Vacation rentals with a pool in Whidbey Island

Whidbey Beachfront Cottage- sand and sunsets

Discover the Beach Cottage at WB, the award winning property on Sweet Retreats, an ABC TV vacation rental series. Set on 155' ft of sandy southwest facing beach, the fully outfitted luxury cabin for two was updated in 2026 with a new queen mattress, new kitchen, and luxurious cotton waffle weave towels and bathrobes. Experience incredible sunsets, Olympic mountain views, bird and wildlife galore, and lapping waves at your feet. Note! Access requires stairs, inquire before booking.

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!

Location · Family · 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.

Family · Location · Indoor spaces

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!

Value · Family · Getting around

Beachfront home with Pool, Hot Tub, and Fire pit

- [Newly FIXED]: Pool AND hot tub overlooking the water - Your own private beach with access from the front yard - Two kayaks with life jackets and paddles - Fully stocked chef’s kitchen and coffee - In-unit washer and dryer The open floor plan and layout allows for connection, regardless of what room you're in. Enjoy the large smart TV's in every room, gas fireplace to keep you warm in the winter, or stay warm while you watch people cook in the incredible kitchen.

Value · Family · Backyard

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.

Family · Value · Comfort

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.

Location · Family · Hospitality

Seaside Suite by Mukilteo Beach

Our studio apartment has a private entrance and a private Juliet balcony to enjoy stunning views of Puget Sound. Sleep in comfort on a Tempurpedic bed with adjustable head and foot lift. Additional sofa bed for extra guests. All necessities provided. Private indoor pool with views out to Puget Sound. Many attractions are within a 10 minute walk, including Mukilteo beach, the ferry terminal, the Sounder train to downtown Seattle or Mukilteo town.

Value · Family · Parks

Walk to Beach & Pool • 2 King Beds • Fenced Yard

✨ Availability LABOR DAY WEEKEND and during Practical Magic 2 showings at the Blue-Fox Drive-In Sep 19-20! • 0.5 miles to beach, minutes to Coupeville & the Port Townsend ferry • Community beach club/pool access • Sleeps 7, 3 bedroom: 2 King, 1 Queen, 1 rollaway*, 2 Bathroom • Fully equipped kitchen, fresh herb garden • Fenced yard (dog friendly!) • Vaulted living space + wood stove • RV parking + power (reservation fee applies)

Family · Value · Nearby

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.

Location · Family · Checkout

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.

Value · Family · Pool

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.

Family · Location · Pets