Pet-friendly holiday rentals in Dunedin

A charming Florida bungalow features a turquoise exterior with natural stone accents. The front porch is accessed by a concrete pathway lined with greenery, including tropical plants. A small entry door and window allow for natural light, framed by neatly placed shutters and landscaping.

4.92 out of 5 average rating, 285 reviews

Wonderful family friendly home in Dunedin FL

Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.

4.96 out of 5 average rating, 204 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

Tiki Hut Cottage

This unit private vacation rental is located on the property, plenty of space for 5 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Conveniently located to the downtown & beach. This unit is pet friendly, we allow 1 dog. Wether your dog is or is not a service dog we have the following guidelines no excessive parking clean up after your pet any physicial damage caused by the pet will be subject to reimbursement

4.97 out of 5 average rating, 392 reviews

The exterior of a coastal cottage is shown, featuring a gravel driveway and tropical landscaping with palm trees. Two wicker chairs are positioned under a covered porch, inviting relaxation. Large windows allow natural light to brighten the welcoming facade.

Cottage in Dunedin

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater Beach, this stylish upstairs 2-bedroom cottage blends modern coastal design with exceptional comfort. Tropical murals, treetop views, two king beds, and a sleeper sectional create a chic and comfortable stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.

4.93 out of 5 average rating, 100 reviews

Apartment in Dunedin

Owl Nest Townhouse-Walk downtown, new POOL!

Our brand-new construction condo offers everything you’ll need for an enjoyable and comfortable stay in Delightful Dunedin! Steps from the heart of downtown Dunedin, our quaint costal town offers amazing restaurants, shops, parks, breweries, festivals, night life, marina and Blue Jays baseball! Close to Honeymoon and Caladesi Islands and Clearwater Beach-award winning beaches! New heated pool! *As of March 4, 2024 Owl unit has been combined with Osprey unit to make a more spacious condo.

4.97 out of 5 average rating, 121 reviews

Dunedin Roost · 1BR Suite · Walk to Pinellas Trail

A private, self-contained suite in Dunedin, FL - your own entrance, patio, and king bed. One block from the Pinellas Trail, two blocks from TD Ballpark (Blue Jays spring training), and a mile to downtown's breweries and restaurants. Grab the cruiser bike and ride to Honeymoon Island or Clearwater Beach. Built in 2023, includes beach gear, room-darkening shades, and everything you need for a real stay, not just a weekend. Dogs welcome ($125 pet fee, payable on arrival through Airbnb).

4.88 out of 5 average rating, 121 reviews

Serenity Bungalow Downtown

Kick back and relax in this stylish bungalow, perfectly situated at the gateway to downtown Dunedin’s vibrant corridor. Explore a variety of shops, microbreweries, pubs, and restaurants, all just steps away. Enjoy the scenic marina and catch fabulous sunsets at the west end of downtown. Located right across the street from a lively restaurant and bar, this bungalow places you in the heart of the action, making it the ideal spot for your Dunedin getaway. Pet fee is per pet.

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

4.9 out of 5 average rating, 176 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

Tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today! Please note that the minimum age requirement to book is 23.

4.74 out of 5 average rating, 294 reviews

A well-appointed room showcases a spacious bed with soft linens against a light-colored wall. Natural light streams through multiple windows, enhancing the comfortable seating area featuring a gray sofa and small white dining table. A touch of greenery is added with a potted plant.

Hotel room in Dunedin

Seaside Artisan *Dog Friendly* 5

This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s. There is no lobby for the guests, however we do list for rent the owner suit with front desk on airbnb as well. You can find it under “Seaside Artisan Motel Owner Suit”. This Airbnb is walking distance from the restaurants, shops and bars in Dunedin. It’s about 4 miles away from Honeymoon Island and about 6 miles from Clearwater Beach.

A serene outdoor space features a heated pool, reflecting the colorful sky during sunset. Strands of lights are draped above, enhancing the inviting atmosphere. Comfortable loungers are placed beside the pool, with dining areas visible in the background, surrounded by lush greenery.

4.96 out of 5 average rating, 135 reviews

Heated saltwater pool|Spacious 4BR/3BA|

Welcome to Cerulean Cottage, our coastal home centrally located in Dunedin, Florida. Whatever brings you to this area, you will find yourself right at home in our comfortable beds, cozy couch, and functionally designed spaces. Have a blast in the pool and game room and wind down in our new 4D massage chair. We are close to conveniences, including grocery stores and many favorite local restaurants and just a short drive from our quaint downtown and beaches.

4.94 out of 5 average rating, 243 reviews

A colorful exterior is framed by lush greenery and tropical plants. A brick pathway leads to the entrance, with a dining area featuring a table and chairs amidst the vibrant surroundings. Sunlight streams through the trees, creating a serene atmosphere.

Apartment in Dunedin

The Coastal Retreat

Studio apartment. Light airy Coastal Eclectic décor. Walk in closet, full size bath, Fully equipped kitchen . Key west style tropical courtyard with fish pond. Off street parking . Gas grill and outdoor dining area. One block off the Pinellas Bike trail, walking/biking to historic downtown Dunedin, Toronto Blue Jays spring training. Minutes to the 3 of the country's best beaches! Clearwater Beach, Honeymoon Island, and Caladesi Island.

Superhost

4.84 out of 5 average rating, 116 reviews

2 Homes- Heated Pool & Pickleball- The Dunedin Duo

Escape to your private resort! This unique Dunedin property features TWO homes perfect for up to 16 guests. Enjoy a heated pool, private mini-golf, and a pickleball court just minutes from Florida's best beaches. With a massive, fully-fenced backyard oasis packed with games and an outdoor kitchen, it's the ultimate group getaway. Ideal for large families seeking endless fun and relaxation near downtown Dunedin and Clearwater Beach

4.95 out of 5 average rating, 223 reviews

Cottage in Dunedin

Best Location! Walk to Dining, Trail & Stadium

Charming 1920s cottage in Dunedin just 3 blocks from the water and lively downtown! Walk 2 blocks to the Pinellas Trail, Fenway Hotel, and TD Ballpark. Enjoy a private outdoor retreat surrounded by lush greenery—perfect for morning coffee. Bright, inviting interiors with a sunny kitchen, spacious living area, and cozy beds make this the perfect getaway for beach days, biking, dining, and sunsets! Book early, dates fill fast!

Popular amenities for Dunedin pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

An inviting living room showcases ample seating with a gray sectional couch and plush ottoman. A cozy dining area is visible outdoors, furnished with a table and chairs under a shaded canopy. The sparkling pool, surrounded by lounge chairs, is highlighted by vibrant tropical landscaping.

4.93 out of 5 average rating, 106 reviews

3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!

4.93 out of 5 average rating, 122 reviews

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.

4.93 out of 5 average rating, 132 reviews

Lakefront home near beaches w/ waterview, pets ok

4.91 out of 5 average rating, 204 reviews

Home in Largo

The Oasis - Arcades - Golf & Games - HTD Pool

The exterior of a retro home is highlighted by a red vintage truck parked in the driveway. Lush greenery, including palm and flowering plants, surrounds the property, while two distinct pathways lead toward the entrance. The warm concrete driveway complements the inviting atmosphere.

5.0 out of 5 average rating, 121 reviews

Sleeps 10, pet friendly/ fenced yard, near beaches

4.96 out of 5 average rating, 111 reviews

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Holiday

Paradise!Renovated waterfront pool home.Sunsets!

A comfortable living area is showcased with a beige sofa adorned with colorful pillows and two green accent chairs. A ceiling fan provides airflow, and natural light filters through large windows. The open layout connects to the kitchen area, creating a bright and inviting atmosphere.

4.93 out of 5 average rating, 158 reviews

Cozy Retreat! Walk to Crystal Beach/Park

4.95 out of 5 average rating, 21 reviews

Walk Downtown & Waterfront | Dunedin's Best Street

Pet-friendly home rentals with a pool

Condo in Clearwater Beach

A spacious outdoor terrace features modern seating arrangements with gray cushions and white wooden frames. Clear glass railings provide unobstructed views of the Gulf of Mexico, while a single palm tree adds a touch of greenery to the coastal setting.

Beachfront on Clearwater Beach!

4.84 out of 5 average rating, 192 reviews

4.92 out of 5 average rating, 173 reviews

Home in Largo

Swim-Out Bedrooms, Waterfall pool, Peace Place

4.88 out of 5 average rating, 147 reviews

Hot Tub, Heated Pool, Minutes to Clearwater Beach

Bungalow in Indian Rocks Beach

A decorative lamp features a mermaid holding a round, glowing orb. The lamp is set against a backdrop of a colorful wave painting and neatly folded towels, adding a touch of coastal charm to the workspace.

Your private Waterfront Pool home!

4.97 out of 5 average rating, 234 reviews

4.78 out of 5 average rating, 107 reviews

Chic|Pool|PuttingGreen|Beaches

A vibrant pool area features playful tiger floaties and white spherical decorations floating on the surface. The pool is surrounded by comfortable lounge chairs and hammocks, with colorful drapes leading to the entrance of the house. Lush greenery and palm trees add a lively touch.

4.9 out of 5 average rating, 236 reviews

Clearwater GLAM | Pool, Games, Hot Pink Oasis!

Bungalow in Indian Shores

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

4.97 out of 5 average rating, 206 reviews

The outdoor area presents a heated swimming pool surrounded by a patio made of stone. Lush greenery and tropical plants frame the pool, while a nearby gazebo offers shaded seating. Bright blue lounge chairs are positioned by the water, creating a relaxing environment.

4.98 out of 5 average rating, 121 reviews

Paradise palms oasis Clearwater

Private, pet-friendly home rentals

4.95 out of 5 average rating, 140 reviews

Bungalow in Clearwater

Cozy Bungalow near Beaches and Downtown Dunedin

4.93 out of 5 average rating, 107 reviews

A covered patio features four comfortable wicker chairs surrounding a glass-top table. Large windows provide views of palm trees and the sunset over the water, creating a serene outdoor space for relaxation.

Apartment in Clearwater

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

4.96 out of 5 average rating, 205 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

4.86 out of 5 average rating, 403 reviews

A cozy interior space features a neutral color palette with a striped bedspread. A serving tray holds two white cups beside a small dish of candy. Natural light fills the room, highlighting a kitchenette in the background, complemented by white cabinetry and a subtle decor.

Cottage in Dunedin

Cozy up in a French Country nest NEAR EVERYTHING

Luxe

An open-concept kitchen and living area showcases modern design elements. A large island with a sink and sleek countertop is highlighted, accompanied by elegant pendant lighting. Expansive windows bring in natural light, while a comfortable seating area and dining space are visible in the background.

Townhouse in Dunedin

Rooftop+Balcony- Luxury Stay in Downtown Dunedin

5.0 out of 5 average rating, 54 reviews

4.94 out of 5 average rating, 31 reviews

A bright and airy living area features a light-colored sofa adorned with decorative pillows, complemented by a stylish round table set for two. Large windows allow natural light to fill the space, showcasing a modern kitchen equipped with updated appliances.

Condo in Dunedin

Quiet Locale King Beds 1 Mile To Honeymoon Island

4.72 out of 5 average rating, 25 reviews

Bungalow in Dunedin

Dunedin Blue Bird Bungalow

A wooden dock stretches over calm water, framed by white railings. One black Adirondack chair is positioned to enjoy views of the water and distant shoreline against a backdrop of a pastel sky at dusk.