Cottage holiday rentals in Sarasota

Cottage in Pass-a-Grille Beach

A serene beach scene shows soft, white sand stretching along the shoreline, meeting gentle turquoise waves under a clear blue sky. A few people are visible enjoying the beach, with vibrant green vegetation and distant structures lining the coast.

4.8 out of 5 average rating, 297 reviews

Sunny PaG Island rental w/bikes-just steps2beach

Welcome to your beach getaway! This cheerful, sun-soaked cottage is steps from the sand—or your next ice cream or seaside meal at a nearby restaurant. Perfect for couples or solo travelers, a comfy queen bed, a breezy living room, and a kitchen and dining area. Sip your morning drink on the upstairs porch as salty breezes drift by, or fire up the BBQ on the downstairs patio. Two bikes are yours to cruise the island like a local—Everything you need for a relaxing, joy-filled beach escape is here

4.96 out of 5 average rating, 106 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, 99 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.

4.9 out of 5 average rating, 163 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

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

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, 280 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.

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.

4.94 out of 5 average rating, 145 reviews

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

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.

4.86 out of 5 average rating, 277 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/ FREE 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 screened lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

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, 137 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.

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.

4.97 out of 5 average rating, 122 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.

4.91 out of 5 average rating, 371 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 Bradenton Beach

A vibrant yellow cottage is surrounded by a sandy area with palm trees. Colorful adirondack chairs in pink, blue, and green are positioned on the white gravel. A covered outdoor seating area is visible to the side, enhancing the beachside environment.

4.99 out of 5 average rating, 222 reviews

Bradenton Beach Sunsets 2, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

4.98 out of 5 average rating, 172 reviews

A row of brightly colored Adirondack chairs is positioned on the sandy beach, facing the tranquil ocean. The hues include yellow, orange, green, blue, pink, and purple. A clear blue sky with soft clouds complements the serene shoreline.

Cottage in Nokomis

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

Popular amenities for Sarasota cottage rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A serene outdoor space showcases a private heated pool and spa, surrounded by lush tropical landscaping. Paved with light-colored stones, the area features several lounge chairs positioned for relaxation under the bright sky. The backdrop includes a white wall and large windows of the house, enhancing natural light.

Cottage in Holmes Beach

5 out of 5 average rating, 3 reviews

Yacht Rock Ranch

4.94 out of 5 average rating, 68 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!

Cottage in Sarasota County

Cozy Cottage Near Siesta Key Village!

Modern Lakefront Getaway – 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

A bright studio space features a spacious king-size bed and a cozy sofa in soft blue tones. Natural light filters through window treatments, highlighting white walls and wooden beams that add warmth. A mirror and wall decor complement the relaxing atmosphere, while a TV is mounted nearby.

4.91 out of 5 average rating, 70 reviews

Cozy Cottage 1 block from Beach

4.91 out of 5 average rating, 77 reviews

Sandy Cottage w/ Hot Tub, 20 min to Beach + Garden

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, 147 reviews

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

Pet-friendly cottage rentals

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, 5 reviews

Charming 2BD Bungalow Close to Crescent Beach!

5 out of 5 average rating, 17 reviews

House with pool 1 block to village, 3blks to beach

A wooden deck extends from the cottage, featuring a sturdy chair positioned for relaxation. The light blue exterior of the house contrasts with the greenery surrounding the space. Steps lead up to the deck, enhancing accessibility to the entrance.

4.87 out of 5 average rating, 70 reviews

Cozy Cottage

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.

4.96 out of 5 average rating, 49 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

5 out of 5 average rating, 36 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

Cottage in Don Pedro Island

4.98 out of 5 average rating, 59 reviews

Island Getaway•Beach House•Dock•Pet Friendly

Cottage in Bradenton Beach

4.86 out of 5 average rating, 104 reviews

Anna Maria Island Tree House

4.98 out of 5 average rating, 98 reviews

An open-concept living area features exposed wooden beams and light hardwood flooring. A dining area with a table and chairs is positioned near a fully equipped kitchen. Glass double doors lead to a cozy sleeping space with a bed and large windows, allowing natural light to fill the room.

Cottage in Cove

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

Private cottage rentals

4.92 out of 5 average rating, 88 reviews

A quaint cottage is nestled among lush greenery, featuring a light-colored exterior and a sloped roof. Two chairs are positioned near the entrance, inviting outdoor relaxation. The setting emphasizes privacy with natural landscaping, creating a serene atmosphere close to the lush garden.

Cottage in Englewood

Private garden cottage

4.9 out of 5 average rating, 20 reviews

A cozy deck is featured with two chairs and a hammock, overlooking the peaceful landscape. Strings of lights enhance the space, while the sky transitions from blue to dusk. Nearby, views of open fields can be seen, creating a tranquil outdoor retreat.

Cottage in Myakka City

New Country Cottage on Lake Manatee Lakewood Ranch

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, 125 reviews

Modern Lakeview Retreat • Near IMG & Beaches

4.95 out of 5 average rating, 37 reviews

A spacious bedroom features a large bed adorned with a blue throw and several pillows. Two framed art pieces are displayed above the headboard. Nightstands with lamps are placed on either side, while a door on the left leads to another room.

Cottage in Lido Key

The All Hands On Deck Cottage at Casa Limonada

4.92 out of 5 average rating, 50 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 spacious screened lanai features comfortable seating options, including wicker chairs and a sofa with striped cushions. Natural light fills the area, creating a bright ambiance, while plants and decorative accents enhance the setting. A wide pocket sliding door connects the lanai to the family room.

4.95 out of 5 average rating, 58 reviews

Discover Hidden Cove #2 - Water Views with Privacy

4.98 out of 5 average rating, 62 reviews

A charming cottage exterior is adorned with peach-colored walls and a welcoming blue front door. Lush green landscaping features palm trees and colorful flowering plants, complemented by a gravel driveway and a well-maintained lawn.

Cottage in Englewood

Magnolia Cottage

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.