Vacation rentals with a pool in Okanagan-Similkameen

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Okanagan-Similkameen

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Guest favorite

Tiny home in Penticton

4.95 out of 5 average rating, 122 reviews

'Suite Skaha Retreat' Modern Pool House (licensed)

This self contained, modern, renovated 'pool house' is a city inspected, licensed (#00112755) suite that offers a private setting, beautiful landscaping, including a real palm tree,🌴 pool and many sitting areas to enjoy the property. Located steps from Skaha Lake, below Skaha Bluffs Provincial Park and walking distance to Painted Rock Winery. Enjoy our kayaks and SUPs as well as a shed to lock your bikes/gear. Here's your opportunity to enjoy the Okanagan lifestyle and all it has to offer.

Aug 19 – 26

G$36,505 GYD per night

Guest favorite

Guest suite in Peachland

4.87 out of 5 average rating, 227 reviews

Poolside Retreat, our mini resort

Our spacious guest suite is situated on the lower floor of our house, where we live, and is one of three unique accommodations offered at the Poolside Retreat our licensed mini resort. Suits families and mature adults wishing for a private, quiet relaxing vacation. Seasonal Pool and lawned badminton area, set in stunning surroundings. Located by scenic farmland ideal for hiking, cycling, and enjoying the menagerie of nearby farm animals, plus only 3 min drive to the lake and Peachland town.

Mar 22 – 29

G$26,153 GYD per night

Guest favorite

Guesthouse in Naramata

4.94 out of 5 average rating, 35 reviews

The French Quarter

We are delighted to share with you our little piece of heaven. Gated 1 acre estate located in the heart of beautiful Naramata with a micro vineyard, salt water heated pool and gorgeous Okanagan lake views. You will have your own private living quarter, 572 sq ft nestled above the detached garage. Less then 10 mins walk to restaurants, downtown Naramata, 3 wineries (Serendipity, Therapy and Kettle Valley)and Manitou beach. Bike/Walk the famous KVR Trail/Wine tour/Swim/Dine/Sleep...REPEAT :)

Jan 3 – 10

G$37,944 GYD per night

Guest favorite

Guest suite in West Kelowna

4.95 out of 5 average rating, 206 reviews

WK Wine Trail: clean & bright with private beach

(Pending City issuing reg #) Large, clean, & bright newly renovated suite with private entrance, king-sized bed, and granny-style kitchen. .5 km to both Quail's Gate & The Hatch wineries. A quick 5-minute drive to over 8 additional award-winning wineries (including the stunning Mission Hills winery), multiple hiking trails, and the Gellatly Bay lake front area (boat launch, walking path, sandy beach). A short 7-minute drive to the bridge to go to downtown Kelowna. Private beach available.

Aug 25 – Sep 1

G$40,954 GYD per night

Superhost

Cabin in Peachland

4.87 out of 5 average rating, 75 reviews

Forest Cabin with Hot Tub in Paradise

Come to Paradise where all your wants and needs are met in a beautiful forest setting. Private HOT TUB on the deck is yours to enjoy! Swimming pool will be closed this year. Enjoy the Mountain Views and serenity. Your cabin is the best location in the entire resort. Entertain yourself in front of a 65" Smart TV with NetFlix, Prime, PS5 or play from a fantastic collection of board games. If you are looking for quiet, relaxing times this place is for you. Paradise in the forest.

Oct 19 – 26

G$26,495 GYD per night

Guest favorite

Vacation home in Kelowna

4.96 out of 5 average rating, 105 reviews

Year-Round Heated Pool Hot Tub Vineyard Lake Views

Welcome to LAVASAN! Kelowna’s most unique LICENSED vacation rental, with a private vineyard and year-round heated pool. Nestled in Lakeview Heights, walking distance to some of the most notable wineries in the Okanagan, our private 4 Bed / 3 Bath home complete with a Private Vineyard, Heated Pool, Waterslide, Hot Tub, Movie and Games Rooms, and ample off-street parking, is yours to enjoy. LAVASAN truly has it all! *Please read our house rules and listing details prior to booking.*

Jan 7 – 14

G$69,742 GYD per night

Guest favorite

Barn in Princeton

4.95 out of 5 average rating, 92 reviews

Romantic couples getaway in the Country

Brand new build offering unique features such as sauna room, deck, large chef's kitchen, generous bathroom, wood burning fireplace. Located 20 minutes from town and golf course. 10 minutes to nearest lake, with approximately 100 more within an hours drive. Bordering access to KVR trail. Outdoor activities include quading, horseback riding, biking, fishing, hunting etc. The list goes on. Leave the city behind and come enjoy the country outdoor experience where the night sky comes alive

Jan 30 – Feb 6

G$21,369 GYD per night

Guest favorite

Guest suite in Kelowna

4.82 out of 5 average rating, 298 reviews

Private, 1 bedroom space, Hot Tub access.

You must be 25 years or older to book this space. 10 mins to downtown. 40 mins to Big White. Clean new fully furnished 1 Queen bedroom . Our newest addition to our already 600+ great hosting experiences with Airbnb. Fully stocked, c/w shower, Living room & dinning table area. Comfy brand new double bed pull out couch in living room folds out for up to 2 extra guests. Comes complete with sheets, quilts & pillows. 36" flat screen, cable & WiFi. dishes, pots pans...everything!

Sep 15 – 22

G$23,147 GYD per night

Guest favorite

Guest suite in Kelowna

4.93 out of 5 average rating, 276 reviews

That Modern 70s Garden Suite - Poolside Retreat

* LEGALLY LICENCED BY THE CITY OF KELOWNA- license number listed* Your reservation won't be cancelled due to the new legislations starting in May 2024 Welcome to the Garden Suite -This is a perfect getaway spot to the Okanagan! This is not your Grandma's house! Updated and modern 70's style suite - this space will take you back a few eras Enjoy a refreshing dip in the pool and a chilled glass of something local in Summer. Private garden entrance studio suite with private bath.

Jul 19 – 26

G$32,903 GYD per night

Superhost

Guest suite in Penticton

4.78 out of 5 average rating, 114 reviews

Your Slice of Penticton Paradise

Looking to have the ultimate Okanagan holiday? This is the space. Whether you're coming for sport or holiday this freshly renovated basement suite has something for everyone in your group! Cabana room, outdoor eating area, pool, aromatherapy hot tub for 8, fresh fruit trees in our fenced yard and organic veggie garden. Centrally located on main bike/run routes. The space is the full basement with ample room for everyone. Centrally located, close to shopping and both lakes!

Sep 28 – Oct 5

G$25,816 GYD per night

Guest favorite

Guest suite in Kelowna

4.89 out of 5 average rating, 444 reviews

Licensed View Suite w/Hot Tub

The self checkin suite is located in the Upper Mission. It’s a private unit in a guest house attached to our home. The room has a separate entrance with keyless entry. It’s within a five minute drive to wineries, beaches and restaurants . This cozy suite includes a queen bed and private three piece ensuite with shower. It has a scenic view of the city and Okanagan Lake. You will have access to our beautiful yard along with pool (seasonal) and 8 person Hot Tub. 2 guests MAX

May 19 – 26

G$33,700 GYD per night

Guest favorite

Condo in Kelowna

4.9 out of 5 average rating, 315 reviews

Downtown Lakefront Condo - Amazing Views BN82776

Business License Valid Through 2024 Indoor and outdoor pools 2 bedroom (2nd bedroom converted from a den) 1 bathroom with standing shower Updated kitchen with stainless steel appliances and granite countertops 2 balconies facing east and west Wifi & Telus TV with Crave & HBO + Chromecast Laptop friendly working space with monitor Washer and dryer Coffee + Espresso Machine 1 underground parking space Central location in Kelowna's downtown waterfront

Jun 24 – Jul 1

G$90,733 GYD per night