Cottage vacation rentals in Clearwater

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

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

FamilyLocationBeach

4.95 out of 5 average rating, 205 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

NO BOOKING FEE! 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 with 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.

FamilyLocationBathroom

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.

FamilyLocationCleanliness

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.

ValueLocationDecor

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 ..

LocationValueOutdoor spaces

4.99 out of 5 average rating, 123 reviews

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

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.

LocationFamilyParking

4.89 out of 5 average rating, 220 reviews

Cottage in Indian Shores

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

This rare ground-floor, direct beachfront one-bedroom sits right on the Gulf of Mexico with unobstructed water views and effortless beach access Step out the door and into a life where the Gulf of Mexico is your backyard — no elevator, no lobby, just you, the sand, and thirty seconds between your pillow and the water. Enjoy your private beachfront patio, a cozy recently remodeled interior, and your own stretch of sand with lounge chairs and front row views right outside your door.

FamilyLocationParks

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.

4.96 out of 5 average rating, 131 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.

FamilyValueCondition

4.79 out of 5 average rating, 138 reviews

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

LOCATION, location! OLD SCHOOL BUNGALOW - 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. Shared gazebo right outside. 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 to public access.

FamilyValueHospitality

Cottage in Clearwater Beach

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.

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.

ValueFamilyQuiet

4.84 out of 5 average rating, 171 reviews

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

3 MIN WALK TO THE BEACH. beach cottage, 2 br, 1 bath, well equipped kitchen, Beautyrest beds, very clean. all included, 4 beach chairs, a cooler, beach toys, 18 towels: 4 beach, 4 shower, 4 hand, 4 face cloths, 2 kitchen towels, no stairs, parking up frond for 4 cars, outdoor sitting+ dining, charcoal grill, private laundry room free, high speed Internet 200 megabytes, cable TV, Wi-Fi, short walk to baseball /pickleball/ tennis/ basketball/ skateboard field, no steps.

FamilyLocationBiking

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, 224 reviews

Beach Cottage | Pool | Walk to Dining & Sunset

Welcome to Coco Cottage! Your coastal cottage retreat in Indian Rocks Beach cottage just a 3-minute walk from the Gulf! Spend your mornings on the sand, afternoons lounging in the heated saltwater pool, and evenings strolling to local coffee shops, restaurants & cocktails. Inside, enjoy a king bedroom, thoughtfully stocked kitchen and relaxed coastal style. Beach chairs, wagon, coolers & more are provided—so pack light and settle into the IRB lifestyle.

LocationValueQuiet

Popular amenities for Clearwater cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a pool

4.88 out of 5 average rating, 177 reviews

The single-family beach cottage features a light yellow exterior with red accents and three prominent windows. Surrounding the home, palm trees and landscaping provide a lush atmosphere. A paved area holds several designated parking spaces in front of the cottage, with a stone picnic table nearby.

Cottage in Madeira Beach

Family Friendly Beach Cottage in Madeira Beach, FL

LocationValueParking

4.88 out of 5 average rating, 101 reviews

Cottage in Madeira Beach

Cozy Cottage on Mad Beach - All Incl Pricing!

LocationFamilyKitchen

The living space features a spacious bed adorned with colorful pillows, complemented by a ceiling fan above. A cozy pink chair and a small dining area with two chairs are visible in the background, alongside modern kitchen equipment peeking from the left.

4.76 out of 5 average rating, 45 reviews

Coquina Studio 2: Heated Pool, Walkable to Beach

LocationValueBeach

The outdoor area features a large heated saltwater pool surrounded by a spacious patio. A tiki bar with seating is visible, along with two red lounge chairs. Lush palm trees add greenery to the setting, creating a relaxed and inviting atmosphere.

4.95 out of 5 average rating, 81 reviews

Seaside Retreat Cottages #3

FamilyLocationGetting around

Cottage in Belleair Beach

Newly Renovated ON Beach/2King Beds&a twin bunk

LocationValueSleep quality

4.93 out of 5 average rating, 44 reviews

4.98 out of 5 average rating, 84 reviews

Endless Summer Cottage 2

FamilyValueSleep quality

5.0 out of 5 average rating, 6 reviews

Cottage in Safety Harbor

2A Newly Renovated 1/1 at Coastal Cottages

LocationGetting aroundHospitality

4.91 out of 5 average rating, 32 reviews

Cottage in Madeira Beach

Private Standalone Beach Bungalow-No Shared Walls!

ValueLocationSleep quality

Cottage rentals with free parking

4.98 out of 5 average rating, 271 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

ValueLocationAmenities

4.98 out of 5 average rating, 125 reviews

Cottage in Gulfport

Cozy Cottage for Lovers

LocationValueGrill

4.95 out of 5 average rating, 223 reviews

Best Location! Walk to Dining, Trail & Stadium

FamilyValueView

4.96 out of 5 average rating, 324 reviews

The charming cottage features a bright yellow front door, flanked by potted plants. A welcoming porch is screened with white framing. The well-maintained yard is adorned with manicured grass and a path leading to the entrance, with a white picket fence visible in the background.

Cottage in Oldsmar

Louisa's Cottage

LocationValueBathroom

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

ValueLocationBiking

Cottage in Redington Beach

Entire home and yard 2 /1 with two sleep sofas

FamilyValueAccess

4.81 out of 5 average rating, 285 reviews

4.96 out of 5 average rating, 127 reviews

Cottage in Largo

The Cottage Stay 3 get 1 FREE

LocationValueQuiet

4.98 out of 5 average rating, 199 reviews

Beach Cottage | Bikes | Walk to Dining & Sunset!

ValueFamilyHospitality

Family-friendly cottage rentals

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

LocationFamilyNearby

4.95 out of 5 average rating, 102 reviews

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.

FamilyLocationAccess

4.83 out of 5 average rating, 142 reviews

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

FamilyValueWifi

Cottage in Pass-a-Grille Beach

The image captures the tranquil waterway with gentle ripples reflecting the sky. In the background, a charming beach cottage is framed by palm trees and boats docked nearby, creating a serene waterfront scene.

Pass-a-Grille Historic Cottage Unit 2

LocationValueParks

4.96 out of 5 average rating, 184 reviews

4.85 out of 5 average rating, 189 reviews

Two light blue beach cruiser bicycles with tan seats are positioned on a concrete surface. A window and a chair in a welcoming yellow tone are visible in the background, framed by greenery. The entrance to the rental is accessible and inviting.

Cottage in Gulfport

Gulfport Getaway-Close to Everything!

LocationFamilyLayout

A family beach house is showcased, featuring a main structure with a covered porch and large windows. Adjacent is a smaller cottage. Both buildings have a light-colored exterior and are surrounded by soft sandy ground and palm trees, highlighting the beachfront location.

4.98 out of 5 average rating, 47 reviews

Kamp Komfort Historic Family Beach House

LocationValueSleep quality

5.0 out of 5 average rating, 66 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

LocationFamilyAccuracy