Sailing holidays

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Sailing holidays (254)

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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254 Holiday homes

Filters applied: Water sports (254)

1 / 4

The Sandgroper - Tonnerre houseboat sleeps 2

Yonne / Tonnerre

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Ask about pets;
Canal Boat in France! Enjoy the Burgundy canals and rivers on our beautifully restored boat. Our boat is based in Tonnerre, Burgundy which is located on the Canal de Bourgogne (Burgundy Canal). Cruise through some beautiful villages, including Ancy Le Franc, Tanlay, Mon  …see more

from £189 / night

£1283 / week

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from £189 / night

(27) Very Good 

1 / 16

Houseboat Pride of Leyden. - Leiden houseboat sleeps 3

South Holland Province / Leiden

2 3 3 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 27 km; 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 £101 / night

£680 - £788 / week

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from £101 / night

1 / 12

Connie - Damazan houseboat sleeps 4

Lot-et-Garonne / Damazan

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Car advised; No pets allowed;
Beautifully restored Dutch Barge with 2 double cabins, shower room with loo and basin.Open plan galley, dining area and saloon.Wheelhouse with dinette.Galley has double sink, 2 fridges, microwave, 4 burner hob, oven, kettle etc.There is a private garden with summer kitc  …see more

Pricing unknown

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Pricing unknown

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(4) Excellent 

1 / 9

Holiday Yacht In Southampton Hampshire - Southampton yacht sleeps 5

Hampshire / Southampton

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
An excellent well cared for 37 foot sailing yacht, located in Port Hamble Marina, Hamble village, Southampton. Port Hamble is situated in the heart of the village of Hamble which is a yachting paradise for sailors and visitors alike. The yacht is very user friendly and  …see more

from £125 / night

£750 - £1275 / week

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from £125 / night

1 / 5

Pas-de-Calais / Bethune

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Not suitable for children; Ask about pets;
 …see more

from £56 / night

£389 / week

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from £56 / night

1 / 4

Province of Messina / Furnari

2 4 3 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Swimming pool; Suitable for children age 5+; Car advised;
 …see more

from £60 / night

£342 / week

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from £60 / night

(4) Excellent 

1 / 18

Watervilla Humpy Dumpy - Oost-knollendam houseboat sleeps 6

North Holland Province / Oost-knollendam

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Car advised;
In the infinity of life take out time for the soul.Dreamy days and quiet nights a romantic getaway a place to call a 'home' away from 'home'an epitome of peace and serenity.That would describe "humpy dumpy"A watervilla/houseboat in Netherla  …see more

from £214 / night

£855 / week

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from £214 / night

1 / 6

Blazing Star - Nieuwpoort yacht sleeps 4

West Flanders Province / Nieuwpoort

3 4 2 nights min stay

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; No pets allowed;
Blazing Star est un voilier classique de 18 m de long construit en 1930 au charme fou, confortable et luxueux.Il est situé au KYCN, à proximité de la Ville et de la plage. A bord, vous vivrez une expérience inoubliable. Blazing Star is a 61-foot classical yacht des  …see more

from £129 / night

£898 / week

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from £129 / night

1 / 24

Bouches-du-Rhone / Sausset-les-Pins

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 5 km; Not suitable for children;
 …see more

from £73 / night

£445 / week

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from £73 / night

(6) Very Good 

1 / 28

Yonne / Joigny

4 12 1 night min stay

  • 4 bedrooms
  • Sleeps 12
  • 1 night min stay
Key info: Beach / lakeside relaxation; Child friendly ; Pet friendly;
 …see more

from £107 / night

£748 / week

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from £107 / night

1 / 19

Province of Fermo / Porto San Giorgio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Car advised;
 …see more

from £428 / night

£2137 / week

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from £428 / night

1 / 6

Arrondissement of Le Marin / Le Marin

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Not suitable for children;
 …see more

Pricing unknown

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Pricing unknown

(15) Excellent 

1 / 22

PORTO DOURO VALLEY SAIL YACHT CRUISES WITH SKIPPER - Porto yacht sleeps 4

Porto District / Porto

1 4 1 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 £163 / night

£642 / week

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from £163 / night

(1) Excellent 

1 / 16

Yacht 'Lady H' - Port-Saint-Louis-du-Rhone yacht sleeps 4

Bouches-du-Rhone / Port-Saint-Louis-du-Rhone

3 4 3 nights min stay

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Child friendly ;
NOTE. PRICES QUOTED INCLUDE FOOD, FUEL, MARINA FEES AND EVEN WINE WITH DINNER. The only added expense is what you choose to spend ashore. A CHANCE FOR A SKIPPERED HOLIDAY AFLOAT. Our 'house' keeps floating and keeps moving so it is difficult to define where we are. Ou  …see more

from £35 / night

£245 - £1155 / week

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from £35 / night

(4) Excellent 

1 / 13

Boat Gina -beautiful narrowboat on River Thames - Henley-on-Thames narrowboat sleeps 6

Oxfordshire / Henley-on-Thames

2 6 3 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car not necessary;
Boat Gina is the perfect boat for anyone who wants to enjoy boating on the River Thames with all the comforts of home. There is nothing quite like the sense of freedom of cruising at your own pace and mooring up when you feel like it, exploring some of England's mo  …see more

from £245 / night

£1265 - £1610 / week

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from £245 / night

(15) Excellent 

1 / 14

Yacht Ngoma - Prickly Bay yacht sleeps 4

St. George's / Prickly Bay

2 4 5 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Child friendly ;
The boat we are running at the moment is a Lavezzi 40 built in La Rochelle to our specification and we've been sailing her for 10 years around the caribbean islands.The space we are offering to you is the Port (left - if you are standing on the boat facing forward)  …see more

from £140 / night

£980 - £3920 / week

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from £140 / night

(2) Excellent 

1 / 13

No Fixed Abode - Knockvicar yacht sleeps 5

County Roscommon / Knockvicar

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Child friendly ; Car advised; No pets allowed;
Hire our boat on Ireland's River ShannonNo Fixed Abode is our privately owned 33 ft cruiser and it is not part of a large hire fleet and is ideal for a family holiday.We aim to give you personal treatment at a very affordable price and we will try to advise you of  …see more

from £107 / night

£599 / week

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from £107 / night

1 / 8

Italian Riviera / Loano

3 7 1 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Child friendly ;
 …see more

from £150 / night

£941 / week

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from £150 / night

1 / 18

Deramore classic motor yacht Superior room - Punta Ala yacht sleeps 2

Castiglione Della Pescaia / Punta Ala

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Not suitable for children;
This is an alternative to staying in a hotel, experiencing the glamour of being on a yacht, master cabin with ensuite bathroom in an Elegant Classic Motor Yacht 77ft with large sunbathing spaces, sitting room, dining room, outdoor dining and lounge areas. Mored in the e  …see more

from £257 / night

£1453 - £2650 / week

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from £257 / night

1 / 23

Houseboat Finland: Houseboat Comfort 32 m2/ 6 pers - Jyväskylä houseboat sleeps 6

Central Finland / Jyväskylä

2 6 2 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: 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 £193 / night

£1539 / week

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from £193 / night

(7) Excellent 

1 / 56

Wooden Sail Boat with Air Conditioning and WiFi - El Barrio yacht sleeps 2

Province of Alicante / El Barrio

2 2 3 nights min stay

  • 2 bedrooms
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 200 km; Not suitable for children;
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 £43 / night

£257 / week

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from £43 / night

1 / 20

Haute-Corse / Saint Florent

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Not suitable for children;
 …see more

from £488 / night

£3411 / week

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from £488 / night

1 / 18

Deramore classic motor yacht master cabin - Punta Ala yacht sleeps 2

Castiglione Della Pescaia / Punta Ala

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Not suitable for children;
This is an alternative to staying in a hotel, experiencing the glamour of being on a yacht, 1 cabin with ensuite bathroom in an Elegant Classic Motor Yacht 77ft with large sunbathing spaces, sitting room, dining room, outdoor dining and lounge areas. Mored in the elegan  …see more

from £214 / night

£1283 / week

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from £214 / night

1 / 4

HALKIDIKI GOLDEN YACHTS - Nea Fokea yacht sleeps 6

Halkidiki Region / Nea Fokea

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
LUXURY VACATIONS... FOR YOUR EYES ONLYEnjoy the luxury of a motor boat with daily or multi-day cruises to Chalkidiki, Skiathos, Skopelos, Alonissos. Flee away from the crowded beaches and discover secluded bays ideal for swimming. Relax and enjoy the sun on the deck as  …see more

from £1283 / night

£8975 / week

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from £1283 / night

1 / 7

Charente-Maritime / La Rochelle

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; No pets allowed;
 …see more

from £116 / night

£808 / week

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from £116 / night

(1) Excellent 

1 / 11

Olbia / Pittulongu

5 5 5 nights min stay

  • 5 bedrooms
  • Sleeps 5
  • 5 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
 …see more

from £86 / night

£599 / week

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from £86 / night

1 / 11

Boat House - Kumarakom houseboat sleeps 4

Kerala / Kumarakom

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Child friendly ;
Your houseboat will be a traditional kettuvallam with two en-suite air-conditioned bedrooms. It is built and furnished from local materials, and we provide you with a luxury cruise whilst minimising our impact on the fragile ecosystems of the backwaters. It runs very qu  …see more

Pricing unknown

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1 / 5

Charente-Maritime / La Rochelle

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Suitable for children age 5+; No pets allowed;
 …see more

from £116 / night

£808 / week

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from £116 / night

(8) Excellent 

1 / 24

Boat Geanna - Henley-on-Thames houseboat sleeps 11

Oxfordshire / Henley-on-Thames

3 11 3 nights min stay

  • 3 bedrooms
  • Sleeps 11
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car not necessary;
This is accommodation with a unique difference. Our boat is a luxury 4 star Canal wide beam fitted to an exceptionally high standard. The interior is spacious with a fitted kitchen, complete with all mod coms (inc dishwasher) and beautiful open plan saloon/dining room.  …see more

from £250 / night

£1410 - £2435 / week

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from £250 / night

1 / 7

Province of Teramo / Giulianova

4 8 2 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Air conditioning;
 …see more

from £419 / night

£2565 / week

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from £419 / night

(1) Excellent 

1 / 19

Private Yacht in St Vincent and the Grenadines - Mayreau yacht sleeps 6

St. Vincent and the Grenadines / Mayreau

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; No pets allowed;
A Private Yacht: KALIMBA, A 2012 Beneteau Oceanis 45 foot. This private yacht, with skipper, will take you on the cruise of a lifetime around the spectacular Grenadine Islands. Starting from Grenada, or picking you up at the location of your choice, the itinerary is up  …see more

from £500 / night

£3000 / week

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from £500 / night

(5) Excellent 

1 / 12

Luxury Motor Yacht in Lymington - Lymington yacht sleeps 4

New Forest / Lymington

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Car advised;
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 £280 / night

£1960 / week

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from £280 / night

1 / 19

Province of Grosseto / Porto Ercole

2 2 1 night min stay

  • 2 bedrooms
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Child friendly ;
 …see more

from £308 / night

£1624 / week

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from £308 / night

(9) Excellent 

1 / 14

Yate Alba - Isla Chiloe yacht sleeps 10

Los Lagos Region / Isla Chiloe

5 10 3 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

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from £2138 / night

(12) Excellent 

1 / 27

Zana Catamaran Bali - Serangan yacht sleeps 6

Denpasar / Serangan

5 6 1 night min stay

  • 5 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 1 km; Not suitable for children;
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 £802 / night

£4504 - £5573 / week

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from £802 / night

1 / 5

Corse-du-Sud / Ajaccio

6 10 7 nights min stay

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
 …see more

from £1020 / night

£7137 / week

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from £1020 / night

(1) Excellent 

1 / 4

Arrondissement of Le Marin / Le Marin

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; No pets allowed;
 …see more

Pricing unknown

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1 / 11

Southampton Hampshire Yacht - Southampton yacht sleeps 5

Hampshire / Southampton

3 5 2 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 10 km; Child friendly ;
An excellent well cared for 37 foot sailing yacht, located in Port Hamble Marina . Port Hamble is situated in the heart of the village of Hamble which is a yachting paradise for sailors and visitors alike. The yacht is very user friendly and a full safety brief will be  …see more

from £125 / night

£750 - £1275 / week

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from £125 / night

1 / 44

52 ft. crewed sailing yacht Blue Sky San Blas Is. - San Blas Islands yacht sleeps 6

Guna Yala Region / San Blas Islands

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; No pets allowed;
Blue Sky is a 52 ft. crewed sailing yacht located in the stunning San Blas islands off the coast of Panama. Our trips include 3 delicious meals a day, snorkeling and fishing gear, 2 single kayaks, and a chance to visit with the indigenous Guna Indians. We enjoy snorkeli  …see more

from £130 / night

£802 - £5344 / week

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from £130 / night

(20) Excellent 

1 / 41

Lanzarote Yacht Hotel - Marina Rubicon yacht sleeps 6

Playa Blanca / Marina Rubicon

3 6 1 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 £83 / night

£575 - £3351 / week

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from £83 / night

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