14

Osprey, FL Homes for Rent under $3,000

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  • /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

    (941) 207-5680

    51 Mac Ewen Dr Unit 1, Osprey, FL 34229
  • /8

    $775 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    8 Bay Ave, Osprey, FL 34229

    Property Id: 1524644Unfurnished 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 EXCEPTIONSLandlord 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

    (914) 281-2489

    8 Bay Ave, Osprey, FL 34229
  • /20

    $1,900 Per Month

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

    236 Woodland Dr, Osprey, FL 34229

    Property Id: 310276AVAILABLE JUNE 15 to AUGUST 15, 2026 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 &

    (941) 845-6331

    236 Woodland Dr, Osprey, FL 34229
  • /20

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,371 Sq Ft
    • House for Rent

    253 Glenwood Ave, Osprey, FL 34229

    Welcome to your new oasis in Osprey! This charming 3-bedroom, 2-bathroom house offers a perfect blend of comfort and convenience, making it an ideal place to call home. With a spacious 1,371 square feet, there's plenty of room for you to spread out and enjoy life.Step inside to discover a bright and inviting living space, complete with modern amenities that make daily living a breeze. The

    (941) 335-5525

    253 Glenwood Ave, Osprey, FL 34229
  • /18

    $1,850

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • House for Rent

    455 Pennsylvania Ave, Osprey, FL 34229

    Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

    455 Pennsylvania Ave, Osprey, FL 34229
  • /14

    $1,995

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    188 Explorer Dr Unit 188, Osprey, FL 34229

    Location, Location, Location. Beautiful, quiet, safe & secure, Newer 2 Bed, 2 Bath, for rent annually, All amenities including all Stainless Steel Appliances, Washer, Dryer, Stove, Refrigerator. Gorgeous Pool, Exercise Room, Clubhouse, great area, five minutes to Sarasota Square Mall, Costco, shopping, and medical facilities. Close to Siesta Key Beach and fabulous restaurants. Special Hurricane

    188 Explorer Dr Unit 188, Osprey, FL 34229
  • /36

    $1,800

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,100 Sq Ft
    • Condo for Rent

    1847 Highland Rd Unit 1839 Highland Rd, Osprey, FL 34229

    Spacious Duplex Villa with community pool in a great area. Close to beaches, shopping & restaurants. Right across Oscar Scherer State Park. Shoreland Park is down the street, where you can launch your kayak.

    1847 Highland Rd Unit 1839 Highland Rd, 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
    • The Residences of Blackburn Bay

    2090 S Tamiami Trail Unit 303, Osprey, FL 34229

    2090 S Tamiami Trail Unit 303, Osprey, FL 34229
  • /21

    $1,695 Per Month

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Condo for Rent

    354 Pine Run Dr, Osprey, FL 34229

    This is an unfurnished 2 bedroom, 2 bathroom condo located in the Pine Run community in Osprey! This upper-level unit features vaulted ceilings, a mix of hardwood and tile flooring, and a distinctive courtyard-style layout that brings the outdoors inside. The kitchen features granite countertops, maple shaker-style cabinets with glass-front uppers, stainless steel appliances, a tile backsplash,

    Todd Roughton SARASOTA MANAGEMENT & LEASING

    354 Pine Run Dr, Osprey, FL 34229
  • /36

    $2,500 Per Month

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

    80 Navigation Cir, Osprey, FL 34229

    Turnkey fully furnished newer built 3 bedroom 2 bathroom one car garage townhouse on the second floor. Hurricane windows, gated community, with community pool, club house and gym room. 15-20 minutes to Siesta Key and about 10-15 to Nokomis Beach, Legacy Trail at the end of the street, Dogpark across the street. Walking distance to 4-5 Restaurants. Walmart across the street 3 Publixes and a Target

    Krisztian Kecskes M&M PROPERTY MANAGEMENT GROUP

    80 Navigation Cir, 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
  • /41

    $2,400 Per Month

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

    4219 Frontier Ln Unit 105, Osprey, FL 34229

    2 bedrooms. 2 baths, 1 car garage. Condo Unfurnished. Available July 1, 2026. Tenant Occupied until June 22, 2026. 2nd floor. Close to Beaches! Located 10 minutes to Nokomis Beach/Casey Key Beach or 15 minutes to Siesta Key Beach. Minutes by bike to Legacy Trail and Casey Key. Water, Sewer & trash included in the rent. This maintenance free community includes gated entry, resort style community

    Tim Weller EXIT KING REALTY

    4219 Frontier Ln Unit 105, Osprey, FL 34229
  • /19

    $2,100 Per Month

    • 2 Beds
    • 2 Baths
    • 2,052 Sq Ft
    • House for Rent

    4062 Westbourne Cir, Sarasota, FL 34238

    SINGLE-FAMILY HOME IN GATED COMMUNITY OF STONEYBROOK ESTATES: Need a place while you look for a place or build your dream home or just want to get away for a few months? This fully furnished single-family home located on Palmer Ranch might be just what you're looking for; two bedrooms, two baths, kitchen, dining area, family room and living room plus a large outdoor lanai with a scenic view of

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE

    4062 Westbourne Cir, Sarasota, FL 34238

Rental Home Trends in Osprey, FL

Rental Home Trends

Number of Homes for Rent
14
Median Rent
$4,000
Median Single Family Home Rent
$3,950
Median Townhouse Rent
$2,500
Median Condo Rent
$2,400
How to Rent a Home