Siesta Homes with 1-7 Days Minimum lease

Welcome to Siesta, a charming subdivision located in the heart of Siesta Key, Sarasota, Florida. Known for its stunning white sandy beaches and vibrant community, Siesta offers a unique blend of luxury living and laid-back island lifestyle.

One of the standout features of the homes in Siesta is the option for short-term rentals with a minimum lease of 1-7 days. This flexibility allows homeowners to capitalize on the bustling tourism industry in Siesta Key, making it an ideal investment opportunity for those looking to generate rental income.

Whether you're looking for a vacation home, a permanent residence, or an investment property, Siesta has something for everyone. From cozy beachfront cottages to modern waterfront estates, the real estate options in Siesta are diverse and cater to a range of preferences.

In addition to its prime location and real estate opportunities, Siesta boasts a strong sense of community and a range of amenities for residents to enjoy. From upscale dining and shopping to outdoor recreational activities, living in Siesta offers the perfect balance of relaxation and entertainment.

Come discover the beauty and charm of Siesta – where everyday feels like a vacation, and the possibilities are endless. Experience luxury island living at its finest in this coveted subdivision in Siesta Key, Sarasota, Florida.

Newest Siesta Homes with 1-7 Days Minimum lease

$3,350,000

Siesta SubDv. ⋅ 34242 Zip Code ⋅ A4677797 MLS ⋅ Active Status

Discover Unrivaled Coastal Elegance Steps from Siesta Key Beach! This rare gem features two meticulously remodeled canal-front homes with stunning partial views of the bay, perfectly situated in a prestigious neighborhood. The main residence boasts a contemporary design with open and spacious layouts, highlighted by soaring 24 ft ceilings adorned with stylish gray wooden accent beams. Culinary enthusiasts will be captivated by the gourmet kitchen, featuring custom-made wood cabinets complemented by exquisite Carrara Quartz countertops. Equipped with top-of-the-line appliances, including a new stainless Thermador refrigerator, Bosch dishwasher, and an impressive center island with a bar area, it truly caters to the most discerning chefs. Zoned RMF2 while located in a single-family neighborhood, this property allows for daily Airbnb rentals, making it an excellent investment opportunity. A private, charming guest cottage serves as an ideal retreat or rental for additional cash flow. Recent upgrades include new Window World Hurricane-rated windows, French doors, and a newly installed seawall (2025), ensuring your investment remains safe and secure. The main house spans 3,005 sq ft, featuring three bedrooms and 2.5 baths adorned with luxurious Panaria marble and 24x48 tile flooring. Bathrooms boast contemporary Miseno vanities and premium Grohe and Hansgrohe fixtures. The decadent master suite invites relaxation with a rain cap shower and a sumptuous soaking tub. Both homes are equipped with new Rheem A/C units, while the property’s outdoor oasis features a large screened lanai overlooking the canal and bay. Dive into the newly resurfaced pool with a stunning stone waterfall or enjoy the expansive outdoor space, surrounded by tropical landscaping. The cozy guest cottage, covering 1,700 sq ft, includes three bedrooms and two full baths, showcasing beach-washed ceramic tile flooring, white wood Shaker cabinets, and modern KitchenAid and Bosch appliances. The new dock provides easy access to pristine boating waters with no bridges obstructing your path to the bay. Siesta Key is a haven for music lovers and foodies alike, while Sarasota delights with its vibrant art scene, ballet performances, the Asolo Performing Arts Center, the Ringling Art Museum, and world-class shopping. Relax with your favorite beverage on the rear patio, shaded by a majestic live oak, or grab your fishing rod, bathing suit, and water toys to fully embrace the Siesta Salt Life. Act fast! This exquisite property offers a luxurious lifestyle and lucrative potential in one of Florida’s most sought-after destinations!

1240 Solitude Lane, Siesta Key

$639,900

2 Beds ⋅ 2 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code ⋅ A4679214 MLS ⋅ Active Status ⋅ Building 1 BLDG.

Reduced over 60K! Excellent resort investment opportunity with a proven rental history at The Beach Club on Siesta Key, located just steps from the world-famous sugar-sand beach. This beautifully maintained residence looks and feels brand new, featuring a functional floor plan, deeded beach access, and a complete 2021 update with elegant sea-inspired décor, flat-screen TVs, free Wi-Fi, and a full kitchen with stainless steel appliances. Owners enjoy up to 120 days of personal use per year while benefiting from professional on-site management or the option to self-manage for added flexibility. TripAdvisor rates the property 4.5 stars with outstanding reviews. Resort amenities include a heated pool, hot tub, and complimentary beach chairs and umbrellas. Built in 2009 on stem walls, the building is elevated and sustained no storm damage. Ideally located mid-island just 1,000 feet south of the Stickney Point Bridge for easy mainland access, and within walking distance to popular restaurants, shops, marinas, rentals, and local favorites such as Captain Curt’s and Daiquiri Deck—making this a true turnkey beach getaway and income-producing investment. Ask your agent for the Rental History attached to the MLS listing too!

6732 Sarasea Circle Unit 104C, Siesta Key

$8,000,000

8 Beds ⋅ 9 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code ⋅ A4635010 MLS ⋅ Active Status

Investor's Dream - Short term rentals allowed here at this amazing Siesta Key home. Designed specifically to cater to large groups, this brand new home comes fully furnished and ready to produce an impressive income. Just steps away from Siesta Key's public beach access onto Crescent Beach, all the boxes are checked here. 8 bedrooms, all en suite with 8 bathrooms and a powder room too. Amazing resort style pool & spa boasting a rain/waterfall feature and impressive outdoor living. Luxury finishes are seen throughout such as an elevator, high end appliances, solid wood cabinetry, stone surfaces, bar, oversized island, and more!

7007 Point Of Rocks Road, Siesta Key

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