Family-friendly holiday rentals in Dunedin

Two modern tiny homes are situated next to each other, featuring a light color palette. Each unit has large glass doors leading to a spacious deck with railings, while lush greenery surrounds the area, providing a natural ambiance.

4.95 out of 5 average rating, 103 reviews

Surf Shack Tiny Home on Pinellas Trail w/ Heated P

Welcome to the Dunedin Tiny House Vacation Rentals! This Vacation Rental property offers daily, weekly or monthly rentals in 4 luxury tiny homes, a 3 bed bungalow & 1 bed cottage. The 6 Units along with a large Heated Pool are all tucked away within a thoughtfully planned, peaceful & wooded lot.... located right on the Pinellas Trail! The front entrance is conveniently located on Bayshore Blvd just north of the crossroad of Wilson. Once you enter the front door of your unit you will enjoy a

Indoor spacesFamilyWi-Fi

4.97 out of 5 average rating, 201 reviews

A spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.

Place to stay in Dunedin

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

FamilyKitchenAccuracy

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

4.99 out of 5 average rating, 389 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint prime downtown street. Private yard with grill in terrific location. Walk to restaurants, breweries, shops, and live music. Walk to Dunedin's gorgeous sunsets or drive minutes to award-winning beaches such as Honeymoon & Caladesi Island & Clearwater Beach. Sleeps 6. Two king bed suites and a luxury leather couch that sleeps 2 more. Loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today!

Indoor spacesKitchenSleep quality

4.93 out of 5 average rating, 176 reviews

A renovated bungalow is presented with a charming front porch, framed by palm trees and lush greenery. Soft lighting highlights the entrance, which features dual doors leading into the home. A landscaped pathway guides visitors to the inviting entrance.

Bungalow in Dunedin

Artisan Island Bungalow / Walk To Downtown

* HOSTED BY GABE & SHANNON * Enjoy your visit to Dunedin (& surrounding areas) in our custom renovated bungalow! Originally built in 1918, this home has been painstakingly revived to reflect our thriving creative community. Much of the home has been built and decorated using the skills of local artisans. Many things - from the front deck to the furniture to the very plates you’ll eat off of - are handcrafted originals. This isn’t just a place to crash. It's a living, breathing work of art.

Indoor spacesKitchenParking

4.91 out of 5 average rating, 317 reviews

A spacious sleeping area features a large bed with a white comforter and decorative throw. A modern lamp illuminates a side table. Soft blue walls complement the artwork depicting a beach scene, while a cozy chair adds a comfortable seating option.

Guest suite in Dunedin

Downtown Coastal Studio, close to great beaches!

The studio has a bright and airy atmosphere, clean and cozy, it is the perfect place to rest and relax. Located in the heart of downtown Dunedin in walking distance to the Pinellas Trail and Main St. Simply park your car and enjoy town on foot or rent a bike and cruise around. We are close to Honeymoon Island and Clearwater Beach. Beach towels, chairs, cooler, and umbrella are provided. There is also a park across the street with a nice path to stroll along the water or take in the sunset.

FamilyKitchenAccess

4.94 out of 5 average rating, 239 reviews

Walkable, fun, local Dunedin experience

Stay in this charming 1920s cottage, where you can walk to local restaurants, breweries, and shops, or take a short walk to the marina for a sunset. Perfectly located in the heart of Dunedin, this home makes it easy to explore the area on foot. Spend your days enjoying nearby beaches, biking the Pinellas Trail, or catching a game at TD Ballpark to watch the Toronto Blue Jays. After a day of beach fun, baseball, or exploring, then enjoy an easy walk for dinner, drinks, or live music downtown.

KitchenIndoor spacesOutdoor spaces

A welcoming outdoor space is highlighted by two red lounge chairs, adorned with floral cushions, positioned on a paved area. Lush greenery, including banana plants, frames the cottage-style villa, while a small seating area is visible in the background, providing a tranquil setting.

4.96 out of 5 average rating, 127 reviews

Adorable Villa 1 min to Downtown Dunedin

Welcome to our 1/1 cottage-style villa, which is minutes from Downtown Dunedin. Only a short walk to Main Street and a 12 min drive to Honeymoon/Caladesi Island! Walk to the Pinellas Trail, breweries, eateries, waterfront marina, and Blue Jay baseball stadium. Enjoy award-winning cuisine, live entertainment, and breathtaking sunsets before returning to the peace and quiet of your own private area. Dunedin is a gulf cart friend city with local rental available to cruise around town.

Indoor spacesFamilyAccess

4.88 out of 5 average rating, 115 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.

KitchenIndoor spacesLocation

A tranquil lagoon pool is surrounded by lush tropical foliage and colorful flowers. A shaded seating area is visible, along with a light-colored house in the background. Multiple palm trees contribute to the serene atmosphere of this private oasis.

4.99 out of 5 average rating, 275 reviews

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Indoor spacesFamilyWi-Fi

4.83 out of 5 average rating, 301 reviews

A spacious room is highlighted by a comfortable bed covered with a soft blanket. Natural light enters through large windows, illuminating the tile floor. A small dining table with a chair and a bedside lamp offers additional convenience. Closet doors are visible against a wooden wall.

Hotel room in Dunedin

Seaside Artisan Apartment 9

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.

Indoor spacesFamilyAir conditioning

A bright, modern living area features a blue couch and two woven chairs, with light streaming in from windows. A round dining table is visible in the background, and the kitchen is partially revealed, highlighting the open floor plan. Decorative elements enhance the coastal theme.

4.95 out of 5 average rating, 129 reviews

Beachy Modern Downtown Getaway I

READY TO HOST YOU! First floor modern unit with vinyl laminate flooring, throughout complemented by beach accents and stainless steel appliances. Very light, bright, and coastal furnishing. Just 1.5 blocks off the main road where you can explore some of Dunedin's finest breweries, and all types of restaurants to fulfill your palate. If shopping makes you happy, we have several local shops to buy the right gift or something special for yourself!

FamilyKitchenTV

A comfortable living area features a beige sofa adorned with decorative cushions and a cozy throw. Two accent chairs sit beside a round coffee table on a soft area rug. Large windows allow natural light, while a potted plant adds a touch of greenery.

4.96 out of 5 average rating, 246 reviews

Comfortable and Convenient | On Main Street

Directly located on Dunedin's Main Street, over Flanagans Irish Pub/Bar. Comfortable and cozy this newly updated unit will have you feeling right at home. Come stay and live like a local with everything you need right out your front door within steps. You'll want to stay and never leave this brand new large 1 bed/ 1 bath apartment. This unit is above a Pub/Bar, noise may be an issue. Please take a look at our reviews.

Indoor spacesFamilyBathroom

Popular amenities for Dunedin family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A screened-in outdoor area features a heated pool and spa accompanied by a spacious dining table set for eight. Vibrant glassware and dining plates are arranged, capturing bright colors against the backdrop of lush greenery and a clear sky.

4.93 out of 5 average rating, 130 reviews

Luxury home ~ Heated pool, hot tub, TWO kitchens

KitchenFamilyBathroom

4.89 out of 5 average rating, 206 reviews

A serene pool area is surrounded by lounge chairs and palm trees, with a view of the water in the distance. Soft lighting from overhead strings enhances the setting. The pool depth is marked at 5 feet, and a sun umbrella offers shade.

Condo in Dunedin

Sunset Resort Condo – Clearwater Beaches & Bikes

FamilyIndoor spacesWi-Fi

4.93 out of 5 average rating, 100 reviews

Owl Nest Townhouse-Walk downtown, new POOL!

KitchenFamilyTV

4.95 out of 5 average rating, 198 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

FamilyIndoor spacesAir conditioning

4.95 out of 5 average rating, 386 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

KitchenIndoor spacesAccuracy

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.

4.91 out of 5 average rating, 171 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

Indoor spacesFamilyParking

5.0 out of 5 average rating, 169 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

KitchenIndoor spacesSleep quality

4.88 out of 5 average rating, 144 reviews

A modern kitchen is presented with navy blue cabinetry and a spacious island featuring seating for four. Quartz countertops and stylish light fixtures add elegance. Natural light streams through a nearby window, illuminating the adjacent dining area with a table and chairs.

Home in Clearwater

Hot Tub, Heated Pool, Minutes to Clearwater Beach

KitchenIndoor spacesCondition

Family- and pet-friendly home rentals

A bright living area features light yellow walls and a cozy beige sofa with colorful cushions. A vibrant striped rug lies beneath a small round table, accompanied by a green accent chair and a wooden chair. Natural light enters through a window and double doors leading outside.

4.97 out of 5 average rating, 118 reviews

Dunedin 1BR: KingBed/walkable/bike trail/NewBuild

FamilyIndoor spacesWi-Fi

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, 131 reviews

Heated saltwater pool|Spacious 4BR/3BA|

FamilyIndoor spacesSleep quality

A spacious living area features a large sectional sofa adorned with various decorative pillows. A light-colored coffee table is positioned in the center, complemented by a decorative basket. Natural light filters through two window blinds, creating a bright and inviting environment.

4.93 out of 5 average rating, 149 reviews

Ocean Sunsets & Downtown Biking Trails

FamilyKitchenQuiet

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, 284 reviews

Wonderful family friendly home in Dunedin FL

Indoor spacesKitchenOutdoor spaces

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.

4.86 out of 5 average rating, 401 reviews

Cozy up in a French Country nest NEAR EVERYTHING

Indoor spacesKitchenBathroom

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, 101 reviews

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

FamilyKitchenGetting around

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.

4.95 out of 5 average rating, 240 reviews

The Coastal Retreat

KitchenFamilyCleanliness

4.99 out of 5 average rating, 125 reviews

A private backyard pool area is featured, showcasing a clear blue in-ground pool surrounded by lounge chairs and sunbeds with striped cushions. Lush greenery and potted plants add a tranquil touch, while a shaded umbrella stands at one end for comfort.

Guesthouse in Ozona

Pvt Pool, Free Kayaks, Wlk to Gulf, Fish, Bike Trl

KitchenIndoor spacesValue

Family-friendly home rentals with a pool

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

5.0 out of 5 average rating, 170 reviews

Coastal Escape: Heated Pool, Playground&Family fun

KitchenFamilyCondition

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

4.94 out of 5 average rating, 118 reviews

Private pool, Golf Cart, Completely Renovated!

Indoor spacesKitchenBarbecue

4.99 out of 5 average rating, 127 reviews

Villa in Palm Harbor

The Palm Haus • Heated Pool • Near Beach • Games

Indoor spacesKitchenAir conditioning

4.94 out of 5 average rating, 158 reviews

Modern Coastal: Pool, Mini-Golf & Backyard Resort

KitchenFamilyValue

4.93 out of 5 average rating, 103 reviews

A screened patio surrounds the inviting pool, providing views of the waterfront. Sunlight glimmers on the clear water, and grassy areas border the pool deck. Nearby boat docks are visible, enhancing the serene atmosphere by the water.

Home in Ozona

Luxe Private Waterfront Getaway with Pool in Ozona

Indoor spacesKitchenTV

4.98 out of 5 average rating, 231 reviews

Home in Clearwater

Specious home W/ Heated Pool ! ! ! Great Location.

KitchenFamilyGetting around

4.92 out of 5 average rating, 106 reviews

A comfortable living area features a gray sectional sofa, accompanied by a matching armchair. A light wooden coffee table sits in the center, topped with decor. Large windows allow natural light to fill the space, complemented by light-colored walls and polished wooden flooring.

Cottage in Palm Harbor

Palm Paradise

Indoor spacesKitchenBarbecue

A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.