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

The Starburst Inn
Bring your family to the luxurious 5 BR 3 Bath oasis in the tranquil and friendly Old Evergreen Highway waterfront area. Visit the exciting attractions, natural landmarks, restaurants, shops, and much more, and then retreat to the lavish oasis that will leave you in awe with its starburst MCM design, backyard, and rich amenity list. ✔ 5 Comfortable BRs ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Swimming Pool ✔ Hot Tub ✔ Game Room ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more belo

Recreational Family Fun & Adventures Await
Entertain outdoors in a covered lit patio with grill and cooler. Stay warm with 2 propane firepits or by the campfire pit. Fenced in yard is pet friendly. Nearby Rec Center offers a Gym, Splash Pad, and Indoor Pool with Water Slide ($7 Day Pass). Enjoy basketball, baseball, soccer, and tennis all walking distance with our sports equipment. Explore many nearby parks with playgrounds and trails with our bicycles. Short drive to Washington Square Mall, restaurants, grocery stores, and more!

Rose City Hideaway
Oasis for the traveler seeking culture, nightlife, music, food, and ease of access to the Oregon Convention Center, Moda Center, Kaiser and Legacy Hospitals, and Portland Expo Center. This tucked away space, with views of the public park with art installations, is located in the entertainment district. The Hideaway is the ideal landing pad for business and pleasure. After exploring, return to RCH for time in the swim spa, gym, outdoor kitchen, or relax by the gas fire pit to end your day!

Garden Apartment in the Heart of Portland
Beautiful and bright basement apartment with AC in relaxing Northeast Portland. The neighborhood has everything you could want with NE Williams Street a short walk away, easy access to the Rose Garden and the Convention Center, and a 10-minute bike ride to Powell's Books in downtown Portland. The community center across the street offers a full-sized pool and gym. Enter through your own gate into a backyard food forest, and enjoy a private entrance to your apartment. Easy checkout.

Cascadia Cabana | Poolside Suite with Spa
Modern Scandi Guest Suite located on a 1/3 of an acre within the Powell Butte Natural Area. Equipped with a Heated Pool, Oversized Hot Tub Spa, Water Slide, Outdoor Shower, & plenty of privacy and room for activities. A grand sculpture arches over the large pool displaying a gorgeous disco ball! It is the perfect feature to swim under or use as a backdrop for a unique photo. The large deck and pool get full sun almost all day. This space boasts total privacy and all the amenities!

Camp out in new RV, with pool/hot tub at our farm
Enjoy сountry Luxury Getaway at Our Miranda's Farm & recreation just a 2 min of downtown Mollala! Watching stars is a must do list on 5 ac farm with beautiful views of the mountains, trees and field. The 32' RV is very spacious, including double bed, sleeper couch, 2 bunk beds, full kitchen, bring your food! Relax on comfy sun beds, go for a swim in our warm pool and soak in power jets hot tub! We have a solar heated outdoor shower! Just relax! What are you waiting for? Book Now

Secluded Suite Surrounded in Beauty
* Queen bed * Private bath * No smokers * Quarters on first floor of house* Shared hallways * Quiet location * 3-room suite in non-smoking home up long driveway not visible from st. Walking distance to WSU-V w/hiking trails and 3 min. drive to Legacy Hosp. 1-acre home w/heated pool during summer. Adjacent private livingroom has sink, frig, microwave and eating area. Shared laundry room -keypad for secure entry. Second bedroom available per request and registration.

Oasis Between City, River & Mountain. Damascus OR
A large & private guest house on lower level of home only 30 min. to Portland. Mt. Hood, Gorge Waterfalls & Scenic hikes within 60 min drive. Super comfortable bed, quiet nights, recliner sofa & relaxing atmosphere make this an ideal place to hang out and rest. We welcome ALL colors, LGBTQ. Must Read all info, house rules & details prior to booking please. Informed guests are happy guests. Can accommodate 3pm check in every day of the week except Tuesdays.

Poolhouse of Portland Architectural Gem
Private guest house adjacent to Pietro Belluschi's "Sutor House", featured in Dec 2017 Dwell Magazine. Pool-house is 750 square feet, and features a master bedroom, full bath, living area with kitchenette, and access to and shared use (With our family) of the swimming pool in summer months (June, July, August). Surrounded by private wooded garden with Japanese plantings and water features. Located in Portland's West Hills, just minutes from Downtown.

Quaint Tiny House In The Trees. Damascus, Oregon.
150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to SE Portland, 45 to PDX, One hour to Mt. Hood, 40 min to waterfalls in the Columbia Gorge. Pool open June 15 through September 5th. Can accommodate a 3pm check-in all days except Tuesdays.

Forestplace Nightly - Studio A
Each magnificent nightly rental comes equipped with: • Queen Size Murphy Bed - Sleeps 2 Guest • No Pets Allowed • Dining area for 2 Guests • Full Bath with linens • Personal Care Kit (Shampoo, body wash etc.) • Toaster • Microwave • Mini Fridge • Keurig Coffee Maker • Air Conditioning • Quartz Counter-Tops • Modern Interiors • Cable TV 150 channels with On Demand • Free Wi-Fi • Free Reserved Parking for one vehicle

Rose City Retreat
Newly constructed basement studio with private entry in 100+ year old NE Portland home in park-like setting. Trendy Beaumont Village neighborhood, walking distance to restaurants and shops, 90 minutes to the coast, one hour to skiing on Mt. Hood. Triple lot, gardens, swimming pool, and patio with BBQ. Non-smoking household. If you are into cold plunging, use our pool during the cooler months for this experience!
Popular amenities for Sherwood rentals with a pool
House rentals with a pool

Orienco home, steps to Intel RA, winter discount!

One level Entertainers Dream *Heated Pool*

Frankie's Place; Walkable Craftsman luxury!

Starlight Lodge with Private Pool & Game Room

An Entertainment Oasis!

3-Bed Cowboy Cabana w/ Soaking Pool + Hot Tub!

Serene Oasis: Swim Spa, Sauna, huge deck and grill

Private house, hot tub & acres of forest trails!
Other holiday rentals with a pool

Octagon Family Retreat - Hot Tub • Games • Pool

Countryside Modern Guest House!

The Art Farm

Salmon Creek Cottage

Home in Wilsonville

Sherwood Bella Retreat / close to GFU - Newberg

Cute practical walkout basement studio

Country equine setting with lovely garden
Quick stats about holiday rentals with a pool in Sherwood
Total rentals
10 properties
Nightly prices starting at
€ 60 before taxes and fees
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Moda Center
- Laurelhurst Park
- Oregon Zoo
- Enchanted Forest
- Silver Falls State Park
- Providence Park
- The Grotto
- Portland Japanese Garden
- Wooden Shoe Tulip Festival
- Beacon Rock State Park
- Wonder Ballroom
- Hoyt Arboretum
- Powell's City of Books
- Tom McCall Waterfront Park
- Oaks Amusement Park
- Pumpkin Ridge Golf Club
- Wings & Waves Waterpark
- Domaine Serene
- Portland Art Museum
- Battle Ground Lake State Park
- Arlene Schnitzer Concert Hall
- Council Crest Park
- Bridal Veil Falls State Scenic Viewpoint
- Stone Creek Golf Club