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, 122 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!

4.93 out of 5 average rating, 220 reviews

Charming Downtown Cottage – Walk to Everything!

Stay in this charming 1920's cottage, where everything is just a stroll away. Walk to the local restaurants, breweries, and shops on Main St, or take a leisurely walk to the marina for sunsets. With its prime location, it is perfect for exploring the heart of Dunedin on foot. Let’s walk and discover all that this vibrant area has! Your beautifully appointed cottage is a great retreat after beach fun, baseball or biking, and is an easy stroll home after an evening enjoying the local music scene.

4.82 out of 5 average rating, 223 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.

4.97 out of 5 average rating, 130 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

2 people max cozy cottage with all the amenities of home with a lakefront view. There's a firepit for those colder nights and kayaks & peddleboats for the more adventurous ones, or just sit back and take in some sun on our beautiful dock. Centrally located in between the Veterans Expressway and I 275, minutes from shopping, Lake Park, Adventure Island and Busch Gardens ...Lutz has something for everyone, don't let your friends and family stay in a hotel, we've got it all waiting right here!

4.97 out of 5 average rating, 176 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, 232 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.

Cottage in Tarpon Springs

The entrance of Palm Cottage features a welcoming red double door with decorative glass panels. Lush green plants and white gravel provide a fresh outdoor aesthetic, complementing the blue siding of the cottage.

4.82 out of 5 average rating, 120 reviews

Palm Cottage * King Bed * Tropical Yard

Located in the heart of historic downtown Tarpon Springs, Palm Cottage (520 sf) is walking distance to the world famous SPONGE DOCKS, and located just blocks away from breweries, restaurants, and the PINELLAS TRAIL. And the BEACH is only 3 mi away! The cottage offers king and twin beds, Wi-Fi, Fire TV, kitchen w/ full stove and fridge, coffee maker, toaster, pots, pans, table, and shared use of the tropical back yard of our 121-year-old Victorian home. 1st time Airbnb guests welcome!

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.

4.77 out of 5 average rating, 176 reviews

Cool Breeze Cottage by the Bay in South Tampa

Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

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.

Cottage in Central Oak Park

4.9 out of 5 average rating, 157 reviews

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

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, 358 reviews

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street, yet tucked away ! Private yard with grill in a prime location. Short walk to Dunedin's waterfront and minutes to beaches. Stroll to Dunedin's restaurants, breweries, shops, and live music. Walk to gorgeous sunsets or drive minutes to award-winning beaches such as Honeymoon Island and Clearwater Beach. Sleeps 6. Enjoy designer décor and two king suites. Loaded with beach & kids’ gear for easy escape. Treat yourself and book this Dunedin favorite today.

Popular amenities for cottage rentals in Safety Harbor

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.96 out of 5 average rating, 197 reviews

A spacious outdoor deck is shown, featuring a hot tub covered with a protective lid. Blue and white lounge chairs, along with bright cushions, are arranged for relaxation. The cottage's vibrant turquoise exterior is complemented by a cheerful yellow door and lush surrounding greenery.

Cottage in Safety Harbor

Harbor Oasis | Hot Tub | Private | Lush Backyard

Cottage in Clearwater 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

4.98 out of 5 average rating, 42 reviews

Beachy Keen Cottage A only steps to the Beach

The outdoor pool area features a clear water pool surrounded by lounge chairs and vibrant umbrellas. A bright blue building is visible in the background, complemented by colorful accents along the poolside. Lush greenery adds to the relaxed atmosphere.

4.92 out of 5 average rating, 138 reviews

Sunny - Key West Vibe Cottage - Pool - Walkable

New Listing Hidden Gem 3 Bedroom Home

Cottage in Clearwater Beach

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, 163 reviews

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

4.83 out of 5 average rating, 109 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.

4.99 out of 5 average rating, 67 reviews

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

Pet-friendly cottage rentals

4.96 out of 5 average rating, 165 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

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, 129 reviews

Artsy guest house; near downtown w/ private patio

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, 194 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, 316 reviews

Vintage Florida Beach Cottage B

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, 220 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!

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.

4.94 out of 5 average rating, 77 reviews

Charming Blue Bungalow With Amazing Yard

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

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)

A collage depicts a vibrant map of Downtown Dunedin, showcasing various local spots. Images show a dining table set for two with wine, complemented by views of greenery and the cottage's inviting bedroom featuring fresh linens and natural light streaming through the window.

4.86 out of 5 average rating, 7 reviews

Downtown Dunedin Cottage Near Beaches + Breweries

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

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.

4.94 out of 5 average rating, 63 reviews

🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️

Cottage in St. Petersburg

A charming cottage exterior is framed by lush trees, with a front porch featuring a welcoming entry door. Decorative potted plants line the gravel pathway, enhancing the appeal of the space. A covered area is visible to the right, providing additional outdoor seating.

4.95 out of 5 average rating, 60 reviews

Old Florida Paradise Secret Lair Cottage

5 out of 5 average rating, 12 reviews

A cozy living area features a light gray sofa with decorative throw pillows, positioned across from a wooden coffee table. A modern artwork adorns the wall, and a flat-screen TV is mounted nearby. Natural light enters through a window, enhancing the calm atmosphere.

Cottage in Tampa

Cozy South Tampa Cottage Near Macdill AFB!