Sailing holidays

Sailing holidays (77)

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

77 Holiday homes

Filters applied: Swimming pool (77)

16

San Blas Islands / El Porvenir

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £106 / night

£740 / week

Book View

from £106 / night

(1) Very Good 

32

Port d'Andratx holiday yacht rental

Port d'Andratx / Cala Llamp

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min
  • 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

£350 / week

Book View

from £50 / night

(25) Excellent 

20

Holiday houseboat with shared pool in Amsterdam

Amsterdam / Jordaan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Pantheos Romantic Houseboat Prinsengracht Amsterdam<br />A public swimmingpool "Het Marnixbad" is located just around the corner.  …see more

from £156 / night

£1207 - £1811 / week

Book View

from £156 / night

(21) Very Good 

28

Halong Bay ski yacht to rent.

Quang Ninh Province / Halong Bay

18 2 1 night min

  • 18 bedrooms
  • Sleeps 2
  • 1 night min
  • 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 £212 / night

£19043 / week

Book View

from £212 / night

(1) Excellent 

30

Holiday houseboat in Marigot Bay

Castries Quarter / Marigot Bay

3 2 4 nights min

  • 3 bedrooms
  • Sleeps 2
  • 4 nights min
  • 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 £66 / night

£456 / week

Book View

from £66 / night

(22) Excellent 

41

Holiday yacht with shared pool in Playa Blanca

Playa Blanca / Marina Rubicon

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Beautiful” We had a fantastic one week holiday,the location was stunning and plenty of restaurants to choose from although we found Lani's the best. Jorge and Raquel are lovely and so friendly.  …see more

from £83 / night

£580 - £966 / week

Book View

from £83 / night

(21) Excellent 

29

Porto holiday narrowboat rental

Porto District / Porto

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Unique way to see a beautiful part of Portugal” We spent a fantastic week exploring the upper Douro Valley on two boat. Our party of 11 hired two boats with skippers. Jose Alberto was an excellent guide and host and is very knowledgable about the regi  …see more

from £164 / night

£561 / week

Book View

from £164 / night

(5) Excellent 

22

Santa Ponsa / Santa Ponsa Marina

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £164 / night

£1147 - £3440 / week

Book View

from £164 / night

(1) Excellent 

14

Kas holiday yacht rental

Antalya Province / Kas

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Looking for a different type of Holiday? Try our Turkish Gullet Accommodation Only. We offer a registered skipper day cruise to one of the beautiful local bays around kaş. on bookings of 3 or more nights. At extra charge, weather permitting. Our beautiful 5 year old  …see more

from £60 / night

£400 - £505 / week

Book View

from £60 / night

20

Arrondissement of Le Marin / Le Marin

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £259 / night

£1811 / week

Book View

from £259 / night

20

Chioggia / Sottomarina

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly

 …see more

from £57 / night

£371 - £1421 / week

Book View

from £57 / night

44

Houseboat rental in Srinagar with golf nearby

Kashmir / Srinagar

27 50 1 night min

  • 27 bedrooms
  • Sleeps 50
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children
kashmir ,houseboats ,travel booking ,car rental, bike rental, tour pakages , treaking, camping etc  …see more

from £98 / night

£732 / week

Book View

from £98 / night

(16) Excellent 

22

Porto holiday yacht rental

Porto District / Porto

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“different sailing holiday” good holiday with great scenery good for very avid sailers sailing up and down river would like to do again from port to adriatic really enjoyed and was welcomed by alberto who did his best for every one thank you  …see more

from £164 / night

£647 / week

Book View

from £164 / night

29

Yacht rental in Brewers Bay with shared pool

Tortola / Brewers Bay

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • 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 View

from £1600 / night

(2) Excellent 

7

Srinagar ski houseboat to rent.

Kashmir / Srinagar

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Ski
  • Child friendly
Houseboat Pamela Group of Houseboats in Srinagar Jammu & Kashmir India<br />The houseboat has cosy rooms with attached bathrooms featuring all modern facilities, wifi 24/7 electricity  …see more

Pricing unknown

Book View

Pricing unknown

(8) Very Good 

9

Holiday yacht with shared pool in Halong Bay

Quang Ninh Province / Halong Bay

12 18 1 night min

  • 12 bedrooms
  • Sleeps 18
  • 1 night min
  • 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 £131 / night

£10244 / week

Book View

from £131 / night

13

Ski yacht to rent in Halong Bay

Quang Ninh Province / Halong Bay

14 32 1 night min

  • 14 bedrooms
  • Sleeps 32
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
The Cruise has fourteen spacious cabins, full of luxury equipment with private en-suite bathroom, a large sundeck, elegant dining room, lounge bar, massage room  …see more

from £309 / night

£2163 / week

Book View

from £309 / night

(5) Excellent 

25

Houseboat rental in Puerto Rico Resort with golf nearby

Gran Canaria / Puerto Rico Resort

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
“Just brilliant!” Everything was fantastic. We were met by Alexis who showed us how everything worked and was just a phone call away if we needed help with anything. The boat is fabulous. Very comfortable, luxurious, clean and it was wonderful to have  …see more

from £130 / night

£906 / week

Book View

from £130 / night

11

Palma de Mallorca holiday yacht rental

Majorca / Palma de Mallorca

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Villa exclusive sea view yacht boat sailing  …see more

from £854 / night

£5518 / week

Book View

from £854 / night

(9) Excellent 

14

Isla Chiloe holiday yacht rental

Los Lagos Region / Isla Chiloe

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
“Toby 2014” Excellent experience. We had typical March Chiloe weather with a mix of sunny and rainy days. The food and service at the boat were great. In fact the sea food was outstanding, Kayaking and using the small motor boats were pluses. Visit to  …see more

from £2277 / night

£15935 - £22765 / week

Book View

from £2277 / night

10

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

 …see more

from £647 / night

£4526 / week

Book View

from £647 / night

48

Holiday yacht with shared pool in Lisbon

Lisbon / Santos

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Yacht for rent in Lisbon with 5 rooms available to spend the night or to enjoy your hollidays in a diferent way. All facilities and luxury conditions in this brand new catamaran. All the safety and silence of the marina beats all the best hotels. Experience the best  …see more

Pricing unknown

Book View

Pricing unknown

7

Magnesia Region / Volos

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £156 / night

£953 / week

Book View

from £156 / night

(1) Excellent 

40

Kas holiday yacht rental

Kas / Kas center

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
All inclusive Crewed sailing yacht rental in Kas. Mediterranean Turkey Sailing Holidays set to your course, your destinations, your schedule. Special Mediterranean Turkey sailing holidays by Evita Yachting. Host your own Mediterranean Turkey sailing holiday in Kas - Kek  …see more

from £300 / night

£2000 - £3500 / week

Book View

from £300 / night

22

Naxos / Naxos Town

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary

 …see more

from £863 / night

£6035 / week

Book View

from £863 / night

(1) Excellent 

10

Communaute d'Agglomeration du Pays Ajaccien / Ajaccio

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.05 km
  • Swimming pool

 …see more

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

10

Holiday yacht with swimming pool in Sliema

Sliema / Tigne Point

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
On-board accommodation, boat accommodation, rent-a-cabin, overnight stay aboard, stay on water. boathouse, botel, sea accommodation,<br />CUTTY JEAN is the most exciting combination of stunning settings, unforgettable adventure and fun.  …see more

from £69 / night

£483 / week

Book View

from £69 / night

14

Road Town holiday yacht rental

Tortola / Road Town

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
Would you like to experience how does it feel to live on a boat? Enjoy a calm and rejuvenating lifestyle Surrounded by 360°of Stunning Views. Pristine Beaches&Crystal Clear Waters.We can take you Sailing, Snorkeling, Diving, Kite/Surfing,etc. Please enquire. Di  …see more

from £130 / night

£906 / week

Book View

from £130 / night

(2) Excellent 

5

Tenerife / Amarilla Golf

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £164 / night

£1026 - £3319 / week

Book View

from £164 / night

(10) Very Good 

36

Bodrum / Bodrum City

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Nearest beach 0.1 km
  • Swimming pool
  • Child friendly

 …see more

from £99 / night

£686 - £8253 / week

Book View

from £99 / night

8

Holiday yacht with shared pool in Gouvia

Corfu / Gouvia

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Sail the Ionian from Corfu in a luxury yacht charter from No Stress Yachting. Flotilla, bareboat or skippered yacht charters available. We also have our luxury villa located above Kassiopi on Corfu. We pride ourselves on our excellent customer service.<br />We pro  …see more

Pricing unknown

Book View

Pricing unknown

7

Magnesia Region / Volos

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £44 / night

£302 / week

Book View

from £44 / 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
Welcome to Themis IV With our boat we offer you a trip on the calm Greek waters, with the ability to sail between beautiful clusters of islands, to anchor in natural protected rare beauty coves and visit inaccessible beaches and swim in waters with unique purity and cl  …see more

from £819 / night

£5173 - £5604 / week

Book View

from £819 / night

11

State of Rio de Janeiro / Angra Dos Reis

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £488 / night

£3415 / week

Book View

from £488 / night

7

Magnesia Region / Volos

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £52 / night

£363 / week

Book View

from £52 / night

11

State of Bahia / Salvador

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly

 …see more

from £163 / night

£814 / week

Book View

from £163 / night

6

Magnesia Region / Volos

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £48 / night

£332 / week

Book View

from £48 / night

5

Yacht accommodation in French Harbour with shared pool

Roatan / French Harbour

3 4 1 night min

  • 3 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
DIVING, SAILING, RELAXING  …see more

from £1118 / night

£4472 / week

Book View

from £1118 / night

8

Magnesia Region / Volos

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool

 …see more

from £190 / night

£1457 / week

Book View

from £190 / night

4

State of Rio de Janeiro / Rio de Janeiro

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £407 / night

£2846 / week

Book View

from £407 / night