Holiday rentals with a pool in Whidbey Island

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Top-rated rentals with a pool in Whidbey Island

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Top Guest favourite

A spacious living area features large windows providing panoramic views of the water. A sectional couch, adorned with plush pillows and throws, offers ample seating. A wooden coffee table sits on a decorative rug, while a telescope is positioned nearby to enjoy the scenery.

Holiday home in Coupeville

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!

4.97 out of 5 average rating, 104 reviews

Top Guest favourite

An aerial view captures a curved shoreline bordered by calm waters, leading to a small grassy island with sparse trees. Pathways are visible along the beach and connecting the surrounding area, with residential buildings situated nearby.

Apartment in Port Ludlow

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!

4.93 out of 5 average rating, 74 reviews

Guest favourite

An aerial view captures the tranquil Port Ludlow Inlet, showcasing a marina filled with boats. Further back, green hills rise against a clear blue sky, while a parking area and neatly arranged pathways are visible along the shoreline.

Condo in Port Ludlow

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.

5.0 out of 5 average rating, 17 reviews

Guest favourite

Home in Coupeville

Walk to Beach • 2 King Beds • Fenced Yard

Fall in love with Whidbey 🍂 Centrally located for all-island adventures! Explore charming Coupeville, local farms & wineries, fall festivals, scenic trails & Practical Magic filming locations! Minutes to the Port Townsend ferry • Sleeps 7 | 2 King, 1 Queen + twin rollaway • Fully equipped kitchen, herb garden • Fenced yard, dog friendly! • Spacious deck, covered porch • Vaulted living space + wood stove • 0.5 miles to community beach + seasonal heated pool • RV parking + power ($65/night)

5.0 out of 5 average rating, 32 reviews

Superhost

An outdoor deck is set with a dining table and chairs shaded by a bright red umbrella. Lush greenery surrounds the area, while glimpses of water can be seen in the background. The space is ideal for al fresco dining and enjoying scenic views.

Home in Coupeville

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!

4.9 out of 5 average rating, 49 reviews

Superhost

A spacious living area is highlighted by large windows offering views of the water. A comfortable sofa is paired with an armchair, and a coffee table sits atop a soft area rug. Decor elements include a painting of ocean waves and a small table with fresh flowers.

Home in Coupeville

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.

4.92 out of 5 average rating, 202 reviews

Top Guest favourite

Home in Coupeville

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.

4.94 out of 5 average rating, 33 reviews

Guest favourite

A modern kitchen area features white cabinetry and open shelving displaying various kitchenware. A round dining table is accompanied by transparent chairs, while a gray sofa with decorative pillows sits in the foreground. Light streams in through large windows, enhancing the inviting space.

Guest suite in Mukilteo

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.

4.97 out of 5 average rating, 592 reviews

Top Guest favourite

A well-lit living area features a large stone fireplace with a cozy fire. Floor-to-ceiling windows offer views of Port Ludlow Bay, while a round dining table is paired with stylish chairs. A comfortable armchair and side table complete the inviting space.

Condo in Port Ludlow

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.

5.0 out of 5 average rating, 26 reviews

Top Guest favourite

Guest suite in Camano

“The Beaver Den” Hot Tub, Kayaks, and Gazebo

Escape to The Beaver Den, a cozy island retreat on beautiful Camano Island. This modern 1,200 sq ft daylight basement suite offers a private, peaceful hideaway surrounded by nature. Enjoy birdwatching right from the windows, relax in the hot tub, or explore nearby beaches, parks, and trails just minutes away by car. Perfect for couples, families, or a quiet getaway, The Beaver Den blends comfort, privacy, and island charm.

4.99 out of 5 average rating, 175 reviews

Top Guest favourite

Home in Camano

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.

4.97 out of 5 average rating, 86 reviews

Top Guest favourite

The exterior of the house features multiple stories clad in gray-blue shingles, with large windows allowing ample natural light. A spacious front yard is surrounded by greenery, and a driveway leads to an elevated entrance beneath the home. Blue skies and distant trees frame the scene.

Home in Coupeville

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.

4.96 out of 5 average rating, 57 reviews