Family-friendly vacation rentals in Safety Harbor

5.0 out of 5 average rating, 112 reviews

Retro Dream Near Clearwater Beach & Pet Friendly

Step into 1960, skip the ordinary vacation rental and stay somewhere your family will actually remember. From the colorful retro diner and vintage décor to the fenced backyard and playful details throughout the home, every room was designed to make you smile, walk to Publix. Just minutes from Clearwater Beach, you'll enjoy modern comforts wrapped in a one-of-a-kind nostalgic Florida experience. This is Not just a place to stay it’s an experience you’ll talk about long after your vacation ends.

4.95 out of 5 average rating, 196 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

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

5.0 out of 5 average rating, 156 reviews

A spacious living room features a large sectional sofa adorned with green pillows and a coffee table placed on a vibrant area rug with palm leaf designs. A flat-screen TV is mounted on the wall, complemented by decorative accents and artwork throughout.

Villa in Safety Harbor

Villa Key West "Villas by Christine"

Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

4.88 out of 5 average rating, 124 reviews

Modern Paradise home near Clearwater Dunedin Beach

Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

5.0 out of 5 average rating, 75 reviews

A charming cottage exterior is framed by a white picket fence. The house features light yellow siding and large windows allowing natural light to fill the interior. Front flower boxes hold plants, while a brick pathway leads to the door, with green trees casting dappled sunlight.

Cottage in Safety Harbor

The Sunshine Cottage - Like Grandma's with WIFI

Walk through the front door of my restored 1948 Sunshine Cottage and you will feel transported back to your grandma's house only with WIFI! Just 3 blocks from Main Street. Enjoy the Sunday market, live music, pier, and 400 year old oak trees! Visit the historical mound in Philippe Park. Ride your bike along the bay. Come experience a magical place. I <3 furbabies. Let me know if you are bringing your pet. I have a limit of two dogs and I do have a cleaning fee associated. Sorry, no cats.

A charming bungalow is depicted, featuring a light blue front door that invites guests in. The home is framed by a white picket fence, with a pebbled walkway leading to the entrance. Lush greenery and clear skies enhance the welcoming exterior.

4.98 out of 5 average rating, 113 reviews

Downtown Gem with Guest House - Walk to Main St!

Experience the best of Safety Harbor in a home designed for connection. Whether you’re planning a multi-generational reunion or a getaway with friends, the Blue Gecko offers the rare combination of togetherness and privacy. The Main House features 3 bedrooms and 2 baths with a chef-ready kitchen. Just steps across the yard, the Guest House provides a private retreat with its own queen bed, bath, and kitchen—perfect for grandparents or those in the group who appreciate a little extra quiet.

5.0 out of 5 average rating, 8 reviews

2/1 Modern City Stay | Best Downtown Location

Beautifully renovated 2-bedroom, 1-bath getaway in the heart of Safety Harbor, right off Main Street. 1 free parking spot. Enjoy a spacious living room with a large pull-out couch, comfortably sleeps 6. Need more room? This unique stay also features an attached private suite through an additional door, offering an extra bedroom, bathroom, full kitchen, and separate living area. The private suite is available for an additional cost and must be booked separately through Airbnb for that unit.

Guesthouse in Safety Harbor

4.74 out of 5 average rating, 219 reviews

Cozy Main Street Hideaway

Safety Harbor Main Street Hide Away. 3 blocks away from the beautiful Safety Harbor Main street and all its charm. Restaurants, boutiques, shops, bars, museums, the famous Safety Harbor Spa and pier, perfect place to spot manatees and have a gourmet coffee cup at the same time! Private Guest House with 900 sqft 1bed/1 bath .Ideal size for 1-2 couples or a family of 4 (Family with kids welcome). Private backyard patio with fire place. This is a non-smoking. Come enjoy! No pets allowed.

Apartment in Safety Harbor

A spacious living area showcases a comfortable sectional sofa adorned with decorative pillows. Natural light filters through sheer curtains over the windows, while a stylish coffee table and TV stand complement the open space. A ceiling fan provides a relaxing ambiance.

4.97 out of 5 average rating, 107 reviews

Newly Renovated Apt in Stunning Safety Harbor!

Tranquility awaits in this beautifully updated 2 bedroom 1 full bath apartment. Tampa Bay's hidden gem is in the heart of Safety Harbor and the perfect place to wind down and relax or explore all the area has to offer. Centrally located just minutes from the beaches, parks, museums, and airports. Just a short walk to downtown to enjoy fantastic dining, festivals, art shows, live entertainment, the pier, the renowned Safety Harbor Resort & Spa, and much more in this quaint little town.

Guest suite in Clearwater

A peaceful outdoor area is surrounded by lush greenery, featuring palm trees and vibrant plants. A simple table and chairs are positioned beneath a canopy, providing a shaded space for relaxation. A whimsical flamingo decoration adds a playful touch to the serene environment.

5.0 out of 5 average rating, 136 reviews

Clearwater Studio Getaway

Welcome to Clearwater Studio Getaway! Enjoy a peaceful and centrally-located space just 15 minutes from Clearwater Beach, Downtown Clearwater, and the Tampa Bay área .Just 7 minutes from Safety Harbor and 14 minutes from Dunedin . Perfect for travelers or couples, this cozy studio features a private bathroom, comfy bed, and essential amenities. Relax after a day of sun and fun, with shops, dining, and attractions all within easy reach. Your perfect Florida stay!

4.9 out of 5 average rating, 71 reviews

Peaceful Hideaway

Welcome to Peaceful Hideaway Home 🏡 in Safety Harbor 🌴—a relaxing retreat blending comfort, modern convenience, Florida charm ☀️, and luxury ✨. Enjoy a fun game area with arcade 🎮, pool table 🎱, foosball ⚽, tic-tac-toe 🧩, Jumbo Jenga 🧱, Jumbo Connect 4 🔴, ping pong 🏓, cornhole, mini golf ⛳, and darts 🎯. Unwind in the hot tub 🛁 or gather around the big fire pit 🔥 for cozy nights. Perfect for families, friends, and memorable stays. Florida 🌅.

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

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Popular amenities for Safety Harbor family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.99 out of 5 average rating, 274 reviews

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.

Apartment in Dunedin

Tropical Paradise

4.89 out of 5 average rating, 170 reviews

Walk to BayCare Ballpark! Pool, Hot Tub, Pets OK

4.93 out of 5 average rating, 128 reviews

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.

Home in Dunedin

Luxury home ~ Heated pool, hot tub, TWO kitchens

4.93 out of 5 average rating, 131 reviews

FREE Heated Pool & Spa l Book your Winter Vacation

4.91 out of 5 average rating, 235 reviews

A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.

Home in Town 'n' Country

Rooms with a Pool

Tiny home in Ybor City Historic District

A rustic tiny house stands within a lush garden, featuring a wooden deck adorned with comfortable seating. The entrance showcases large glass doors, framed by greenery, while a charming pathway of stones leads toward the entrance. Subtle decorative elements enhance the inviting outdoor space.

4.98 out of 5 average rating, 618 reviews

Cozy AF Tiny-House Oasis

4.98 out of 5 average rating, 312 reviews

Home in Largo

TIKI•Hot Tub•SAUNA•Pool• 9 min ocean 2 KING beds

4.96 out of 5 average rating, 384 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

Family- and pet-friendly home rentals

4.95 out of 5 average rating, 116 reviews

A view from inside the house shows a spacious deck overlooking the lake, with sunlight reflecting off the water. Outdoor seating is positioned beneath a shaded area, and a serene atmosphere is created by the surrounding natural landscape.

Home in Oldsmar

Fountain House On Timberbay Lake

4.97 out of 5 average rating, 384 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

A modern living room features a comfortable sofa and an accent chair. A large wall-mounted television displays a serene beach scene. A decorative table holds a small plant, and a piece of abstract art adorns the wall, enhancing the space's inviting atmosphere.

4.9 out of 5 average rating, 110 reviews

Clearwater House!Near the beach!Newly renovated!

A welcoming basket sits on a light-colored countertop, filled with snacks and bottled water. A decorative sign reads 'Welcome to Our Little Piece of Paradise.' A small potted plant is positioned nearby, and the kitchen's modern appliances are visible in the background.

4.98 out of 5 average rating, 102 reviews

Harbor Breeze Hideaway 4/2 King size bed!

4.99 out of 5 average rating, 121 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

Superhost

4.77 out of 5 average rating, 105 reviews

Chic|Pool|PuttingGreen|Beaches

Superhost

The spacious studio cabin features wooden accents and high ceilings with exposed beams. Large windows allow natural light to fill the room. A comfortable sofa, a flat-screen TV, and a queen bed are present, alongside a small side table and two chairs.

Apartment in Dunedin

4.91 out of 5 average rating, 227 reviews

Downtown Dunedin B&B - Rustic Cabin Studio with He

4.96 out of 5 average rating, 45 reviews

Casa Artista | 5 Min Walk Downtown | Art & Nature

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, 169 reviews

Coastal Escape: Heated Pool, Playground&Family fun

4.99 out of 5 average rating, 104 reviews

A screened-in pool area is highlighted by clear blue water and a unicorn float. Surrounding greenery adds a natural touch, while shaded seating is positioned on the deck. Sunlight filters through the enclosure, creating a bright, inviting space for relaxation and leisure.

Guesthouse in Westchase

Cottage in Paradise.

A spacious outdoor area features a heated pool surrounded by a screened enclosure. Two lounge chairs are positioned beside the pool, and a barbecue grill is visible near the edge, providing an ideal setting for relaxation and meals.

4.85 out of 5 average rating, 139 reviews

Heated Pool Home | Close to Clearwater Beach

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

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.

4.95 out of 5 average rating, 115 reviews

Private pool, Golf Cart, Completely Renovated!

4.98 out of 5 average rating, 229 reviews

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

A heated pool is surrounded by lush palm trees, providing a sense of seclusion. A stone statue and decorative elements are featured along the pool's edge. Sunlight reflects off the water, creating a serene atmosphere in this private outdoor oasis.