Zumper

260 Hidden Bay Dr
260 Hidden Bay Dr, Osprey, FL 34229, USA

Condo for rent
Monthly rent
$4,850–$5,000
Beds2–3
Baths2
Sqft1,950–2,168
modified
5+ Days Ago

Property Overview

Set in a gated community with a resort-style pool, fitness center, BBQ grills, and a large kitchen with breakfast bar, the home pairs everyday comfort with appealing amenities. Strong value per square foot and 143 listing photos help convey quality and transparency to prospective renters. Common areas for meetings, high-speed internet, large windows, and a quiet environment support remote-work needs alongside leisure and relaxation.

This summary uses Zumper’s proprietary data. “Things you’ll love” and “Great for” are based on our internal analyses of market trends and renter insights.

Things you’ll love

  • More space
  • Extra Storage
  • Images available

Great for

  • Work-from-home

Highlights

  • fitness center
  • large kitchen
  • breakfast bar
  • gated community
  • resort style pool
  • bbq grills

Units

260 Hidden Bay Dr Osprey, FL

Available

504

2 Beds

2.5 Baths

$5,000

Listed on 09/08/2025
Listed by Annual Turnkey 3/3 penthouse on waterfront in Osprey
Days on market: 227
Annual Turnkey Furnished or seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French doors, and powder room in an open floor plan. The kitchen is large with solid wooden soft close, shaker style cabinetry topped with slab granite counters with a breakfast bar on peninsula with seating for 4. This room has a tray ceiling and is complimented with stainless steel appliances. The dining area will seat six comfortably and has your amazing water views. The condo also features a large laundry room with sink, granite counters for folding, hanging rack and upper and lower extra storage, as well as assigned parking garage for one with adjacent huge storage closet. This is a secure community with gated access to the community, and controlled lobby access, and for your weather concerns there are catagory 5 hurricane grade windows recently installed. The amenity package in this community is impressive, with a large clubhouse with full catering kitchen, lounge, library, fitness center, resort style pool with tables and umbrella's and a covered shaded area, BBQ grills and outdoor dining area in a Tiki Hut, and a board walk leading to an island with fountains spraying! Tennis or pickleball-YES! You will also find yourself convenient to shopping, dining, Siesta Key Beach, and downtown Sarasota with theater, opera, museums and more fun! This amazing space can now be rented during HIGH SEASON (December thru April) at $6000/month + 13% tax for an unforgettable vacation. Call today for your incredible home!

Available

401

3 Beds

2.5 Baths

$4,850

Listed on 03/07/2026
Days on market: 48
Experience the beauty of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking Little Sarasota Bay. Thoughtfully designed for both comfort and flexibility, the home includes a private den or home office, convenient in-unit laundry, and generous living spaces perfect for relaxing or entertaining. Nestled within Hidden Bay, a private 14-acre waterfront community, residents enjoy a peaceful coastal setting directly on the bay—just across from the pristine beaches of Casey Key and the Gulf of Mexico. At the heart of the community is a beautifully renovated clubhouse featuring elegant gathering spaces, a catering kitchen, fitness center, reading library, and dining room. Outside, unwind by the heated pool and spa, gather with friends at the Tiki hut grilling area, or relax beside the tranquil pond with cascading water features. For recreation and adventure, Hidden Bay offers tennis and pickleball courts, a kayak launch, pet park, and car wash station. A scenic elevated boardwalk winds through lush mangrove preserves, leading to a long fishing pier where residents can enjoy peaceful water views, cast a line, or simply take in the area’s breathtaking sunsets. Hidden Bay offers more than a home—it offers a true waterfront lifestyle. Rental rate includes basic cable, internet (expanded services available), water, trash, and pest control. Call for a private tour today. Amenities: community pool, community fitness, kayak launch, tennis courts, fishing pier, boardwalk, clubhouse with catering kitchen, community grills, pickle ball courts, gated comunity, hot tub, tiki hut, waterfront community, car wash station

Occupied Units

Occupied

204

3 Beds

2.5 Baths

$4,000

Listed by Laura Davis
Days on market: 338
Property Id: 1812458 3 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has laundry room with washer, dryer, sink. The kitchen has granite counter tops ,fully equipped. . The master suite has a king size bed, 2 large walk in closets, en-suite bathroom with walk in shower, and more amazing water views. The 2nd bedroom is nicely furnished with a queen size bed, walk in closet and en-suite bathroom. The 3rd room can be used as a den or bedroom as it has a desk and trundle bed/sofa with 2 twin mattresses . Located in a private gated community that offers a clubhouse fitness center, pool, hot tub, tiki hut with BBQ grills, tennis courts and pickle ball courts. This unit is situated on the border of Osprey and Sarasota. It's only minutes to the beautiful beaches of siesta key, Nokomis and Venice, shopping, dining and downtown Sarasota.