Vacation Rentals By Owner In Osprey, FL

Decisions, decisions...which beach to go to today Siesta Key, Nokomis, Venice, Lido, Englewood.... Or bike ride on the Legacy Trail to the beach, perhaps kayak on Little Sarasota Bay (water sport rentals avail nearby). Did someone say Siesrs Key Rum tour Or the Ringling Tour Regardless of how you choose to vacation. Enjoy morning coffee on the lanai watching birds and the sun rise above the tree line. Relax in bed gazing Florida's tropical jungle while giant butterflies float by. Grill and chill on the deck. Smoke and Pet free unique property has a style all its own, including native wildflower/herbal garden and beach gear. Nestled away in the ole' Florida fishing Village of Osprey you'll learn about a piece of history staying at this quaint quiet Fully Furnished Turn Key 2/1 offers upgraded kitchen, stainless steel appliances, granite counters, new washer/dryer, enclosed sun porch with great proximity to and walking bicycling distance of: groceries, shoppes, excellent eateries tiki bars ice cream shoppe, canoe kayak launch, fishing pier, yoga, Legacy Bike Trail with access into Oscar Scherer St Park, churches, museums, historic sites, libraries, attractions. Yet centrally located between downtown's of Venice and Sarasota, many golf courses, and amenities galore. Local Farmers Markets. 6-20min to famous beaches and easy access to I-75. Flexible, short and long term available.

Fall is the best time! To vacation here,nAvail ALL Autumn till NYE 2025!

Osprey, Florida, United States

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Exceptional(39)

$357.57

Mid-century home located midway between Sarasota and Venice FL. Peaceful views of South creek flowing into the Sarasota inter coastal waterway. Tranquil and calming home perfect for couples or families looking to escape the daily hustle and unwind. Cool off in the pool during the day or take a dip in the evening. Kayaks available to launch off private dock. Kayak directly into Oscar Scherer State Park or the inter coastal . Manatees can be seen moving along the canal. Nokomis beach is a 10 minute drive south and Siesta Key a 20 minute drive north. After a day at the beach enjoy a nightcap around the outdoor fire pit or pool deck. Home is fully furnished and ready to enjoy.

Mid-century Waterfront Home with pool

Osprey, Florida, United States

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Exceptional(5)

$585.83

Look no further than this private guesthouse that is a great retreat for the family. Enjoy the pool, hot tub on a nice warm day. Go swing the tennis racket on the private courts. Or take a quick drive to Nokomis Beach to lay out, catch some rays, or enjoy the water. This 3 bedroom private guesthouse will be perfect for the family vacation. Enjoy the newly renovated home with custom kitchen, waterfall showers, high speed internet and a private balcony. You will not want to miss this!

Family Guesthouse with Pool Views minutes from Nokomis Beach

Osprey, Florida, United States

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Bath

Sleeps

Exceptional(4)

$194.36

Have fun with the whole family at this brand new, modern private free standing guest house. Full bedroom with king size bed, with a finished loft including a queen bed. There’s also a queen pull out sofa in the living area. Enjoy your privately fenced backyard with a hot tub and putting green.

Private guest house with king bed & loft. Deck with hot tub and putting green

Osprey, Florida, United States

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$326.57

pNestled in Osprey, this vacation home brings it all within your reach. Fans of nature and the outdoors will love being 3 minutes by car from Jim Neville Marine Preserve and 4 minutes from Oscar Scherer State Park. You'll easily make the quick 2-minute drive to Historic Spanish Point or the 3-minute drive to Sarasota Square. /ppWhile you're here, you can enjoy all the comforts of home and more, including WiFi and air conditioning, as well as a dryer and an ironing board. Other amenities include towels, soap, toilet paper, and a hair dryer. /p

Warm & Cozy Family Home in a Quiet Neighborhood

Osprey, Florida, United States

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Bath

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Exceptional(4)

$140.45

Great location at Osprey Harbor Villas located at the swing bridge going onto Casey Key. Located between Siesta Key and Venice and is a great area for walking, biking, boating and kayaking. Gated, secure and quiet complex with 2 under building parking spaces. You will enjoy the well laid out 1900 sqft suite. The master bath is gorgeous with a walk in shower and double vanities. Kitchen has new appliances and lots of cabinets, counter and bar space. Island serves as dining area. Large laundry room with new washer and dryer. Enjoy the sunsets from the spacious lanai .brA short walk to the well known Casey Key Fish House and Tiki Bar.brComplex association requires renter application and background check allow 20 days for this prior to your arrival date.

Luxury Condo on the water with Intercostal view

Osprey, Florida, United States

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Bath

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Exceptional(2)

$245.01

Relax in this stylish 2BR/2BA private unit (duplex) just 10 minutes from Nokomis Beach. Enjoy a private lanai, fast Wi-Fi, full kitchen, and Smart TV with Netflix. Perfect for couples, families, or mid-term stays. Close to Siesta Key, Venice, and St. Armands. Sleeps 6 people.brbrThe spacebrbrAs hosts, we've ensured this space includes everything needed for a quality and memorable experience for up to 6 guests. We love helping our guests find fun things to do, unique dining experiences, and other memorable activities nearby. We’ve made sure to furnish the entire interior with amenities to elevate our guests’ experiences for families, groups, business professionals, and all other fellow vacationers.brbrFor all of our guests, we provide the following complimentary amenities to enhance your stay:brbr• Complimentary coffee & tea starter packbr• Complimentary entertainment channels: Netflixbr• Fast and free Wi-Fibr• Fully stocked kitchenbr• Free ParkingbrbrSleeping Accommodations:brMaster bedroom sleeps 2, 1 king bed, private attached en suite full bathroombrGuest Bedroom: Sleeps 2, 1 queen bed, hallway full bathroombrLiving Room: Sleeps 2, Sleeper sofa with mattress pad, sheets, blanket, and pillows providedbrbrLiving Area:brThis comfortable living area is perfect for starting the day with your cup of coffee or winding down your night with a drink. The 65 Smart HDTV has a complimentary Netflix subscription to keep you up-to-date with the latest show you've been bingeing. Whether you're looking to kick back and relax or catch up on your favorite shows, this living area has everything you need. You also have a full-sized washer and dryer in this unit.brbrKitchen:brThe kitchen comes with all your essential cooking equipment, dishware, silverware (bowls, plates, cups, etc.), a refrigerator, microwave, stove, oven, toaster, and Keurig coffee machine.brbrDining Area:brThe dining area is furnished with a sleek table, and 6 comfortable chairs. Conveniently located next to the kitchen. This area will be perfect for your morning meals or evening sit-down dinners with your family or friends.brbrBathrooms:brMaster Bathroom:brThis bathroom features a walk-in shower and includes all bathroom essentials and complimentary toiletries like plush white bath towels, a 5x magnifying makeup mirror, a plush makeup towel, and a travel-size hair dryer. Both showers are equipped with a soap dispenser filled with a sulfate-free, 100% vegan shampoo, conditioner, and body wash.brbrGuest Bathroom:brTake a soak or shower in our shower-tub combo bathroom. You'll have access to all bathroom essentials and complimentary toiletries like plush white bath towels, a 5x magnifying makeup mirror, a plush makeup towel, and a travel-size hair dryer. Both showers are equipped with a soap dispenser filled with a sulfate-free, 100% vegan shampoo, conditioner, and body wash.brbrWhat's Nearbybr• Oscar Scherer State Park (1.8 miles): We love walking the Oscar Scherer's trails and enjoying lunch at one of the picnic spots.br• Nokomis Beach (5.7 miles): As our go-to beach for breathtaking coastal views, this is an excellent spot for taking gorgeous pictures.br• Legacy Trail (6 miles): Whether it’s dawn or dusk, this popular biking trail offers unforgettable scenic views from Venice to Sarasota.br• Siesta Key Beach (8 miles): Bury your toes in powdery white sands and swim in turquoise waters at this renowned beach.br• The St. Armand's Circle (14 miles): You’ll fall in love with St. Armand’s vibrant atmosphere as you check out unique boutiques, art galleries, and various restaurants.brGuest accessbrYou have exclusive access to the entire unit, nothing is shared. This property is a part of a Duplex, but you will not share the space with anyone. You will have privacy during your stay. Park easily and enter with self-check-in.brAdditional Information:brbrTo ensure a smooth and secure experience for all our guests, we charge a mandatory damage protection fee of $35. This helps cover accidental damage that may occur during your stay and gives everyone added peace of mind.brbrThese measures are in place to maintain a high standard of care for the home and our guests.brbrThank you for your understanding and cooperation!

Charming Osprey Home

Osprey, Florida, United States

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Sleeps

Exceptional(14)

$166.93

This beautiful 2 bedroom and 2 full baths condo is overlooking the water and canals, large screened in lanai with gorgeous sunsets, unit is on the top floor, elevator, big kitchen with all you need to make your meals and a large living room. The master bedroom has a king size bed and queen size in guest bedroom. Washer and dryer is in the unit. Located between Sarasota and Venice close to beaches, boating, golfing, shopping and many excellent restaurants. The amenities of this luxurious gated community are heated pool, tennis and pickleball courts, workout gym and nature trails for jogging.

Just South of Sarasota Gorgeous Waterfront Condo 2 Bedrooms, 2 Baths.

Osprey, Florida, United States

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Bath

Sleeps

Exceptional(6)

$250.71

Step into a sunlit, single-story retreat with two inviting bedrooms and two modern bathrooms. Designed for families or groups of friends, our home seamlessly blends comfort with elegance. Located just moments away, dive into the vibrant St. Armand's Circle or unwind on the pristine sands of Siesta Key and Nokomis Beaches.brbrThe spacebrbrAs hosts, we've ensured this space includes everything needed for a quality and memorable experience for up to 6 guests. We love helping our guests find fun things to do, unique dining experiences, and other memorable activities nearby. We’ve also made sure to furnish the entire interior with necessities to elevate our guests’ experiences. We are committed to creating an enhanced experience for families, groups, business professionals, and all other vacationers who choose to stay at this lovely home.brbrFor all of our guests, we provide the following complimentary amenities to enhance your stay:brbr• Contact-free check-inbr• 24/7 guest supportbr• Free and fast Wi-Fibr• Free parkingbr• Fully equipped kitchenbr• Complimentary coffee & tea starter packbr• Complimentary Netflix accessbrbrAccommodation Detailsbr• Bedroom 1: Queen Bed (sleeps 2), en suite full-bathroom, walk-in shower, bathroom essentials, shampoo, conditioner, body wash, makeup towel, hair dryerbr• Bedroom 2: Queen Bed (sleeps 2), hallway full-bathroom, shower and bathtub, bathroom essentials, shampoo, conditioner, body wash, makeup towel, hair dryerbr• Living Area: sleeper sofa (sleeps 2 medium adults or children), mattress pad for additional comfort, 60 Smart HDTV, board games, throw blanketsbr• Kitchen: cookware, dishware, silverware, a stainless steel refrigerator, microwave, stove, oven, toaster, rice cooker, and Keurig coffee machinebr• Dining Area: dining table, 4 dining chairs, additional 4 counter top seatsbr• Laundry room: Full-sized washer and dryer, complimentary detergent and bleachbrbrbrWhat's Nearbybr• Oscar Scherer State Park (1.8 miles): We love walking the Oscar Scherer's trails and enjoying lunch at one of the picnic spots.br• Nokomis Beach (5.7 miles): As our go-to beach for breathtaking coastal views, this is an excellent spot for taking gorgeous pictures.br• Legacy Trail (6 miles): Whether it’s dawn or dusk, this popular biking trail offers unforgettable scenic views from Venice to Sarasota.br• Siesta Key Beach (8 miles): Bury your toes in powdery white sands and swim in turquoise waters at this renowned beach.br• The St. Armand's Circle (14 miles): You’ll fall in love with St. Armand’s vibrant atmosphere as you check out unique boutiques, art galleries, and various restaurants.brGuest accessbrAt this property, you have full access to all areas and amenities, ensuring a completely private and exclusive experience. From the moment you arrive, every part of the property is yours to enjoy, with no shared spaces or amenities.brOther things to notebrThis home is part of a duplex, with its own driveway.brbrExclusive Offer for Pet Owners:brWe're thrilled to offer a discount on the pet fee for guests who bring more than one pet. Our standard fee is $95 per pet for the duration of your stay. If you're planning to bring multiple pets, please contact us for a special discount.brbrFor the comfort and safety of all our guests, we have specific pet policies. While we adore all dogs, we are unfortunately unable to accommodate Wolf hybrids, Pit Bulls, Rottweilers, German Shepherds, and Doberman Pinschers. We appreciate your understanding and cooperation with these guidelines to ensure a pleasant experience for everyone staying with us.brbrAdditional Information:brbrTo ensure a smooth and secure experience for all our guests, we charge a mandatory damage protection fee of $84. This helps cover accidental damage that may occur during your stay and gives everyone added peace of mind.brbrThese measures are in place to maintain a high standard of care for the home and our guests.brbrThank you for your understanding and cooperation!

Sunny Coastal Escape

Osprey, Florida, United States

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$414.62

Fishing on SunshinebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your serene getaway in Osprey, Florida—an inviting retreat tucked away in a quiet cul-de-sac offering the perfect mix of tranquility and convenience. This spacious, family- and dog-friendly home is ideal for both relaxation and outdoor adventure. With direct access to a secluded waterway leading to the Gulf, a private boat dock, and a nearby boat ramp and marina, boating and fishing enthusiasts will find everything they need just steps away. The outdoor area features a refreshing saltwater pool and a furnished patio with a gas grill, perfect for enjoying Florida’s sunshine and family barbecues.brbrInside, you’ll find a well-appointed home equipped with modern amenities designed for comfort and convenience. The fully equipped kitchen includes all the essentials for easy meal prep, while the cozy living room and private dining area offer ample space to unwind. Enjoy central air conditioning, high-speed WiFi, and a washer/dryer. Two kayaks are available for guest use—perfect for exploring the nearby waterways and natural beauty of the area.brbrLocated just 0.09 miles from Oscar Scherer State Park, the home places you near an unexpected oasis of natural Florida. The park is a haven for wildlife—home to bald eagles, Florida scrub-jays, and 15 miles of scenic trails for walking, biking, or birdwatching. It’s also a key stop on the Legacy Trail, a popular cycling route that stretches from the Venetian Waterway in Venice to Downtown Sarasota. Ride south to Caspersen Beach to hunt for shark teeth and explore Venice Island, or head north and discover Sarasota’s vibrant eateries and parks. Whether you’re seeking adventure or a tranquil retreat, this Osprey home is the perfect launching point for your Florida vacation.brbrIf you are bringing a dog on your trip, the pet fee is already included in your quote when selecting ‘Yes’ to pets. If you would like to add more dogs, please contact us.brbrParking notes: There is free parking available for 3 vehicles.brbrSecurity camera details: EntrancesbrbrDock details: brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Waterfront home with pool, dock accessible to Gulf, dog friendly with AC & WD

Osprey, Florida, United States

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Bath

Sleeps

Exceptional(5)

$248.41

Welcome to LIME ON GREEN! CLEAN! Entire 2, 1 home centrally located between Sarasota & Venice. Siesta Key & Nokomis Beach are less than 6 miles away. Casey Key 2 miles away. WIFI & smart televisions in each room. Washer & dryer located in garage. The kitchen has everything you need! Neighborhood is peaceful, friendly & pet friendly! New Bay Steet Dog Park is located within walking distance. We also have a Ford Focus that you can rent. Check it out on Turo. Host lives near & is available 24/7 should you need anything. ENJOY!

Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM

Osprey, Florida, United States

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Sleeps

$318.29

While staying here, you will be able to walk over to Casey Key by crossing the romantic swing bridge each morning. Take in the view and sightings of pelicans, dolphins, and mullets jumping in the intercostal. You can walk over to the famous Casey Key Fish House or Deep Lagoon Seafood Restaurant. Rent a waterski jet, kayak, SUP or hire a water taxi and explore the beautiful intercostal waterways. Sit in the balcony or take a short drive down to the Nokomis Beach and North Jetty to catch a techno color sunset. Amenities include heated swimming pool, two hot tubs, outdoor shower, kayak launch, picnic area with gas grill, gym, sauna, and clubhouse with a pool table. Located right across from the Blackburn Point Park. Come and experience this paradise!

Luxurious 3/2 Waterfront Retreat in Osprey, FL!

Osprey, Florida, United States

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Exceptional(13)

$227.1

Exclusive Single Family Home, private, electrically heated pool, close to beaches.br3 BR, 2BA, 6 people, garden, covered outside dining area.brYou will find 3 bedrooms, a living room with separate dining space and 2 bathrooms on one floor. In the living room, there is a fireplace and a Smart-TV. Free WiFi throughout the house. In the pool area you can dine and relax under a covered seating area, your food prepared directly on the BBQ next to it.brFrom the caged pool area you have a view of the North Creek and our boat dock. The kitchen is fully equipped with dish washer, microwave, stove and oven, coffee machine, juicer, slow cooker and much more. In the laundry room there is a washing machine and a dryer and in the 2 car garage you will find beach chairs, umbrella and a cooler.brThere is a pet fee of USD 50.00 per week plus 13% taxes.brThe electrical pool heat is optional and will be charged with USD 100.00 per week plus 13% taxes with a pool heater setting to 86°F. Please let us know if you want the pool heated with your booking so we can make sure to have it heated upon your arrival.

Creekside Paradise, 3BR, 2BA, private heated pool, North Creek boat dock

Osprey, Florida, United States

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Bath

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Exceptional(17)

$644.59

Sparkling pool view, tennis courts, and ample open space on Blackburn Bay. 2 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 tastefully renovated condominium. Large Enjoy sunsets every night on the screened in Balcony. There is no better peaceful quiet location to spend the season in style.

3 Bedroom Penthouse with Stunning Sunset Views of Blackburn Bay!

Osprey, Florida, United States

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Bath

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Exceptional(2)

$218.03

Escape to our relaxing 2-bedroom home in Osprey, Florida, just minutes from the stunning beaches of the Gulf of Mexico, pristine golf courses and MLB spring training. This peaceful retreat sleeps up to 7 adults and offers a perfect blend of comfort & convenience. The master bedroom features a queen bed and the second bedroom has a bunkbed sleep system with a queen mattress on bottom and twin mattress elevated above. There is also an office with a daybed & trundle for additional sleeping space.

Cozy beach bungalow

Osprey, Florida, United States

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Exceptional(2)

$193.72

Home away from home while you visit Osprey, Venice, and Siesta Key attractions. This perfectly located property boasts 3 bedrooms and a fully fenced yard with lush landscaping. With 2 modern bathrooms and a fully equipped gourmet kitchen, guests will feel right at home. Enjoy the soothing atmosphere of this quaint house and all that the Sarasota area has to offer. Less than a 5-minute drive to beaches, kayak access, bars, and local fares. Garage Parking, Outdoor Dining and Easy access to Legacy Trail for outdoor adventures.

Newly Renovated Tranquil 3-Bdrm Home in Osprey- Close to Beaches Dogs Okay

Osprey, Florida, United States

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Bath

Sleeps

Exceptional(4)

$193.23

We think you will thoroughly enjoy your stay at this comfortable two bedroom, ground floor condo with a lovely water view to look forward to. The condo features a den with a queen size sofa bed, along with two televisions for your enjoyment. The master bedroom features a king size bed, a large bathroom with a walk-in shower, dual sinks and two walk-in closets and a water view. The second bedroom features a queen sized bed, walk-in closet and direct access to the second full bath. The unit features luxury vinyl and tile flooring throughout. The spacious kitchen is fully furnished with a stove, dishwasher, microwave, a large fridge, as well as a wine fridge and ample storage. There is a round dining table with seating for six people. The lanai is full enclosed with a water view and patio table for your enjoyment. Spacious laundry room in unit. All of the comforts of home!

2 Bedroom Ground Floor Condo in Osprey - lots of light & beautiful water view!

Osprey, Florida, United States

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Bath

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Exceptional(13)

$216.32

Welcome to your ideal Florida escape—a fully renovated coastal-style home just a short drive from the world-famous white sands of Siesta Key Beach, Nokomis Beach, and Casey Key. Whether you're seeking a peaceful retreat, a family vacation, or a remote work getaway, this thoughtfully designed home offers the perfect combination of style, comfort, and location. brbrEnjoy serene mornings with a cup of coffee in the shaded garden, sunny afternoons at the beach, and cozy nights grilling with friends in your private backyard.

3 BR Charming cozy coastal house minutes away from Siesta Key & Venice beach

Osprey, Florida, United States

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$244.84