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Vacation rentals with a pool in Simcoe County

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Top-rated rentals with a pool in Simcoe County

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

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Guest favorite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 421 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Top guest favorite
A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.
Condo in Innisfil
4.99 out of 5 average rating, 182 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Top guest favorite
An open layout of the studio unit is displayed, featuring a modern kitchen with a breakfast bar and sleek cabinetry. The cozy living area contains a pullout sofa with decorative cushions, and a spacious king bed is situated in the corner, complemented by subtle green accent walls.
Apartment in The Blue Mountains
4.99 out of 5 average rating, 187 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convection oven combo along with a stove top *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

Guest favorite
Cottage in Tiny
4.96 out of 5 average rating, 140 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Guest favorite
A serene bedroom features a dark headboard positioned against light gray walls. Three botanical prints hang above a cozy bed with soft blue bedding. On either side, glass lamps provide gentle illumination, and a potted plant adds a touch of greenery near the window.
Condo in Innisfil
4.93 out of 5 average rating, 196 reviews

The Friday Flat | Sunny Escape by the Marina

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

Top guest favorite
A spacious open-concept living area is highlighted, featuring a large dining table set for meals. The kitchen is equipped with modern appliances and black cabinetry. Natural light enters through multiple windows, enhancing the inviting atmosphere of the space.
Condo in The Blue Mountains
4.98 out of 5 average rating, 187 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

Beautifully Newly Renovated Condo Located in Rivergrass on Fairway Crt, which is in the heart of Blue Mountain and Steps to the Village! Condo features 3 bedrooms(One king, two Queen and Two Twin beds with trundle pullouts), 2 full baths, kitchen, washer/dryer, living room, and dining room. Outdoor Pool (Open from June 1 to Sept 20) and Hot Tub(All Year). Short walk or take the shuttle bus to the village. Our cleaners are extensively disinfecting and sanitizing between each booking.

Superhost
An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.
Condo in Innisfil
4.87 out of 5 average rating, 170 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Experience the allure of Friday Harbour! Stay in this gorgeously furnished 1-bedroom condo, complete with a pullout sofa bed. Enjoy the stunning outdoor relaxation area that overlooks the courtyard pool. The condo features a spacious bedroom with a closet and a large bathroom. Its layout is perfect for both relaxation and entertainment, with an open concept living area and a kitchen featuring an island. Embrace the ultimate indoor and outdoor living experience at Friday Harbour!

Guest favorite
Aerial view of a charming multi-unit building surrounded by lush greenery. The structure features a combination of yellow and white exteriors, with distinct architectural details. A paved parking area is visible in the foreground, providing ample space for vehicles.
Condo in Oro
4.88 out of 5 average rating, 279 reviews

Spacious 1-br w jacuzzi at Horseshoe Valley

Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

Top guest favorite
An open-concept studio unit is shown, featuring a cozy living area with a dark sectional sofa and a wooden coffee table. The king bed is visible in the background, accompanied by modern bedding. The kitchen area includes a bar with stools and is equipped with countertop appliances.
Apartment in The Blue Mountains
5 out of 5 average rating, 115 reviews

Alpine Bliss: King Bed/Pool/HotTub/Shuttle

Newly renovated studio unit at the mountainside North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * Double Pull Out Sofa * Remodeled Washroom *Equipped Kitchen with Keurig * Modern, Stylish Decor *Shuttle Service *Year Round Hot Tub *Pool (closed for the winter season- to reopen Spring '26) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)!

Guest favorite
The spacious living area features a comfortable couch and an additional patterned armchair. Two side tables with lamps are present, providing soft lighting. Large windows with sheer curtains allow natural light to fill the room, while a flat-screen TV is mounted on the wall.
Apartment in Shanty Bay
4.84 out of 5 average rating, 104 reviews

Spacious Hideaway in Nature

Welcome to the charming Shanty Bay area! Embrace the relaxed vibes surrounded by natural beauty. Enjoy leisurely walks by Lake Simcoe or explore nearby parks like Oro-Medonte Rail Trail. Discover local shops and eateries, or indulge in water activities and outdoor adventures. Our cozy Airbnb accommodates 4 guests, with a king-size bed and comfy couches. Experience the best of both worlds - a laid-back getaway and exciting local attractions.

Top guest favorite
A living room features a flat-screen television mounted on a stone accent wall above a small fireplace. A cozy armchair and a wooden dining table with matching chairs are visible. Natural light filters in through a window adorned with soft curtains.
Condo in Oro
4.95 out of 5 average rating, 163 reviews

Pet-friendly, 1 BR condo in Horseshoe Valley

All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

Top guest favorite
The living area is designed with a cozy sectional and an armchair, accompanied by a coffee table. A television is mounted above a stone fireplace. Large windows provide ample natural light and views of the surrounding hills and golf course.
Condo in The Blue Mountains
4.95 out of 5 average rating, 925 reviews

Stunning Mountain View- Pool, Hot Tub, WalkToBlue

SHUTTLE, HOT TUB, SEASONAL POOL 5-7 minute walk to the Blue Mountain Village. This cozy 2 bedroom condo gives you immediate access to the action or a quiet place to relax by the fireplace while looking out at the mountain views. ★ ★ SMART TVs in living room (WIFI and Cable) and bedrooms (WIFI) ★ Family Ready! Games, booster seat, packnplay etc ★ Resort hot tub with indoor changeroom and washrooms Pool closed for the season

Popular amenities for Simcoe County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
A spacious bed is adorned with a textured white bedspread and a decorative 'welcome' pillow. Behind the bed, a scenic mural displays misty mountains and lush forests, enhancing the room's atmosphere. Two sleek reading lights are positioned on either side, adding functionality to the space.
Home in The Blue Mountains
4.84 out of 5 average rating, 107 reviews

Cozy Corner Townhome | Shuttle To The Village

Guest favorite
Home in The Blue Mountains
4.89 out of 5 average rating, 253 reviews

Large 4 Br - 4.5 Bathroom: 2 King beds/Sauna/games

Guest favorite
A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.
Home in Innisfil
4.89 out of 5 average rating, 84 reviews

2 Bd Boardwalk Condo Patio Oasis

Top guest favorite
Home in The Blue Mountains
4.89 out of 5 average rating, 107 reviews

Rivergrass Oasis: Across from Blue Mtn | Hot Tub!

Guest favorite
A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.
Home in Shanty Bay
4.86 out of 5 average rating, 100 reviews

King Bed, Pool, Gym, Ravine View, Your Getaway!

Guest favorite
The living area features large windows allowing natural light to illuminate the space. A modern sectional sofa with colorful pillows and a decorative throw faces a sleek coffee table. A cozy fireplace is positioned beneath a wall-mounted TV, creating a warm environment.
Home in The Blue Mountains
4.88 out of 5 average rating, 128 reviews

Blue Mountain Retreat In Historic Snowbridge

Guest favorite
The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.
Home in Barrie
4.91 out of 5 average rating, 116 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

Guest favorite
A master bedroom features a spacious bed adorned with a blue and white comforter. Light wooden flooring is complemented by a decorative nightstand and a stylish chandelier. Large windows allow natural light to fill the room, offering views of the greenery outside.
Home in The Blue Mountains
4.94 out of 5 average rating, 217 reviews

Serene mountainside home with View/Shuttle Bus

Condo rentals with a pool

Guest favorite
The open concept living area features a spacious sofa with blue accent pillows, a flat-screen TV mounted above a modern fireplace, and large windows providing natural light. A dining area with bar stools is visible, complemented by a rustic wooden table.
Condo in The Blue Mountains
4.82 out of 5 average rating, 207 reviews

Blue Escape | Ski-In-Out, Hot Tub & Shuttle

Top guest favorite
A cozy family room features a spacious gray sectional sofa and a wooden coffee table. Light-colored walls and a patterned rug create a welcoming atmosphere. In the background, a kitchen area is visible, equipped with modern appliances and seating for two.
Condo in The Blue Mountains
4.93 out of 5 average rating, 310 reviews

Cozy Studio Mountainside stay in Blue Mountains

Guest favorite
A modern kitchen area features blue cabinetry with open shelves displaying neatly arranged dishes. A central island with seating for two is complemented by sleek bar stools. Stainless steel appliances are integrated into the kitchen layout, providing a functional and inviting cooking space.
Condo in The Blue Mountains
4.87 out of 5 average rating, 469 reviews

Base of Blue Mountain, Modern Studio

Guest favorite
The open concept living area features a modern sofa and armchair arranged around a glass coffee table. A gas fireplace is centered on the wall beneath a mounted TV. Light streams through large windows, illuminating the space.
Condo in The Blue Mountains
4.88 out of 5 average rating, 275 reviews

Hidden Haven - Shuttle to the Village & Ski lifts

Top guest favorite
A bright living area features large windows that allow natural light to fill the space. Comfortable seating is arranged around a central coffee table, with a modern fireplace and a wall-mounted TV providing amenities. Soft, neutral tones dominate the décor, creating a relaxed atmosphere.
Condo in The Blue Mountains
4.97 out of 5 average rating, 110 reviews

3 Peaks at Blue Mountains, your luxury staycation!

Superhost
The studio features a spacious living area with a comfortable sofa and a modern armchair. A king bed adorned with blue and yellow linens is positioned in the background. Natural light filters through the window treatments, enhancing the serene ambiance.
Condo in The Blue Mountains
4.83 out of 5 average rating, 431 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Superhost
A modern kitchen area is showcased featuring sleek white cabinetry and stainless steel appliances. A stone countertop provides space for meal preparation, complemented by four red stools. A bowl of green apples adds a fresh touch to the dining area, enhancing the inviting ambiance.
Condo in The Blue Mountains
4.9 out of 5 average rating, 559 reviews

Blue Mountain Studio with Summer Pool

Superhost
A spacious bedroom features a large bed with a light floral-patterned coverlet. Two bedside tables with lamps are positioned on either side, while soft light filters through a window adorned with light curtains. A framed artwork hangs above the bed, contributing to a calming atmosphere.
Condo in Blue Mountains
4.83 out of 5 average rating, 283 reviews

Private Backyard/Shuttle/Pool/10min walk 2 village

Other vacation rentals with a pool

Top guest favorite
An open living area is highlighted by a spacious sectional sofa and a round coffee table. Floor-to-ceiling windows offer views of the marina. A dining table with chairs is positioned nearby, and a stylish kitchen island with a marble countertop completes the space.
Condo in Innisfil
4.98 out of 5 average rating, 64 reviews

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

Guest favorite
A multi-level building showcases a welcoming entrance with a staircase leading to the upper floors. White railings and balconies are visible on each level, surrounded by manicured greenery and a stone pathway that enhances the inviting appearance.
Apartment in Oro-Medonte
4.97 out of 5 average rating, 58 reviews

Oro-Medonte/(ski),in/out pool 1

Guest favorite
A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.
Cottage in Wasaga Beach
4.95 out of 5 average rating, 295 reviews

GATED RESORT COTTAGE

Top guest favorite
An open concept living and dining area features a comfortable grey sectional sofa and two circular coffee tables on a textured area rug. The kitchen bar is equipped with four high-backed chairs. Large windows allow natural light to illuminate the space, with views of lush greenery outside.
Townhouse in The Blue Mountains
4.94 out of 5 average rating, 537 reviews

3BR Sierra Scandi Chic - Closest to Village

Top guest favorite
The living area features a light-colored sofa paired with a stylish armchair, placed on a neutral-toned area rug. Large glass doors provide access to the private patio, allowing natural light to fill the space. An elegant coffee table is centered in the area, complemented by modern decor.
Condo in Innisfil
4.96 out of 5 average rating, 73 reviews

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

Top guest favorite
A modern living area features a gray sofa adorned with decorative pillows, accompanied by a glass coffee table and a patterned area rug. Wall shelves display decorative items and potted plants, adding a fresh touch to the muted backdrop.
Apartment in Innisfil
4.98 out of 5 average rating, 48 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

Top guest favorite
A cozy living area features a spacious sectional sofa adorned with soft pillows, complemented by a minimalist coffee table. Natural elements are highlighted by an accent wall showcasing a scenic forest mural. The nearby sleeping area includes a neatly made bed with fresh linens.
Condo in Shanty Bay
4.99 out of 5 average rating, 78 reviews

Wildwood HotTub+Indoor/Outdoor Pool+Sauna+GameRoom

Guest favorite
A modern living space features a sleek television mounted above a stylish wooden media console with drawers. A comfortable chair with a cushion is positioned nearby, complemented by a small potted tree. Natural light fills the area through large windows.
Apartment in Innisfil
4.93 out of 5 average rating, 54 reviews

Beautiful 2 Bed/2 Bath Condo, Private Balcony

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Rentals with pools