31

Homes for Rent in ZIP Code 34229

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  • /51

    $6,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,799 Sq Ft
    • Condo for Rent

    14041 Bellagio Way Unit 214, Osprey, FL 34229

    Virtually Staged. Welcome to paradise! Osprey's most desirable luxury community at the Villas at the Osprey Harbor Village with direct access to the Little Sarasota Bay is available for 3 months to 12 months lease. Residences will have direct access to the Interacoastal Waterways, 10 minute boat trips to famous Midnight Pass, Blackburn Point Park, and picturesque Casey Key for morning stroll.

    Agent Photo

    Veronica Lee

    COLDWELL BANKER REALTY

    14041 Bellagio Way Unit 214, Osprey, FL 34229
  • /20

    $4,431

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,389 Sq Ft
    • Condo for Rent

    111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229

    The advertised rate of $4,432/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 11, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    111 Tina Island Dr Unit SI ID1591462P, Osprey, FL 34229
  • /10

    $2,500 Per Month

    • 1 Bed
    • 1 Bath
    • 623 Sq Ft
    • Condo for Rent

    51 Mac Ewen Dr Unit 1, Osprey, FL 34229

    ***AVAILABLE MAY 2026 THRU JULY 2026 AND THEN AGAIN IN NOVEMBER 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.

    Agent Photo

    Anthony DeLuca

    AUDREY RAIN RENTALS, INC

    51 Mac Ewen Dr Unit 1, Osprey, FL 34229
  • /51

    $11,036 Per Month

    • 3 Beds
    • 3 Baths
    • 2,260 Sq Ft
    • Condo for Rent

    521 Habitat Blvd Unit SI FL1-ID1624235P, Osprey, FL 34229

    The advertised rate of $11,037/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 30, 2026. Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    521 Habitat Blvd Unit SI FL1-ID1624235P, Osprey, FL 34229
  • /47

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,568 Sq Ft
    • Condo for Rent

    293 Hidden Bay Dr Unit 203, Osprey, FL 34229

    AVAILABLE 2027 SEASON. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer & dryer

    Agent Photo

    Alba Lange

    WAGNER REALTY

    293 Hidden Bay Dr Unit 203, Osprey, FL 34229
  • /8

    $775 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    8 Bay Ave, Osprey, FL 34229

    Property Id: 1524644 Unfurnished Room with private bath for rent, for 1 person, utilities included. No pets, no alcohol drinks, no drugs, no visitors allowed inside the house. House rules to follow, NO EXCEPTIONS Landlord requires 1st, last month rent plus $455 security deposit due at the sign of the lease. Information to verify employment, references from previous landlord and

    8 Bay Ave, Osprey, FL 34229
  • /23

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Condo for Rent

    236 Woodland Dr, Osprey, FL 34229

    Property Id: 310276 In 2027, AVAILABLE BEGINNING MAY 15. 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 Casey Key, Blackburn Point Park & Intracoastal

    236 Woodland Dr, Osprey, FL 34229
  • /14

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 595 Sq Ft
    • Condo for Rent

    51 Mac Ewen Dr Unit 8, Osprey, FL 34229

    Come lounge around in one of the finest golf communities where everyday can feel like a vacation. This elegant loft has a lovely view of the lake with the rolling green right behind it. Enjoy endless summer days basking in the sun at the pool which is only steps away! This loft is equipped with granite countertops, a full size washer and dryer, stainless steel appliances, fixtures and fittings, a

    Deserea Hardy ROSSI & COMPANY INC

    51 Mac Ewen Dr Unit 8, Osprey, FL 34229
  • /46

    $13,000 Per Month

    • 4 Beds
    • 6 Baths
    • 9,081 Sq Ft
    • House for Rent

    854 MacEwen Dr, Osprey, FL 34229

    Set on a quiet private cul-de-sac in The Oaks, this beautifully revitalized estate embodies the elegance of refined Florida living. Bright, open interiors and thoughtful updates create a welcoming flow from the chefs kitchen through the main living areas and out to the lanai, where sweeping golf course views frame the heated pool, spa, and fully equipped outdoor kitchen perfect for year-round

    854 MacEwen Dr, Osprey, FL 34229
  • /32

    $5,750 Per Month

    • 3 Beds
    • 2 Baths
    • 2,271 Sq Ft
    • House for Rent

    293 Turquoise Ln, Osprey, FL 34229

    **RARE RENTAL OPPORTUNITY (UNFURNISHED)** This STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the SECURE GATES of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank,

    Mark Lyda GENEROUS PROPERTY

    293 Turquoise Ln, Osprey, FL 34229
  • /25

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • House for Rent

    152 Navigation Cir, Osprey, FL 34229

    Rented FEB-MAR 2027 / available all other months / 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, with all living space on the 2nd floor. The extra windows flood the unit with natural sun light. The

    152 Navigation Cir, Osprey, FL 34229
  • /21

    $2,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,244 Sq Ft
    • Property for Rent

    184 Explorer Dr Unit 184, Osprey, FL 34229

    Property available for $2300 from April 1,2024 till November 30,2024. Tenant pays electricity and internet. Available for season 2024/2025 for $4500. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this darling two-bedroom, two-bath, impeccably maintained, property move-in ready. Located on the

    Claudia Dybala DALTON WADE INC

    184 Explorer Dr Unit 184, Osprey, FL 34229
  • /27

    $2,599 Per Month

    • 2 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Condo for Rent

    2090 S Tamiami Trail Unit 303, Osprey, FL 34229

    Stunningly updated and professionally curated and designed 2 Bed 2 Bath condominium with over 1500 sq ft, sparkling pool view, tennis courts, and ample open space on Blackburn Bay. Oversized Master EnSuite with King sized bed, walk in closet, and private access to enlarged screened patio. Dedicated garage parking space in building with direct access to elevators. Enjoy exquisite finishes in this

    2090 S Tamiami Trail Unit 303, Osprey, FL 34229
  • /42

    $5,900 Per Month

    • 3 Beds
    • 3 Baths
    • 2,545 Sq Ft
    • Condo for Rent

    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

    3603 N Point Rd Unit 602, Osprey, FL 34229
  • /49

    $5,900 Per Month

    • 3 Beds
    • 2 Baths
    • 2,306 Sq Ft
    • House for Rent

    124 Turquoise Ln, Osprey, FL 34229

    Welcome to this unfurnished 3 bedroom, 2 bathroom home in Emerald Woods at the GATED Oaks Preserve community in Osprey!The SCREENED-IN POOL & LANAI creates a private outdoor retreat surrounded by lush landscaping. Enjoy a HEATED POOL, spacious patio, and an outdoor kitchen equipped with a gas grill and small refrigerator.Inside, the UPDATED KITCHEN features GRANITE COUNTERTOPS, a

    124 Turquoise Ln, Osprey, FL 34229
  • /39

    $6,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft
    • Townhouse for Rent

    101 Woodland Place, Osprey, FL 34229

    Now AVAILABLE FOR LEASE PINE RUN Condominiums in OSPREY, Florida! 3BR/2.5BA Great SARASOTA Vacation Location! West of the Trail, Pine Run is an active community set in a tropical oasis of 20+ acres of wooded Florida landscape. This spacious corner unit townhouse is well FURNISHED. Beautifully decorated and full of light and color with vaulted ceiling in the main Great Room. Custom designed

    Patrice Ivan WAGNER REALTY

    101 Woodland Place, Osprey, FL 34229
  • /35

    $4,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,261 Sq Ft
    • House for Rent

    1279 Thornapple Dr, Osprey, FL 34229

    Annual unfurnished single-family pool home available in Willowbend! Gorgeous Lee Wetherington-built three-bedroom, two-bath home located in the maintenance-free neighborhood of Willowbend in Osprey. The home features a gourmet kitchen with gas cooktop and double oven, 12-foot ceilings, plantation shutters, a solar-heated pool, and spacious lanai with lake view. Willowbend amenities include lawn

    Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1279 Thornapple Dr, Osprey, FL 34229
  • /25

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Condo for Rent

    152 Navigation Cir Unit 107, Osprey, FL 34229

    BACIK ON THE MARKET HIGH SEASON NOW AVAILABLE!! 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

    Cody Smith RENT SARASOTA

    152 Navigation Cir Unit 107, Osprey, FL 34229
  • /45

    $4,395 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,168 Sq Ft
    • Condo for Rent

    260 Hidden Bay Dr Unit B 401, Osprey, FL 34229

    Flexible Lease Terms Available 6-12 monthsExperience the best of Florida’s Gulf Coast from this spacious, fully furnished 3-bedroom, 2.5-bath waterfront condominium overlooking beautiful Little Sarasota Bay. Designed for comfort, convenience, and coastal living, this inviting residence features a private den/home office, in-unit laundry, and generous living areas ideal for relaxing or

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    260 Hidden Bay Dr Unit B 401, Osprey, FL 34229
  • /31

    $2,250 Per Month

    • 1 Bed
    • 1 Bath
    • 623 Sq Ft
    • Condo for Rent

    51 MacEwen Dr Unit 12, Osprey, FL 34229

    For Lease at THE OAKS CLUB WINDSOR LODGE. Private sanctuary rarely available for rent at one of Sarasota's most exclusive private country clubs. This lovely sunny Second floor end unit is fully turnkey furnished and ready for MOVE IN. Completely updated one bedroom, resort suite style studio, condominium with sweeping Water Views of the Lakefront of the 18th fairway on the Eagle Course. A

    Patrice Ivan WAGNER REALTY

    51 MacEwen Dr Unit 12, Osprey, FL 34229
  • /27

    $3,295 Per Month

    • 4 Beds
    • 3 Baths
    • 2,370 Sq Ft
    • House for Rent

    4401 Conchfish Ln, Osprey, FL 34229

    Welcome to this beautifully maintained 4-bedroom, 3-bathroom home with a 2-car garage, ideally situated on a desirable corner lot in The Palms of Casey Key, just a short walk to the nationally ranked Pine View School. Built in 2018, this residence offers thoughtful upgrades throughout, including updated flooring in every room, custom window treatments, and elegant light fixtures. The open-concept

    Klara Mrcela COMPASS FLORIDA, LLC

    4401 Conchfish Ln, Osprey, FL 34229
  • /65

    $4,995 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,771 Sq Ft
    • Condo for Rent

    6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

    Experience elevated coastal living in this beautifully furnished waterfront residence, available for seasonal (DEC-APR - $6995) or long-term/annual rental (off-season rental $4995 MAY-NOV) in the exclusive Blackburn Harbor community. Located on the second floor with elevator access, this spacious 3-bedroom plus den, 3-bath condominium offers over 3,700 square feet of elegant living space with

    Angelic Tassos CORCORAN DWELLINGS REALTY

    6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
  • /15

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,648 Sq Ft
    • House for Rent

    2068 Preymore St, Osprey, FL 34229

    Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in

    Kenia Rivas PREFERRED SHORE LLC

    2068 Preymore St, Osprey, FL 34229
  • /34

    $2,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,244 Sq Ft
    • Condo for Rent

    4219 Frontier Ln Unit 105, Osprey, FL 34229

    Welcome to this immaculate 2-bedroom, 2-bathroom condo with a private 1-car garage, offering beautiful pond views from every window and a peaceful, resort-style setting.Ideally located just minutes from some of Florida’s most beautiful Gulf Coast beaches:10 minutes to Nokomis Beach and Casey Key15 minutes to the world-famous Siesta Key BeachOutdoor enthusiasts will love

    Tim Weller EXIT KING REALTY

    4219 Frontier Ln Unit 105, Osprey, FL 34229
  • /55

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,306 Sq Ft
    • House for Rent

    124 Turquoise Ln, Osprey, FL 34229

    Welcome to this unfurnished 3 bedroom, 2 bathroom home in Emerald Woods at the GATED Oaks Preserve community in Osprey!The SCREENED-IN POOL & LANAI creates a private outdoor retreat surrounded by lush landscaping. Enjoy a HEATED POOL, spacious patio, and an outdoor kitchen equipped with a gas grill and small refrigerator.Inside, the UPDATED KITCHEN features GRANITE COUNTERTOPS, a

    Benjamin Schwab KEYRENTER SARASOTA PROPERTY MANAGEMENT

    124 Turquoise Ln, Osprey, FL 34229
  • /44

    $5,900 Per Month

    • 3 Beds
    • 3 Baths
    • 2,266 Sq Ft
    • House for Rent

    521 Habitat Blvd, Osprey, FL 34229

    Stylish 3BR Pool Home w/ Office – 10 Mins to Beach -- 90 Day minimum stay, Peak Season at $7,900/mo plus taxes and fees; Off Season at $5,900/mo plus taxes and fees. NOTE: Jan, Feb and March 2027 are Not Available. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

    Dave Holt PMI SOUTHWEST FLORIDA

    521 Habitat Blvd, Osprey, FL 34229
  • /15

    $2,195 Per Month

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • Condo for Rent

    4248 Expedition Way, Osprey, FL 34229

    Welcome home to this beautiful 3-bedroom, 2-bathroom condo in the sought after gated community of Bay Street Village!Experience comfortable Sarasota living in this well-appointed condo, featuring neutral paint, ceiling fans throughout, tile flooring in the main living areas, and carpeted bedrooms. The open-concept living and dining area flows seamlessly into the kitchen, complete with

    Brandon Green PMI SOUTHWEST FLORIDA

    4248 Expedition Way, Osprey, FL 34229
  • /51

    $7,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 4,519 Sq Ft
    • House for Rent

    852 MacEwen Dr, Osprey, FL 34229

    **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

    Mark Lyda GENEROUS PROPERTY

    852 MacEwen Dr, Osprey, FL 34229
  • /14

    $2,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft
    • Condo for Rent

    4271 Expedition Way Unit 103, Osprey, FL 34229

    Welcome to Bay Street Village, a gated community in desirable Osprey! This well-maintained second-floor condo offers 2 bedrooms, 2 full baths, an attached garage, and a private entrance with an interior staircase leading to the main living level. The open-concept floor plan features high ceilings, abundant natural light, and a spacious living and dining area.The kitchen is equipped with

    Yunfei Liu DALTON WADE INC

    4271 Expedition Way Unit 103, Osprey, FL 34229
  • /41

    $3,750 Per Month

    • 4 Beds
    • 3 Baths
    • 2,077 Sq Ft
    • House for Rent

    534 Oak Bay Dr Unit 1, Osprey, FL 34229

    AVAILABLE AUGUST 25, 2026 AS UNFURNISHED RENTAL. Very nice light and bright 4 bedroom pool home with private secluded lot in the quaint community of Oak Bay Estates in Osprey. Great access to Sarasota and Venice without having to get on I-75. New interior paint and new ceiling fans throughout. Enjoy this great home and the private pool in your spare time as the pool care and lawn and landscaping

    Brian ODonnell,PLLC REALTY BY DESIGN LLC

    534 Oak Bay Dr Unit 1, Osprey, FL 34229
  • /87

    $7,500 Per Month

    • 3 Beds
    • 2 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

    CLOSE TO NOKOMIS BEACH! BOOKED JAN/FEB/MAR 2027. AVAILABLE APR 2027 $7,000/MONTH. Beautiful direct waterfront 5th Floor condo located in Blackburn Harbor Residences with 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

    Chrissie Cummings JENNETTE PROPERTIES INC

    5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
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