Holiday rentals with a pool in Trent Hills

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Trent Hills

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

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Top Guest favourite

Guest suite in Keene

4.96 out of 5 average rating, 122 reviews

Welcome to Paradise on Rice Lake!

Welcome to Paradise on Rice Lake Unique, semi-detached cottage has a heated pool, southern exposure, private deck with glass railing overlooking the lake. Included: 3 beds total, King, Queen Murphy bed with Tempur-Pedic + pull out Queen sofa bed All S/S appliances, W&D, dishwasher, gas stove, firewood available $15, propane BBQ, outdoor dining area overlooking the lake. boat dock in front, great fishing, 5min to Keene for LCBO, Pharmacy, Gen Store, ATM, 1:20 from Toronto, :20 to Peterborough

Guest favourite

Home in Stirling-Rawdon

4.86 out of 5 average rating, 37 reviews

★Stylish Chalet | Pool | Scenic Views |♛Royal Beds

1960's Style Chalet 10 Mins to Stirling 10 Mins to Campbellford Beautiful setting in the country. Spacious living room Relaxing spot for a get-away. Patio & BBQ Property sits on 5 acres with 3 buildings The Chalet is fully fenced, so perfect for dogs and has private drive. *On-Site Chef* Delicious Catering Available Menu's Available for "Room Service" Call Ahead to place orders Other buildings are roughly 200ft away so plenty of private space. Shared pool on-site with other guests.

Guest favourite

Home in Campbellford

4.98 out of 5 average rating, 43 reviews

Moon River

“Moon River, wider than a mile. I’m crossing you in style”. Located at a 5-star location, this historic home was freshly designed by a professional interior designer. The stunning emerald tiles in each bathroom reflect the color of the river running outside. While enjoying a warm bath in a freestanding bathtub in the bedroom, you’ll be amazed by the bright moon above the peaceful river outside the window. “Moon River” is ideal for a large family(up to 16) vacation or a romantic getaway for 2.

Top Guest favourite

Apartment in Havelock-Belmont-Methuen

4.94 out of 5 average rating, 203 reviews

Belmont Lake Getaway

8 + acres w/ Fully Private separate entry facing pond & lake ,one bedroom with queen bed, living room with queen pull out couch , TV etc, dining room, full kitchen, and bathroom is wheelchair accessible, host main house above, Summer: kayaks and canoes , fishing, ducks & pond , full gardens. Pizza night is every Saturday . Winter: snow shoes skating, ice fishing ,curling ,lots of winter activities. Local Chocolate & Cheese factories, Wineries, We added an Eco Pool with beach for swimming.

Top Guest favourite

Cottage in Bailieboro

4.9 out of 5 average rating, 108 reviews

Majestic Lake Haven ~ Heated Pool~Hot Tub~Dock

As if emerging straight out of a fairy-tale fantasy, this 6-bed lakefront retreat exudes luxury and unmatched privacy like no other. Envision a place of solitude nestled on an enormous grassy lawn, with a heated swimming pool + bubbling hot tub, a private dock for spontaneous swims & fishing, plus a BBQ & fireplace for evenings under a starlit sky. The interior is just as awe inspiring, boasting a 1500 sq. ft. interior, complete with a 52" smart HDTV, mini golf & board games for all around fun!

Top Guest favourite

Home in Keene

5 out of 5 average rating, 260 reviews

Spacious Lower Level Walkout in the Country

Beautiful lower level walkout in COUNTRY 15K from downtown Peterborough. Reflective waterfall/pond & gardens or if you like to be active pool(summer) & woodland hiking trails. Nearby boat launch on Otonabee River, excellent fishing. Large pool accommodates an active family(summer). Spacious family room with 60" HDTV (Bell Express & Netflix), kitchen & eating area. 4 bedrooms should be ample space for family/ friends. NO PETS & NON SMOKERS ONLY. WE LIVE ON MAIN LEVEL & DO NOT LIVE IN THE CITY.

Top Guest favourite

Home in Prince Edward

4.97 out of 5 average rating, 157 reviews

Prince Edward Landing

Victorian Home in PEC gets a full renovation to become a one of a kind vacation home. Featured in the Globe & Mail the house is a 2018 restoration of old-world charms with as many contemporary comforts as one wishes. From the gorgeous landscape and a screened-in, white-trim front porch to the fully modern spectacular interior The back of the house is a stunning starkly contemporary black box, designed by architect Jay Pooley, a lecturer at the University of Toronto’s school of architecture.

Top Guest favourite

Farm stay in Kawartha Lakes

4.88 out of 5 average rating, 124 reviews

Luxury, One-of-a-kind Pool and Zen with Horses

Luxury spaces for the whole family, YEAR ROUND Zen with horses in our heated barn, magnificent views. Private suite, Fire Pit, Hiking Trail, outdoor kitchen and BBQ. Billiards, shuffleboard, trampoline, table tennis, basketball and more. Book an archery tag or axe throwing game! Search horse experiences Sky Haven Equestrian in Bethany. Kids Stay Free! When booking enter number of adults only. Wutai Shan Bhuddist Garden is 4 min. away. Great for entertaining. Inquire about our event space.

Top Guest favourite

Guest suite in Kawartha Lakes

4.93 out of 5 average rating, 144 reviews

Hidden Acres - a Stay and Play Retreat!

Are you looking for some nature therapy? You'll be nestled in several acres of forest, where you can hear the birds and enjoy the private backyard. The hot tub and campfire* beckon in all seasons, and the heated inground pool is open from mid-June to Labour Day each year. We are dog friendly, but cannot accept other pets due to allergies. Please be sure to read our house rules before booking. **We are excited to share that we now offer a Level 2 EV outlet!** * except during bans, April

Guest favourite

Cottage in Hastings ,Trent Hills

4.94 out of 5 average rating, 18 reviews

Cheerful 2 bedroom cottage with indoor fireplace.

Relax with the whole family at this peaceful rustic cottage that is situated on 21 acres with trails in the beautiful County of Trent Hills. Cottage is fully furnished with fully equipped kitchen with appliances, pots and pans, microwave, BBQ with patio table and chairs and gazebo. 3 piece bathroom. Wood stove inside for those chilly nights. Cottage has wifi. Large outdoor fire pit to be enjoyed in the evenings. Small above ground pool to cool off. Hot tub for you to relax and unwind.

Top Guest favourite

Home in Marmora

5 out of 5 average rating, 8 reviews

Stone House Manor

Jackson Venues is excited to list its second AirbnbThe Stonehouse Manor. It shares a riverview waterfront with Cabin On The Crowe. The combined venues have 9 beds to accommodate 16 people. A five time Superhost with all 5 star reviews, you won't be disappointed. Located within a 2 hr drive from Toronto and a 2.5 hr drive from Ottawa and less than an hour to Prince Edward County. Surrounded by lakes and rivers. Bring family and friends to this great place with lots of room for fun.

Guest favourite

Home in Prince Edward

4.94 out of 5 average rating, 197 reviews

Dragonfield House: a beautiful stay in central PEC

Dragonfield House: STA License No. ST-2024-0206 Featured in Canadian House and Home, March 2015, Dragonfield House was designed with a contemporary approach to country living. It is a four bedroom split-level country house, plus a guest yoga retreat with all the amenities of a city home. It features a heated salt-water pool (Mid May until Mid October) and a brand new year round hot tub for six people! There are three work/desk areas within the house ideal for remote working.