Cottage holiday rentals in Safety Harbor

A cozy living space features a well-equipped kitchenette with modern appliances, including a coffee maker and microwave. A dining table with two chairs is positioned beside expansive windows. A spacious bed occupies the corner, complemented by light-colored bedding and gentle lighting from ceiling fans.

4.95 out of 5 average rating, 140 reviews

Walk to beach shops food drinks “The Sweet”

Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, private full bath, kitchenette, sofa sleeper, large back yard with fire pit, bbq grill, beach chairs, wagon and cooler. Zoning permits 2 people per bed only and one on futon. All guests must be listed on the reservation. No Pets allowed. Florida State License # DWE6215889

Cottage in Tarpon Springs

The exterior of the cabin is showcased, featuring a white façade and a welcoming front porch. Decorated with colorful plants, the walkway leads to the entrance, framed by lush greenery and tall trees providing natural shade.

4.98 out of 5 average rating, 121 reviews

Cooper Cabin: Cute, Adorable, Standalone Studio

Cooper Cabin is a super cute and sparkling clean stand alone studio with a full eat-in kitchen and bath. 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! Located within walking distance of all things Tarpon Springs and just a short 7 min drive to Fred Howard Beach, Cooper Cabin is decorated with fun decor and a relaxing front porch balcony with bistro set. Bikes and beach gear provided!

Cottage in Seminole Heights

4.95 out of 5 average rating, 408 reviews

Lovely Loft Close to Everything in Tampa

A perfect balance between suburban serenity & urban convenience in this historic Tampa neighborhood. Central air, Roku, strong Wi-Fi, coffee, tea, snacks. Easy self-check-in. The ideal home base for your Tampa adventures. Quick 10 min drive to TPA Airport, Busch Gardens, Fla Amphitheater, Raymond James Stadium, Aquarium, Cruise Port, USF, UT, Ybor City, Armature Works & Downtown. 35 min to countrys best beaches, 70 min to Orlando. Plus great restaurants & breweries within walking distance.

4.82 out of 5 average rating, 221 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.

4.95 out of 5 average rating, 213 reviews

Perfect Location Cottage in Delightful Dunedin

Discover a charming 1920's cottage nestled in the heart of Dunedin, 3 blocks from the water and downtown. This delightful cottage is ideally located 2 blks from the Pinellas Trail, the Fenway Hotel, and the Blue Jay's stadium. Surrounded by lush greenery, the cottage boasts a private outdoor space perfect for you to enjoy your coffee. Inside, you'll find a sunny kitchen, a spacious living and dining area, and comfortable beds to ensure a wonderful stay. Come and enjoy a memorable stay here!

4.99 out of 5 average rating, 135 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.

Welcome to my little cottage in the city. The house was built in 1926 but has been fully remodeled with modern style, while keeping the charm of an older home. Even though it's close to everything Tampa has to offer, it still has the feeling of that little, quiet neighborhood near the river. This is my get away home. I love the front porch to sit on with a cold beverage and watch neighbors stroll by walking their dogs. The river park is very close by which is a nice walk from the cottage.

Cottage in Euclid Place - St. Paul

A cozy living room features a tan sofa positioned across from a purple armchair. A round coffee table is centered on a light-colored rug. Colorful artwork adorns the wall, while a floor lamp provides warm lighting. The space is brightened by natural light through a window.

4.95 out of 5 average rating, 125 reviews

Artsy guest house; near downtown w/ private patio

This uniquely decorated guest house is a private oasis with a lovely, private patio. The house is decorated with Latin American art from the owner's collection & travels. Only 11 blocks to downtown and very close to grocery stores, art galleries and all the night light life St. Pete offers. The home has a full kitchen and a very comfortable bedroom for one or two people. A perfect location for those that want to experience a comfortable and relaxing place. Only 12 block walk to Tropicana.

4.97 out of 5 average rating, 174 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

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

4.97 out of 5 average rating, 227 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

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, 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 curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

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.

4.95 out of 5 average rating, 101 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.

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, 353 reviews

Walk to Downtown and Waterfront - Private Yard

Private yard with grill. Steps to Main Street, short walk to Dunedin's waterfront. Minutes to beaches. Enjoy beautiful décor and two king suites. Stroll to Dunedin's restaurants, breweries, shops, and live music. Enjoy gorgeous waterfront sunsets or drive minutes to award-winning beaches such as Honeymoon Island and Clearwater Beach. Sleeps 6. Loaded with beach and kids’ gear for a seamless escape. Treat yourself and book this Dunedin guest favorite by Lucky Guest today.

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.

4.97 out of 5 average rating, 158 reviews

𖤓Updated Stilt home: just steps to the beach!𖤓

Experience a stylish and relaxing beach vacation at our vacation retreat! We are a very popular spot for Honeymooners and anniversaries! As a 4-year Superhost, we offer a charmingly renovated home just steps away from the beach and local restaurants. Explore Indian Rocks Beach with our provided bikes and unwind in the bubbly spa. Escape the everyday and find paradise here! BTR #2292

Popular amenities for cottage rentals in Safety Harbor

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A thatched Tiki hut is illuminated at night, surrounded by lush tropical plants. Wooden picnic tables are positioned under the hut, creating a casual gathering area. A 'Vacancy' sign is visible above, highlighting the inviting atmosphere of the property.

4.74 out of 5 average rating, 209 reviews

Tiki Cottage Sleeps 6, Pets OK, Steps to Beach

A charming duplex features a bright pink exterior with white awnings. A swing and patio chairs are located in the front yard, surrounded by potted plants. Bicycles are parked nearby, enhancing the inviting atmosphere of this beachside property.

4.78 out of 5 average rating, 157 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

A small private patio area is displayed, featuring two light-colored chairs positioned beside a sliding glass door. The patio is paved with antique bricks, and lush greenery surrounds the space, creating a cozy entrance to the cottage.

4.74 out of 5 average rating, 224 reviews

Lemon Cottage Steps from Beach

4.98 out of 5 average rating, 42 reviews

Beachy Keen Cottage A only steps to the Beach

4.91 out of 5 average rating, 100 reviews

A private hot tub is positioned on a wooden deck, outfitted with two black chairs and a small table. The cottage features a light blue exterior with a white door framed by two towels. A pergola with climbing plants is visible in the background.

Cottage in Safety Harbor

Heart of Safety Harbor | Hot Tub | Luxe Comfort

The exterior view of a charming blue cottage is presented, featuring white accents and shutters. Two light-colored lounge chairs are positioned on the paved front area. Lush greenery surrounds the property, enhancing the inviting beach house vibe.

4.78 out of 5 average rating, 162 reviews

Corner Cottage Sleeps 5, Steps to Beach, Pets OK.

4.84 out of 5 average rating, 107 reviews

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

A bright and airy seating area features a hanging chair and a cozy sofa, adorned with colorful cushions. Natural light floods in through large windows, complemented by light-toned wooden flooring and a textured pink area rug that adds warmth to the space.

4.98 out of 5 average rating, 66 reviews

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

Pet-friendly cottage rentals

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.

4.76 out of 5 average rating, 173 reviews

Cool Breeze Cottage by the Bay in South Tampa

4.96 out of 5 average rating, 164 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

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, 192 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

A single-story cottage features a pink exterior with large windows allowing natural light. A landscaped garden with decorative stones is visible in the front. White chairs are placed near the entrance, and ample parking spaces are provided in the driveway.

4.9 out of 5 average rating, 313 reviews

Vintage Florida Beach Cottage B

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, 373 reviews

Cozy up in a French Country nest NEAR EVERYTHING

4.93 out of 5 average rating, 58 reviews

A spacious bedroom is complemented by a king-sized bed with a light quilt. The room features a ceiling fan, air conditioning unit, and a well-equipped kitchen area with a refrigerator, stove, and sink. Natural light enters through the window, enhancing the bright decor.

Cottage in Safety Harbor

6B Newly Renovated Casita at Coastal Cottages!

A charming cottage exterior is highlighted by vibrant blue accents on the door and window frames. Lush palm trees surround the property, and a pathway of red bricks leads to the entrance. Gravel landscaping complements the home, enhancing its welcoming appearance.

4.7 out of 5 average rating, 219 reviews

Beachy Paradise

4.99 out of 5 average rating, 280 reviews

The cottage exterior features a light teal facade with white trim and multiple windows allowing natural light. A welcoming front porch includes a central entry door flanked by two large windows. The address is displayed prominently above the door. Lush greenery surrounds the base of the structure.

Cottage in Gulfport

Gulfport Art District - One Block From Beach!

Private cottage rentals

4.91 out of 5 average rating, 32 reviews

A tranquil salt-water pool is framed by lush tropical foliage, offering a serene retreat. Sunlight filters through a striped awning, providing shaded seating areas. The circular pool is accompanied by a stone patio, creating a welcoming space for relaxation.

Cottage in Palm Harbor

Coral Cottage pool/firepit 2 bedr 2 bth sleeps 6

A spacious living area features a light-colored couch and a coordinating armchair, positioned on a decorative area rug. A wooden TV stand holds a flat-screen television. Wall art adds color, while a ceiling fan provides comfort. Natural light filters through the windows.

4.81 out of 5 average rating, 72 reviews

Cottage by the Coast 2 bd - Pet Friendly

The living space features a light-colored queen size bed with decorative pillows, accompanied by a comfortable armchair and side table. A ceiling fan is present above, and a kitchenette is visible in the background. A dining table with two vibrant yellow chairs is situated nearby.

4.62 out of 5 average rating, 37 reviews

Tropical Coquina Cove Studio #3 5min Walk to Beach

A glass table is set with two wine glasses and a bottle of red wine, inviting relaxation. The backdrop features a picturesque view of the surroundings, with lush greenery and a sunset sky visible in the distance.

5 out of 5 average rating, 23 reviews

Cozy Cottage Downtown + near Waterfront

4.96 out of 5 average rating, 72 reviews

A welcoming porch area features a small round table and two chairs under a shaded awning. A hanging planter with vibrant flowers adds color. Lush greenery lines the perimeter, and a path of natural mulch leads away from the entrance.

Cottage in Tampa

Tranquil Guesthouse Hideaway (Near MacDill AFB)

4.85 out of 5 average rating, 13 reviews

A spacious area features a comfortable seating arrangement, including a grey sofa and patterned accent chairs. In the background, a large bed is flanked by bedside tables with lamps. Natural light filters in through patterned curtains, enhancing the inviting room ambiance.

Cottage in Palm Harbor

Private Oasis Luxury King Bed Walk To Restaurants

Cottage in Tarpon Springs

The exterior of a charming blue bungalow features a pink front door. A pink chair is positioned next to the door, adorned with greenery and colorful florals. The landscaped yard showcases a stone pathway, bordered by plants and palm trees, creating an inviting entrance.

4.93 out of 5 average rating, 75 reviews

Charming Blue Bungalow With Amazing Yard

A light and airy living room features cozy seating, including a gray armchair and a beige couch adorned with a knitted throw. Sunlight enters through shuttered windows, illuminating warm wooden floors. A dining area is visible in the background, showcasing a chandelier and a dining table.