Pet-friendly vacation rentals in Osprey

We are a couple traveling to see new interesting places. Spend most of the day exploring the area, just need a quiet place to rest, sleep and cook dinner. This place was good for our purposes: quiet, private and close to many attractions of Sarasota.

My sister and I had a lovely stay at El Tropicale. We were attending a yoga retreat in Lakewood Ranch so the location was perfect. Very spacious and the pool is great! All communication was prompt and friendly. Would definitely stay here again.

The space allowed our family to be together, but also have privacy. Michael was an excellent host and cared about our family’s needs. We were in town for our son’s wedding and the “Family Fun House” was truly special!

Sonia & Daniel's house exceeded all our needs for our son's stay visiting his grandparents in Venice. The house was very clean, nicely decorated and comfortable. Everything he needed was there, and he enjoyed a quiet place to relax. The screened in lanai was a nice place to enjoy morning coffee. The neighborhood was very peaceful, and our son was happy to be able to do a morning run down through Shamrock Park, which is on the water. Sonia and Daniel were very responsive to our messages. We would definitely consider renting this house again!

Great stay! Quiet and off the beaten path but still close to many fun activities and restaurants. Would definitely recommend and stay again!

Romualda’s home was very clean, beautiful, and modern. She was very communicated from the time we booked the AirBnb, to the time we checked in, and the time we checked out. We felt right at home as she had many ameneties that were offered and more. We will definately book again next time we are in town.

we came to Relax at the Beach and Christopher's place had everything we needed to do that. From coffee to Beach towels, He thought of everything.! We enjoyed our trip.

Joe's place feels like a real home - many AirBnBs can feel like a hotel with a little more space - Joe's house was not that! Complete with a ton of my personal favorite books, tons of kitchen utensils/supplies, a desk, and more. The huge fenced in backyard was perfect for grilling and our dogs. The location is right off of a main road that takes you to shopping/amenities within minutes. If you're looking for a great place to feel comfortable while visiting Sarasota, we'd recommend Joe's property to anyone!

What a beautiful home and neighborhood. It was perfect for our needs. The pool was a huge plus and we swam every day.

Mary was so easy to talk to and very responsive. We chatting before and during our arrival. She has a lovely, Clean, organized home. She has been so gracious and we loved our stay there.

This place was perfect for a relaxing vacation. Beautiful home with a wonderful pool area. Nicole was a perfect host. We would definitely recommend and/or stay here again!

Lovely home with a large fenced backyard and a warm pool. Conveniently located near Robinson Preserve and Anna Maria Island. Michelle was quick to answer any questions. We enjoyed our stay.

Really great accommodation! Stayed with a group of friends. Loved the pool and outdoor space! Kitchen had all the amenities needed. Host was very responsive when we had a minor issue with the pool. Game room and laundry was a bonus! Beach is close but lots of traffic getting on/off Anna Maria Island. Beautiful beaches, recommend Coquina!

We are repeat guests at Rancho Relaxo, and we will continue to return as long as they have us. I highly recommend Lynn's place if you're looking for a place to relax and unwind. We enjoyed the heated pool every night, and our dogs loved the gated backyard. The location is private, yet it's conveniently close to shopping and restaurants. We can't wait to go back!

This was the cutest home and was absolutely perfect for our stay. The home was clean, well stocked, and in a quiet neighborhood. The pool was crystal clear. The beds were comfortable. The listing was just as described. We truly enjoyed our stay!

Ryan’s place was just right for our escape from the Wisconsin winter! We walked every morning to the Shamrock park and Nature center. Great restaurants and shopping in Venice.

First I would like to say thanks so much to William and Terri. What a beautiful home you have. My family and a great stay at your house I would have to say the pool was the big hit. The boys absolutely loved it. The area was beautiful the shopping in downtown Venice has tons of shops to go and check out. Manasota Key Beach was fun as well shark tooth exploring and shell hunting was great it's kind of a must do if your there. Can't say enough had a great stay beds were comfy. Thanks again William and Terri.

Mario's place was a great set up for our family. It's a little smaller than what we thought it was going to be but the island is so beautiful that we didn't really spend a lot of time inside anyways. We had a blast on our trip for a week. The only thing we didn't enjoy was the neighbor directly behind their place didn't like any noise at all. In the instructions it states that the "quiet" time is from 10:00 PM - 7:00 AM. There were two nights that we were being "loud" at 7:30ish PM outside in the pool having fun with our kids and she used choice words after banging on the fence to get us to quiet down. A few nights later around the same time she threatened to call the cops. We were enjoying our vacation, we weren't being rude at all, I think she is what I would consider the "Sherrif of No Fun" but other than those two nights we would highly recommend Mario and his place. It was a great location and we were able to enjoy your stay.

We loved the house and the hosts. One of my best Airbnb experiences. It was exactly as expected. Love it!

Great cottage. Close to IMG and Anna Maria island. Very responsive hosts, would recommend!

The apartment was very roomy, clean and we loved the well-stocked kitchen with the beautiful countertops and all the cooking utensils that you could want. Renee is an excellent host, very responsive! It was great to enjoy morning coffee out on the balcony!

Gigi provided so many little touches that made their Airbnb stand out. A basket of snacks, freshly baked cookies, bottles of water in the fridge and bags of ice in the freezer. So much attention to detail elevating this cottage to the highest level in accommodations. My two sons (8 and 10) especially enjoyed the Squishmallows and the wonderful tree swing out front. The couches in the living room were so comfortable and the shower was quite relaxing. 10/10 would go back again if in Sarasota.

We enjoyed our two month stay at Viktoriya’s beautiful new home. The house is well maintained - the kitchen has all the amenities allowing you to feel like you’re at home. The neighborhood is very quiet and we enjoyed our walks. Viktoriya is a wonderful hostess and is very welcoming and responsive to any questions you might have. Looking forward to our stay in 2026.

Had a wonderful stay! Place was in great location for what we wanted out of our vacation: golf, beach and bike trail! The accommodations were clean and roomy. Siesta Key Prop Mgmt was very responsive and brought us an extra beach chair and umbrella for our beach day! Would highly recommend!