Vacation rentals in Osprey

4.98 out of 5 average rating, 57 reviews

Home in Bradenton

Sunshine Family Paradise With Heated Pool, Hot Tub

KarolinaRating, 5 stars2 weeks ago

We had a great time staying at this house with our family. Everything was clean and well taken care of. The pool was a big enough -perfect for relaxing and letting the kids have some fun. Overall, it was a great value for the money. We would definitely stay here again!

4.89 out of 5 average rating, 57 reviews

Home in Sarasota

Lakefront Getaway in Sunny FL

ChrisRating, 5 stars2 weeks ago

What a wonderful week we had at this place! The surroundings and nature with the lake were unreal! The pool was spectacular and the entire family enjoyed every minute of our stay! So close to everything you need and some of the best beaches in Florida! Would recommend this home to anyone looking for a peaceful oasis getaway!

Tiny homes in Port Charlotte

5 out of 5 average rating, 6 reviews

Minutes to Sand, Dog Friendly, Hot Tub Luxury

EricRating, 5 stars6 months ago

We transferred over to Richard’s Airbnb location seamlessly during the last hurricane. The place was very spacious, comfortable, with high end finishings, easily accommodating myself, daughter, granddaughter, and pet. Richard was a great host especially considering the circumstances. Very responsive and openly communicative when needed or necessary. We would definitely stay at Richard’s Place again when in the area. Eric - out of state traveler

5 out of 5 average rating, 3 reviews

Apartment in Bradenton

Five Beach Retreat * Best Value @ Shorewalk Resort

LisaRating, 5 stars1 month ago

this Airbnb was extremely well appointed with a full kitchen and everything and anything you could need! I’ve been to many Airbnb’s where I have to go out and buy toilet paper paper, products, wine, openers dishwasher soap, laundry soap, and that can add to the expense. This place had it all which I thought was very thoughtful by the owner.! The unit was extremely clean many condos. I’ve been and have very dirty floors, but not this one also very nicely decorated with a coastal style. The bed was very comfortable. I would most definitely recommend and stay here again myself. !

4.77 out of 5 average rating, 104 reviews

Apartment in Siesta Key

Gertrude's Siesta | Patio & 1-min to Beach/Village

KatarzynaRating, 5 stars4 months ago

Our apartment was very clean, sheet as well. The kitchen had everything what you need, there were plenty of towels in the apartment and beach supplies were helpful. The contact with the landlord was very good, he was nice and answered quickly, Is also access to a new washer and dryer. The only minus was the mess in the garden and old junks that were everywhere, as well as the neglected greenery. 9/10

4.97 out of 5 average rating, 37 reviews

Condo in Sarasota

Siesta Key Village & Beach w pool & pet friendly

NatalieRating, 5 stars7 months ago

Great location, exactly as listed. Came with all the essentials plus more. The condo was perfect for us and our 18 month old and the brand new pack and play was much appreciated. Very friendly beach town with the softest white sand!

4.92 out of 5 average rating, 294 reviews

Home in Sarasota

❤ Villa & Garden in Downtown ~ 5 Min to Beaches

ZalmonRating, 5 stars2 months ago

I arrived late after dark but Chris’ guest duplex had a light on. Also there is attractive landscape lighting both front and in the enchanting private backyard patio. It felt magical entering this lovely place located in one of the best neighborhoods in Sarasota. This duplex was spotless and attractively furnished. It was equipped with everything you could possibly need. Chris is a responsive, helpful host who respects the guest’s privacy. This is the place to stay if you ever visit Sarasota.

4.91 out of 5 average rating, 11 reviews

Home in Sarasota

Slowtide Cottage on Siesta Key

MichaelaRating, 5 stars1 week ago

“Better than the Ritz” MAGICAL sunrises that are visible from just about anywhere on the property. Enjoyed peaceful evenings by the glistening water that surrounds. Enjoyed chatting with my 2 teenagers at the dining table on the screened in porch. My 14 year old son loved that he could fish all day and night. (Bait shop was only a 5 min drive) All 3 beds were luxuriously comfortable. Loved that each bedroom had its own bathroom tucked into it with luxury showers and tastefully simplistic design. The cottage is built with AUTHENTIC wood (cedar i think?) that adds to the feeling of being grounded in nature. Nice pool steps from the back door. Sunsets on the beach are an easy walk across the street. The “Our Place” toaster oven/air fryer works great. Cooking with a view is much more enjoyable! Wish I could live here and would love to return asap. Thank you Jack for your hospitality!!!

Vacation rentals for every style

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Houses

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Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Osprey vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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 vacation rentals in Osprey

5 out of 5 average rating, 8 reviews

Home in Placida

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.

4.93 out of 5 average rating, 28 reviews

Home in Nokomis

Last minute May ,house 2 Mil beach .Pets welcome

ErinRating, 5 stars6 days ago

Great location, clean and cute. A great size for a large or small group of people

4.89 out of 5 average rating, 27 reviews

Home in Venice

Second home vacation rental

BrendaRating, 5 stars3 weeks ago

Our stay at Leroy's place was just great. It was a great location. Easy to find. Easy check in. The place was clean. Kitchen was clean with all the amenities you need. Lots of clean linens ans towels. Bed was very comfortable. The air-conditioning was always cool and big ceiling fans. The bathroom was very clean and good size. The washer and dryer was an awesome thing to have. We loved the screened in back porch and enjoyed our evenings out there. The neighborhood was nice and great. No sirens ans loud cars or cars going by with loud music. It felt very respectful of one another. Leroy's place was not close to our venue, but it was such a nice stay for a great place, we would DEFINITELY stay again and highly recommend to others!

5 out of 5 average rating, 4 reviews

Home in Bradenton

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!

4.99 out of 5 average rating, 83 reviews

Camper/RV in Sarasota

HOME HOME ON THE RANCH. SARASOTA FL.

CarlRating, 5 stars1 month ago

this was a great location.

5 out of 5 average rating, 6 reviews

Home in Bradenton

Luxury ~ Heated Pool ~ Games ~ near AMI, IMG, SRQ

MichaelRating, 5 stars1 month ago

Beautiful home, very clean, and very nicely decorated with all the modern amenities. The neighbourhood was great too, close to shopping and restaurants. The host was really welcoming and responsive. Overall super happy with our stay! Thank you!

4.76 out of 5 average rating, 136 reviews

Home in Venice

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!