Cottage vacation rentals in Longboat Key

A fenced-in outdoor area features a swimming pool surrounded by a red brick patio. Sun loungers are positioned beside the pool, and a pool house is visible in the background, complemented by lush greenery and large trees draped with moss.

4.96 out of 5 average rating, 104 reviews

1930s Cottage + Pool 12 miles to Beach

Located in the heart of historic Palmetto FL, you will find this adorable cottage. This home has 2 bedrooms & 1 bath in the main home with a pull out sofa, as well as, a pool house with a full bath & daybed. You will love the southern charm of this home while relaxing by the pool or having morning coffee on the front porch. There are many restaurants & shops w/in walking distance as well as local parks & preserves. If you love the beach, this home is just a short drive to FL's beautiful beaches.

4.85 out of 5 average rating, 146 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

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Cottage in Indian Beach-Sapphire Shores

The cottage features a welcoming exterior with a screened-in lanai, framed by decorative beams and charming window boxes. Lush greenery surrounds the property, and a large tree adds to the tranquil setting. A pathway leads to the front door, enhancing the inviting atmosphere.

4.8 out of 5 average rating, 275 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

4.94 out of 5 average rating, 140 reviews

A circular pool is surrounded by a landscaped area featuring vibrant plants and red stones. Lounge chairs offer seating nearby, while a shaded umbrella provides relief from the sun. Inflatable rings float in the clear water, and a view of the canal can be seen in the background.

Cottage in Bradenton

Waterfront+Pool+Putting Green+Beach Gear! 2BR/2BA

• Perfect for couples, families, or remote work escapes • Unwind by the water • Fish from dock • Well equipped kitchen (no food items) • Starter supplies: coffee, tea, paper goods & toiletries • 2 bd / 2 ba • Selfie Wall • Keyless Entry • Pool • Putting Green *Tap the 🖤 in the corner to save this listing and find it faster later* • 10 miles to beach, *Award Winning Ana Maria Island • 7 miles to IMG Academy • 11 miles to SRQ Airport • 2 miles from Pittsburgh Pirates Training Camp

Cottage in Indian Rocks Beach

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, 115 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.

Cottage in Pass-a-Grille Beach

A wooden boardwalk leads directly to the beach, framed by sandy dunes and swaying grass. The clear blue sky meets the calm waters of the Gulf, creating an inviting scene for beachgoers. The soft beach sand stretches out, blending seamlessly into the horizon.

4.88 out of 5 average rating, 179 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Welcome to your island beach escape! This charming coastal abode boasts all the island vibes you need for a relaxing getaway. Enjoy the quaint historic village (5 houses wide) while being just steps away from the most beautiful beach in Florida! Take a stroll through the picturesque streets of Pass A Grille and soak up the old beach charm. The rental home has hardwood floors, a screened-in porch, and a sun patio, 2 bikes to cruise around the area! open-concept kitchen + bar and smart TVs.

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.

4.97 out of 5 average rating, 233 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.

An aerial view captures the expansive Siesta Key coastline, showcasing a stretch of sandy beach meeting calm blue waters. Nearby buildings and lush greenery punctuate the landscape, highlighting the serene environment just minutes away from the cottages.

4.79 out of 5 average rating, 146 reviews

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) ONLY A 4 MINUTE WALK TO SIESTA KEY BEACH #1 in USA (no major streets to cross): First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!

Cottage in Bellevue Terrace

A private pool is surrounded by a paved area, featuring two lounge chairs positioned near the water. Green foliage adds a natural touch, while a white fence encloses the space, creating a secluded atmosphere. The clear blue water reflects the sky, inviting relaxation.

4.93 out of 5 average rating, 135 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

4.89 out of 5 average rating, 203 reviews

A cozy dining area is framed by large windows, offering a direct view of the beach and ocean. Two light-colored chairs surround a round wooden table. Outside, lounge chairs are positioned on the sand, with stunning sunset colors reflecting on the water.

Cottage in Indian Shores

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*

Step out the door and into the sand! Ground floor DIRECT beachfront one- bedroom/one-bath cottage nestled in the sand directly on the Gulf of Mexico with awesome amenities for the perfect Gulf Beach getaway! Enjoy a cozy bedroom, living/dining area, fully-equipped kitchen, beachfront patio and private beach area with lounge chairs. Conveniently located near a trolley stop for easy access to local restaurants, shops, and attractions. Book now for an unforgettable beach vacation!l

4.97 out of 5 average rating, 347 reviews

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.

Cottage in Dunedin

Walk Downtown and to Waterfront, Mins to Beaches

Experience modern coastal luxury in this stylish, spacious upstairs 2-bedroom cottage with magazine worthy decor. Steps from Main Street Dunedin, short stroll to gorgeous sunsets at the waterfront, quick drive to award winning beaches--Honeymoon Island & Clearwater Beach. Walk to restaurants, shops, & breweries. Pet-friendly w/ 2 king beds, a sleeper sectional, & lovely treetop views. Treat yourself! Book your getaway at the Barefoot Parrot Cottages.

Popular amenities for Longboat Key cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

The entryway features warm wooden floors and natural light streaming through large windows. A vibrant blue door adds a pop of color, while a stylish desk and lamp provide a functional workspace. A wooden cabinet with glass doors showcases decorative items and greenery.

4.94 out of 5 average rating, 49 reviews

Charming Home w/ Hot Tub, 20 min to Beach + Garden

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

4.92 out of 5 average rating, 138 reviews

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.

Cottage in Dunedin

Sunny - Key West Vibe Cottage - Pool - Walkable

A modern park model home is shown with a red convertible parked in front. Lush palm trees surround the property, providing shade. A spacious patio area with outdoor seating is visible, complementing the vibrant landscaping and inviting exterior.

5 out of 5 average rating, 6 reviews

Sarasota Cottage Near Beaches, Downtown & Airport

4.91 out of 5 average rating, 101 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

4.84 out of 5 average rating, 110 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

4.99 out of 5 average rating, 67 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

4.91 out of 5 average rating, 35 reviews

Cottage in Palm Harbor

Cozy Cottage Near Beach | Hot Tub • Pet Friendly

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, 176 reviews

Cool Breeze Cottage by the Bay in South Tampa

Cottage in Independence Square

The living area features a high, wooden ceiling with a decorative octagonal window, allowing natural light to fill the space. Comfortable seating includes a blue sofa and a floral-patterned chair, positioned near large windows that frame views of the outdoor patio.

4.76 out of 5 average rating, 37 reviews

Yachtsman Beachfront Cottage w/ Heated Pool

The front view of the bungalow features a welcoming entrance framed by tall palm trees. The light blue exterior contrasts with the lush greenery surrounding the property. A driveway leads to the entrance, inviting visitors to explore the charming cottage just steps away from the beach.

5 out of 5 average rating, 4 reviews

Charming 2BD Bungalow Close to Crescent Beach!

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

4.96 out of 5 average rating, 47 reviews

An aerial view highlights the river house set amid lush greenery, featuring a large wooden deck and fenced yard. The property is bordered by the Braden River, with its tranquil waters reflecting the surrounding trees and homes.

Cottage in Bradenton

2/2 Charming Riverfront Cottage w Deck & Kayaks

4.83 out of 5 average rating, 118 reviews

A modern kitchen features a blend of grey and white cabinetry, with a stainless steel dishwasher and sink. Countertops are adorned with kitchen essentials. A coffee maker and kettle are visible, along with stylish lighting fixtures above the island, creating a functional and inviting space.

Cottage in Bradenton

Modern Lakeview Retreat • Near IMG & Beaches

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 Bradenton Beach

A two-story elevated property is shown with a wooden exterior painted in light tones. A spacious deck with blue accents overlooks the ground level, which features a sandy area bordered by greenery. Steps lead up to the entrance, providing access to the living space.

4.86 out of 5 average rating, 104 reviews

AMI Tree House

Private cottage rentals

Cottage in Indian Beach-Sapphire Shores

A screened lanai is presented with light-colored wicker furniture, featuring green striped cushions. A small coffee table is positioned between the two seating areas, and a bicycle can be seen tucked in the corner, complementing the lush garden views visible through the screens.

4.81 out of 5 average rating, 67 reviews

Walk to Bay light filled private Cottage King bed

The living room features a spacious sectional sofa and a central round coffee table. A ceiling fan is present above, and natural light enters through large windows adorned with patterned curtains. A desk and chairs provide workspace, while art and decor enhance the inviting ambiance.

4.93 out of 5 average rating, 43 reviews

Historic Cocoanut Art Cottage

4.96 out of 5 average rating, 89 reviews

The exterior of a cottage features light-colored siding and a turquoise door, framed by shade from a large oak tree. The entrance is surrounded by white gravel, with lounge chairs and beach equipment visible. Bright sunlight illuminates the scene, enhancing the tropical atmosphere.

Cottage in Siesta Key

Surf Shack- Walk to Village/Boat Dock Included

The entrance features a charming porch with a white front door framed by tall windows on either side. A simple welcome mat lies in front of the door, and colorful landscaping with plants and red foliage completes the inviting exterior.

4.98 out of 5 average rating, 83 reviews

Central Quiet Bright Cottage, near Skyway Bridge.

The exterior of a brightly colored cottage features a pale blue facade with navy blue shutters and a welcoming front porch. A U.S. flag is displayed on the porch, while lush greenery surrounds the home. A driveway provides access to an open carport.

4.92 out of 5 average rating, 48 reviews

Aqua Breeze Cottage - Winter retreat 2 bd, 2 ba

A charming beachfront bungalow features a mint green exterior with a vibrant door, surrounded by well-maintained landscaping. The front yard is enclosed by a white picket fence, with tropical plants and decorative stones enhancing the inviting atmosphere.

4.58 out of 5 average rating, 12 reviews

Chic Peaceful 3BD Cottage - Walk to Siesta!

4.97 out of 5 average rating, 31 reviews

A bright living area features a comfortable seating arrangement with a light-colored sofa and armchair, complemented by decorative pillows. A coffee table sits centrally, and a television is mounted on a white console. Natural light flows in through large windows, with views of the outdoor patio visible.

Cottage in Holmes Beach

Sailfish Gulf Suites #2, Beachfront, Steps to the