$3,800 per month
- 2 Beds
- 2 Baths
- 2,143 Sq Ft
- Condo for Rent
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229$3,800 per month
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229$2,500 per month
51 Mac Ewen Dr Unit 1, Osprey, FL 34229
51 Mac Ewen Dr Unit 1, Osprey, FL 34229$5,000 per month
293 Hidden Bay Dr Unit 203, Osprey, FL 34229
293 Hidden Bay Dr Unit 203, Osprey, FL 34229$3,200 per month
14041 Bellagio Way Unit 414, Osprey, FL 34229
14041 Bellagio Way Unit 414, Osprey, FL 34229$1,900 per month
236 Woodland Dr, Osprey, FL 34229
Property Id: 310276AVAILABLE MAY 15 to SEP 15, 2026 / $100 discount for term of 2 or more months: Light, airy home in Pine Run overlooks established native landscaping. Copious sliding doors, windows & high ceilings. Beautifully updated kitchen offer views to outdoors. Carport + 1 visitor parking space. A nature lovers paradise, this laid-back, quiet & desirable community is close to
$2,500 per month
2313 Jessie Harbor Dr Unit 2302, Osprey, FL 34229
ANNUAL UNFURNISHED VILLA AVAILABLE FOR LEASE IN BLACKBURN HARBOR IN OSPREY! This beautiful 2BR 2BA villa has a large lanai with peaceful views over Blackburn Harbor and features Brazilian Cherry hardwood floors, stainless steel appliances and a private one car garage. The entire condo has been freshly painted. Blackburn Harbor is a gated community and offers many amenities, which include a
Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY
$1,800 per month
294 Hidden Bay Dr Unit 203, Osprey, FL 34229
Unfurnished light and airy 2 Bedroom 2 Bath with Den condo on 2nd floor. Lease terms negotiable with 7 months minimum. In the Lovely gated Hidden Bay Community that covers 12 beautiful acres located on Little Sarasota Bay with waterfront access for kayaking (including storage) and boardwalk to fishing pier. Recreational center includes pool, spa, fitness center, library, clubhouse,
$2,250 per month
4256 Expedition Way Unit 107, Osprey, FL 34229
Welcome to Bay Street in Osprey! This 3-bedroom, 2-bath condominium offers the comfort of single-level living on the second floor of a two-story building. Enjoy an open layout filled with natural light and peaceful lake and fountain views from nearly every room. The kitchen is equipped with newer stainless steel appliances, plus a washer and dryer. Additional features include ceiling fans
Geri Scheckner BRIGHT REALTY
$2,995 per month
127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229
Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage
$6,000 per month
409 N Point Rd Unit 802, Osprey, FL 34229
**TURNKEY FURNISHED, PENTHOUSE Condo Unit has been FULLY RENOVATED** This 8TH FLOOR, Light and Bright, 3-BEDROOM plus 3 FULL BATH dwelling with screened balcony is available beginning in September, 2025. The 2055sf floorplan is tastefully furnished and offers superb views of the Intracoastal Waterway and Gulf. This unit was fully renovated in 2023 with updated oak hardwood flooring, new kitchen
Mark Lyda GENEROUS PROPERTY
$2,200 per month
304 Pine Run Dr, Osprey, FL 34229
Stunning annual unfurnished 2 bed/2 bath ground floor condo located at Pine Run in Osprey, FL. Water, sewer/trash, lawn maintenance, washer/dryer, and pest control included. Available now for $2,200 a month. Application fee for each adult $50, association application fee of $50(10-day association approval process), $ 2,200 security deposit, and $100 administrative fee. 1 pet allowed
AnaElizabeth Fernandez A & R PROPERTY MGMT, LLC
$5,000 per month
260 Hidden Bay Dr Unit B-504, Osprey, FL 34229
Annual Turnkey Furnished 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
Henry Rossi RENT SARASOTA
$4,200 per month
280 Hidden Bay Dr Unit 202, Osprey, FL 34229
READY FOR IMMEDIATE OCCUPANCY! Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota Bay Step into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space for your
Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE
$4,200 per month
280 Hidden Bay Dr Unit 302, Osprey, FL 34229
NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood
Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE
$4,000 per month
Unlisted Address
NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood
Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE
$4,200 per month
Unlisted Address
NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood
Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE
$4,000 per month
280 Hidden Bay Dr Unit 303, Osprey, FL 34229
One or more photo(s) has been virtually staged. *** PRICE REDUCED*** Annual Rental. This newly constructed 3rd floor condo is available for immediate occupancy at Hidden Bay in Osprey. This gorgeous 3 Bedroom PLUS a Home Office is light, bright and very spacious! Wood and tile floors throughout- NO CARPETING! The Primary suite features 2 walk-in closets, sliding glass doors leading to the lanai
Jaime Barcelo GULF COAST REALTY & MANAGEMENT
$7,000 per month
5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
This beautiful 5th Floor condo located in Blackburn Harbor Residences is now available for Season 2026! There are breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and 2 bathrooms. As you step inside the
Chrissie Cummings JENNETTE PROPERTIES INC
$5,000 per month
14041 Bellagio Way Unit 218, Osprey, FL 34229
Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from Midnight Pass beach, Snake Island and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space with breath taking harbor and sunset views from every room. Designed with both comfort and style
Kelli Eggen COLDWELL BANKER REALTY
$5,900 per month
3603 N Point Rd Unit 602, Osprey, FL 34229
**FURNISHED, 3-BED / 3-FULL BATH, Over 2500sf CONDO with FANTASTIC VIEW** features an Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Spacious interior which boasts beautiful Crown Moldings, Hardwood Floors, a well-equipped Kitchen with granite
Mark Lyda GENEROUS PROPERTY
$7,500 per month
14041 Bellagio Way Unit 316, Osprey, FL 34229
NOW AVAILABLE FOR APRIL AND OFF-SEASON MONTHS 2025 AND JAN-APRIL 2026! Welcome to BELLAGIO at Osprey Harbor Village, offering luxurious waterfront living! This turnkey direct waterfront condo has 3 beds/2 baths plus a den is the perfect place for your next Florida vacation, located in a private gated community. As you step off the elevator, you are basically outside this 3rd floor end unit. Upon
Chrissie Cummings JENNETTE PROPERTIES INC
$4,500 per month
152 Navigation Cir Unit 107, Osprey, FL 34229
Seasonal and short term rental Get out of the cold and into the sunshine in this newer 3/2 condo in the gated community of Bay Street Village in Osprey. This condo is an end unit with an open floor plan for ease of entertaining and family time. The extra windows flood the unit with natural sun light. The kitchen is a natural gathering point with solid wooden cabinetry, topped with slab granite
Henry Rossi RENT SARASOTA