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condos
Last updated December 2 2022 at 12:54 AM

130 Condos for rent in Osprey, FL

Finding condos for rent in Osprey is almost no different than renting an apartment in a big complex. The real difference is the ownership. Condos are owned by individuals within t... Read Guide >
294 HIDDEN BAY DRIVE Photo Gallery 1
1 of 29
2 Bedrooms
$2,695
1568 sqft
This is a second floor two bedroom, two bath with den condo located in the gated waterfront Hidden Bay community. The split floor plan condo features an open living area featuring large sliding doors to a screened in patio with preserve views. The U-shaped kitchen is located between the Dining Room and Breakfast area features white countertops, white cabinets and a triple-wide pantry. The master bathroom features a garden tub and walk-in shower. There is also a guest suite with direct access to the 2nd bathroom. In addition, an office or den with French doors at the front of the condo. There is a full size laundry room with washer and dryer and a one car separate garage. Hidden Bay is a 12 acre waterfront community on the Little Sarasota Bay with a social-rich clubhouse and pool, tennis and pickleball courts, kayak racks and launch, a renovated fitness center, and a 500-yard boardwalk and fishing pier. Hidden Bay is located near Venice Beach, Historic Spanish Pointe, Oscar Scherer State Park and The Legacy Trail. Rent includes: Water, Sewer, Basic Cable TV, and Internet. Tenants are not allowed pets. No boats, trucks over 3/4 tons, commercial vehicles, trailers, recreational vehicles or other pickup trucks unless they fit in the garage. Please allow up to 4 weeks before move-in for the HOA to process their own application. This home is being leased by Sarasota Management & Leasing, however the Owner will be managing the home and the tenant that is placed.
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228 EXPLORER DRIVE Photo Gallery 1
1 of 55
2 Bedrooms
$4,500
1244 sqft
Furnished-Turnkey, Condo Close to Beaches! Available Febuary 1, 2023 thru March 31, 2023. 2 month minimum. Located 10 minutes to Nokomis Beach or 15 minutes to Siesta Key Beach? Minutes by bike to Legacy Trail and Casey Key. Professionally decorated 2 bedrooms. 2 baths, 1 car garage located on the second floor. All utilities such as electric, Cable and internet are included in the price. This maintenance free community includes gated entry, resort style community pool, cabana, fitness room, and club room. The construction is concrete block, impact resistant glass windows, tile roof, and paver driveway. The community is conveniently located to Sarasota, Venice, Casey Key, the beaches, dining, shopping, the Legacy Trail, Oscar Scherer Park, and A+ Pineview School!
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4226 FRONTIER LANE Photo Gallery 1
1 of 15
2 Bedrooms
$3,000
1244 sqft
Available for NOVEMBER and DECEMBER 2022 .Please check the 3D matter port tour, all the utilities are included in the rental amount .Start enjoying the Florida lifestyle at Bay Street! The spacious floor plan makes great use of space with two bedrooms, two baths, and an attached one car garage. Oversized windows allow Florida sunshine to fill this home with light. Beautiful 18x18 ceramic floor tile in the main living areas. Kitchen features a large center island, 42” Espresso cabinetry, under cabinet lighting, granite countertops, tile back splash, and stainless steel appliances. Bathrooms have matching cabinets and ivory cultured marble counters with integral sinks. Double slider opens to screened corner balcony. Master suite features large walk-in closet and tiled bathroom with double vanity. Maintenance free community includes gated entry, resort style community pool, fully equipped fitness room, and community club room. Conveniently located between downtown Sarasota and Venice, close proximity to the Legacy Trail, Oscar Scherer Park, the areas top-rated beaches, and numerous dining and shopping venues.
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293 HIDDEN BAY DRIVE Photo Gallery 1
1 of 45
2 Bedrooms
$4,500
1568 sqft
SORRY RENTED JAN. FEB. AND MARCH 2023. APRIL 2023. 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 inside unit. Nicely renovated with closet barn doors. Stainless appliances. Detached one car garage immediately in front of condo and plenty of parking. PET OKAY with owner approval and non refundable pet fee. Resort style community pool, heated spa, fitness room, tennis courts, reading room, BBQ area with covered bar for guests, community clubhouse with kitchen. Short distance to shores of Little Sarasota Bay, Casey Key, Siesta Key. Fishing pier. Easy commute to shopping, restaurants and more. NOTE: SORRY BOOKED ALL DECEMBER 2022 Till APRIL 2nd 2023. NO CATS. OWNER HAS ALLERGIES.
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Results within 1 mile of Osprey
4106 CENTRAL SARASOTA PARKWAY Photo Gallery 1
1 of 11
2 Bedrooms
$3,100
1100 sqft
Vacation in paradise at this beautifully furnished 2 bedroom 2 bath GROUND FLOOR condo at Bella Villino. Centrally located to Sarasota beaches and shopping, this condo has it all. A beautiful pool, spa, community room, fitness center, racquetball and basektball court. Plus your just steps away from Legacy Trail for biking and fitness without all the cars. Many restaurants and shops are within a short drive as is famous Siesta Key Beach. No pets. No smoking.
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5713 FOSSANO DRIVE Photo Gallery 1
1 of 55
3 Bedrooms
$2,895
1863 sqft
THIS IS AN ANNUAL RENTAL Located in The Isles on Palmer Ranch. This 2nd floor, spacious 3 bed/2 bath condo has 1,863 square feet of living space with generously sized living and dining areas. Significant upgrades including granite and stone countertops, tiled backsplashes, updated light and fan fixtures, wood cabinets, and more! Eat-in kitchen as well as a dining room - so either could also be used as office space for those who work remotely. The rear screened lanai possesses an exceptional unobstructed lake view. Attached one-car garage, and ample parking outside with a dedicated driveway/street parking. The community itself is "amenity filled" with a clubhouse, fitness center, community pool, lighted tennis and pickleball courts, plenty of communal parking, a kitchen and private room which can be used for functions and lastly a pergola with a lake view. Located in prestigious Palmer Ranch, it's conveniently located to Osprey/Nokomis/Venice, I75, various restaurants, shopping, walking trails and other amenities. 1st/Last/Security required for move in. Credit/background/eviction search checks on all applicants.
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1617 BAYHOUSE COURT Photo Gallery 1
1 of 14
2 Bedrooms
$2,500
1216 sqft
Great opportunity to rent this conveniently located unit tucked away in a gated community! The landlord is seeking a (3 Month Minimum). Enjoy the tranquility in the popular community of Pelican Cove! Available June through December 2022. Tons of amenities, and just minutes away to Siesta Key for your leisure. Shopping and restaurants are nearby as well. No pets. Call for your showing today!
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9651 CASTLE POINT DRIVE Photo Gallery 1
1 of 20
1 Unit Available
2 Bedrooms
$3,700
1661 sqft
AVAILABLE OFF-SEASON ONLY. NEWLY UPDAT3D Exceptional 2nd floor Abbey offering 2 bedrooms, 2 baths with den/office (currently used as a bedroom) vacation rental within gated Stoneybrook Golf & CC. Enjoy the outstanding views of the golf course from the glassed and screened lanai offering an outstanding golf course view. There is plenty of room in this turnkey-appointed unit with recently updated kitchen, new flooring, and the coveted den/bedroom. There is a one-car garage and the heated community pool is just a short distance from your front door. The golf membership transfers if desired for $250.00, there is an impressive clubhouse with fine and casual dining, Har-Tru lighted tennis courts, a premier Arthur HIlls designed golf course, a fitness center and a large heated pool. The Legacy walking and biking trail is just a block from the community, and it is less than 15 minutes to the sugar sandy beaches of Siesta Key. You can be downtown in less than 30 minutes to enjoy all the cultural activities that Sarasota has to offer.
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9611 CASTLE POINT DRIVE Photo Gallery 1
1 of 40
1 Unit Available
2 Bedrooms
$4,800
1661 sqft
RENTED DEC. JAN. FEB. MARCH, 2023. AVAILABLE NOW THROUGH NOVEMBER, rarely available Abbey model, end unit, beautifully furnished and so well decorated, eating space in kitchen, king bed in primary bedroom and guest bedroom, tub and glassed-in shower in master bath, the coveted den offers that so needed extra space and has a sleeper sofa, desk, and doors that can provide privacy when needed (end unit offers windows in the den and guest bedroom not available in interior units) allowing for a bright and cheerful atmosphere. You will not want for a thing in this well-equipped kitchen, kitchen is open to the dining area, there are sliding glass doors that open onto a tiled and screened lanai from the living area and the primary bedroom offering a private preserve view, The one-car garage is perfect for your beach chairs and pool toys as well as your vehicle, and the Fairway Veranda's community pool is just a skip and a hop from your front door. The golf membership transfers for a nominal fee to the clubhouse allowing you to participate in an array of social activities, play golf and or tennis, swim in the large heated club pool and enjoy the dining facilities at the impressive clubhouse restaurant. The Legacy walking and biking trail access is about two blocks from the gated entrance to the community, the world famous Siesta Key beach is less than a 15 minute drive, and you can be downtown to take in all of the cultural activities, restaurants, theaters, museums, that Sarasota has to offer.
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8921 VERANDA WAY 322 Photo Gallery 1
1 of 37
1 Unit Available
2 Bedrooms
$4,400
1333 sqft
RENTED JAN, FEB., MARCH 2023. Exceptional vacation condo on the second floor, 2 bedrooms, two baths, Queen in master suite, twin plus trundle bed in guest room. Condo is comfortably furnished, there is internet access, flat-screen TVs, the interior is freshly painted, bright and cheerful. There is a golf course view from the screened lanai. The heated pool is a short walk from the condo. You'll find everything you need for a few months in the sunshine. Golf membership transfers for $250 if desired. The complex is gated and boasts an impressive clubhouse with fine and casual dining, a fitness center, a large heated pool, a premier 18 hole golf course, Har-Tru tennis courts, is located approximately seven miles from Siesta Key beach, shops, and restaurants and the Legacy walking and biking trail access is just a block from the entrance. CALL FOR OFF-SEASON RATES
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4240 CENTRAL SARASOTA PARKWAY Photo Gallery 1
1 of 24
2 Bedrooms
$2,300
1147 sqft
AVAILABLE JUNE 1 2023 THROUGH DEC. 30, 2023. Spend six months in Paradise in this absolutely picture-perfect 2nd-floor condominium at desirable Plaza de Flores on Palmer Ranch. Master suite with king bed and adjoining bathroom with two sinks and walk-in shower, guest bedroom with queen bed and easy access to guest bath. Efficiently designed kitchen with all new stainless steel appliances and a window above the sink allowing for bright and cheerful surroundings. The dining area is open to kitchen and living room and the living room is furnished for comfort and style. The high ceilings enhance the living space and the icing on the cake is the awesome lanai running the entire length of the condo accessible from the living room or the master bedroom. Both beds have brand new mattresses and are sleep number beds, you will have the luxury of sleeping in your own desired comfort zone. You're sure to love this amazing tree-top retreat! The location is ideal, close to shops and restaurants, the YMCA, and just minutes from the Legacy walking and biking trail access. The world-famous Siesta Key beach is less than 15 minutes from the gated complex and you can be downtown in less than 25 minutes to enjoy all that Sarasota has to offer. Plaza de Flores offers a heated swimming pool and spa, tennis courts, a clubhouse with catering kitchen, and a well-equipped fitness room.
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12414 OSORIO COURT Photo Gallery 1
1 of 24
2 Bedrooms
$6,000
1526 sqft
LOCATION, LOCATION, LOCATION. Absolutely stunning 2/2+ den with a one care garage, available in the sought after community of Esplanade of Palmer Ranch. Fully turnkey furnished and ready for your stay. This neat as a pin condo has square feet 1526 , 2 bedrooms plus a den(pull out couch), 2 bathrooms, open floor plan, The kitchen has stainless steel appliances, The master bedroom has a king size bed,walk in closet with a on suite bathroom with a walk in shower, double sinks and a garden tub. The guest bedroom has a queen sized bed, guest bathroom has a tub/shower combination. Walkable to the amazing community pool. Enjoy resort style living, Lagoon style pool, full service Tiki Bar, State of the Art Fitness Center, Day Spa, Tennis Courts, Pickle Ball and much, much more! Call today as this will not last long!!Available for both seasonal and annual. Annual rent is $4,000 per month.
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5424 CICERONE STREET Photo Gallery 1
1 of 15
2 Bedrooms
$3,000
1650 sqft
Available APRIL 1, 2023 ----LEASED Season thru MAR 31 2023******RESORT SEASONAL IN ESPLANADE OF PALMER RANCH - brand new spacious 2B+Den with sofa sleeper, beautifully furnished. Come stay in sunny Sarasota just 15 min to the Gulf of Mexico for sunsets every night. This condo has high vaulted ceilings, stainless steel appliances, granite and tile. Esplanade has a luxury pool with cabanas, a spa, Child Splash Pad, Resistance Pool, the Bahama Bar Restaurant with music every Friday eve, towel service for pool & gym, state-of-the-art fitness center with classes. Here you can enjoy bocce ball, pickle ball, tennis courts, walking paths around the grounds with quick access to the Legacy Trail. Pet allowed. ****Note: high season rate $4500 Jan-Apr. May is $3500; June - November is $3000 and December is $3500.
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9050 MIDNIGHT PASS ROAD Photo Gallery 1
1 of 30
2 Bedrooms
$7,000
1251 sqft
SEASON SPECIAL $7000 PER MONTH AVAIALBLE Nov. 1, 2022 - Jan. 31, 2023. SPECTACULAR WATER VIEWS WITH LARGE DEEP WATER BOAT DOCK! Great opportunity to stay in a recently remodeled 2 bed/2 bath furnished WATERFRONT condo on the uncrowded south end Siesta Key in the Moorings. Just a short cruise to the Gulf of Mexico so bring your boat or rent one nearby for some world class fishing or just hanging out on the sandbars. Turtle Beach is only a 10 min walk with all of it's amenities. Be enchanted by the breathtaking sunsets from the west facing living room, master bedroom and screened lanai. Impressive water views of Blind Pass Lagoon and Turtle Beach just beyond. Open floor plan with living/dining area and new luxurious kitchen. Wake up to serene views from the master suite through the large sliding glass doors and step directly out onto the lanai to enjoy the gulf breezes. Bathrooms are updated with stylish new vessel sinks and handcrafted tile showers. Interior laundry for your convenience and two dedicated parking spaces, one under carport and storage locker. Our quaint complex has a heated pool and grill area. Stroll across the street to Ophelia's for fine dining or drop down to Turtle's Pub for a cold libation. Take the free trolley and hop up to Siesta Key Village for shopping and live entertainment. The perfect place to stay for the winter in the first time rental!
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4170 CENTRAL SARASOTA PARKWAY Photo Gallery 1
1 of 36
1 Bedroom
$1,975
829 sqft
3 Bedrooms
$3,000
1280 sqft
Available September 2022. Available long term. Immaculate 2nd floor condo in gated community of Bella Villino on Palma Ranch. The vaulted ceilings gives a spacious feel and the large, screened lanai adds some outdoor living area. Enjoy the lake view from the living room, lanai, master bedroom and one of the guest rooms. The third bedroom has a locked owner's closet. With all new appliances, granite counters, new hard surface flooring, remodeled bathrooms, and very tastefully decorated this home makes for a very comfortable winter retreat or a year-round furnished home. The resort style amenities include heated pool and spa, clubhouse, tennis/pickle ball courts, basketball courts, racquetball court, fitness room, and billiard room. This great location is close to the beautiful beaches of Siesta Key! Wide open availability and still available for season 2023.
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4216 CENTRAL SARASOTA PARKWAY Photo Gallery 1
1 of 34
2 Bedrooms
$3,200
1147 sqft
This adorable 2 bedroom 2 bathroom furnished condo is adorned with a beach theme and features an open floor plan with high ceilings, granite countertops, stainless steel appliances, and beautiful white cabinets with chrome fixtures. This home is fully equipped with a washer & dryer, overhead lighting, fans throughout, flat screen tv's in every room, king size beds, and tile flooring. Also featuring an oversized screened in lanai with a lake view just perfect for your morning cup of coffee! The community grounds are gated and have fountains, gazebos, and bike racks throughout. Community amenities include a tennis court, a pool, spa, gym, clubhouse and kitchen, and a card room. Conveniently located just 1 minute from the Legacy Trail, Lowes, and a shopping plaza with Siesta Key Beach just 6.5 miles away. No pets will be considered. 6 month minimum as per HOA rules and regulations. Call now to book a showing!
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1717 PELICAN COVE ROAD Photo Gallery 1
1 of 12
2 Bedrooms
$3,400
1112 sqft
Located in Pelican Cove community. This community is gated with a guard 24 hours a day. Lush mature foliage create a relaxing atmosphere. Walking trails along with boardwalks throughout the community. There are 6 Pools, 4 tennis courts, shuffleboard and a basketball court that are all available to you while staying at Pelican Cove. An 86 slip boat harbor is also within the community. Just a short drive to Siesta Beach which has been voted #1 beach in the USA, restaurants, shopping and downtown area. No Pets. No Smoking. No Trucks/RV/Motorcycles/Golf Carts. Association requires a 2 month minimum stay. Call for off season availability and rates.
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1700 GLENHOUSE DRIVE Photo Gallery 1
1 of 13
3 Bedrooms
$3,500
1370 sqft
Located in beautiful Pelican Cove. Come and stay and watch the sunsets. Located minutes from Siesta Beach, voted #1 in USA. This condo is a ground floor end unit. The floor plan is actually a three bedroom but set up as a two bedroom with a den (No sleeper sofa). Unit has been renovated and includes granite counter tops. Has a garden view, inside utility which includes washer and dryer. No Pets, No Smoking. Vehicle Restrictions, No Trucks, Trailers, Recreational Vehicles, Golf Carts, Motorcycles, Commercial Vehicles. Gated community with 24 hour guard at gate.
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9630 CLUB SOUTH CIRCLE Photo Gallery 1
1 of 31
1 Unit Available
2 Bedrooms
$4,300
1230 sqft
AVAILABLE OFF-SEASON ONLY: Delightful ground floor updated condo at Club South Cir., beautifully furnished, freshly updated kitchen, bright and cheerful interior and great view from the screened lanai, everything you need for a few months in the sun. Rental includes internet access, flat-screen TVs, one covered parking space, and the heated pool and tennis courts are right outside your door. Stoneybrook G&CC is one of Sarasota's most popular golf and tennis clubs featuring an impressive clubhouse with fine and casual dining, a fitness center, Har-Tru lighted tennis courts, a premier 18 hole challenging golf course, and all of the activities you would expect from a country club. The golf membership transfers for $250 if desired. RENTED NOV. 2022
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9300 CLUBSIDE CIRCLE Photo Gallery 1
1 of 31
1 Unit Available
2 Bedrooms
$4,300
1106 sqft
RENTED JAN. FEB. MARCH 2023. Available off-season. Exceptional ground floor vacation condo, two bedrooms, two baths, screened lanai with view of lake and golf course, nicely furnished, King bed in master, queen in guest bedroom, new living room furniture, plank wood look flooring, freshly painted, bright and cheerful unit, well-appointed, internet access, flat-screen in living room, one covered parking space, golf membership transfers if desired for $250. Complex is close to the access to the Legacy walking and biking trail, grocery stores, shops, restaurants, there is a Sprouts food market and it's only minutes to the world-famous sugary sands of Siesta Key beach. It's just a short drive to downtown Sarasota and all of the cultural activities Sarasota has to offer. Call for off-season rates.
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8750 OLDE HICKORY AVENUE Photo Gallery 1
1 of 16
2 Bedrooms
$4,300
1238 sqft
RENTED NOV THROUGH APRIL 2022-23. Soak in the golf course view from the screened lanai overlooking the fabulous golf and lake view. Two bedrooms, two baths, large flat screen TV in living room, flat screen in the master bedroom, internet access, nicely furnished with all you need for a great winter stay. The community pool is just outside your door along with the tennis courts. The community offers golf, tennis, heated pools and clubhouse with premier restaurant and it is just Minutes to the sugar sandy beaches of Siesta Key, shopping and restaurants. The Legacy walking and biking trail access is right outside the complex and it is a short drive to downtown Sarasota for all the cultural activities Sarasota has to offer. RENTED NOV THROUGH APRIL, 2022.
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4639 CHAPEL HILL DRIVE Photo Gallery 1
1 of 24
1 Unit Available
2 Bedrooms
$5,000
1414 sqft
RENTED JAN., FEB., MARCH 2023. One of the prettiest views in Stoneybrook overlooking the 3rd hole on the golf course. This is special!! This second floor “Barrington” model veranda offers over 1400 sq. ft. of open living space, two bedrooms, two full baths, plus den/office, and is newly furnished and decorated, flat screen TVs, internet access, there is new engineered wood flooring in living and dining area and den. There is a screened entry and rear lanai, a one car detached garage and is conveniently located just a short distance from the heated community pool and tennis courts. The clubhouse is something to be proud of and features casual and formal dining, a grill room, piano lounge and meeting rooms, there is a well-equipped fitness room, a library, a large heated pool and spa. The community is conveniently located less than two blocks from the access to the Legacy Bike and Walking Trail and is minutes away from the famed sugary sand beaches of Siesta Key, shops and fine restaurants. You can be downtown in 20-25 minutes to take in all the cultural activities Sarasota has to offer. The golf membership can be transfered for $250 for the duration of your stay. CALL FOR OFF SEASON RATES
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9320 CLUBSIDE CIRCLE Photo Gallery 1
1 of 21
1 Unit Available
2 Bedrooms
$4,400
1106 sqft
RENTED JAN. FEB., MARCH 2023. Beautiful, 2nd-floor condo features 2 bedrooms, 2 baths, upgraded kitchen with great view from the screened lanai, nicely furnished and appointed, flat-screen TVs, internet access, golf membership transfers for $250 if desired, one covered parking spot, close to pool and tennis courts. Gated complex with impressive clubhouse offering formal and informal dining, fitness center, newly renovated premier golf course, tennis courts, and close to the Legacy Walking and Biking Trail access offering miles of biking trails, and just minutes from the sugar sandy beaches of the world-famous Siesta Key beaches, shops, and restaurants. You can be downtown in 20-25 minutes to take in all of the cultural activities Sarasota has to offer CALL FOR OFF-SEASON RATES
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9330 CLUBSIDE CIRCLE Photo Gallery 1
1 of 21
1 Unit Available
2 Bedrooms
$4,300
1106 sqft
RENTED JAN., FEB, MARCH, APRIL 2023. Beautiful view from the screened lanai, two bedrooms, two full baths, new furniture, new carpeting, internet access, flat-screen TVs, very nicely appointed, everything you need for your Florida getaway, one covered parking space, golf membership transfers for $250 if desired. Amenity-rich community, heated pool, tennis court nearby, clubhouse with dining facilities, fitness center, large heated pool, close to Legacy walking and biking trail and just minutes to Siesta Key beaches, shops, and restaurants. CALL FOR OFF SEASON RATES
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City Guide for Osprey, FL

The laid back town of Osprey, Florida, the site of the irreplaceable outdoor museum Historic Spanish Point, is located at the same latitude -- 27 degrees -- as Dibrugarh, India.

Home to 6,100 people at the time of the 2010 Census, Osprey is a small town steeped in history and culture. More accurately, it is not actually an incorporated town at all, but rather a census-designated place within the limits of Sarasota County. See more

What to keep in mind when looking for condos in Osprey, FL

Finding condos for rent in Osprey is almost no different than renting an apartment in a big complex. The real difference is the ownership. Condos are owned by individuals within the same building. However, apartments in a large complex are owned by a single landlord or property management group.

Sometimes the price of condos in Osprey may prove cheaper. The owners are often moving onto a new home or leaving the city and just need someone to cover the costs. Apartment complexes are designed to deal with tenant issues, make repairs, and care for the property. Condo owners will still deal with repairs and upkeep but may need more time to address a problem, especially if they don’t live nearby. However, condo owners have a more vested interest in the property and keeping their tenants happy to reduce turnover.

Choose the best condos for rent in Osprey that meet your wishlist for budget, amenities, and layout. You probably won’t notice the difference between the condos and apartments you tour.