Holiday houses in Osprey

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Popular amenities for Osprey holiday rentals

Stay near Osprey's top sights

Historic Spanish Point42 locals recommend
Casey Key Fish House45 locals recommend
Stoneybrook Golf & Country Club4 locals recommend
Turtles Restaurant7 locals recommend
Turtle Beach Grill Restaurant4 locals recommend
Max's Table20 locals recommend

Other great holiday rentals in Osprey

Superhost
Home in Placida
5 out of 5 average rating, 8 reviews

Bay view and possible two family rental!

ArleneRating, 5 stars1 month ago
we had a wonderful time at Robert's place. Everything was as described. the island is a perfect getaway for anyone that wants to go on an adventure and get away from the hustle and bustle. The kitchen had everything you would need to cook, it was perfect! Everything was well thought of in this home. On a side note, golf carts need to be booked months in advance and are pretty pricey and we hoped to walk around the island but we're told upon checkin that was not allowed. we could only go to the beach and back to the property. You could walk along the beach though.
Guest favourite
Home in Nokomis
4.93 out of 5 average rating, 28 reviews

Last minute May ,house 2 Mil beach .Pets welcome

ErinRating, 5 stars1 week ago
Great location, clean and cute. A great size for a large or small group of people
Guest favourite
Home in Venice
4.9 out of 5 average rating, 29 reviews

Second home vacation rental

JasonRating, 5 stars2 days ago
I highly recommend staying at this location very clean very nice well-maintained. Highly recommended.
Superhost
Home in Bradenton
5 out of 5 average rating, 4 reviews

Cottage by the Sea

LukeRating, 5 stars4 months ago
Pam and Bailey were super helpful and responsive. The place was incredible and the extra touches made it feel like home! Super private backyard and friendly neighbors. Would definitely stay there again!
Guest favourite
Home in Venice
4.76 out of 5 average rating, 136 reviews

Vacation home by Shasta Rd

JudithRating, 5 stars1 month ago
The house was comfortable, and the kitchen was well stocked with all the dishes and cookware we needed. The location overlooking the pond is a highlight. The many kinds of birds that come onto the lawn and right onto the patio are fun to watch. As are the turtles and alligators that swim by all the time! The water in the area isn’t great, so there is a reverse osmosis filter in the kitchen for drinking and cooking water. But the water in the rest of the house isn’t filtered, so the water in the tub and toilets and laundry is a little amber colored. It didn’t affect our clothes in the laundry, and we used bottled water to brush teeth, so it was fine. Overall, we really enjoyed our stay, and would come back again!
Superhost
Guesthouse in Bradenton
4.73 out of 5 average rating, 60 reviews

Roxy’s Village 1

KeilaRating, 5 stars1 week ago
Alexander was kind and attentive at all times.
Top Guest favourite
Home in Port Charlotte
4.97 out of 5 average rating, 185 reviews

Full home, Low Cleaning fee, heated salt pool.

ChrisRating, 5 stars5 days ago
Fantastic stay. Great home and great hosts all around.
Top Guest favourite
Home in Rotonda West
4.96 out of 5 average rating, 53 reviews

Waterfront 3bdr 2ba Beaches Golfing Fishing

KaylaRating, 5 stars1 month ago
Home was very clean and tidy, I liked the space and all the accommodations it had. Although the home still had left over food from previous guests it was still clean. The only issue i had was finding where the “pool” was that was shown in the listing aswell as a hammock, bikes and beaches were farther than anticipated. Aside from that we were very comfortable and would recommend to future guests!!

Quick stats about holiday rentals in Osprey

  • Total rentals

    80 properties

  • Nightly prices starting at

    $77 AUD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    50 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sarasota County
  5. Osprey