Sailing holidays - holiday homes with moorings, boats and yachts

Sailing holidays (259)

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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259 Holiday homes

Filters applied: BBQ (259)

1 / 5

Holiday yacht in St. Petersburg

St. Petersburg / St. Pete Beach, St Petersburg

2 4 1 night min stay

Yacht / 2 bedrooms / sleeps 4 / 1 night min stay

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from £173 / night

£1207 / week

Book

from £173 / night

(5) Excellent 

1 / 40

Holiday yacht in West End

Grand Bahama Island / West End

3 8 7 nights min stay

Yacht / 3 bedrooms / sleeps 8 / 7 nights min stay

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from £444 / night

£3104 - £5863 / week

Book

from £444 / night

1 / 15

Yacht rental in Faa'a

Tahiti / Faa'a

21 46 7 nights min stay

Yacht / 21 bedrooms / sleeps 46 / 7 nights min stay

Add to shortlist

from £316 / night

£2207 / week

Book

from £316 / night

1 / 14

Holiday yacht in Key West

Florida Keys / Key West

3 6 7 nights min stay

Yacht / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £276 / night

£1932 / week

Book

from £276 / night

1 / 4

Holiday yacht in St. Petersburg

St. Petersburg / St. Pete Beach, St Petersburg

1 2 1 night min stay

Yacht / 1 bedroom / sleeps 2 / 1 night min stay

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from £104 / night

£725 / week

Book

from £104 / night

1 / 21

Holiday yacht in Sainte-Luce

Arrondissement of Le Marin / Sainte-Luce

4 8 Min stay varies

Yacht / 4 bedrooms / sleeps 8 / Min stay varies

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from £462 / night

£2770 - £3077 / week

Book

from £462 / night

1 / 20

Holiday yacht in Saint Florent

Haute-Corse / Saint Florent

3 6 7 nights min stay

Yacht / 3 bedrooms / sleeps 6 / 7 nights min stay

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from £439 / night

£3070 / week

Book

from £439 / night

1 / 14

Holiday yacht in Miami

Florida / Miami

3 8 3 nights min stay

Yacht / 3 bedrooms / sleeps 8 / 3 nights min stay

Add to shortlist

from £259 / night

£1811 / week

Book

from £259 / night

1 / 20

Holiday yacht with swimming pool in Le Marin

Arrondissement of Le Marin / Le Marin

1 2 Min stay varies

Yacht / 1 bedroom / sleeps 2 / Min stay varies

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from £231 / night

£1616 / week

Book

from £231 / night

(5) Excellent 

1 / 16

Sorrento holiday yacht rental

Province of Naples / Sorrento

4 8 1 night min stay

Yacht / 4 bedrooms / sleeps 8 / 1 night min stay

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from £246 / night

£592 - £11770 / week

Book

from £246 / night

1 / 12

Holiday yacht in Bocas Town

Isla Colon / Bocas Town

3 6 1 night min stay

Yacht / 3 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £345 / night

£2414 / week

Book

from £345 / night

1 / 32

Holiday yacht rental

Florida Keys / Key West

2 4 1 night min stay

Yacht / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £276 / night

£1932 / week

Book

from £276 / night

1 / 21

Holiday yacht rental

Bequia / Port Elizabeth

6 8 7 nights min stay

Yacht / 6 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £418 / night

£2924 - £2962 / week

Book

from £418 / night

1 / 19

Holiday yacht in Geneva

Canton of Geneva / Geneva

6 6 1 night min stay

Yacht / 6 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £174 / night

£1216 - £6806 / week

Book

from £174 / night

1 / 58

Holiday yacht rental

St. Thomas / East End

3 6 Min stay varies

Yacht / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £1359 / night

£9311 - £14690 / week

Book

from £1359 / night

1 / 10

Le Marin holiday yacht rental

Arrondissement of Le Marin / Le Marin

4 8 7 nights min stay

Yacht / 4 bedrooms / sleeps 8 / 7 nights min stay

Add to shortlist

from £577 / night

£4039 / week

Book

from £577 / night

1 / 4

Ski yacht to rent in Antiparos

Cyclades / Antiparos

4 12 1 night min stay

Yacht / 4 bedrooms / sleeps 12 / 1 night min stay

Add to shortlist

from £1588 / night

£11114 / week

Book

from £1588 / night

1 / 12

Holiday yacht with golf nearby in San Diego

California / San Diego

2 5 2 nights min stay

Yacht / 2 bedrooms / sleeps 5 / 2 nights min stay

Add to shortlist

from £169 / night

£1035 - £1455 / week

Book

from £169 / night

1 / 16

Houseboat rental in Boston

Massachusetts / Boston

1 6 Min stay varies

Houseboat / 1 bedroom / sleeps 6 / Min stay varies

Add to shortlist

from £121 / night

£828 - £1380 / week

Book

from £121 / night

1 / 26

Holiday yacht in Le Marin

Arrondissement of Le Marin / Le Marin

4 8 1 night min stay

Yacht / 4 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £216 / night

£1385 / week

Book

from £216 / night

(2) Excellent 

1 / 30

Holiday yacht rental

San Blas Islands / El Porvenir

4 8 2 nights min stay

Yacht / 4 bedrooms / sleeps 8 / 2 nights min stay

Add to shortlist

from £966 / night

£6759 / week

Book

from £966 / night

1 / 21

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

7 14 2 nights min stay

Houseboat / 7 bedrooms / sleeps 14 / 2 nights min stay

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from £539 / night

£3000 / week

Book

from £539 / night

(5) Excellent 

1 / 9

Holiday yacht rental

Grand Terre / Noumea

3 6 1 night min stay

Yacht / 3 bedrooms / sleeps 6 / 1 night min stay

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from £651 / night

£4556 / week

Book

from £651 / night

(2) Very Good 

1 / 78

Holiday houseboat in Amsterdam

North Holland Province / Amsterdam

3 5 2 nights min stay

Houseboat / 3 bedrooms / sleeps 5 / 2 nights min stay

Add to shortlist

from £116 / night

£808 / week

Book

from £116 / night

1 / 38

Holiday yacht with golf nearby in San Diego

California / San Diego

1 4 2 nights min stay

Yacht / 1 bedroom / sleeps 4 / 2 nights min stay

Add to shortlist

from £166 / night

£1035 - £1315 / week

Book

from £166 / night

1 / 14

Puerto Pollensa ski yacht to rent.

Puerto Pollensa / Puerto Pollensa Marina

4 8 2 nights min stay

Yacht / 4 bedrooms / sleeps 8 / 2 nights min stay

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from £424 / night

£2962 / week

Book

from £424 / night

(3) Excellent 

1 / 21

Copenhagen holiday houseboat rental

Zealand / Copenhagen

4 8 2 nights min stay

Houseboat / 4 bedrooms / sleeps 8 / 2 nights min stay

Add to shortlist

from £424 / night

£2693 / week

Book

from £424 / night

(85) Excellent 

1 / 47

Holiday houseboat in Amsterdam

Amsterdam / Central Amsterdam

2 4 Min stay varies

Houseboat / 2 bedrooms / sleeps 4 / Min stay varies

Add to shortlist

from £104 / night

£770 - £1808 / week

Book

from £104 / night

1 / 24

Holiday yacht rental

Tenerife / Las Galletas

3 6 7 nights min stay

Yacht / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £385 / night

£2693 / week

Book

from £385 / night

(2) Very Good 

1 / 22

Holiday yacht in Kas

Antalya Province / Kas

4 8 1 night min stay

Yacht / 4 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £481 / night

£3077 - £4231 / week

Book

from £481 / night

(14) Excellent 

1 / 19

Holiday yacht in El Porvenir

San Blas Islands / El Porvenir

2 4 3 nights min stay

Yacht / 2 bedrooms / sleeps 4 / 3 nights min stay

Add to shortlist

from £249 / night

£1738 - £3138 / week

Book

from £249 / night

(1) Excellent 

1 / 13

Holiday houseboat with shared pool in Tavernier

Key Largo / Tavernier

2 6 2 nights min stay

Houseboat / 2 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £173 / night

£1035 / week

Book

from £173 / night

(1) Excellent 

1 / 26

San Diego holiday houseboat rental

California / San Diego

1 4 2 nights min stay

Houseboat / 1 bedroom / sleeps 4 / 2 nights min stay

Add to shortlist

from £172 / night

£1203 / week

Book

from £172 / night

1 / 8

Holiday yacht in Fort Myers

Southwest Gulf Coast / Fort Myers

3 6 7 nights min stay

Yacht / 3 bedrooms / sleeps 6 / 7 nights min stay

Add to shortlist

from £79 / night

£552 / week

Book

from £79 / night

(1) Excellent 

1 / 10

Holiday yacht in Dar es Salaam

Dar es Salaam / Masaki Peninsula

3 6 1 night min stay

Yacht / 3 bedrooms / sleeps 6 / 1 night min stay

Add to shortlist

from £828 / night

£5794 / week

Book

from £828 / night

1 / 19

Seattle holiday houseboat rental

Washington / Seattle

1 4 1 night min stay

Houseboat / 1 bedroom / sleeps 4 / 1 night min stay

Add to shortlist

from £121 / night

£725 - £1476 / week

Book

from £121 / night

(2) Excellent 

1 / 21

Holiday yacht in Lipari

Aeolian Islands / Lipari

3 10 1 night min stay

Yacht / 3 bedrooms / sleeps 10 / 1 night min stay

Add to shortlist

from £1000 / night

£6924 / week

Book

from £1000 / night

1 / 23

Yacht rental in Petersburg

Alaska / Petersburg

6 12 7 nights min stay

Yacht / 6 bedrooms / sleeps 12 / 7 nights min stay

Add to shortlist

from £481 / night

£3363 - £40376 / week

Book

from £481 / night

1 / 8

Holiday yacht accommodation

Tortola / Road Town

4 8 1 night min stay

Yacht / 4 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £1380 / night

£9656 / week

Book

from £1380 / night

(3) Excellent 

1 / 19

Amsterdam holiday houseboat rental

North Holland Province / Amsterdam

2 6 3 nights min stay

Houseboat / 2 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £212 / night

£1193 - £1516 / week

Book

from £212 / night

1 / 16

Holiday houseboat rental

Mashonaland West Province / Kariba

3 8 1 night min stay

Houseboat / 3 bedrooms / sleeps 8 / 1 night min stay

Add to shortlist

from £828 / night

£5794 / week

Book

from £828 / night

(5) Excellent 

1 / 39

Manaus holiday houseboat rental

Amazon River / Manaus

1 6 1 night min stay

Houseboat / 1 bedroom / sleeps 6 / 1 night min stay

Add to shortlist

from £12 / night

£78 - £464 / week

Book

from £12 / night

1 / 58

Spanish Town holiday yacht rental

Virgin Gorda / Spanish Town

3 6 Min stay varies

Yacht / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £1359 / night

£9311 - £14690 / week

Book

from £1359 / night

1 / 58

Holiday yacht rental

Tortola / Road Town

3 6 Min stay varies

Yacht / 3 bedrooms / sleeps 6 / Min stay varies

Add to shortlist

from £1359 / night

£9311 - £14690 / week

Book

from £1359 / night

(1) Poor 

1 / 17

Holiday houseboat in Tavernier

Key Largo / Tavernier

2 6 2 nights min stay

Houseboat / 2 bedrooms / sleeps 6 / 2 nights min stay

Add to shortlist

from £173 / night

£1035 / week

Book

from £173 / night

1 / 5

Holiday yacht in La Rochelle

Charente-Maritime / La Rochelle

2 4 1 night min stay

Yacht / 2 bedrooms / sleeps 4 / 1 night min stay

Add to shortlist

from £104 / night

£727 / week

Book

from £104 / night

1 / 77

Holiday yacht in Honolulu

Oahu / Honolulu

3 5 3 nights min stay

Yacht / 3 bedrooms / sleeps 5 / 3 nights min stay

Add to shortlist

from £200 / night

£1276 - £1359 / week

Book

from £200 / night

1 / 15

Holiday houseboat in Manaus

Amazon River / Manaus

1 6 1 night min stay

Houseboat / 1 bedroom / sleeps 6 / 1 night min stay

Add to shortlist

from £12 / night

£78 - £464 / week

Book

from £12 / night

(1) Excellent 

1 / 21

Holiday yacht in Annapolis

Maryland / Annapolis

4 8 Min stay varies

Yacht / 4 bedrooms / sleeps 8 / Min stay varies

Add to shortlist

from £338 / night

£2366 / week

Book

from £338 / night

(2) Excellent 

1 / 20

Holiday yacht in Fort Pierce

Florida / Fort Pierce

2 6 3 nights min stay

Yacht / 2 bedrooms / sleeps 6 / 3 nights min stay

Add to shortlist

from £156 / night

£932 - £1221 / week

Book

from £156 / night

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