Sailing holidays

Sailing holidays (21)

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.

View larger 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

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
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

21 Holiday homes

Filters applied: Heated pool

(7) Excellent 

21

Key West holiday houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great location and boat!” First time for us renting a boat and previous reviews proved accurate. Location in marina at end of pier was nice. Arranged for a captain to take us out for one day (at additional fee) which was a great way to spend a day enj
…see more

from £317 / night

£1954 - £5196 / week

Book View

from £317 / night

14

Yacht rental in Ajaccio

Communaute d'Agglomeration du Pays Ajaccien / Ajaccio

3 8 6 nights min

  • 3 bedrooms
  • Sleeps 8
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £110 / night

£658 - £6027 / week

Book View

from £110 / night

10

Le Marin holiday yacht rental

Arrondissement of Le Marin / Le Marin

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £653 / night

£4566 / week

Book View

from £653 / night

44

Houseboat rental in Srinagar with golf nearby

Srinagar District / Srinagar

27 50 1 night min

  • 27 bedrooms
  • Sleeps 50
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children

from £94 / night

£698 / week

Book View

from £94 / night

31

Holiday yacht in Skiathos Town

Skiathos / Skiathos Town

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Air conditioning

from £827 / night

£5218 - £6957 / week

Book View

from £827 / night

(1) Excellent 

10

Ajaccio holiday yacht rental

Communaute d'Agglomeration du Pays Ajaccien / Ajaccio

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Swimming pool

from £603 / night

£4218 / week

Book View

from £603 / night

24

Holiday yacht in Cogolin

French Riviera - Cote d'Azur / Cogolin

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £517 / night

£2586 / week

Book View

from £517 / night

25

Holiday yacht in Charlotte Amalie

St. Thomas / Charlotte Amalie

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

from £508 / night

£3555 / week

Book View

from £508 / night

(1) Excellent 

20

Marina del Rey holiday yacht rental

California / Marina del Rey

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

from £79 / night

£547 / week

Book View

from £79 / night

(3) Excellent 

26

Holiday houseboat in Tuakau

Waikato Region / Tuakau

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £550 / night

£3844 / week

Book View

from £550 / night

(1) Excellent 

24

Holiday narrowboat in Ruskin

Florida / Ruskin

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly

from £71 / night

£430 - £540 / week

Book View

from £71 / night

18

Holiday houseboat in Naples

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £117 / night

£937 / week

Book View

from £117 / night

14

Holiday yacht in Pompano Beach

Broward County / Pompano Beach

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

from £153 / night

£1016 / week

Book View

from £153 / night

9

Holiday yacht rental

Florida Keys / Key West

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £269 / night

£1500 - £2039 / week

Book View

from £269 / night

13

Holiday yacht rental

Southwest Gulf Coast / Cape Coral

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £235 / night

£1172 - £1719 / week

Book View

from £235 / night

(3) Very Good 

32

Holiday houseboat in Tuan Chau Island

Halong Bay / Tuan Chau Island

20 2 1 night min

  • 20 bedrooms
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £209 / night

£1460 / week

Book View

from £209 / night

23

Houseboat rental in Lake Ozark

Lake of the Ozarks / Lake Ozark

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £408 / night

£1852 - £3395 / week

Book View

from £408 / night

25

Holiday yacht in Road Town

Tortola / Road Town

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

from £504 / night

£3528 / week

Book View

from £504 / night

4

Renmark holiday houseboat rental

South Australia / Renmark

5 2 3 nights min

  • 5 bedrooms
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £6 / night

£41 / week

Enquire View

from £6 / night

16

Fort Lauderdale holiday houseboat rental

Broward County / Fort Lauderdale

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £622 / night

£4348 / week

Book View

from £622 / night

6

Holiday yacht in Bavaro

Punta Cana / Bavaro

1 1 1 night min

  • 1 bedroom
  • Sleeps 1
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £24 / night

£180 / week

Book View

from £24 / night

1