Sailing vacations

Sailing vacations (1130)

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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1,130 Vacation rentals

(15) Excellent 

77

Vacation houseboat in Amsterdam

North Holland Province / Amsterdam

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Nearest beach 25 mi
  • Child friendly
  • Pet friendly
A lovely old cargo ship in the nautic centre of Amsterdam port. Nearby the old city with a beautiful view on the famous canals. The National Maritime Museum and the Mill of Brewery 't IJ in sight. The Artis Zoo, the Nieuwmarkt area with its charming cafés, b  …see more

from $188 / night

$1311 / week

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from $188 / night

(3) Good 

11

Marne-la-Vallee / Torcy

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Pet friendly

 …see more

from $43 / night

$268 - $718 / week

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from $43 / night

(3) Excellent 

10

Vacation houseboat in Srinagar

Kashmir / Srinagar

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
( The taste of Home, where we treat you like Family)  …see more

from $11 / night

$75 / week

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from $11 / night

(15) Excellent 

12

Vacation yacht with golf nearby in Puerto de la Duquesa

Manilva / Puerto de la Duquesa

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Vivione III is our pride and joy, moored in the harbor in Duquesa on the southern coast of Spain's Costa Del Sol. This is the perfect location to enjoy the beautiful surroundings, right in the heart of the harbor, with it's shops, restaurants and nightlife. &  …see more

from $159 / night

$1037 - $1550 / week

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from $159 / night

23

Vacation houseboat in Jyväskylä

Central Finland / Jyväskylä

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Would you like to spend summer on a peaceful lake, in the pristine wilderness of Finland? On a Houseboat you can easily get to great fishing spots, beaches or discover different Finnish villages and towns . You can sunbath on the roof, make food in the kitchen and take  …see more

from $332 / night

$1921 - $2885 / week

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from $332 / night

(4) Excellent 

11

Amsterdam Vacation houseboat rental

North Holland Province / Amsterdam

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Have breakfast, lunch and diner in the steering cabin watching the boats pass by like you are a part of Amsterdam. The ultimate Amsterdam experience! Our well equipped apartment with lots of light and high ceilings give you a very spacious feeling with a great view on  …see more

from $300 / night

$2098 / week

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from $300 / night

18

Gran Canaria / Mogan

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+

 …see more

from $86 / night

$514 - $664 / week

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from $86 / night

16

San Blas Islands / El Porvenir

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from $130 / night

$910 / week

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from $130 / night

(5) Excellent 

12

Vacation yacht in Lymington

New Forest / Lymington

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
Your luxurious motor yacht is available on an accommodation only basis. She is located at the prettiest marina in Lymington with amazing sea views towards the Isle of Wight. She was commissioned in 2013 and is fitted out to the highest standard. Step through the glass  …see more

from $342 / night

$2392 / week

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from $342 / night

(37) Very Good 

18

Kumarakom Vacation houseboat rental

Kerala / Kumarakom

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 70 mi
  • Child friendly
Our houseboat `Aqua Jumbo` is a floating palace which is a modified form of traditional Kettuvallams. It contains 2 luxurious well furnished & bath attached bed rooms, sun bath-deck, lounge cum dining room and a hygienic kitchen. In the royal kitchen, we prepare del  …see more

from $200 / night

$1451 - $2821 / week

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from $200 / night

(1) Excellent 

87

Houseboat rental in Dublin

Dublin / Dublin 2

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
You must contact Dublin Barge Hire at least 48 hours before you arrive to arrange a time to meet at the marina etc €250 damage deposit if cruising. €100 damage deposit if using the barge for accommodation only. NO CRUISING OCT-MARCH Central Heating for those  …see more

from $177 / night

$1199 - $1723 / week

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from $177 / night

(1) Excellent 

15

Henley-on-Thames Vacation narrowboat rental

Oxfordshire / Henley-on-Thames

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Suitable for children age 5+
  • Pet friendly
Cruise and explore some of the most stunning parts of the River Thames at your own pace. Boat Gema is a delightful 4 star narrowboat that has a fresh and modern feel but without losing the quaint charm of an English narrowboat. Cruise to Henley-On-Thames, Marlow and Win  …see more

from $370 / night

$1647 - $2140 / week

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from $370 / night

(32) Excellent 

12

Vacation houseboat rental

Amsterdam / Central Amsterdam

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
This friendly houseboat is a complete floating apartment. There is a lounge room, open-plan kitchen, separate bedroom with double bed, and bathroom with full-length bath and shower. Perfect for 2 people, with a sofa bed for 2 more guests.Situated on the beautifu  …see more

from $161 / night

$964 - $2248 / week

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from $161 / night

36

San Blas Islands / El Porvenir

3 2 2 nights min

  • 3 bedrooms
  • Sleeps 2
  • 2 nights min
  • Child friendly

 …see more

from $441 / night

$3081 / week

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from $441 / night

(10) Excellent 

24

Vacation yacht in East Molesey

Surrey / East Molesey

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
EXCLUSIVE USE, and available all year round, this perfectly appointed liveaboard moored in the most idyllic palm fronted Hampton Court marina. “Eucala” is a very beautiful and cleverly laid out classic French motor yacht with a really rich heritage. We h  …see more

from $129 / night

$897 / week

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from $129 / night

(148) Very Good 

15

Vacation houseboat in Alappuzha

Kerala / Alappuzha

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
Pournami houseboats have been operating houseboat cruise since 2007 in Alleppey and Kumarakom. We are rated as one of the best houseboat operators in Alleppey. We focus on the quality of service provided to our guest. Our new 4 bedroom houseboat is a full featured lux  …see more

from $305 / night

$1801 / week

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from $305 / night

33

San Blas Islands / El Porvenir

3 2 2 nights min

  • 3 bedrooms
  • Sleeps 2
  • 2 nights min
  • Child friendly

 …see more

from $441 / night

$3081 / week

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from $441 / night

(2) Excellent 

7

Vacation houseboat in Mallacoota

Gippsland / Mallacoota

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
Mallacoota wilderness houseboats offers customers a unique experience on Mallacoota Inlet. Wake up on the water at one of many Parks Victoria jetties located at varios locations around the lake. Listen to the Koalas at night and witness the beauty of far east Gippsland  …see more

from $196 / night

$942 - $1733 / week

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from $196 / night

(10) Excellent 

40

Yacht accommodation in Puerto Calero

Lanzarote / Puerto Calero

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Do not miss the opportunity of sleeping onboard this beautiful and classic sailing yacht in exclusive for you. Vientos del Sur is rented entirely as a private holiday letting and only you and your friends or familiy will stay onboard. The yacht is equipped with all the  …see more

from $65 / night

$450 - $630 / week

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from $65 / night

(25) Excellent 

20

Vacation 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
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 $193 / night

$1499 - $2248 / week

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from $193 / night

(16) Excellent 

12

Vacation houseboat in Amsterdam

Amsterdam / Eastern Docklands

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
Annie's Boat is suitable for 2 people and maximum 2 children.Children up to 12 years stay for free. For children up to the age of 3 years there is a cot present. For children from 3 up to 12 years is a thick luxury air mattress (2x 1pers. mattress) of very good  …see more

from $129 / night

$643 / week

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from $129 / night

(17) Excellent 

23

Yacht rental in San Blas Islands

Guna Yala Region / San Blas Islands

5 8 1 night min

  • 5 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Aboard Cinco, we want you to feel at home in the perfect setting San Blas islands offer : warm waters, world class snorkeling spots , beautiful empty islands, white sand and coconut trees, great food ;) Guna culture, and most of all, our constant attention to make your  …see more

from $500 / night

$3500 / week

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from $500 / night

(29) Very Good 

16

Leiden Vacation houseboat rental

South Holland Province / Leiden

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 27 mi
  • Child friendly
Houseboat Pride of Leyden is fully equipped with every comfort, from a well stocked kitchen, to central heating and air conditioning, a TV and Wifi internet, and a veranda with a spectacular view. The main bedroom sleeps two in a king-size bed, the study sleeps one on a  …see more

from $127 / night

$851 - $986 / week

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from $127 / night

(2) Excellent 

10

Houseboat rental in Chertsey with golf nearby

Surrey / Chertsey

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Welcome aboard the beautiful widebeam barge The Time Machine, moored in a private garden on the River Thames near Chertsey. 5 mins from Thorpe Park theme park, 15 mins from Heathrow Airport and easy access to the M25, M3 and M4 and the South East. 15 mins drive to Heat  …see more

from $86 / night

$732 - $989 / week

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from $86 / night

(10) Excellent 

25

Province of Naples / Sorrento

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $333 / night

$2141 / week

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from $333 / night

(22) Excellent 

41

Vacation 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
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.  …see more

from $103 / night

$720 - $1199 / week

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from $103 / night

(3) Excellent 

46

San Diego Vacation houseboat rental

California / San Diego

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Suitable for children age 5+
Sleep on the water! Enjoy this unique opportunity to stay at Pelican Place - a floating home on this beautiful bay. Enjoy this 84 sq meters floating 2-story home. House sleeps 4 adults or 2 adults with up to 3 children works well too. House details: On the bottom f  …see more

from $249 / night

$1743 / week

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from $249 / night

15

Newtown, Alderney Vacation yacht accommodation

Alderney / Newtown, Alderney

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Car not necessary
Presented by Static Boat Holidays. The price is for the whole boat and is exceptionally good value. The boat is situated in Braye harbour, Alderney. She is on a swing mooring, but you have access to a tender and water taxi. She has three double cabins, a kitchen living  …see more

from $127 / night

$824 / week

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from $127 / night

(9) Very Good 

24

Houseboat accommodation in Henley-on-Thames

Oxfordshire / Henley-on-Thames

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This is a self drive boating holiday with a unique difference. Our boat is a luxury Canal widebeam, fitted to an exceptionally high standard, an ideal holiday for families or groups of friends holidaying together.Pets are welcome too. You pick the boat up from our base  …see more

from $305 / night

$1843 - $2636 / week

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from $305 / night

(6) Excellent 

21

Copenhagen Vacation houseboat rental

Zealand / Copenhagen

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets
Have you ever thought about living on a houseboat? Now you can try it.It's different, it's supercool- and right in the heart of Copenhagen. Only 5 min. walking distance to city hall and TIVOLI Garden. 125 square meters inside the passenger ferry build  …see more

from $589 / night

$3746 / week

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from $589 / night

(2) Very Good 

11

Vacation houseboat in Amsterdam

North Holland Province / Amsterdam

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
The Manta is a beautiful 120 years old Dutch sailing ship, It is still in very good condition, centrally heated, 100m2, With thge atmosphere of the old ships, but modern and comfortable as well. It has a well equiped kitchen, a large living room, central heating, plen  …see more

from $177 / night

$964 - $1338 / week

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from $177 / night

14

Vacation yacht in Fort Myers

Southwest Gulf Coast / Fort Myers

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly
My Yacht is located as close to down town Fort Myers As you can get. This 50 ft Floating Condo has lots of room for six guest's or more and is right in the center of the River District The B.B.Q is located on the large back deck. It has a washer and dryer .. m  …see more

from $172 / night

$1201 / week

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from $172 / night

4

Vacation yacht in Ta' Xbiex

Island of Malta / Ta' Xbiex

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Car not necessary
Spend your holiday on a Yacht 14m and well equipped as much as apartment. Airy and bright with standing headroom. Layout comprises two comfortable sofa beds in salon with 32" TV, kitchen dinette two fridges and one freezer, master cabin with ensuite, front cabin &a  …see more

from $108 / night

$739 / week

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from $108 / night

(4) Excellent 

28

Yacht rental in San Sebastián de la Gomera

La Gomera / San Sebastián de la Gomera

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Suitable for children age 5+
PLEASE READ THE WHOLE LISTING PLEASE NOTE: The yacht is available for accommodation only and not for any kind of chartered sailing. If you are looking for a different type of holiday accommodation and perhaps a bit off the beaten track, then Brego is just the thing f  …see more

from $58 / night

$402 / week

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from $58 / night

11

Falkirk / Banton

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

 …see more

from $182 / night

$1273 - $2009 / week

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from $182 / night

(2) Excellent 

11

Olbia / Pittulongu

5 5 5 nights min

  • 5 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $108 / night

$750 / week

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from $108 / night

(1) Excellent 

30

Vacation 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 mi
  • 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 $81 / night

$561 / week

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from $81 / night

9

Aude / Marseillette

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 35 mi
  • Child friendly
  • Pet friendly

 …see more

from $91 / night

$637 - $750 / week

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from $91 / night

13

Monaco-Ville

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $396 / night

$2772 / week

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from $396 / night

(3) Excellent 

67

Vacation yacht in Road Town

Tortola / Road Town

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Allinclusivecharter provides the perfect getaway on your own private crewed luxury motor yacht in the Caribbean area. Being the only guests on our board, you are treated like royalty. Do what you really want, when you want. Your voyage is personalized and is a customize  …see more

from $2400 / night

$16500 - $22100 / week

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from $2400 / night