Cottage holiday rentals in Clearwater Beach

4.95 out of 5 average rating, 141 reviews

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.

Cottage in Largo

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!

4.82 out of 5 average rating, 225 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, 131 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!

A sandy path leads from a grassy area to the shoreline, flanked by light vegetation. The vibrant blue sky is dotted with clouds, while the gentle waves of the ocean are visible in the distance.

4.76 out of 5 average rating, 117 reviews

#5 Beach Front Cottage w view- Indian Rocks Beach

LOCATION, location! Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples getaway. Enjoy some of Florida’s best beaches. Minimalistic living. *Kitchen recently updated* Shared gazebo & picnic table next door. Shared Washer & dryer takes quarters. Walking distance to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next 2 public access.

4.78 out of 5 average rating, 165 reviews

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

1925 beach house just steps to the beach. . All shops and resturaunts just a few blocks walk. Beach is 120 steps away. Part of Clearwater Cottages, a group of historic beach houses. This is an entire small house that will sleep 4 Restored antique kitchen. Just cute as a button. Families with pets welcome shared commercial hot tub in recreation area. has queen size bed in private master bedroom and pull out sofa bed in living room . as well as an additional twin bed in the living room

4.97 out of 5 average rating, 239 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.

4.97 out of 5 average rating, 177 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.

An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.

4.96 out of 5 average rating, 167 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

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, 206 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

4.95 out of 5 average rating, 101 reviews

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.

Cottage in Dunedin

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.

An open-concept kitchen and dining area features modern fixtures and wooden accents. A large island bar is surrounded by high-backed chairs, with a dining table visible in the background. Light blue walls and stylish light fixtures create a bright atmosphere.

4.98 out of 5 average rating, 160 reviews

New Beach Retreat– Hammock, PAC-MAN, Steps 2 Sand!

Sandy Feet Cottage is a newly remodeled beach retreat just 2 minutes from Indian Rocks Beach. Enjoy an open layout, new furnishings, a spa-style bath, and a private yard with fire pit, hammock, and patio. Walk to dining, bars, and shops—your stylish Gulf Coast escape. ***NEW AIRBNB PRICING UPDATE*** Starting mid-October 2025, Airbnb will display all-in pricing—including a 15.5% Airbnb service fee (charged directly by Airbnb to the host), plus cleaning and pet fees if applicable!

Popular amenities for Clearwater Beach cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.97 out of 5 average rating, 201 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

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, 212 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

4.74 out of 5 average rating, 227 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, 105 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

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

4.83 out of 5 average rating, 111 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

4.99 out of 5 average rating, 69 reviews

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.

Cottage in Largo

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.

4.77 out of 5 average rating, 181 reviews

Cool Breeze Cottage by the Bay in South Tampa

4.96 out of 5 average rating, 167 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, 130 reviews

Artsy guest house; near downtown w/ private patio

4.91 out of 5 average rating, 128 reviews

A serene sunset over the Little Manatee River is captured, with vibrant hues of orange and pink reflecting on the water surface. The dark outline of trees defines the horizon, creating a peaceful natural backdrop.

Cottage in Ruskin

Little Manatee River Cottage

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, 318 reviews

Vintage Florida Beach Cottage B

4.86 out of 5 average rating, 378 reviews

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.

Cottage in Dunedin

Cozy up in a French Country nest NEAR EVERYTHING

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.

4.71 out of 5 average rating, 221 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

4.96 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)

4.98 out of 5 average rating, 62 reviews

A vibrant pink cottage is surrounded by lush tropical landscaping and palm trees. A staircase leads to the rooftop patio, while the exterior features large windows and cheerful accents. The beachfront neighborhood is visible in the background, showcasing a relaxing coastal atmosphere.

Cottage in Indian Shores

Cottage with Rooftop Patio & Private Beach Access

5 out of 5 average rating, 57 reviews

A contemporary cottage is illuminated at night, showcasing large glass panels that reveal a warm interior. Surrounding the cottage, a manicured lawn features stone pathways and lush greenery, creating a serene outdoor environment.

Cottage in Safety Harbor

Safety Harbor Cottage

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.

4.94 out of 5 average rating, 78 reviews

Charming Blue Bungalow With Amazing Yard

4.73 out of 5 average rating, 92 reviews

A colorful antique home features a vibrant mural on its exterior, blending coastal themes with geometric patterns. A palm tree stands in front, complementing the inviting façade. A small detached garage is visible to the right, with a door painted in soft pink, adding character to the property.

Cottage in Clearwater

The Bitchin' Beach House

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, 61 reviews

Old Florida Paradise Secret Lair Cottage