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Whidbey Island Luxury Holiday Rentals

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    Travellers to Whidbey Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    19 Matching Rentals in Whidbey IslandView all 131 rentals
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    Harbor Villa Waterfront Estate - Sleeps 141 / 11
    (1)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Whidbey Island Beachfront -Luxury on a Sandy Beach1 / 34
    (7)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Harbor Retreat Waterfront Home1 / 8
    (3)Average
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Luxury Cape Cod on Low Bank Sandy Beach,  faces SW1 / 34
    (3)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Waterfront
    • Mountain Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whidbey Beach Retreat is one of the most spacious and luxurious beach homes on Whidbey Island. With the Olympic Mountains as a backdrop, and a sandy beach right in front of the house, the location is stunning. Views to the south include a perfectly pink Mt Rainier with the alpenglow of...
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    Location Information
    Clinton, Whidbey Island 98236
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    What an opportunity to taste a new lifestyle! Come stay on beautiful Whidbey Island in luxury. Frank Lloyd Wright style main house - freshly painted inside & out, new carpet, marble floors, & more. Stunning water views from almost every room. Private setting on almost 5 acres of peace & quiet. 180...
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    Greenbank, Whidbey Island 98253
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • DVD Player
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to ‘Barranco’ (named after a charming high bank neighborhood in Lima, Peru)! This contemporary waterfront home, high on the south west facing bank, is just a stone throw from South Whidbey State Park and situated on one of the most magical and secluded spots on Whidbey Island. With...
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    Greenbank, Whidbey Island 98253
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 13
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    5 Bedrooms & 4 Baths1 / 33
    (34)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2018
    End of the road haven with beautiful private yard, view of the Sound, comfortable furnishings. Great for gatherings! You can't go just once!
    Reviewed 5 September 2018
    We used this house for a recent Whidbey Island wedding event. The bride's large family enjoyed this special lodging. Beautiful house on beautiful Useless Bay. The beach and...
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    About this property
    HERON'S CROSSING is a charming beachfront Cape Cod style home on Sunlight Beach, Useless Bay. 5 bedrooms sleep 10. 2 Full baths, a 3/4 bath with walk in shower and a 1/2 bath. If your group is bigger, talk to us about overflow rentals close by. Check in is at 4PM. Check out at 11AM. -This...
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    Clinton, Whidbey Island 98236
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Beach Hideaway - Waterfront Beach Home1 / 15
    (6)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Outdoor Dining Area
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Waterfront
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2016
    This was our second time staying at the property. The location and seclusion can not be beaten. You are literally right on the water. The outside deck, fire-pit and beach are...
    Reviewed 22 June 2015
    We found a little piece of Heaven at the Beach Hideaway. This is the most romantic, secluded, heavenly property we have ever stayed at. There is complete seclusion and privacy...
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    About this property
    Designed by famed waterfront architect Robert Maloney, the Beach Hideaway will take your breath away. With its two bedrooms, 2.5 baths, gourmet kitchen, 42' Plasma HDTV in the living room, massive river rock fireplace, decks to the water, and private hot tub, this bungalow sits on a private...
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    Freeland, Whidbey Island 98249
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Harbor Chalet Waterferont Home1 / 6
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Central Heating
    • DVD Player
    • Internet Access
    • Hot Tub
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2014
    This place was pretty great! Very spacious and well-maintained. We had a great time, and would definitely book again. The only drawback would be that the beach wasn't very...
    Reviewed 3 June 2014
    My friends from college andI all decided to do a weekend getaway on Whidbey. This house was a perfect spot for us. The family room was spacious and there were plenty of bedrooms...
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    About this property
    The Harbor Chalet has become one of the most popular luxury vacation homes on Whidbey in a very short time, and a true superstar of the Whidbey Retreat's (WR) family of luxury homes. The reasons for its success are simple: it was built from the ground up to take advantage of spectacular...
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    Freeland, Whidbey Island 98249
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Your Private Resort / Waterfront Vacation Home1 / 31
    (13)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    excellent in every respect. particularly struck by cleanliness, ample supplies, and handicap accessibility.
    Reviewed 31 March 2016
    This property is incredible. Perched on top of a bluff on the Southeast side of Whidbey Island. As you drive in, the first thing you notice is how tucked away the house is. When...
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    About this property
    Harbor Hideaway is a waterfront, executive home located on the west shore of Holmes Harbor on Whidbey Island, adjacent to the Holmes Harbor Golf community. 3,600 SQ FT, 4 Bedrooms & 5 Bathrooms. Ideal for 8 to 11 persons. Comfortably sleeps up to 15. The grounds will blow you away: Gazebo,...
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    Location Information
    Freeland, Whidbey Island 98249
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 15
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    Captain's Cabin Waterfront Home1 / 10
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Internet Access
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2018
    Captain's Cabin is a beautiful cottage situated on a bluff overlooking the water. Large French doors in the living room and bedrooms open to expansive decks. The hot tub was...
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    About this property
    Perched on a bluff with bald eagles around, the Captains Cabin waterfront home commands an enviable perch with a view that goes forever. The entry way is through a vine covered arched trellis opening onto a cobblestone courtyard. Upon entry, you are surrounded by a courtyard filled with the...
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    Location Information
    Greenbank, Whidbey Island 98249
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bay Cottage Waterfront Home1 / 20
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Patio
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 June 2017
    Could not ask for more perfection getaway! Marvelous view, spacious deck with hot tub and BBQ, comfy beds, awesome baths with heated floors, and well appointed kitchen. Eagles...
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    About this property
    Perched dramatically on a cliff overlooking Honeymoon Bay, sits the enchanting Bay Cottage. It is a magical setting with such a unique charm and peaceful feel...there is a gentle spirit to the house and setting that one cant miss. It is calming. Upon your arrival you may be thrilled by the cry of...
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    Freeland, Whidbey Island 98249
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • DVD Player
    • Washer
    • Patio
    • Grill
    • Waterfront
    • Central Heating
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The sound of the waves, deep sandy waterfront and grassy front lawn, spacious deck and gorgeous home are just a few of the perks of ONCE UPON A TIDE beach house. Once you get off the ferry on Clinton, you will have the sigh of relief from the hustle and bustle of the city. This beautiful...
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    Clinton, Whidbey Island 98236
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Historic Restored Farmhouse With Spectacular Views - Now with an EV charger1 / 48
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • Mountain Views
    • DVD Player
    • Internet Access
    • Waterfront
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2016
    Me and my 4 girlfriends stayed at Marty's for a long girls weekend getaway. Just driving up to the house was impressive, it is very large and the view from the driveway alone...
    Reviewed 20 April 2016
    We arrived at MARTY'S PLACE and discovered the wonderful photos online told only half the story. This is a terrific house, warm and inviting, with great views and grounds. The...
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    About this property
    Hello and welcome to Marty's Place at Strawbridge Farm, a 5 bedroom plus vacation rental with room for a few people or your entire family. This newly restored 1909 farm house has all the amenities of a modern home, but has maintained its rustic sensibilities. Come and enjoy the breathtaking views...
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    Langley, Whidbey Island 98260
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the entire family! 3000 Sq ft, 5 bed, 3 bath, spacious summer home available to host multi-generational gatherings, groups of friends for wine tasting, or a weekend getaway with close companions. This custom home can sleep 11 with 2 king beds, 1 queen, 1 full, and 3 twin beds. Air mattress...
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    Location Information
    Langley, Whidbey Island 98260
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blueberry Hill Retreat is an expansive 5 bedroom, 4 1/2 bath home with remarkable views of blueberry fields, Puget Sound and the Olympic Mountains. Nestled in a quiet grove of towering fir trees, this home has both privacy and easy access to 3 of the most popular beaches on Whidbey Island. Enjoy a...
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    Freeland, Whidbey Island 98249
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    217 - Vineyard House1 / 29
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 December 2017
    This place was even better than advertised. Love how peaceful it was and enjoyed walking the grounds. Everyone at the winery was so very nice and helpful. Only compliant was...
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    About this property
    When your car turns off of historic Newman Road and in through the open gates of Dancing Fish Vineyards, you know you’ve entered a six-acre Whidbey Island paradise. The unique and luxurious amenities offered at the Vineyard House cannot be found anywhere else--you'll find yourself at your very own...
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    Location Information
    Freeland, Whidbey Island 98249
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Washer
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This immaculately maintained English Tudor Home is nestled on 5 manicured and forested acres. Located in South Whidbey's up and coming Porter District, minutes from the Mukilteo Ferry Terminal. This private property rests on the south end of South Whidbey Airpark and allows you the additional...
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    Langley, Whidbey Island 98260
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    View, beach, vintage farmhouse, alpacas, birds, sunrise & sunset -- get it all1 / 46
    (14)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Central Heating
    • Mountain Views
    • Washer
    • Ocean Views
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2017
    We've just returned from our third visit to the Aerie and it was better than ever which is saying a lot. I had a few quiet days with my teenage daughter walking on the beach...
    Reviewed 17 August 2016
    This was our fifth visit to the farm, and, as always, we enjoyed a relaxing, rejuvenating experience. There's something so calming about feeding the gentle alpacas, drifting off...
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    About this property
    Perched on a ridge with sunrise and sunset views, this vintagel farmhouse is exquisitely sited on 740 feet of high bank waterfront on 25 acres overlooking Useless Bay and the Olympic Mountains to the west, and the Maxwelton Valley to the east. It perches like the eagles nest beside it, taking in...
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    Location Information
    Clinton, Whidbey Island 98236
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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