add to shortlist

from £92 /night

£642 - £3847 / week

View

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

24 Photos

Houseboat | 24 Bedrooms | sleeps 48

Min stay varies

Add to shortlist

from £185 /night

£1291 - £1521 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
  • Ski
  • Great for children of all ages
  • 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

4 Photos

Yacht | 4 Bedrooms | sleeps 8

Min stay varies

Add to shortlist

from £733 /night

£5130 / week

View

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