Vacation Home Rentals By Owner In Osprey, FL

Showing 25 Of 25 Vacation Rentals

$147.59

4-bedroom heated pool house 5 minutes to the beach

Osprey, Florida, United States

Relax at this peaceful place to stay. The little heated pool is a big hit, outdoor kitchen and lanai is a great hang, Take a kayak to the beach bar, take a bike ride down the beautiful neighborhood or go to the beach Nokomis 5 min away siesta 15 min away. Breweries, grocery stores and Oscar Scherer park all nearby. Lots of space and fast wifi. Plenty of space for a big group to spread out. 2 master bedrooms both go out to the pool deck. We want to make this the best trip you ever have!

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Exceptional(2)

$208.01

/ Nightly

Private Vacation Home

Cozy beach bungalow

Osprey, Florida, United States

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.

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Exceptional(3)

$476.38

/ Nightly

Private Vacation Home

4-bedroom heated Pool house in lovely Osprey, 5 minutes to the beach

Osprey, Florida, United States

Picture yourself paddling a canoe to the Casey key fish house after you take a dip in your own large heated pool with room for your whole family to have a great time. Make dinners in the outdoor kitchen and check out the sunset at Nokomis beach 5 minutes away or siesta key beach 20 minutes away. 85 inch tv with room for everyone and dining room seats 12. 3 bathrooms to make everyone happy, the perfect place for a walk or a bike ride in serene Osprey. Your close to grocery stores, breweries and the highway if you need it. Plenty of room for your boat, RV, camper and vehicles. The large yard has beautiful trees and an 8 foot vinyl privacy fence all the way around to keep pets and family happy. We have everything you need to leave your worries behind and have a great stay.

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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.

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Exceptional(13)

$216.32

/ Nightly

Private Vacation Home

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

Osprey, Florida, United States

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.

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Rent a place that suits your needs

Private vacation home

View 23 Private vacation home

Most popular vacation rentals in Osprey

Exceptional(13)

$343.13

/ Nightly

Private vacation home

Mid-century Waterfront Home with pool

Osprey, Florida, United States

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Exceptional(13)

$136.57

/ Nightly

Condo

Cozy 1-bedroom condo in Osprey, near Nokomis Beach, WiFi, AC, Pool, Tennis

Osprey, Florida, United States

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Exceptional(13)

$139.69

/ Nightly

Condo

Luxury Condo on the water with Intercostal view

Osprey, Florida, United States

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Exceptional(13)

$164.53

/ Nightly

Private vacation home

2-bedroom Spacious townhome in Osprey

Osprey, Florida, United States

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Exceptional(13)

$168.53

/ Nightly

Private vacation home

Sunny Coastal Escape

Osprey, Florida, United States

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Exceptional(13)

$177.54

/ Nightly

Private vacation home

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

Osprey, Florida, United States

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Exceptional(13)

$193.23

/ Nightly

Condo

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

Osprey, Florida, United States

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Exceptional(13)

$193.72

/ Nightly

Private vacation home

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

Osprey, Florida, United States

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Exceptional(13)

$195.37

/ Nightly

Private vacation home

Charming Osprey Home

Osprey, Florida, United States

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Exceptional(13)

$279.24

/ Nightly

Private vacation home

Pet-Friendly Modern Retreat Near Siesta Key

Osprey, Florida, United States

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Vacation Home Rentals By Owner In Osprey, FL

$147.59

$208.01

$476.38

$414.62

$216.32

Rent a place that suits your needs

Most popular vacation rentals in Osprey

$343.13

$136.57

$139.69

$164.53

$168.53

$177.54

$193.23

$193.72

$195.37

$279.24

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