Cottage vacation rentals in Safety Harbor

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.

4.97 out of 5 average rating, 392 reviews

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.

4.84 out of 5 average rating, 264 reviews

A bright living area features a lavender sofa and a coral ottoman, complemented by a light blue armchair. Natural light fills the space through multiple windows, with a small indoor plant accentuating the coffee table. A patterned area rug adds texture to the hardwood floor.

Cottage in Clearwater

Clearwater Cottage Short Drive to Beach & Dunedin!

Perfectly nestled between the quaint town of Dunedin & Clearwater. Just a short drive across the bridge & you’ll be Sinking your toes into the beautiful white sandy beaches of Honeymoon Island State Park or Clearwater Beach. Enjoy Honeymoon Island natural beauty or exciting tourist attractions of Clearwater beach! Take a cruise on the dinner boats to watch the beautiful sunset. Walk or rent a bike & explore the Pinellas trail. Kayak or jet ski the Gulf. Max 5 Adult guests with government ID.

Cottage in Tarpon Springs

The front exterior of Cooper Cottage features a welcoming porch with two black rocking chairs and potted plants. A pathway leads to the entrance, while large windows allow natural light to illuminate the space. Lush trees provide shade and a tranquil atmosphere.

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

4.99 out of 5 average rating, 194 reviews

Cottage in Seminole Grove Estates

The three-story guesthouse features a blend of wood siding and large windows, surrounded by lush greenery. A spacious balcony is present on the second level, offering a shaded outdoor space. Tropical plants and trees frame the entrance, enhancing the serene ambiance of the property.

Florida Guest House

Seminole Oaks House...Beautifully appointed new construction 2-story Guesthouse located in a very quiet setting 10 minutes from Indian Rocks Beach. Walking/biking distance from Walsingham Park and Lake and the Pinellas Trail. Enjoy your morning coffee or evening glass of wine on the balcony..or tree shaded rear Patio w/BBQ grill..Great location for exploring all Pinellas has to offer including the Beaches, Downtown St. Pete,and open air Markets..dedicated parking..very peaceful and private ..

4.99 out of 5 average rating, 123 reviews

4.98 out of 5 average rating, 270 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage, Private Dock, Romantic, Fishing

You’ll have the Entire 500sq ft Cottage & private entry, deck and fishing dock, charcoal grill, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout drapes, luxury quality hair products, high thread count linens. Fully stocked kitchen, reverse osmosis drinking water, k-cup/drip coffee machine. The lake has bass, complimentary fishing poles/tackle box. Rentable Canoe & Kayaks.

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, 403 reviews

Cozy up in a French Country nest NEAR EVERYTHING

Very private, romantic and Stylish Apt w/free WiFi & Parking in a very walk/run/bike/golf carting friendly area. PERFECT LOCATION in the heart of everything! 10 mins away from Clearwater Beach, HONEYMOON & CALADESI ISLANDS, 10 mins walk from Downtown Dunedin with its Unique Restaurants, Boutiques & Breweries & 7mins to Blue Jay Stadium. Pinellas Trail is across the street from the apt and only 2 blocks down from the waterside! It's a perfect central place to cozy up away from home!

4.76 out of 5 average rating, 110 reviews

A spacious living area is presented with a light-colored couch, complemented by two patterned chairs. A wooden coffee table sits in the center, while a flat-screen television is mounted on the wall. Natural light fills the room through multiple windows, enhancing the airy ambiance.

Cottage in Ozona

Bright, Clean and Cozy Coastal Home in Ozona

Discover Old Florida Charm with Modern Luxury in Ozona. This newly renovated 2021 “Old Florida” fishing home blends turn-of-the-century charm with bright, contemporary interiors for a coastal escape. Walk to top restaurants, pubs, and the Pinellas Trail; stroll or bike to Honeymoon Island, and a short drive to Clearwater Beach. Sleeps 6–7 in stylish, relaxed spaces. Boat trailer-friendly, golf-cart neighborhood, and easy access to boat/kayak rentals. Unwind, explore, and reconnect.

A cottage-style home is framed by lush greenery and colorful flowering plants, creating a vibrant outdoor setting. A paved area provides ample space for parking, while a cozy patio area is visible nearby, inviting outdoor relaxation amidst the natural beauty.

4.96 out of 5 average rating, 112 reviews

Charming Newly Reno 1 min to Downtown Dunedin

Welcome to our cottage-style home, 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.

The cottage exterior features a vibrant green facade with a welcoming front porch. Lush landscaping includes palm trees and ornamental plants framing the entrance. Paver stones lead to white steps that connect to the front door, while a wooden fence provides privacy.

4.92 out of 5 average rating, 240 reviews

Historic Keylime Cottages

Step into the charm of a historic 100-year-old home, once surrounded by orange groves and lovingly preserved with original wood floors and timeless character, now in vibrant downtown Dunedin, steps from everything. This is a true historic home with natural quirks and is not newly renovated. Enjoy an upgraded bathroom, full kitchen with coffee and tea, two Queen bedrooms, washer/dryer, porch rockers, and parking for two cars. Ideal for guests who value charm over new finishes.

Superhost

A sandy pathway leads through beach grass and wildflowers, with palm trees framing the scene. The azure ocean and clear blue sky serve as a backdrop, inviting guests to enjoy the nearby beach.

Cottage in Clearwater Beach

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

4.84 out of 5 average rating, 170 reviews

4.95 out of 5 average rating, 223 reviews

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!

The exterior of the vibrant blue cottage features a welcoming patio with brightly colored Adirondack chairs and a table, surrounded by dappled sunlight from the overhead trees. A storage unit is visible, labeled with a cheerful sun design, enhancing the inviting atmosphere.

4.98 out of 5 average rating, 118 reviews

LUNA Retreat • Fall Special - Owner Managed

LUNA – This fully renovated 1946 Indian Rocks Beach cottage blends historic charm with modern comfort. Just 177 steps to the white sand beach, and minutes to Clearwater and St. Pete Beach. Walk to coffee shops, shopping, and great restaurants. Each bedroom includes a white noise machine for restful sleep. Enjoy fast Wi-Fi, smart TVs, and a cozy outdoor space—perfect for relaxing after a day in the sun.

Popular amenities for Safety Harbor cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

The porch features a circular daybed with decorative cushions, accompanied by a small table and two chairs. Direct views of the bright blue sky and nearby palm trees are visible, enhancing the outdoor relaxation space.

4.98 out of 5 average rating, 203 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

A welcoming entryway features a large, round planter filled with vibrant greenery, placed beside stone steps leading to the front door. The area is adorned with a mix of leaves and decorative stones, while two blue adirondack chairs invite relaxation.

4.97 out of 5 average rating, 378 reviews

Private Heated pool/spa home!

4.91 out of 5 average rating, 65 reviews

A hot tub sits on a spacious patio, surrounded by comfortable dark wicker seating and a picnic table. Lush green fields and trees are visible in the background, contributing to a peaceful outdoor setting under a partly cloudy sky.

Cottage in Palm Harbor

Hot tub cottage near Honeymoon Island

4.98 out of 5 average rating, 49 reviews

Beachy Keen Cottage A only steps to the Beach

4.88 out of 5 average rating, 128 reviews

Cottage - Pool - Free Parking - Walkable

A charming coastal cottage is depicted, featuring a welcoming front porch with rocking chairs and vibrant seating. Lush plants in decorative pots frame the entrance. The exterior is painted in soft grey tones, complemented by white shutters and a serene pathway leading to the door.

Cottage in Crystal Beach

Happy Camper Cottage | Cozy Oasis with Hot Tub

4.69 out of 5 average rating, 158 reviews

A shaded outdoor dining area features a glass table surrounded by decorative metal chairs. Lush greenery and colorful flowers adorn the space, with a wooden structure visible in the background. The garden offers a feeling of seclusion and connection to nature.

Cottage in Downtown St. Petersburg

Castle Keep Guest House

4.56 out of 5 average rating, 36 reviews

Cottage in Sunset Beach

Sunset Beach Cozy Cottage

Pet-friendly cottage rentals

A vibrant tropical mural featuring large flowers adds a pop of color to the room, while a cozy seating area includes a sofa adorned with decorative pillows. A small dining table with tropical-patterned chairs provides a space for meals. The outdoor area showcases a lit pool, creating a serene evening ambiance.

4.99 out of 5 average rating, 223 reviews

Beach Cottage | Pool | Walk to Dining & Sunset

Cottage in Tarpon Springs

The exterior of the Blue Bungalow showcases a charming blue facade with a pink front door. Lush greenery and colorful plants surround the entrance. A small, inviting chair is placed beside the door, adding to the welcoming appearance.

Charming Blue Bungalow With Amazing Yard

4.95 out of 5 average rating, 102 reviews

4.95 out of 5 average rating, 204 reviews

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

Beautiful Beachfront Cottage on the Water

4.95 out of 5 average rating, 176 reviews

The cottage features a welcoming front porch adorned with vibrant flowers and lush greenery. A stone pathway leads to the entrance, framed by well-maintained landscaping. Large windows allow ample natural light, enhancing the charm of the remodeled exterior.

Cottage in Tampa

Wonderful 2-Br, 2 Bath Cottage near the river.

4.97 out of 5 average rating, 179 reviews

A spacious backyard is featured, bordered by a wooden fence for privacy and lined with tropical plants and trees. A concrete patio area is included, which features a grill covered for protection. The lawn is open and well-maintained, providing a serene outdoor space.

Cottage in Gulfport

The Pelicans Roost / Gulfport

Superhost

4.83 out of 5 average rating, 142 reviews

Coral Sands I -2/2 Porch, Pool Tbl, Best Location!

4.79 out of 5 average rating, 138 reviews

#5 Cottage on the beach-*Water View* -Indian Rocks

Cottage in Bayshore Beautiful

A comfortable seating area features two light-colored sofas with throw pillows, arranged around a rustic wooden coffee table. A decorative screen provides partial division from other spaces, and a textured rug is laid beneath the furniture, enhancing the warm ambiance of the room.

Good vibes Cottage block from Beautiful Bayshore

4.79 out of 5 average rating, 209 reviews

Private cottage rentals

4.98 out of 5 average rating, 125 reviews

Cottage in Gulfport

Cozy Cottage for Lovers

4.97 out of 5 average rating, 145 reviews

A serene lakefront view is framed by tall trees draped with Spanish moss. A wooden dock extends into the calm water, providing a space for relaxation. Soft shadows are cast across the lush green lawn, inviting guests to enjoy the peaceful surroundings.

Cottage in Lutz

A little piece of Heaven

4.98 out of 5 average rating, 199 reviews

2-Min Walk to Beach | Private Yard & Bikes

4.89 out of 5 average rating, 220 reviews

Cottage in Indian Shores

Ground-floor, direct beachfront 1BR | on the Gulf

A comfortable living area is depicted, featuring a light-colored sofa accompanied by two side lamps on small tables. A ceiling fan is visible, and a round piece of wall art echoes a coastal theme. Natural light filters in through the window with white blinds.

4.94 out of 5 average rating, 233 reviews

Kooky Coconut Cottage, Indian Rocks Beach

4.95 out of 5 average rating, 154 reviews

Cottage in Largo

Stay 3 get 1 FREE at “The Sweet”

A well-equipped kitchen features wooden cabinets and a spacious granite countertop with seating for two. Stainless steel appliances, including an oven, microwave, and coffee maker, are visible. Natural light streams in, highlighting the modern design and warm tones of the space.

4.9 out of 5 average rating, 164 reviews

B - BEACH HOUSE 3 MIN WALK TO THE BEACH