Sink into the warm 85° (year‑round heated) cocktail pool, framed by cafe lights, tropical foliage and the glow of your tiki bar. From above, you’ll spot City Cottage tucked into the vibrant heart of Sarasota—just minutes from the bay, beaches, and downtown buzz. Glimpse your private retreat from above—lush landscaping, a sparkling cocktail pool, and charming 1920s bungalow all your own. Sip evening cocktails at your own tiki bar under strung lights, the mood set for conversation and coastal ease. As golden hour fades, your private tiki bar comes alive with string lights and warm ambiance. As dusk settles in, the heated cocktail pool glows inviting you to slip in for a serene evening soak. City Cottage welcomes you with classic 1920s charm in a walkable Sarasota neighborhood. Relax on the porch with coffee or cocktails and the gentle Florida breezes. Unwind beneath the original eaves on this breezy front porch. Step through the vintage front door into a thoughtfully restored cottage where historic charm meets modern comfort. Gather in a sunlit living room where original hardwood floors, crown molding, and a classic fireplace create cozy, timeless character. Curl up beside the fireplace in a light‑filled living space of tall ceilings, original hardwoods, and timeless elegance. Relax by the glowing fireplace in a spacious living area filled with natural light and vintage elegance. See the clean lines of your living room—versatile, stylish, and ready to transform with the queen Murphy bed tucked away. Sunlight streams through large windows, casting a warm glow over the refined blend of classic and contemporary decor. Admire the timeless crown molding and tasteful accents that elevate your stay with subtle sophistication. Find your favorite spot to unwind in a cozy corner filled with soft textures and thoughtful lighting. Breathe easy in an airy living room that balances open space with intimate comfort for every guest. Discover the charming details that add personality and warmth to the inviting living space. Curl up in the oversized Papasan chair, the perfect nook to relax with a book or enjoy a quiet moment. Gather around the elegant dining table, where sunlight and style set the scene for memorable meals with family and friends. Share stories over dinner with the fully equipped kitchen just steps away, blending convenience and charm seamlessly. Enjoy open-concept living as you dine, with inviting views back to the cozy living room. Cook together in the retro‑modern kitchen while light pours through windows, blending historic character and fresh style. Enjoy seamless flow between the living space and dining area, perfect for entertaining or relaxing after a day in Sarasota. Cook and connect in a bright, open kitchen featuring sleek countertops and plenty of space to prepare your favorite meals. Enjoy the seamless blend of vintage charm and modern appliances in this thoughtfully updated kitchen. Store your groceries with ease in the spacious stainless-steel fridge, ready for everything from beach snacks to gourmet dinners. From the dishwasher to the stove, every feature is designed for effortless cooking and cleanup during your stay. Bedroom 1, where you wake to gentle morning light. Step into a spacious bedroom where comfort meets classic style and thoughtful touches for your stay. Enjoy easy access to your private ensuite bathroom, seamlessly connected to a restful bedroom retreat. A spacious, light-filled bedroom that combines classic charm with cozy comfort for a peaceful retreat. Sink into the clawfoot soaking tub—your own spa moment—complete with charming tile accents. Refresh in a beautifully updated shower that blends retro style with contemporary convenience. A bright, elegant space featuring a classic vanity with ample lighting and thoughtful touches. Step into a stylish ensuite bathroom where vintage charm meets modern comfort in every detail. From the ensuite, enjoy a seamless connection to the serene bedroom, creating a harmonious retreat filled with vintage charm. Rest easy in the second queen bedroom, with warm textures, calming tones, and a cozy refuge after exploring the city. Relax in a bright and inviting bedroom featuring a comfortable queen bed and tasteful decor. Enjoy thoughtful touches and ample natural light for restful stays. Refresh in a well-appointed hall bathroom featuring a modern shower, sleek fixtures, and a bright, clean design for guest convenience. The third bedroom is ideal for kids or friends, this twin room feels bright and airy—smartly appointed for comfort and flexibility. Cozy and charming, this twin bedroom offers two comfortable beds perfect for friends or family sharing a peaceful space. Enjoy total relaxation in your private heated cocktail pool, surrounded by lush greenery and inviting outdoor seating. Enjoy the best of outdoor living with a private cocktail pool, sunny patio, and comfy chaise lounges—your own tropical escape in the heart of Sarasota. Soak up the sun on a row of comfy chaise lounges, then fire up the grill and gather around the shaded seating area for easy, al fresco dining. Kick back at your private tiki bar—complete with barstools, twinkle lights, and island vibes. Start the day island-style at your private tiki bar, a sunny spot for sipping coffee, smoothies, or a midday cocktail in the breeze. Just steps from the pool, the BBQ area offers the ideal hangout for grilling, relaxing, and soaking up Sarasota’s easy going vibe. Fire up the grill and enjoy a laid-back meal in this inviting outdoor space, perfect for family cookouts or casual sunset dinners. As the sky turns shades of violet and rose, City Cottage glows with warmth and welcome—your perfect Sarasota retreat as evening falls. Framed by a dreamy twilight sky, the front porch invites you to slow down, settle in, and savor the magic of golden hour. Unwind on the front porch under the glow of soft outdoor lighting—an inviting space to end the night with quiet conversation or a final glass of wine. Cool off in the cocktail pool, then rinse off under the open-air shower. As dusk arrives, your pool and tiki bar glow under soft lighting, the perfect backdrop for quiet evening ambiance. As the sun sets, the cocktail pool sparkles under twilight skies—creating the perfect backdrop for a peaceful evening dip. Linger poolside as the sky fades to dusk, with chaise lounges ready for stargazing, cocktails, or simply soaking in the serenity. Festive party lights twinkle over the tiki bar, casting a warm glow that beckons you to unwind and celebrate. Twilight bathes the barbecue and sitting area, creating an inviting spot to savor grilled meals and warm conversations as day turns to night.

City Cottage – 1745

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Overview Amenities Availability Location Room Details Reviews

Description

City Cottage – Cocktail Pool + Walk to Downtown

Why You ll Love This Home

Step back in time without sacrificing comfort. City Cottage blends 1920s charm with upscale, modern updates, including a heated cocktail pool, clawfoot soaking tub, and tiki bar, all nestled in a walkable downtown Sarasota location.

Perfect For

Couples, small families, or friend groups looking for a stylish, walk-to-everything Sarasota escape with vintage flair.

️ Imagine This

You arrive at City Cottage and step through the front door into a storybook bungalow 9-foot ceilings, crown molding, and soft natural light pouring in through oversized windows. Drop your bags, kick off your shoes, and feel the easy rhythm of Old Florida take over. Morning starts with coffee on the front porch, birdsong in the background. Afternoons unfold with dips in the heated cocktail pool, sun-soaked lounging, or a mid-day refresh under the Al Fresco shower. As evening falls, mix a drink at your private tiki bar before heading downtown for a sunset dinner. End your day soaking in the clawfoot tub, wrapped in nostalgia and peace.

Where You ll Sleep

Main Bedroom: Queen Bed, Ensuite Bath with Clawfoot Tub/Shower

Bedroom 2: Queen Bed, Shared Bath

Bedroom 3: Two Twin Beds, Shared Bath

Living Room: Queen Murphy Bed Main Living Area

Explore the Area

0.4 Miles to Main Street Sarasota Walk to Dining, Art, Entertainment

0.6 Miles to Marie Selby Botanical Gardens

1.8 Miles to Bayfront Park Marina Jack

3.0 Miles to Lido Beach

3.2 Miles to St. Armands Circle

Access to Free Sarasota Bay Runner Trolley

⌛ Don t wait this home books fast. Your reservation includes peace of mind with 6-hour deep clean and 35-point inspection.

Need to Know: This pool is heated to 85 degrees year round. This unit is DTWN zoned by the City of Sarasota.

Availability

  • Today
  • Booked
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Location

Room Details

Room Beds Baths TVs Comments
Bedroom 1
Bedroom 2
Bedroom 3
Bathroom 1
Bathroom 2

Reviews(11)

Tim

03/16/2026
The house and its location were great, the team was very responsive for a minor snafu getting the pool heating working.

Sybil

02/17/2026
Excellent location, easy walk to restaurants and grocery. Spa was a great addition. Super responsive host. Definitely recommend.

Julia

01/30/2026
We had a wonderful time staying at the City Cottage. The location was amazing and walkable to restaurants, grocery stores and the downtown area. The house itself was as advertised and very clean with plenty of amenities. Our hosts were helpful and responsive throughout our stay. I would highly recommend this airbnb!

Judy

01/20/2026
Spacious, clean, cozy

Susan

01/12/2026
Every thing was wonderful! I would definitely be back to this adorable little place!

Maria Fernanda

10/23/2025
Good place to stay in Sarasota area, located near restaurants and downtown.

Hali

07/07/2025
Great place, close to many breakfast places and walkable to the trolly and grocery store.

Gus

04/14/2025
Great place near downtown Sarasota. Could walk to shops/restaurants on Main street, catch the trolley to Siesta Key Beach or Lido Beach. Centrally located. Plenty of room and a nice back yard. Would stay there again.

William

03/24/2025
Fabulous location and home. Fantastic service from the hosts!

Chris

01/20/2025
We had an excellent stay and highly recommend!

Peter

12/30/2024
Great location.
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