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Pet-friendly vacation rentals in The Annex, Old Toronto

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in The Annex, Old Toronto

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.

Home in The Beaches

4.99 out of 5 average rating, 142 reviews

Heated Pool-tub Open 365 Days

** Ask about MID WEEK Specials. Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

A bright and airy kitchen and dining area features large glass doors that open to a lush outdoor space. A dining table with modern chairs is set beside sleek cabinetry. Natural light fills the room, highlighting minimalist decor and a comfortable seating area.

Apartment in Roncesvalles Village

4.94 out of 5 average rating, 120 reviews

TreeTops! Sunny Style for 8-14. HighParkHomes .ca

*Here's why people choose @HighParkHomes .ca - better value for top location. *Sleeps 8. Sleeps 14 booked w Garden Suite. Message HighParkHomes .ca for detail. *Walk: Dundas W, Queen W, Trinity Bellwoods, Little Italy, Roncy, High Park, Bud Stage. *Sublime Scandi decor. *Dine surrounded by 8-foot windows. *BIG bedrooms + Den. 4 queen mattresses. *Full chef's kitchen. *2 decks. BBQ. *2 full baths. Rain showers. Italian bidet. *Heated floors. Oak, stone, marble finishes. *Cable TV and apps

The exterior view features a modern two-story house with a stone facade and a welcoming front porch. A neatly landscaped yard with shrubs and a tree provides a touch of greenery. The double garage doors are prominently displayed, complementing the home's elegant design.

Home in Churchill Meadows

4.9 out of 5 average rating, 41 reviews

Holiday retreat in Toronto

Make memories at this one-of-a-kind, family-friendly haven. With 5 bedrooms and 3.5 baths, it offers ample space. Only 2 kms from RIDGEWAY PLAZA and Meadowvale Town Centre. On a quiet street yet only 2 kms from the largest restaurant cluster in entire Toronto. An experience not comparable to anything in entire Canada. The fully equipped kitchen and the high-end mattresses ensure restful sleep. The tasteful decor adds a special touch. House is professionally cleaned between bookings.

A spacious living area features modern furnishings, including a sleek black sectional sofa and a non-reflective coffee table. Natural light enters through a window adorned with shutters. A round mirror reflects the room's warmth, while a light fixture illuminates the space. A playground is visible outside.

Home in Brampton

4.92 out of 5 average rating, 24 reviews

Comfortable Stay Near Airport - Brampton 5B/3.5B

Experience luxury and comfort at our Modern Brampton Getaway Near Airport —book now before it's gone! ★ Top-tier furnishings throughout ★ High-speed internet up to 500 Mbps ★ Free dedicated parking ★ Smart TVs in the living room ★ Luxurious queen and double beds with premium mattresses ★ Fully equipped kitchen with essentials ★ Dedicated remote workstation ★ Prime location near the Airport (15 minutes), Vaughan Mills Mall, Wet n Wild, Canada's Wonderland, Parks, and shops.

A cozy outdoor seating area features comfortable gray wicker furniture arranged around a wooden deck, with decorative flower boxes enhancing the backdrop. Surrounding greenery provides a serene atmosphere, complemented by clear blue skies and a nearby heating element for cooler evenings.

Apartment in The Beaches

4.92 out of 5 average rating, 117 reviews

One bedroom vacation rental at The Beaches

Welcome to Our Cozy Retreat! Escape to our relaxing, perfectly situated in a prime location at the Beaches, a few minute walk to the: - Beautiful beaches - The vibrant waterfront boardwalk - Bike path and parks - A variety of delicious restaurants, pubs and shops Local Amenities including such as: - Spa and wellness services - Nail and hair salons - Flower, gift, and clothing shops - Grocery stores - Yoga studio - History Toronto (concert venue) - Theatre

A wooden outdoor dining table is set for four, featuring plates, wine glasses, and a bottle of champagne. Sunlight filters through the leaves, creating dappled patterns on the table. A cozy atmosphere is enhanced by surrounding greenery and wooden fencing.

Home in Toronto

4.87 out of 5 average rating, 53 reviews

Hotel Inspired Relaxing Oasis w/Parking

Adorable Historic Home with Private Patio & Parking. ♡ 3 bedroom & 1 bath (1 King & 1 Queen & 1 Twin) ♡ Hotel Inspired Home with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Steps from St. Clair transit line ♡ 90/100 Walk Score ♡ 100/100 Transit Score ♡ Close to Casa Loma | Rated #1 by BlogTO of Places to Visit in Toronto ♡ Flexible Check in Check out - Message for Details Smart TV ♡ A/C ♡ Laundry ♡ Fully Equipped Kitchen ❤ Book today!

The exterior view presents a charming bungalow surrounded by greenery and flowering trees. A neatly paved driveway leads to the entrance, with a vibrant garden lining the pathway. The residence features a blend of brick and light-colored siding, creating an inviting first impression.

Apartment in The Beaches

4.91 out of 5 average rating, 290 reviews

Honey House in the Beach

A clean, private two bedroom apartment in the fully finished basement of our funky and well kept bungalow. A great backyard with a hot tub, several decks and a 3-season garden room to share- all great places for a morning coffee or late night drink. The private washroom has just been totally renovated - new everything! Two bedrooms, each with one double bed. Sleeps four. *a heads UP for tall guests, this is a basement apartment 7foot ceilings

The exterior of the urban home is presented, featuring a dark blue façade and a sloped roof. A small, neatly landscaped front yard is enclosed by a black picket fence. Large windows allow for natural light, with a Canadian flag displayed proudly outside.

Home in Leslieville

4.96 out of 5 average rating, 72 reviews

Cozy Leslieville 2-Bedroom Home

Unique urban home located right next to Greenwood Park where the Leslieville Farmer's Market happens May - October. Perfect for families with children and dogs as the dog park is less than 1 minute away. Convenient access to Queen St. restaurants and the streetcar 5 minutes away. Be downtown Toronto in 15 minutes. Free parking behind house. Explore all Leslieville has to offer.

An outdoor deck is furnished with a sofa adorned with patterned cushions, a wooden table, and several potted plants. Vibrant flowers and greenery surround the area while a pet relaxes on the deck, offering a peaceful spot with a view of the landscape beyond.

Guest suite in South Parkdale

4.93 out of 5 average rating, 96 reviews

Lakeside in the city

Over 1300 square feet apartment with views. Located on a quite dead end street with amazing lake views but in the heart of trendy parkdale highpark area. Only 20 minutes from Scotia Arena via 504 king streetcar , 15 min walk to high park, Sunnyside pool, shops and restaurants on Roncesville. Close to great walking trails along the lake, High park and the Martin Goodman trail.

A modern living room features a minimalist design with a cozy sectional sofa and a contemporary armchair. A dark coffee table is centered on a striped rug, while a flat-screen television sits on a sleek shelf. Natural light enters through a large window adorned with light blinds.

Home in Yonge and Eglinton

4.93 out of 5 average rating, 29 reviews

Luxury Modern House with EV Charger in Mid-Town

Available for a long-term rental from mid-August. This modern home is located in one of the most desirable, affluent and safest neighborhoods of Toronto. Bright and sunny, it's beautifully decorated and has a cozy backyard/oasis in the heart of the city. 2 min walking distance to trendy and vibrant area with shops, cafes, casual/fine dinning, bus stop, etc.

The outdoor space is highlighted by a saltwater pool enclosed by a safety fence. Paved patio areas provide seating options, complemented by grassy lawns and mature trees that enhance privacy. The side of the house features a warm brick exterior and a barbecue area.

Home in Clarkson

4.85 out of 5 average rating, 41 reviews

Clarkson Place with pool

Located in the lakeshore area of Mississauga. Minutes away from QEW and walking distance to lakeshore in highly sought after Clarkson Village. Placed on a large corner lot of a quiet street, fully fenced large yard complimented with pool, patio & walk out living room. 20 mins downtown Toronto, 5 min walk to the GO Transit.

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Popular amenities for The Annex, Old Toronto pet-friendly home rentals

Free parking on premises

Air conditioning

Pet-friendly house rentals

The entrance features a welcoming porch with light-colored railings and potted flowers. A mix of vibrant plants and flowers provide color, while a wooden path leads to the entrance. Hanging plants and outdoor decor add charm to the inviting exterior.

Home in Roncesvalles Village

4.92 out of 5 average rating, 152 reviews

Cozy one bedroom apartment in Roncesvales village

Top guest favorite

A spacious living area features light wood flooring and neutral-toned furnishings. A comfortable sofa is positioned alongside a small dining table and chairs near the window. Artwork adorns the walls, and natural light enters through the door, which has a decorative glass design.

Home in North York

4.92 out of 5 average rating, 25 reviews

One Bedroom street level unit/separate entrance

A well-lit bedroom features a spacious bed dressed in a floral-patterned quilt. Natural light filters through large windows, illuminating the room's modern decor, including a comfortable seating area and sleek furniture. The walls are adorned with tasteful artwork, enhancing the serene atmosphere.

Home in Downtown Toronto

4.95 out of 5 average rating, 111 reviews

Victorian Home Downtown Toronto, Cabbagetown

A well-maintained backyard is visible, featuring a neatly mowed lawn covered with fallen leaves. Surrounding greenery adds a natural feel, complemented by a wooden fence providing privacy. A portion of the back deck is seen in the foreground, enhancing the outdoor space.

Home in Richmond Hill

4.73 out of 5 average rating, 11 reviews

Theniceday - Family Friendly House

A wooden staircase leads to the upper floor, enhanced by detailed railings. A vintage wooden writing desk is positioned against the wall, showcasing a rich finish. Warm wooden flooring runs throughout the space, creating a cohesive and inviting entryway.

Home in Toronto

5 out of 5 average rating, 4 reviews

3 bdr home + bsmt in Swansea/High Park

Top guest favorite

The inviting living area features modern furnishings, including a blue sofa and a circular coffee table. A dining table with chairs is positioned near the kitchenette, which has sleek cabinets and a stainless steel refrigerator. Ambient lighting adds to the cozy atmosphere.

Home in Scarborough

5 out of 5 average rating, 15 reviews

Cozy Basement Suite 20 min near Downtown

Top guest favorite

A well-lit entryway features a staircase leading to the upper level, framed by sleek white walls. A mirror adorns one wall, while a storage rack for shoes and a hanging area for coats are positioned nearby. Natural light filters in through a shuttered window.

Home in North York

5 out of 5 average rating, 51 reviews

Spacious N Bright 3Bd/1.5Ba Updated Suite/Parking

Top guest favorite

A cozy living area is presented with a large gray sofa adorned with a red plaid pillow. A coffee table sits in front, accompanied by indoor plants of varying heights. Sunlight filters through the nearby windows, enhancing the warm atmosphere of the space.

Home in Leslieville

4.98 out of 5 average rating, 131 reviews

4 BR, 3BA Modern Toronto Home | Offices, Espresso

Pet-friendly home rentals with a pool

A modern living area features a plush gray sectional sofa accompanied by a decorative rug. Large windows provide ample natural light and showcase a city skyline view. A dining table with dark chairs sits nearby, complemented by a wall-mounted art piece and a potted plant.

Condo in Fort York

4.96 out of 5 average rating, 132 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

A modern living area is furnished with a large gray sectional sofa, paired with a light coffee table and rug in soft blue shades. Two framed artworks decorate the wall, while a dining table with chairs is visible in the background, creating a functional and inviting space.

Condo in Mississauga

4.86 out of 5 average rating, 207 reviews

🔥Charming 1 BR Condo🔥 Steps To Square One!👌

A private backyard features a grassy area with a children’s playground, including a slide and swing set. Mature trees provide shade, while colorful plantings add vibrancy. A saltwater pool is visible in the background, enhancing the outdoor space for relaxation and recreation.

Home in Central Etobicoke

4.89 out of 5 average rating, 9 reviews

Luxury 2bedroom Unit in the city/heated salt pool.

The outdoor area features a large in-ground swimming pool surrounded by a stone patio, with bright yellow chairs positioned nearby for relaxation. Lush greenery and wooden fencing provide privacy, creating a tranquil space ideal for outdoor enjoyment.

Home in Scarborough

4.95 out of 5 average rating, 101 reviews

New Cstm Bld 2 BDRM Cozy Suite-Heated Flrs-Game Rm

A spacious grassy area is framed by large trees, providing a natural backdrop. The section is bordered by a wooden fence, ensuring privacy and security. The scene encompasses a tranquil setting ideal for relaxation or gatherings.

Home in Scarborough

4.94 out of 5 average rating, 16 reviews

Lakeview Cottage in the City with Pool

A spacious yard is enveloped by lush green grass, with mature trees providing shade and a serene atmosphere. The home is visible in the background, harmonizing with the surrounding greenery. A variety of plants and flowers can be seen, enhancing the natural beauty of the landscape.

Home in Cooksville

5 out of 5 average rating, 13 reviews

The Retreat

A balcony view showcases a bustling urban landscape, featuring modern buildings of varying heights and designs. The foreground includes a glass railing, while street activity and greenery can be seen below, suggesting a lively city atmosphere.

Apartment in Downtown Toronto

5 out of 5 average rating, 46 reviews

Stylish Condo in the Heart of Downtown Toronto

A private balcony is shown with a white sofa set against green turf. Floor-to-ceiling glass doors provide views of the cityscape, featuring modern buildings with reflective glass exteriors. A large potted plant adds a touch of greenery to the outdoor space.

Condo in Downtown Toronto

4.97 out of 5 average rating, 105 reviews

FREE Parking! CN Tower Views! Amazing Condo

Private, pet-friendly home rentals

Top guest favorite

A spacious sitting area features a large circular coffee table atop a striped rug. A comfortable red couch adorned with colorful cushions provides seating. Soft lighting highlights the decor, while an open space leads toward the back of the basement apartment.

Apartment in East Danforth

4.94 out of 5 average rating, 406 reviews

1 Br Basement Apartment/next to Subway - Full Apt

A spacious living area features a comfortable dark sofa facing a modern electric fireplace. A large screen displays local weather. Natural light enters through large windows, and a dining space is visible through an archway, complemented by a decorative wall art piece.

Home in Brampton

4.9 out of 5 average rating, 21 reviews

Luxury 3+1 Bedrooms Home…

A cozy sitting area features a light-colored sofa adorned with patterned cushions and a woven throw. A clock with a minimalistic design showcases numbers without hands on the wall above. A floor lamp stands beside the sofa, contributing to the bright ambiance.

Home in Scarborough

4.88 out of 5 average rating, 25 reviews

2 Beds lower lvl apt w/Parking

The backyard features a spacious grassy area bordered by a wooden fence, offering privacy. Lush greenery, including a large tree and a small ornamental maple, enhance the natural setting. A stone pathway leads to a firepit, creating a welcoming space for outdoor relaxation.

Bungalow in North York

4.77 out of 5 average rating, 31 reviews

Chic 2-Bedroom Bungalow

A living area features a gray sofa adorned with a decorative pillow. A coffee table with wooden legs is placed on a patterned rug, while a blue seating group is visible in the background. Soft lighting from recessed fixtures highlights the space.

Home in Richmond Hill

5 out of 5 average rating, 6 reviews

Stylish unit, Your Cozy Getaway!

A bright office space is furnished with a simple wooden desk and a black office chair. A laptop is placed on the desk. Natural light filters through large windows, enhancing the clean and functional atmosphere. A sleek photograph of sailboats adorns the wall.

Townhouse in Oakville

4.83 out of 5 average rating, 6 reviews

Executive 3 Bedroom & Prof Office Townhouse

A cozy living area features a patterned sofa arranged in front of a modern electric fireplace. A wooden coffee table with decorative items occupies the center space. Elegant shelving above the fireplace displays a selection of plants and artwork, enhancing the room's design.

Home in Streetsville

4.89 out of 5 average rating, 27 reviews

Riverfront home,sauna,gym.15 min Airport. Sleeps 8

Guest suite in East York

4.86 out of 5 average rating, 14 reviews

The Hideaway Hub (2 bdrm basement)

Quick stats about vacation rentals that are pet-friendly in The Annex, Old Toronto

Total rentals
40 properties
Total number of reviews
960 reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
Royal Ontario Museum, Yorkville Village, and Lee's Palace

Destinations to explore