2BR Beachy Speakeasy In St Armand's w/ Rooftop Deck. Walk to Lido Beach

Book Your SUMMER 2026 GETAWAYS! Step into your getaway now at a Sarasota paradise nestled in the heart of St Armand's Circle! This isn't just any rental, it's an experience waiting to unfold!

*Please note our "Moderate Cancellation Policy" listed only applies to bookings during mid season from May through August . See our Custom Seasonal Cancellation Policy at the bottom of this description and in our Rental Agreement.

Picture this: A Beach Vacation Getaway in a hidden, 1-of-a-kind apartment with a Beachy Speakeasy Vibe that is located on the rooftop of a retail store. It features a rooftop deck, outdoor dining under a gazebo with string lights, with a lounge area complete with cushioned lounge chairs, a single daybed, a double daybed with clamshell canopy, and a retro vintage umbrella. Plus, it's a 5min walk to the pristine sands of Lido Beach, and surrounded by the charm of boutiques, and eateries within walking distance!

Welcome to the Beachy Speakeasy! Thanks for checking us out!

The Beachy Speakeasy is a recently updated 2-bedroom, 1-bath Sarasota hideaway with a rooftop deck, beachy style, speakeasy-inspired touches, and a walkable location near St. Armand's Circle and Lido Beach.

Stay a few days, a week, a month, or longer. Stays of 28+ nights receive a 35% discount.

This unique second-floor apartment was updated in 2026 with fresh paint throughout, new furniture additions, new bedding, new linens, new towels, and a brand-new blue linen pull-out sleeper sofa in the living room.

Please note before booking: this is a second-floor walk-up with no elevator. The entrance is located on the rear/service side of the retail shops, near dumpsters and trash cans used by neighboring businesses. It is safe, well-lit, and part of the quirky hidden speakeasy-style arrival - but it is not a traditional hotel lobby entrance. We disclose this clearly so guests know exactly what to expect.

Your stay begins at an unassuming rear entrance behind the retail shops. From there, you’ll enter an ocean-blue concrete-floor corridor with vibrant blue walls, pass the hidden washer/dryer area, our provided beach essentials area and head up a small two-flight stairway to your private second-floor Beachy Speakeasy.

Inside, you’ll find a bright, updated, thoughtfully designed 2-bedroom retreat that blends coastal style with speakeasy character.

The living area includes a brand-new blue linen pull-out sleeper sofa, 2 blue velvet chairs, coastal accents, a streaming TV, and a coffee table with 2 pop-up laptop/eating surfaces. It’s a great spot to relax after Lido Beach, stream a movie, catch up on work, or use the sofa bed for additional guests.

The kitchen is fully equipped with the essentials for meals, snacks, coffee, and beach-day prep. You’ll have a drip coffee maker, Vertuo Nespresso machine with frother, cookware, dishes, utensils, and the basics needed for a comfortable stay.

A dedicated workspace is available with a chair, laptop desk, and printer/scanner. A computer is also being added for guest convenience.

Fast, free T-Mobile 5G Wi-Fi is provided throughout the Speakeasy.

Sleeping Arrangements

Tortuga Morada Suite / Purple Turtle Suite:
The primary bedroom has that beachy vibe and features a memory foam queen bed, hotel-style sheets, new beachy comforter, 4 new pillows, smart streaming TV, smart speaker, sound machine, dehumidifier, wireless chargers, USB charging, alarm clock, luggage racks, dresser, robes, and extra seating. There is also a blue velvet futon sofa with a rolling laptop desk.

Pineapple Room:
The second bedroom has a moody speakeasy vibe and has been newly painted and designed. This room does not have a window, which makes it great for guests who enjoy a darker room for sleeping in. It includes a comfortable queen bed with high-end memory foam topper, new bedding and pillows, mirrored wall, pineapple lamps and decor, remote-controlled crystal fandalier, smart TV, smart speaker, sound machine, luggage rack, dresser, clothing rack, robes, and champagne-gold nightstands.

Living Room:
The living room includes a brand-new blue linen pull-out sleeper sofa for additional sleeping space.

The home sleeps up to 6 guests total with 2 bedrooms plus the living-room sleeper sofa. Reservation rates are based on 4 guests. Extra guest charges apply for reservations over 4 guests, up to a maximum of 6.

Bathroom

The bathroom is small but very functional, with a walk-in shower featuring new LifeProof non-slip Carrera marble mosaic tile flooring and a spacious single vanity.

We provide shampoo, conditioner, soap, hair dryer, flat iron, towels, and other essentials to make your stay easier.

Rooftop Deck

The rooftop deck is one of the best parts of the Beachy Speakeasy.

Enjoy morning coffee, breakfast, lunch, dinner, evening drinks, rooftop yoga, sun-soaked lounging, or a light workout with the provided mats and free weights.

The rooftop includes a dining table with umbrella and 4 chairs on the wooden deck under string lights inside the new gazebo, plus multiple lounge areas when you step down the stairs of the deck.

The rooftop garden lounge area features 2 lounge chairs with cushions, a daybed with vintage umbrella, a side table with hidden ice chest, tropical plants, areca palms, pygmy palm, blooming hibiscus, and a manicured AstroTurf lawn.

There is also an additional AstroTurf sitting area with 2 Adirondack chairs and a queen-sized daybed with cushions and clamshell canopy.

Beach Gear

We provide beach chairs, a beach umbrella, cooler/ice chest, and beach wagon so you can walk to Lido Beach without dealing with beach parking.

Lido Beach is about a 7-minute walk from the property, and St. Armand's Circle shops, restaurants, cafes, and nightlife are very close walking distance since the property is located on a spoke of the circle

Location

The Beachy Speakeasy is in one of Sarasota’s most walkable and convenient areas, literally on St. Armand's Circle and close to Lido Beach.

You’ll be close to:

Lido Beach
St. Armand's Circle
Restaurants, boutiques, galleries, cafes, and nightlife
South Lido Park
Mote Marine Aquarium
Downtown Sarasota
Marina Jack
Longboat Key
Siesta Key Beach
SRQ Airport

A free trolley connects St. Armand's Circle to downtown Sarasota and nearby areas, making it easy to explore without relying only on a car.

Electric scooters and bike rentals are also available nearby.

Parking

There is no dedicated parking space for this unit.

However, there are many nearby free and paid street parking options within walking distance, generally about 150–200 feet from the entrance. Parking is not an issue, regardless of season, but guests should expect street parking rather than private assigned parking.

This location is especially convenient for guests who enjoy walking, using Uber/Lyft, biking, scooters, or the trolley.

So come, dive into the Beachy Speakeasy experience - it's not just a rental, it's a lifestyle waiting to be embraced!

I am also a licensed Realtor with a team at Berkshire Hathaway HomeServices, so feel free to reach out if you are looking to buy in the area. I'm always happy to help.

There is NO POOL on the property but there is a public pool located on Lido Beach for a small daily fee

Important: Before you arrive you will be asked to complete guest verification through third-party provider Truvi. This is done to ensure we are keeping up-to-date with short-term rental regulations as well as providing both our guests and our properties with extra protection. Truvi will contact you via email and/or text to complete the verification. Please do so prior to arriving at the property to enable a quick and easy check-in process. You will also be given the choice between a security deposit or a non-refundable damage waiver. There is also a separate rental agreement that is sent for e-signing.

Our custom seasonal cancellation policy and our refund policy:

January - April : Strict - *Partial refund 60 days before check-in; No refund after 60 days before check-in.
May-August: Moderate: *Partial refund 30 days before check-in; 50% refund 14-30 days before check-in. No refund after 14 days before check-in.
September - October: Relaxed *Partial refund up to 14 days before check-in. 50% refund for cancellations between 7 and 14 days. No refund after 7 days before check-in.
November - December: Firm - *Partial refund 60 days before check-in; 50% refund 30-60 days before check-in. No refund after 30 days before check-in.

*Partial refunds are further defined as 100% refunds minus processing fees incurred by the merchant - Stripe

The Host recommends that all guests obtain appropriate travel and personal insurance coverage to cover these charges in case of a cancellation.