Holiday rentals with a pool in Island County

Beach Dreams on Whidbey! Beachfront! 2 King Beds

Stunning Beachfront Paradise! This architectural mid-century modern home sleeps 8+ with vaulted ceilings offering panoramic views of the ocean, Olympics, Coupeville Ferry, marine traffic and all the wildlife you can imagine! Beachcomb, watch dolphins, whales, seals, porpoises, eagles and all types of native birds. Adventure out kayaking, ride bikes to jump on ferry to Port Townsend or explore Fort Casey. Bring the whole family or enjoy the seclusion yourself in the hot tub or at the firepit!

3 BR Condo w/Water Views - Steps to Dining + Beach

Come enjoy a beautiful and quiet stay at the Hudson, a recently remodeled Port Ludlow condo steps away from the beach! 3 bedrooms with ensuites are perfect for two families or couples looking for a getaway. Relax at the beach or at the beach club where you'll find two heated pools (outdoor and indoor), an exercise facility, tennis and pickle ball courts. Outdoor pool is open Memorial Weekend to early Sept. This is the perfect place to disconnect from the city and enjoy comfortable amenities!

Comfy Condo in Port Ludlow

Nestled in the picturesque Port Ludlow Inlet, this charming home offers a perfect retreat for those seeking a relaxing getaway with scenic views. Relax on the patio with a good book or go on an exhilarating hike; this condo has something for everyone. With 27 miles of trails and golf available nearby, there's no shortage of activities to enjoy. You'll have access to the resort's many shared amenities, including indoor and outdoor pools, pickleball courts, a hot tub, sauna, and fitness center.

Olympic View Retreat

Whatever "escape" means to you, this home can be your perfect getaway. Spacious enough for a small family or group of friends, but still very comfortable. Hiking, biking, fishing, and other outdoor activities surround you. Just 10 minutes away, the dreamy town of Coupeville offers delicious dining options, shops, galleries, and more. Need to connect to work for a bit, or just want to hunker down and read, play games, or watch movies? This home is configured to meet your needs. Enjoy!

Walk to Beach•2 King Beds•Community Pool

Welcome to Tide & Timber, your next Whidbey Island getaway! • 0.5 miles to the beach • Sleeps 7: 2 King beds, Queen bed, twin bed* • Fully equipped kitchen + wood stove • Fenced yard (dog friendly!), herb garden • Community beach, fire pits & seasonal pool • RV parking + power Minutes to Coupeville & the Port Townsend ferry for easy exploring. Community beach: The outdoor pool is open ~June-September, salmon fishing access, fire pits, park/playground, basketball, and horseshoes.

Ebey Landing Ocean View Retreat on Whidbey Island

Relax & enjoy your Whidbey Island Getaway. Spacious, Open design and newly renovated. Unforgettable sunsets and relaxing views of the Olympic Mountains and the Juan de Fuca Strait. Melt into the couch while watching eagles soaring throughout the sky, ships quietly passing by, and the waves break against the bluff. Highspeed internet for remote work and entertaining. Modern kitchen, formal dining, spacious living are await for you to enjoy a great vocation stay.

The Nest - Whidbey Island

Escape to this stunning waterfront home on Keystone Ave, Coupeville. Enjoy panoramic views of the Puget Sound & Olympic Mountains from your private deck or hot tub. Watch whales, dolphins, and eagles daily. Perfect for families, friends, or romantic getaways. Steps to private beach, world-class fishing, kayaking, and hiking. Minutes from Coupeville, Port Townsend ferry, and Langley. Fully stocked for summer fun or cozy winter stays—this is Whidbey at its best.

Seaside Escape - 2 + Bedrooms

Relax at this unique and tranquil getaway. Enjoy the beautiful views of Port Ludlow Bay. There are 2 bedrooms on the main floor, each with a bathroom. For a small additional fee the 2 upstair bedrooms, each with a bathroom, can be included. The entire condo sleeps 10 with 4 bathrooms. Information on how to access the two upstairs bedrooms can be found by clicking "Show More". Full kitchen. Many fun activities in the area.

Waterfront Gamble Bay House +Seasonal Heated Pool

Take a break with people you love! Enjoy the wrap around porch and two balconies over looking Port Gamble Bay (part of the Hood Canal). In the evenings enjoy beautiful sunsets over the forest on the other side of the bay and in the morning, fall in love with the fog that clings to the trees across the water. In the summer months enjoy the private outdoor heated pool. Guests can expect a heated pool May- October ish.

Luxury Waterfront: Pool, Beach & Theater

Discover a luxurious multi-level beachfront villa on Camano Island's Madrona Beach. This serene coastal home offers direct beach access, a private heated pool (seasonal), a fire pit overlooking the Puget Sound, a dedicated theater room, and modern amenities for an unparalleled retreat. Perfect for families seeking tranquility and comfort, it comfortably accommodates a small group looking for a premium island escape.

Admiral's Seaglass Sanctuary

Admiral’s Seaglass Sanctuary is located in the center of the island so you can enjoy all Whidbey has to offer. Perfectly located for walk on ferry enthusiasts to Port Townsend, hikers, cyclists, historians, and those who enjoy bird watching or sea life. Regarding the "Other Details to Note" category below please contact the owner for website to review the schedule. The schedule is posted one week in advance.

Unique Open Concept Log Home

Make some memories at this unique getaway. Family friendly home with access to a private beach, pool (seasonal) and playground. A true nature lover's getaway. The grand ceilings add to the serenity that this home exudes. Enjoy the sunsets from the covered porch or on the sand. Centrally-located we are a short drive to just about everything on the island. Lots of things to do close by as well.