Cottage holiday rentals in Sarasota

4.96 out of 5 average rating, 113 reviews

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.

Cottage in Palmetto

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.

An open living area features tiled flooring and soft lighting, with comfortable seating arrangements including a sofa and armchairs. A dining area is visible, showcasing a wooden table with chairs. Decorative touches such as artwork and a side cabinet enhance the space's charm.

4.99 out of 5 average rating, 107 reviews

Quaint Cottage,150 steps away from Crescent Beach!

Nestled on the serene Crescent Street, this classic 1969 cottage, is just a short walk to the ground quartz sands of Siesta Key. The 500 sq foot private brick paver and stone backyard off the screened in lanai is fully fenced with custom built stainless outdoor kitchen, featuring a large grill, refrigerator, custom built stone bar with seating for 8 . Nearby is a blue glass gas fire pit with a seating area, over sized (9 ft. diameter) in ground "spool", loungers and a large circular daybed.

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, 288 reviews

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. This is a 101 year old home. It has not been renovated. 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 as well.

An inviting outdoor area features a heated pool surrounded by lounge chairs. A two-story blue building with a covered balcony offers a view of the pool. Lush palms and landscaping line the pool's perimeter, creating a relaxing environment.

4.94 out of 5 average rating, 129 reviews

The Marlin: Heated Pool, 4 Houses to Beach

This apartment is a 2nd story unit with vaulted ceilings in the living room and an open floor plan that sleeps 2 with a maximum of 4 people. The bed makeup in this rental is a king bed in the master and a queen size sofa sleeper. This rental is great for longer stays or guests who like to cook since you have a full kitchen and all the items to cook any meal. There is also a washer/dryer in the apartment private for your use. Beach chairs and umbrellas are supplied to you at no charge.

4.79 out of 5 average rating, 154 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!

An open living space features a fully equipped kitchen with wooden cabinetry, a dining table, and seating area. A flat-screen TV is mounted on the wall. Light-colored flooring enhances the spacious feel, while natural light brightens the room through multiple windows.

4.87 out of 5 average rating, 296 reviews

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

4.98 out of 5 average rating, 109 reviews

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage—set in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

A mobile home with a welcoming front porch is surrounded by lush greenery and colorful flowering plants. The structure features a light exterior, complemented by a decorative element above the porch. A carport for vehicle parking is visible, alongside a well-maintained pathway.

4.96 out of 5 average rating, 132 reviews

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.

4.87 out of 5 average rating, 187 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

Three blue Adirondack chairs are positioned on a grassy area overlooking a tranquil canal. The chairs face the water, enhancing the serene environment. A white picket fence borders the space, with greenery and trees visible in the background.

4.94 out of 5 average rating, 156 reviews

Waterfront Retreat•Pool•PingPong•Near AMI Beaches

Relax at this cozy waterfront cottage with a private pool, & a short drive to Anna Maria Island’s white-sand beaches. 2BR/2BA with two living areas include a bright Florida room overlooking the canal. Enjoy ping pong and a putting green ⛳. Start your mornings with coffee on the dock, watching fish jump out of the water. Fast WiFi, workspace, beach gear, and a kitchen with cooking essentials. Perfect for beach days, family getaways, or a relaxing coastal escape.

4.9 out of 5 average rating, 383 reviews

Serene Suite*Walk 2 Dwtn/Riverfront/Dining*AMI*IMG

Our private, old Florida, suite located in historic downtown Bradenton with spacious back deck, king bed, sitting area, kitchen, fast FREE WiFi & parking. Walk to the Riverfront where you will enjoy dining, shopping and some amazing waterfront views. Just minutes to AMI beaches, shops, and endless fun. Walkable to local museums, Planetarium, IMG and other local favorites. Nestled in a quiet neighborhood this suite makes for an enjoyable, peaceful stay.

Cottage in Bellevue Terrace

4.92 out of 5 average rating, 146 reviews

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴 Cert# VR24-00152

Popular amenities for cottage rentals in Sarasota

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.95 out of 5 average rating, 56 reviews

Cottage in Palmetto

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

4.96 out of 5 average rating, 275 reviews

A private outdoor space featuring a heated pool and spa, surrounded by palm trees and lounge chairs. The vibrant blue cottage is visible in the background, complemented by carefully arranged landscaping. A pathway of stepping stones leads toward the entrance of the cottage.

Cottage in Anna Maria

Turtle Cottage - Anna Maria Island

Cottage in Anna Maria

Over the Moon

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, 9 reviews

Sarasota Cottage Near Beaches, Downtown & Airport

4.95 out of 5 average rating, 76 reviews

A coastal-style duplex is framed by lush tropical landscaping, featuring palm trees and colorful flowering plants. The exterior showcases light-hued siding, a spacious front porch with railings, and two garage spaces below. A clear blue sky enhances the inviting atmosphere of the property.

Cottage in Holmes Beach

Close to the Beach+ Private heated pool and spa!

5 out of 5 average rating, 3 reviews

Cozy Cottage Near Siesta Key Village!

Cottage in Sarasota County

5 out of 5 average rating, 3 reviews

Lake Ibis Retreat-Resort Perks Included

A charming cottage is seen with a porch featuring a white railing and a blue and white striped umbrella. The exterior showcases light blue siding and a screened-in lanai. Lush green grass frames the entrance, adding to the welcoming appeal of the home.

4.67 out of 5 average rating, 3 reviews

Cozy Cottage at Sun Outdoors Sarasota

Pet-friendly cottage rentals

Cottage in Pass-a-Grille Beach

An inviting dining space displays a wooden table paired with white chairs, complementing light blue walls. A small sideboard houses essentials, while natural light streams through a large window. The open layout connects to a cozy living area with a television and tasteful decor.

4.81 out of 5 average rating, 308 reviews

Sunny PaG Island rental w/bikes-just steps2beach

4.96 out of 5 average rating, 171 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.

4.96 out of 5 average rating, 143 reviews

Artsy guest house; near downtown w/ private patio

4.9 out of 5 average rating, 144 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

4.91 out of 5 average rating, 175 reviews

An aerial view captures the coastline of Manasota Key, showcasing the blue-green waters and sandy beach. The surrounding area features a mix of residential buildings and green spaces, with multiple boats visible in the water and a bridge connecting to nearby islands.

Cottage in Englewood

Unit #1 Free kayak/bikes/walk to beach/fullcottage

4.97 out of 5 average rating, 59 reviews

Old Florida River Cottage 2/2 - Kayaks & Huge Deck

5 out of 5 average rating, 37 reviews

A cozy living area features a light grey sofa adorned with throw pillows, complemented by two round coffee tables. A floor lamp and a potted plant add warmth. Natural light floods the room through large windows, enhancing the welcoming atmosphere.

Cottage in Holmes Beach

Hibiscus Villa by Beach Boutique Rentals

4.99 out of 5 average rating, 283 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

Cottage in Redington Shores

An expansive view of a sandy beach stretches under a clear blue sky. Soft dunes with tall grass line the shore, while gentle waves can be seen lapping at the sand, creating a serene coastal atmosphere.

4.9 out of 5 average rating, 21 reviews

2BR Charming Beach House Steps To The Beach 2nd FL

4.97 out of 5 average rating, 32 reviews

A comfortable living space features a light grey sofa with two blue cushions and a yellow accent pillow. A round mirror hangs on the wall, reflecting natural light. The white coffee table displays a decorative bowl, with a woven rug beneath providing texture to the floor.

Cottage in Englewood

Oystercatcher 3min walk to sunset, bikes, kayaks

A single-story cottage is highlighted by warm sunlight, showcasing a welcoming front porch with white railings. Lush palm trees flank the entrance, complementing the structure's light exterior. The driveway leads up to the home, set against a clear blue sky.

5 out of 5 average rating, 20 reviews

Cozy cottage 15 min from the beach

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.

4.82 out of 5 average rating, 147 reviews

Modern Lakeview Retreat • Near IMG & Beaches

5 out of 5 average rating, 16 reviews

A welcoming living area features a light-colored sectional sofa with decorative pillows and a contrasting green area rug. Large windows provide views of the outdoor patio, while a flat-screen TV is mounted against the wall. Lush plants and modern decor complete the space.

Cottage in Holmes Beach

Sailfish Gulf Suites #1, Beachfront, Steps to the

Cottage in Don Pedro Island

4.99 out of 5 average rating, 69 reviews

Island Getaway•Beach House•Dock•Pet Friendly

4.92 out of 5 average rating, 60 reviews

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.

Cottage in Palmetto

Aqua Breeze Cottage - Winter retreat 2 bd, 2 ba

A comfortable seating area features a dark leather sectional sofa with decorative pillows and a matching recliner. A central ottoman provides additional comfort, while two table lamps illuminate the space. Natural light filters through the blinds, complementing the artwork on the walls.