Sailing holidays

Close

Sailing holidays (80)

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

Price per night

Price per night

to

Bedrooms

Bathrooms

Location

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
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

80 Holiday homes

Filters applied: Swimming pool (80)

(12) Very Good 

1 / 26

Western Cape / Knysna

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £70 / night

£487 - £775 / week

Book Book View

from £70 / night

(14) Excellent 

1 / 20

Pantheos Romantic Houseboat - Jordaan houseboat sleeps 4

Amsterdam / Jordaan

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Pets welcome;
This was a truly unique experience to stay on a houseboat. I grew up in Amsterdam but never had the opportunity to stay or even visit a houseboat. I stayed here for 10 days at the end of April and was very fortunate to be blessed with great weather. My stay was excellen  …see more

from £152 / night

£1177 - £2269 / week

Book Book View

from £152 / night

(2) Excellent 

1 / 9

Roanoke Island / Manteo

2 bedroomsSleeps 43 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £152 / night

£955 - £1146 / week

Book Book View

from £152 / night

1 / 61

Castrignano del Capo / Santa Maria di Leuca

1 bedroomSleeps 3Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £126 / night

£0 / week

Book Book View

from £126 / night

(20) Excellent 

1 / 41

Lanzarote Yacht Hotel - Marina Rubicon yacht sleeps 6

Playa Blanca / Marina Rubicon

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
You have the opportunity to rent a magnificent Yacht-Hotel entire for you! She has 3 double cabins, 2 full bathrooms with hot water shower, galley with vitroceramic hob and microwave oven, fridge, dining room, outside lounge, solarium, cd player and air conditioning. Th  …see more

from £81 / night

£565 - £3295 / week

Book Book View

from £81 / night

1 / 32

A unique experience in Mallorca - Live the dream!

Port d'Andratx / Cala Llamp

3 bedroomsSleeps 41 night min stay

  • 3 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.1 km; Swimming pool;
Annette Rosenkilde is a lovely traditional Danish Fishing vessel, converted to a live-a-board cruising and charter vessel. She has a fantastic deck space with dining area, comfortable seating area and sunbeds. There are high bulwarks around the entire deck making her sa  …see more

from £50 / night

£0 / week

Book Book View

from £50 / night

(7) Very Good 

1 / 38

Florida / Miami Beach

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £138 / night

£909 - £1107 / week

Book Book View

from £138 / night

1 / 16

Corsaro, our 5* luxury cruiser houseboat, Kariba

Mashonaland West Province / Kariba

3 bedroomsSleeps 81 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Swimming pool; Suitable for children age 5+; Car not necessary;
Corsaro is the Kariba Cruise Company's 5* houseboat on Lake Kariba. There is no better way to explore the shores of this enchanting place than from her decks. Fall asleep to the sounds of Africa from one of two double ensuite rooms, or in one of her two single bunks or  …see more

from £917 / night

£0 / week

Book Book View

from £917 / night

(1) Excellent 

1 / 30

Classic yacht houseboat in beautiful Saint Lucia

Castries Quarter / Marigot Bay

3 bedroomsSleeps 24 nights min stay

  • 3 bedrooms
  • Sleeps 2
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.1 km; Swimming pool;
This is an opportunity to experience life in our private classic 41 foot yacht which is moored to the dock in beautiful Marigot Bay in Saint Lucia. We also have a 4x4 jeep available if you wish to go out and explore the island. The boat has a classic teak wood interior  …see more

from £65 / night

£0 / week

Book Book View

from £65 / night

(15) Excellent 

1 / 29

PORTO DOURO CANAL BOAT HIRE - DOUROVOU LTD

Porto District / Porto

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Swimming pool;
CANAL BOAT HIRE DOURO RIVER WATER WAY PORTO Portugal.ATTENTION: PLEASE CHECK AVAILABILITY BY EMAIL The company owns a small Marina "Douro Fluvina" at Ferradosa - Sao Joao da Pesqueira.The boat is a 26ft Yachts ideal for a couple or a family with children.You c  …see more

from £160 / night

£547 / week

Book Book View

from £160 / night

(4) Excellent 

1 / 30

Sailing Adventure Amalfi Coast and Flegree

Province of Naples / Procida Island

4 bedroomsSleeps 2Min stay varies

  • 4 bedrooms
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
"CONTACT US FOR ONE PAX AND MORE THAN TWO PAX AVAILABILITIES. PRICES ARE FOR 2 PERSONS GROUPS, PRIVATE QUOTES FOR LARGER GROUPS. Classic Sailing Ketch of 20 meters based in Ibiza & Formentera. Why to rent a villa if you can have your private sailing yacht or share  …see more

from £211 / night

£1446 / week

Book Book View

from £211 / night

(15) Excellent 

1 / 22

PORTO DOURO VALLEY SAIL YACHT CRUISES WITH SKIPPER

Porto District / Porto

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Swimming pool;
YACHT CHARTER DOURO RIVER WATER WAY PORTO Portugal.ATTENTION: PLEASE CHECK AVAILABILITY BY EMAIL The company owns a small Marina "Douro Fluvina" at Ferradosa - Sao Joao da Pesqueira.Our boats are 28ft Yachts ideal for a couple or a family with children.You can  …see more

from £160 / night

£631 / week

Book Book View

from £160 / night

(1) Excellent 

1 / 14

beautiful 3 bedroom gullet berthed in kas marina

Antalya Province / Kas

3 bedroomsSleeps 51 night min stay

  • 3 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Looking for a different type of Holiday? Try our Turkish Gullet Accommodation Only. We offer a free registered skipper day cruise to one of the beautiful local bays around kaş. on bookings of 3 or more nights. It would be possible to pay extra for a cruise further afi  …see more

from £60 / night

£400 - £605 / week

Book Book View

from £60 / night

(5) Excellent 

1 / 22

Santa Ponsa / Santa Ponsa Marina

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £160 / night

£1118 - £3353 / week

Book Book View

from £160 / night

1 / 20

California / Marina del Rey

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 1 km; Swimming pool; Great for children of all ages ;
 …see more

from £77 / night

£0 / week

Book Book View

from £77 / night

1 / 44

Florida Keys / Key West

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 4 km; Swimming pool;
 …see more

from £535 / night

£0 / week

Book Book View

from £535 / night

1 / 15

Galveston Island / Galveston

1 bedroomSleeps 41 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Swimming pool;
 …see more

from £153 / night

£802 / week

Book Book View

from £153 / night

(2) Excellent 

1 / 9

Massachusetts / Boston

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £382 / night

£2291 / week

Book Book View

from £382 / night

(9) Excellent 

1 / 14

Yate Alba - Isla Chiloe yacht sleeps 10

Los Lagos Region / Isla Chiloe

5 bedroomsSleeps 103 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
The Alba is a traditionally made wooden 66 foot motor boat that provides full accommodations for 10 guests with all inclusive service, incredible meals, the best chilean wines and international spirits, our guests are tended by 4-5 (fluent English speaking Captain, Coas  …see more

from £2138 / night

£14962 - £21375 / week

Book Book View

from £2138 / night

(1) Excellent 

1 / 11

Maryland / Baltimore

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £210 / night

£1069 - £14428 / week

Book Book View

from £210 / night

(10) Very Good 

1 / 7

Choeng Thale / Bang Tao Beach

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £184 / night

£1069 / week

Book Book View

from £184 / night

1 / 24

Stylish luxury houseboat - Puerto de Mogán

Mogan / Playa de Mogan

3 bedroomsSleeps 52 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Swimming pool; Suitable for children age 5+; No pets allowed;
Spectacular luxury houseboat for up to 5 people (4 adults and 1 child).In the best and exclusive port in the south of Gran Canaria (Puerto de Mogan), this houseboat will do your holidays unforgettable forever. With all which you need to have a relax and wonderful stay:  …see more

from £130 / night

£910 - £1645 / week

Book Book View

from £130 / night

1 / 20

Arrondissement of Le Marin / Le Marin

1 bedroomSleeps 2Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £253 / night

£0 / week

Book Book View

from £253 / night

1 / 58

St. Thomas / East End

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £1833 / night

£12596 - £22214 / week

Book Book View

from £1833 / night

1 / 44

royal heritage houseboats - Srinagar houseboat sleeps 50

Kashmir / Srinagar

27 bedroomsSleeps 501 night min stay

  • 27 bedrooms
  • Sleeps 50
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Ask owner if suitable for children;
Offering a massage parlour, Royal Heritage Houseboats is located in Srīnagar and is 500 metres from Zabarwan Park. Free wired internet is available. The property offers free parking.The accommodation will provide you with a TV, a heater, a minibar and cable channels. F  …see more

from £92 / night

£688 / week

Book Book View

from £92 / night

(5) Excellent 

1 / 25

LUXURY HOUSEBOAT. - Puerto Rico Resort houseboat sleeps 3

Gran Canaria / Puerto Rico Resort

2 bedroomsSleeps 37 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
Spectacular luxury houseboat for up to 3 people (2 adults and 1 child).In the best private and exclusive port in Gran Canaria ( ANFI DEL MAR ), this houseboat will do your holidays unforgettable forever.With all which you need to have a relax and wonderful stay: beach w  …see more

from £127 / night

£883 / week

Book Book View

from £127 / night

1 / 5

Aeolian Islands / Lipari

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £72 / night

£505 - £589 / week

Book Book View

from £72 / night

(1) Excellent 

1 / 26

Waikato Region / Tuakau

6 bedroomsSleeps 121 night min stay

  • 6 bedrooms
  • Sleeps 12
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £540 / night

£0 / week

Book Book View

from £540 / night

1 / 63

Florida Keys / Key West

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £1833 / night

£12596 - £22214 / week

Book Book View

from £1833 / night

1 / 10

Arrondissement of Le Marin / Le Marin

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £631 / night

£4412 / week

Book Book View

from £631 / night

1 / 13

Southwest Gulf Coast / Cape Coral

3 bedroomsSleeps 64 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £230 / night

£1146 - £1680 / week

Book Book View

from £230 / night

(19) Very Good 

1 / 28

Royal Palace Cruise - 1 Deluxe Room for 2 People

Quang Ninh Province / Halong Bay

18 bedroomsSleeps 21 night min stay

  • 18 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 5 km; Swimming pool;
The boutique beauty of the cruise will charm all the guests at the first glance. Among hundreds of boats and cruises in Halong Bay. We can say for sure that the Royal Palace Cruise is the unique one which was designed specially like a Royal Palace, Totally different wit  …see more

from £199 / night

£17880 / week

Book Book View

from £199 / night

1 / 15

Maryland / Baltimore

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £191 / night

£993 / week

Book Book View

from £191 / night

1 / 8

Maryland / Davidsonville

2 bedroomsSleeps 42 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £191 / night

£1069 / week

Book Book View

from £191 / night

1 / 29

⛵ Sail charter Catamaran NEW! Caribbean BVI's

Tortola / Brewers Bay

1 bedroomSleeps 25 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
Sail La Vie 46 foot Catamaran a perfect blend of lavish & comfortable combined with speed & performance she is perfect for those looking for a luxury yacht vacation. Each Cabin has a Refined & Contemporary Interior. RATE is per cabin for 2 people min 7n. ***********  …see more

from £1600 / night

£6395 / week

Book Book View

from £1600 / night

1 / 48

Catamaran - Santos yacht sleeps 12

Lisbon / Santos

5 bedroomsSleeps 12Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
Brand new catamaran from 2014 with 3 double rooms and 2 indivuduals. Excellent conditions for charter traveling in the Atlantic or just to spend a few nights in Lisbon. With crew included feel free to try this new way to stay in Lisbon and take advantage of the best loc  …see more

from £757 / night

£4118 / week

Book Book View

from £757 / night

1 / 5

EXPECTATIONS43 CATAMARAN - French Harbour yacht sleeps 4

Roatan / French Harbour

3 bedroomsSleeps 41 night min stay

  • 3 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
SAILING CATAMARAN LOCATED CARIBBEAN 43 FEET LONG AND 25 FEET WIDE SET UP FOR DIVING, FISHING. UP TO 4 GUESTS ON DAY TOURS UP TO 20 PERSON. YOU WILL TRAVEL FROM PORT TO PORT TO ENJOY LOCAL PLACES TO SEE. LOT OF NICE SNORKELING LET US SHOW YOU ROATAN OR BELIZ  …see more

from £1050 / night

£4199 / week

Book Book View

from £1050 / night

(4) Very Good 

1 / 9

Halong Imperial Classic Cruise - Halong Bay yacht sleeps 18

Quang Ninh Province / Halong Bay

12 bedroomsSleeps 181 night min stay

  • 12 bedrooms
  • Sleeps 18
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
Halong Imperial Classic Cruise is a traditional sail boat, built of wood with modern facilities and firt class service, is perfect for exploring Halong Bay on Imperial Classic Cruise. The main food in Imperial Classic Cruise is Vietnam traditional dishes made of local s  …see more

from £123 / night

£9619 / week

Book Book View

from £123 / night

1 / 15

Jersey Shore / Atlantic City

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £306 / night

£0 / week

Book Book View

from £306 / night

1 / 17

Province of Guanacaste / Nosara

7 bedroomsSleeps 14Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £786 / night

£5499 - £14886 / week

Enquire Enquire View

from £786 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page