16

Osprey, FL Condos for Rent

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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
  • /34

    $4,285

    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 $4,285/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

    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
  • /20

    $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
  • /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
  • /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
  • /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
  • /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
  • /34

    $2,100 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
  • /15

    $2,245 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
  • /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
  • /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

Frequently Asked Questions

How much does it cost to rent a condo in Osprey, FL?
The median rent for a condo in Osprey, FL is $2,599 per month, though prices vary by neighborhood, size, and property type. As of September 2026, townhouses tend to be the most affordable option while condos and single-family homes are currently more expensive.
How much do you need to make to afford rent in Osprey, FL?
To comfortably afford the median rent in Osprey, FL, a household needs to earn roughly $180,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $4,500 per month in Osprey, FL, renters typically need to show $13,500 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Osprey, FL?
In Osprey, FL, the price-to-rent ratio is 12.0, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Osprey, FL are best for renting a condo?
The best neighborhood for renting in Osprey, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a condo include Vamo, Coral Cove/Holiday Harbor, South Sarasota, Ridge Wood Heights and Heritage Oaks Golf & Country Club, each with its own character and price range.

Rental Home Trends

Number of Condos for Rent
16
Median Condo Rent
$2,599
Median 1 Bedroom Condo Rent
$2,250
Median 2 Bedroom Condo Rent
$2,300
Median 3 Bedroom Condo Rent
$4,448
How to Rent a Home