Home Vacation Rentals By Owner In Osprey, FL

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$139.9

/ Nightly
Private Vacation Home

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

Osprey, Florida, United States

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.
Bed 2

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Bath 1

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Sleep 4

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Exceptional(2)

$245.01

/ Nightly
Private Vacation Home

Charming Osprey Home

Osprey, Florida, United States

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!
Bed 2

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Bath 2

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Sleep 6

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Exceptional(6)

$250.71

/ Nightly
Private Vacation Home

Sunny Coastal Escape

Osprey, Florida, United States

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!
Bed 2

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Bath 2

Bath

Sleep 6

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$414.62

/ Nightly
Private Vacation Home

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

Osprey, Florida, United States

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.
Bed 4

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Bath 2

Bath

Sleep 12

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$244.84

/ Nightly
Condo

Charming 3-bedroom condo with WiFi, AC in tranquil Osprey

Osprey, Florida, United States

Welcome to Edgewater at HIDDEN BAY COMMUNITY, offering luxurious waterfront living. This 3 bedroom 2.5 bath waterfront condo is immaculate and the perfect place for a seasonal snow bird rental, annual rental or Florida vacation (1 month minimum). Relax on the spacious lanai that reveals a view of the bay and AMAZING SUNSETS. The unit has an elegant foyer and comes with a separate laundry room with washer, dryer, sink and plenty of storage. There is a 1/2 bath off of the kitchen and a separate walk in pantry. The unit also comes with secure under building parking and a large storage unit. The kitchen has granite counters, stainless steel appliances and comes fully equipped. Off the kitchen is the living/dining area with sliding doors opening onto the large lanai overlooking the bay. The master suite has a king size bed, 2 large walk in closets, en-suite bathroom with walk in shower, and more amazing water views. The 2nd bedroom is nicely furnished with a queen size bed, walk in closet and en-suite bathroom. The 3rd room can be used as a den or bedroom as it has a desk and trundle bed/sofa with 2 twin mattresses . Located in a private gated community that offers a wealth of amenities, including a clubhouse with a catering kitchen, state-of-art-fitness center, inviting pool, hot tub, tiki hut with BBQ grills, tennis courts and pickle ball courts. This unit is ideally situated on the border of Osprey and Sarasota. It’s only minutes to the beautiful beaches of siesta key, Nokomis and Venice, shopping, dining and the vibrant downtown Sarasota area.
Bed 3

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Bath 2

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Sleep 6

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