Windwardside Rentals

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160 Houses

Romantic Beachfront Condo - Waterside 402

Holder's Hill apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$255

201 Sapphire Beach dover st lawrences gap

St. Lawrence Gap apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great Condo on Beach for Vacation Rental” Condo is even nicer than photos. A very spacious and relaxing 3 bedroom condo on Dover beach. End unit so master bedroom and patio has a wrap around view - a bonus. However, could be a little noisy with music on Friday nights from beach bar next door as at public beach entrance however, music only heard outside from patio, not when inside condo. Condo was very clean through out and the Condo building was very well maintained and secure. All staff encountered, including anita were warm and very helpful. Great location, just off the St. Lawrence Gap and lots of nearby restaurants and the like (ideally you would need to rent a car). Would recommend 100%

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Price per night from

$426

EXCLUSIVE Beach FRONT 1 BEDROOM GROUND FLOOR BEACH APARTMENT

Black Rock apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 2

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Price per night from

$719

Modern Beachfront Condo with Pool - Sapphire 211

St. Lawrence Gap apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$391

Vida Mejor West Pool

Holetown villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 5

“Perfection” This was the first time we have booked a private villa and were a little nervous as to what to expect - our concern was unfounded, the villa "did exactly as it said on the tin"! Carlton was excellent and nothing too muc trouble. The location is perfect, near to all restaurants and bars, beach etc. We really didn't want to leave and are looking forward to returning.

Responds fast! avg. 2 hours 55 minutes

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Price per night from

$322

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$240

Beachfront Villa with Plunge Pool - Church Point 2

Holetown villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$800

Beachfront Bliss Getaway with Pool - Nelson Gay

Speightstown villa

  • 6 bedrooms
  • 8 bathrooms
  • sleeps 12

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Price per night from

$2,650

Modern Beachfront Condo with Pool - Sapphire 209

St. Lawrence Gap apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“We had an amazing stay at Sapphire Beach.” The concierge team made sure our arrival went smoothly - our driver was waiting for us on arrival and a member of the team was waiting to greet us at Sapphire Beach. The apartment is beautiful and has everything you could wish for. The location is great and it was a wonderful, relaxing holiday.

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Price per night from

$391

Charming Beachfront Villa - Sunset Reach (2 bed)

Mullins villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$550

Vida Mejor --Waterfall Pool villa

Holetown villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Very good location” Carlton was very easy to talk to and ask for help on anything to do with the island. He did all this even before I met him for the first time. So this was setting me up as too how it was to be in person and he was just as pleasant and helpful when we arrived. The house is in a great location and an easy walk to everything you need. We did not see monkeys in the garden but they were on the street in front of the house a few times which was a thrill for us. You will feel very safe in the area where the rental is located as well. The only thing I would have to say that was not up to my liking were the beds. They were really hard and needed a pad on the top of them for more comfort . After being there a week you really felt your back getting sore. One other thing that could have been better was the house keeping. The lady was so sweet and nice to be around I did not dare ask her to do a better job on the floors. It was so minor and we were only there a week so I chose to over look it. I would not even consider staying at another place if I ever get the chance to return. Carlton has my business and I have told others to rent as well from this same place. Well worth the look. Thank You Carlton for the chance to stay at your rental.

Responds fast! avg. 2 hours 55 minutes

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Price per night from

$322

Seascape, Gibbs, St. Peter, Barbados - Beachfront

Gibbes villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$928

Modern Beachfront Condo with Pool - Sapphire 118

St. Lawrence Gap apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$298

“Best Of Barbados Cathy & Tony 2012” We recently had the great pleasure of staying in condo Palm Beach Condos. Condo #1. This wonderful condo is owned by a lovely couple whom live there part time and share it with others for enjoyment. It is off the main hwy and very private, quiet and secluded. Condo #1 is very unique in that it is the only corner property facing the the beach with a wonderful balcony with great views of the sunset by evening and water activities by day. Lies 10ft from the beach. There are plenty of water activities available as well as just strolling on the beach and relaxing with restaurants available along the beach. There is a fresh water pool as well. It has a dining/living rm combination which is open air with multiple fans for excellent ventilation for tropical breezes and cooling. The condo is immacuately kept and well furnished. Kitchen has everything thing for cooking equisite meals. The bedroom has a king size bed and is cooled(air con) with multiple fans and very confortable for sleeping with the open windows for the wonderful sound of the surf. It is located within walking distance to grocery shopping, excellent restaurants of various meals,and gift shopping. Bus service is located on main street to take you all over the island. This was a 65th birthday gift for Cathy which will be remembered for a life time. We want everyone to know that is coming to Barbados this is the best place to come and stay. We hope to return soon and will be making our reservation only for condo # 1. The owners and Care taker Pat are a dream to work with and go out of their way to make your stay in their home most enjoyable. Thanks Dayle and George.

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Price per night from

$196

Beachfront Tropical Retreat - Belair

Mullins villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Great villa, beautiful place, a place to go and go back!” We loved - the villa and its situation - the rooms/beds which were very comfortable - the decoration and all amenities We loved less the fact - that the house was not really clean when we arrived (fridge, doors, loo, etc.) - that the cook, despite being a true sweetheart, was not very qualified and was totally unable to cook a full meal for 9 people 3 times a day, in fact note even one meal a day! - that the housekeepers, despite being asked not to do so, kept changing towels and sheets too often - that the whole staff is very little concerned about saving nature and environment We also think that the sharing of tasks should be reviewed, the staff shouldn't wash the dishes with soap under running hot water before putting them in the dishwasher and wipe them again afterwards (!), the cook shouldn't have to clean the kitchen, pots and so on, the 2 other ladies would have plenty of time to do so! A laundress is certainly not necessary, especially if sheets and towels wouldn't be changed so often. Who does this at home? Their working hours should be reviewed. Impossible to have a cooked breakfast before the arrival of the cook at 9, and then she does the pots/stove from the night before! Impossible to have a proper dinner cooked, served and the kitchen cleaned with someone very slow working from 5 to 8 pm. Cooking, eating and cleaning cannot be achieved in 3 hours! We ended up cooking, cleaning, etc., ourselves and gave the afternoon off to the staff many days! Impossible to have 3 meals between 9 am and 8 pm, including preparation , eating and cleaning!

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Price per night from

$1,210

Modern Beachfront Condo with Pool - Sapphire 112

St. Lawrence Gap apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$298

Modern Beachfront Condo with Pool - Sapphire 203

St. Lawrence Gap apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$391

Modern Beachfront Condo with Pool - Sapphire 311

St. Lawrence Gap apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$391

Luxury Beachfront Villa - Bonavista

Gibbes villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,600

Beachfront Luxury - Coral Cove 2

Paynes Bay apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

“Perfect!” The Mahogany Tree accommodation was just perfect! The unit was clean and every amenity taken care of. Jasmine, our housekeeper, was awesome and her cooking just amazing! We traveled to Barbados for our wedding and we could not have been happier with our choice for accommodation. Walk out to the beach and sunsets by the pool..what else is there?!

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Price per night from

$425

The Condominiums at Palm Beach, Apt 408, Christ Church, Barbados

Hastings apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$502

Modern Beachfront Condo with Pool - Sapphire 102

St. Lawrence Gap apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$298

Beachfront Rooftop Penthouse with Plunge Pool - Reeds House 1

Reeds Bay apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

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Price per night from

$425

Beachfront Bliss with Spa Pool - Reeds House 9

Reeds Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$375

Beachfront Villa with Plunge Pool - Harmony House

Gibbes villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$1,100

Classic Beachfront Home - Arcadia

Worthing villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$450

On The Water's Edge - Easy Reach

Mullins villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$700

Traditional Beachfront Style - Clearwater

Gibbes villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$610

Beachfront Condo with Pool - Sapphire Beach 509

St. Lawrence Gap apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great location, fantastic apartment with breathtaking ocean view” We've spent in this apartment 12 days right before Xmas 2013. We had great stay, apartment, location, size, view, surroundings etc. was matching 100% our expectations. We will be back for sure :)

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Price per night from

$391

Chic Beachfront Apartment - Bora Upper

Paynes Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$285

GOBAJAC VILLA.....WONDERFUL PANORAMIC VIEWS OF OCEAN ( SLEEPS 6 GUEST)

Oistins villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Vacation Stay” I enjoyed my stay tremendously. The accommodations gave me the feeling that I was at still at home. I found that all of the amenities made my stay very comfortable and relaxing. The view from my room was breathtaking especially at night along with the sweet tropical breeze that came along with the view. I am looking forward the spending some more time at this location because of the enjoyment that I experienced.

Responds fast! avg. 2 hours 20 minutes

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Price per night from

$99

Private Beachfront Oasis - Reeds House 1 (3 bed)

Reeds Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$530

Finest Beachfront Villa in Babados - Crystal Springs

The Garden villa

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 20

“Paradise” A fabulous Villa with great character with probably the best location on the island.The private beach is totally private it is very difficult for outsiders to get to it from the public beaches.Staff very friendly and efficient and a fabulous chef/cook. Eight of us stayed there and each couple had their own space.Well worth the money as when split between 4-5 couples works out better value for money than staying in a five star hotel.

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Price per night from

$13,500

Coco, Mullins Bay, St. Peter, Barbados

Mullins house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$777

Mirador, Fitts Village, St. James, Barbados

Fitts villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$1,905

Uninterrupted Beachfront Views - Schooner Bay 207

Speightstown apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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Price per night from

$860

Modern Beachfront Condo with Pool - Sapphire 109

St. Lawrence Gap apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$304

Fosters House, Lower Carlton, St. James, Barbados - Beachfront

Lower Carlton villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$3,659

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