Family-friendly holiday rentals in Safety Harbor

Cozy Main Street Hideaway 4 guests, queen bed

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 (kids are welcome). Private backyard patio.This is a non-smoking. Come enjoy! No pets allowed. Queen bed and a Murphy double bed

Family · Indoor spaces · Biking

Coastal Escape: Heated Pool, Playground&Family fun

★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras

Family · Kitchen · Check-in

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

Indoor spaces · Family · Quiet

Dream Retro | Near Beaches | Pets Welcome-fenced!

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.

Indoor spaces · Kitchen · Comfort

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.

Family · Indoor spaces · Bathroom

Villa at Harbor House "Villas by Christine"

Welcome to The Villa at Harbor House, located just steps from Safety Harbor’s Main Street, ranked the #10 Main Street by USA Today in 2025. Enjoy convenient walkable access to charming shops, dining, and pubs. This villa is perfect for solo travelers or couples, offering a queen bedroom, fully stocked kitchen, spacious living room, smart TVs, full laundry, and more. Pet-friendly ($100 fee). Beach gear included. For larger groups, consider booking Villa Key West or Villa Italia, steps away.

Indoor spaces · Kitchen · Decor

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.

Family · Indoor spaces · Getting around

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.

Family · Indoor spaces · Parking

Heated Pool • 4BR • Near Clearwater Beach

Welcome to your private Safety Harbor getaway—perfect for families and groups of up to 8. Enjoy 4 comfortable bedrooms, 2 baths, a private heated pool maintained around 86°F, fast Wi-Fi, a fully equipped kitchen, spacious living areas, and free driveway parking. About 15–20 minutes from St. Pete–Clearwater Airport, 20–25 minutes from Tampa International Airport, and convenient to Clearwater Beach, shopping, dining, and local attractions. Easy self check-in with a smart lock.

Kitchen · Family · Long stay

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!

Indoor spaces · Kitchen · Checkout

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

Family · Indoor spaces · Comfort

Tiny House Oasis - 2 Min Walk to Main Street

Experience unique tiny home living in the heart of downtown Safety Harbor! This stylish 132 sq. ft. retreat for two features soaring ceilings and a large, private outdoor oasis with a firepit and a one-of-a-kind outdoor shower. Just steps from Main Street's shops, restaurants, and the beautiful waterfront pier. Perfect for a memorable, walkable getaway.

Kitchen · Indoor spaces · Check-in