
Holiday rentals with a pool in Oak Harbor
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oak Harbor
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Poolside Cabana at the Sunburnt Mermaid
Poolside Cabana is a uniquely modified 26' traveler, 1 BR 2 BA w/private deck, sparkling water views of Westsound from our pool and hot tub. Guests can also take float plane or personal boat direct to Westsound marina within walking distance, We provide transportation to and from marina or Eastsound Airport. Kayak rentals available from our beach and tidelands. Organic vegetable gardens and fruit orchard. Microwave, instapot, toaster, fridge, tea kettle, hot plate, internet and ROKU TV Max 2
FamilyLocationOutdoor 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!
LocationValueParks

Colorful Container Home on 13 acre estate
Modern, yet cozy 1BR/1BA container home in Gardiner, WA—perfectly situated between Sequim and Port Townsend, with easy access to Olympic National Park. Features a full kitchen, bright open layout, and a sunny deck with dining area and views of Discovery Bay and the San Juan Islands. Minutes from 7 Cedars casino, yet tucked away on a peaceful country estate. Come expeirence one of the best rated AirBnB's in the world! 5.0 rating with over 200 reviews! We look forward to hosting you.
ValueFamilyAmenities

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 Puget Sound) 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. Explore the shore down the steps and harvest some oysters for dinner! In the summer months enjoy the private outdoor heated pool. Guests can expect a heated pool May- October ish.
LocationValueAccess

Contemporary Poolside Paradise w/ Hot Tub
Our beautiful home features a backyard oasis with a pool—perfect for relaxing or entertaining. Inside, you’ll find a modern design with spacious living areas, a fully equipped kitchen, and comfortable bedrooms for a seamless stay. Conveniently located near local attractions, dining, and shopping, it offers both comfort and accessibility. The pool is heated to 85°F from April through October and is closed during the rest of the year. The hot tub is fully heated between 6pm - 6am.
FamilyLocationHeating

Walk to Beach•2 King Beds•Community Pool
Welcome to Tide & Timber, a true 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.
ValueFamilyNearby

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.
FamilyLocationQuiet

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.
ValueFamilyTV

Rosario Condo - Views/Two Queen Beds
Recently renovated upscale Rosario condo with stunning views of Cascade Bay & the Rosario Mansion. Features two NEW queen beds, private deck, parking, and trail access to Moran State Park next door. Enjoy luxury bedding, 50" 4K Roku TV, Blu-ray, Nespresso, ice maker, fridge, microwave, electric fireplace, and private bath. Stay at The Residences— former Rosario Resort & Spa rooms reimagined for comfort, with infinity bay views!
ValueLocationView

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.
LocationFamilyBreakfast

Modern luxe beachfront w/ Pool & Spa
A luxe modern coastal home on the beach with a heated indoor pool and spa with sweeping views of Discovery Bay, Protection Island, the Strait of San Juan De Fuca, and a lagoon. Located in the rain shadow directly between Port Townsend and Sequim. Pool & Spa are heated year-round, Pool at 85 degrees, Spa at 100 degrees. Enjoy Sequim and Port Townsend. 4 kayaks and a rowboat to launch from the private beach.
FamilyValueHot tub

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.
ValueLocationWalkability
Popular amenities for Oak Harbor rentals with a pool
House rentals with a pool

2BR Bayview Whidbey Island Dog Friendly | Pool
FamilyLocationParks

Historic Waterview Home. Hot tub, pets welcome
LocationFamilyQuiet

Charming house with lake access
FamilyValueCleanliness

Whidbey Island Retreat
FamilyLocationHeating

Luxury Waterfront: Pool, Beach & Theater
LocationFamilyLong stay

Private Pool, Pickleball/BBall, Putting Green+
LocationValueBarbecue

Oceanside Cottage Est. 1860s
LocationFamilyAmenities

The Nest - Whidbey Island
LocationFamilyHot tub
Condo rentals with a pool

I Love Mukilteo
LocationValueCleanliness

Mutiny Bay Condo by AvantStay | Walk to the Beach
LocationFamilyHospitality

Water Views & Marina Access: Port Ludlow Getaway
FamilyViewHospitality

Comfy Condo in Port Ludlow
FamilyLocationWalkability

1BR ground-floor condo with indoor/outdoor pools
FamilyLocationAmenities

3BR Bayview 1st-Floor | Deck | Pool
ValueLocationSleep quality

4BR condo with waterfront views
ValueSleep qualityCheck-in

Lovely bayview 2BR with pickleball, hot tub, pools
ValueLocationIndoor spaces
Other holiday rentals with a pool

Private Pool Retreat Near Coupeville

Beach Dreams on Whidbey! Beachfront! 2 King Beds
LocationFamilyHeating

Cozy Condo | Steps from Martha Lake!
ComfortHospitalityQuiet

Dapper Swan Landing- Private Entry Suite
FamilyValueComfort

Beachfront Abode at Admiralty Bay
FamilyLocationBeach

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

Luxury glamping on Marrowstone Island
FamilyLocationAmenities

Barndominum 14+ guest, pool, Galbraith, Lake!
LocationFamilyPool
Destinations to explore
- Pet-friendly rentals Oak Harbor
- Rentals with a washing machine and dryer Oak Harbor
- Rentals with outdoor seating Oak Harbor
- Cottage rentals Oak Harbor
- Rentals with a patio Oak Harbor
- Family-friendly rentals Oak Harbor
- House rentals Oak Harbor
- Rentals with a fireplace Oak Harbor
- Rentals with pools Island County
- Rentals with pools Washington
- Rentals with pools United States
- University of Washington
- Space Needle
- Seattle Center
- Climate Pledge Arena
- Woodland Park Zoo
- Chateau Ste. Michelle Winery
- Bear Mountain Golf Club
- Seattle Aquarium
- University Of Victoria
- Birch Bay State Park
- Salt Creek Recreation Area
- Marymoor Park
- Discovery Park
- Moran State Park
- Lake Union Park
- Olympic Game Farm
- 5th Avenue Theatre
- Deception Pass State Park
- Amazon Spheres
- Willows Beach
- Waterfront Park
- Golden Gardens Park
- Port Angeles Harbor
- Westlake Center





