Sailing vacations

Sailing vacations (1123)

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

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,123 Vacation rentals

(17) 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 $186 / night

$1298 / week

Book View

from $186 / night

(5) Very Good 

11

Vacation houseboat in Alappuzha

Kerala / Alappuzha

3 2 1 night min

  • 3 bedrooms
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Ask about children
Welcome to Alleppey Backwater Kerala in the God's Own Country ! . Our new AC Premium houseboat had 3 bed/3 bath,living room, dinning and kitchen fully covered glass which PROTECT FROM MOSQUITO AND INSECT in the night. We are located 2 minutes from Alleppey town  …see more

from $101 / night

$1412 / week

Book View

from $101 / 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 $350 / night

$2450 / week

Book View

from $350 / 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 $223 / night

$1484 - $2225 / week

Book View

from $223 / 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 $329 / night

$1902 - $2855 / week

Book View

from $329 / 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 $85 / night

$509 - $657 / week

Book View

from $85 / night

(11) 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 $64 / night

$445 - $623 / week

Book View

from $64 / night

6

Vacation houseboat in Alappuzha

Kerala / Alappuzha

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Check into the finest Houseboats in God's own Country with Gold Star Rating Alapuzha (Venice of the East) or Alleppey as it is popularly known is the most prominent township in the backwaters. The Backwaters of Kerala is a network of interconnected canals, rivers  …see more

from $197 / night

$1311 / week

Book View

from $197 / night

4

Rhineland-Palatinate / Meuspath

1 50 1 night min

  • 1 bedroom
  • Sleeps 50
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from $11 / night

$75 / week

Book View

from $11 / night

(1) Excellent 

14

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 $379 / night

$1688 - $2193 / week

Book View

from $379 / night

(53) Excellent 

30

Vacation narrowboat rental

Salford / Worsley

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly
Now taking bookings for 2017. From November 2017 to April 2018 'Gloria' will be available for a 5 month, static, houseboat hire only at our base - our other boat 'Queenie' will still operate as normal. We offer 2 unique, bright, clean and cosy narr  …see more

from $213 / night

$1488 / week

Inquire View

from $213 / night

(38) 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 $202 / night

$1462 - $2844 / week

Book View

from $202 / night

(5) Excellent 

42

Vacation yacht in Unterterzen

Canton of St. Gallen / Unterterzen

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
You’ll love MAYA because sleeping overnight on a beautiful classic yacht, is a night to remember. FULLY HEATED, privacy, romantic soft lit atmosphere, you'll find the cosy, comforting great nights sleep much needed to recharge your batteries for your next da  …see more

from $64 / night

$445 / week

Book View

from $64 / night

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 $132 / night

$918 / week

Book View

from $132 / 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 $338 / night

$2119 / week

Book View

from $338 / night

(6) Excellent 

24

Vacation houseboat in Amsterdam

North Holland Province / Amsterdam

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary
  • Ask about pets
Are you looking for a comfortable apartment for 2 people? Our apartment is a self-contained part of a water villa. It has a living room and open plan kitchen with all modern equipment. The living room has patio doors directly to the water. On the ground floor there is a  …see more

from $122 / night

$795 - $848 / week

Book View

from $122 / night

(1) Very Good 

10

Chester / Broxton

2 5 Min stay varies

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

 …see more

from $180 / night

$1260 - $1989 / week

Book View

from $180 / 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 $128 / night

$636 / week

Book View

from $128 / night

(18) Excellent 

27

Vacation yacht in Barcelona

Barcelona / Port Forum

5 11 Min stay varies

  • 5 bedrooms
  • Sleeps 11
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Suitable for children age 5+
Unique & Special 80ft Boat to stay during your holiday or business trip in Barcelona. Spacious sundecks with Jacuzzi, peaceful surroundings, fully air-conditioned luxury cabins with private bathrooms. Fully equipped kitchen. Only 10 min from center Barcelona, near C  …see more

from $313 / night

$2188 / week

Book View

from $313 / night

(6) Very Good 

32

Vacation houseboat in Alappuzha

Kerala / Alappuzha

2 7 1 night min

  • 2 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
ITINERARY» Guests can check in at 12:00 hrs, we will welcome you with welcome drink and start cruise after a short briefing introduction, relax and enjoy the canals, rivers and backwater, at 13:00 hrs houseboat will stop for lunch, with lavish menu of traditional  …see more

from $202 / night

$1412 / week

Book View

from $202 / night

(3) Excellent 

15

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 $88 / night

$750 - $1013 / week

Book View

from $88 / 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 $125 / night

$843 - $976 / week

Book View

from $125 / night

(13) Excellent 

24

Houseboat rental in Amsterdam

Amsterdam / Eastern Docklands

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Child friendly
Welcome on board our fully renovated boat & breakfast, 'de Dageraad' (Dutch for 'daybreak'). We offer two luxury, 100% smoke-free rooms, both featuring amenities such as floor heating, en suite bathroom, LCD-television, and free Wifi. In the mo  …see more

from $223 / night

$1558 / week

Book View

from $223 / night

(3) Excellent 

43

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
  • Child friendly
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

Book View

from $249 / 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 $163 / night

$1063 - $1588 / week

Book View

from $163 / night

36

San Blas Islands / El Porvenir

3 2 2 nights min

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

 …see more

from $444 / night

$3105 / week

Book View

from $444 / night

(23) 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 $102 / night

$712 - $1187 / week

Book View

from $102 / night

(5) Excellent 

15

Pangkalan Bun Vacation houseboat rental

Central Kalimantan / Pangkalan Bun

6 10 2 nights min

  • 6 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 10 mi
  • Child friendly
  • Air conditioning
Borneo Eco Tour Houseboat is has 3 houseboat. 1 standard houseboat, 1 Deluxe Houseboat and 1 Super Deluxe Houseboat.Standard houseboat with 1 open deck CabinDeluxe Houseboat with 1 Cabin with Air Condition and 1 Open Deck CabinSuper Deluxe Houseboat with 2 C  …see more

from $350 / night

$2188 - $8488 / week

Book View

from $350 / night

(7) Excellent 

56

Vacation yacht in El Barrio

Province of Alicante / El Barrio

2 2 3 nights min

  • 2 bedrooms
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 200 mi
  • Car not necessary
Classic wooden sailing yacht right in the city center of Alicante...10 meters LOA 4 meters beam, good for two people, one double bed and 2 singles... great views. Close to restaurants and bars. Very close to he beach. Secure parking inside the marina, security and vi  …see more

from $53 / night

$318 / week

Book View

from $53 / night

(32) Excellent 

12

Vacation houseboat rental

Amsterdam / Central Amsterdam

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
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 $159 / night

$954 - $2225 / week

Book View

from $159 / night

20

Marseille / Les calanques

2 4 2 nights min

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

 …see more

from $43 / night

$265 - $477 / week

Book View

from $43 / night

(3) Excellent 

21

Key West Vacation houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and fre  …see more

from $409 / night

$2521 - $6704 / week

Book View

from $409 / night

(12) Excellent 

27

Yacht rental in Serangan

Denpasar / Serangan

5 6 1 night min

  • 5 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
S/Y Zana is a high tech construction 40ft catamaran, the fastest sailing boat in Bali. Zana is a catamaran built for speed, a carbon and kevlar epoxy infused foam sandwich construction weighing in at just under 4 tonnes. Two 20hp Honda 4 stroke outboards push her alon  …see more

from $1050 / night

$5900 - $7300 / week

Book View

from $1050 / night

(4) Excellent 

23

Oost-knollendam Vacation houseboat rental

North Holland Province / Oost-knollendam

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Wonderful houseboat with typical Dutch landscape view, while located only 20 minutes from Amsterdam. Enjoy the unique stay on this tasteful designed houseboat. and experience the comfort of living in a house on water.  …see more

from $265 / night

$1060 - $1166 / week

Inquire View

from $265 / night

6

Corse-du-Sud / Porto-Vecchio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 5 mi
  • Car not necessary

 …see more

from $43 / night

$297 / week

Book View

from $43 / night

(26) 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 $133 / night

$927 / week

Book View

from $133 / night

(1) Good 

24

Vacation yacht in Amsterdam

North Holland Province / Amsterdam

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The accommodation makes the perfect choice for a family or a group of friends desiring the chance to enjoy a traditional old houseboat experience. Blending authentic elements with a wooden finish and only basic amenities, the lodging offers a simple space after a busy d  …see more

from $181 / night

$1261 / week

Book View

from $181 / night

(2) Very Good 

30

Houseboat rental in Amsterdam

North Holland Province / Amsterdam

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
WE ACCEPT MAX. 4 ADULTS!!! This beautiful Arc is 135 square meters big. It is very light, has an outside terrace and 3 bedrooms. It is an excellent stay for 2 couples or a family of 4. LOCATION Located 3,5 kilometres from central station in the east part of Amsterd  …see more

from $105 / night

$735 / week

Book View

from $105 / night

(1) Very Good 

38

Vacation houseboat in Amsterdam

Amsterdam / New West

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
Lady Luck is located directly connected to the Jordaan, the historic centre of Amsterdam. Shops, cafes and restaurants are only minutes away. Very comfy stay with living, kitchen, comfortable bathroom and a outdoor deck. There is one bedroom with a 2 person bed and a bi  …see more

from $223 / night

$1484 - $1928 / week

Book View

from $223 / night

22

Vacation houseboat in Amsterdam

North Holland Province / Amsterdam

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 35 mi
  • Suitable for children age 5+
Our large houseboat is especially suitable for groups up to 14 people.It's located in a quite neighborhood in the north of Amsterdam but close to the town center.7 bedrooms and a large living area gives you enough space for a joyful time in Amsterdam.Ne  …see more

from $742 / night

$4132 / week

Book View

from $742 / night