Fitness-friendly holiday rentals in Osprey

We had a great time at the Villas. This neighborhood is very peaceful and has all you need. We enjoyed being able to go to the pool and hot tub. The location is perfect - close to the beach and restaurants. Bea was quick to communicate and was helpful. Will be coming back.

Very relaxing atmosphere…comfortable bed…everything worked:AC, TV, and Denise was very responsive . She suggested excellent restaurants within walking distance. It’s a quiet neighborhood within walking distance of downtown. Museums and Selby Gardens within walking distance.

Fabulous! The beach is across the street and there are beach chairs, towels, umbrellas, noodles,cooler, wagon,etc. The view of the Gulf of Mexico from the Lanai is stunning .The Village is a mile away with lots of fun bars and restaurants . We loved this place!

Ewelina’s property was both beautiful and functional. The kitchen was large and well stocked. The condo was tastefully decorated. The location is ideal for us, as it is close to downtown and not far from the beaches and the ballpark. Ewelina is an excellent host. She reached out in advance of our stay, communicated very clear instructions for entry, and stayed in touch while we were there. She responded very promptly to all the questions we had. We would love to return to Ewelina’s property again!!

We had a wonderful stay at this apartment! Everything was spotless, well-equipped, and exactly as described—if not better. Robert clearly went above and beyond to make sure we were comfortable and had everything we needed. Communication was smooth and responsive throughout our stay. The location was perfect for our vacation, and we felt right at home. Highly recommended!

Had a great stay at Susanna's. It was comfortable, clean and in close proximity to the beach. Will definitely come back

This stay was amazing. Extremely beautiful, clean, comfortable, well stocked condo with everything you need for a family vacation. The one swimming pool is diagonal from the condo and just a short walk to the private beach. Perfect location and very close to the village. Richard was extremely responsive and helpful throughout our stay. We loved staying here! We will be booking this again for next year!

Caitlyn's home is amazing! It is extremely clean and has everything you need. Well furnished and exactly what the pictures show. We stayed with 3 children ranging from 1-9 years of age and it accomodated everything we needed for the stay. Everything from a high chair and playpen. Lots of extra towels, kitchen and bathroom supplies and everything you need for the beach as well. Perfect location as it is near highly rated local cuisine and also 5 minute drive to downtown and a few minutes drive to Lido Key and Siesta Key beach. The pool and gym and other amenities were great and were always clean. Very private and quiet ambience and the security to get in makes the property extremely safe. Caitlyn is always ready to respond to any inquiries and made communication so easy from check in to check out. We would definitely recommend this property and would love to return in the future. Thank you Caitlyn for being a wonderful host! Our family had an amazing vacation! 🌅☺️

Great price, great place! Easy walk to the ocean. Great for fishing. Close by to ice cream and restaurants.

Super clean, quiet, comfy bed. We enjoyed the bayside pool. Nice views. Palm Bay club nice benefit as after a short walk over to the beach we enjoyed the chaises delivered and set up close to the water and hole drilled for our beach umbrella. Amazing sand is not over rated. Warm gulf waters and easy entry and exit. Breeze Trolley with their app made getting around without driving convenient . Lots of fun food and shops minutes away. This bayside spot a was a delight.

The location was great, close to village as well as crescent beach. Lots of restaurants, bars, and excursions close by. Private beach which is wonderful, they offer umbrella rentals for a very reasonable price. Two pools which allowed for plenty of space as neither pool was crowded. The condo came with adequate linen/towels with an exchange halfway through the week which was great. There were extra beach toys, umbrellas, and a cooler in the closet we found a few days in that came in handy.

This was an amazing condo for our family trip! Pictures and listing were very accurate and it was so lucky to find a property on Siesta Key that was actually on the beach. We would absolutely stay here again! The beach is stunning and the two pools are wonderfully maintained Some things worth mentioning (they are disclosed in the listing) - you must provide your own beach/pool towels but there are plenty of shopping options nearby - beach chairs are free and located once you get down to the beach - for a fee, you can reserve/rent an umbrella and have it set up for you during your stay. The guys are out there early (7-7:30am) but then come in around lunch time so if you want an umbrella, I suggest going out in the morning to get it setup - dish soap, dishwasher tablets, hand soap are provided but you’ll need to purchase everything else (salt/pepper, spices, oil, ziplocks, shampoo/conditioner, etc). Super central location and very secure property! Would definitely stay here again!

Such a beautiful place to stay! Very clean! The kitchen was stocked with all the dishes you will need. The view was amazing!!! The free trolly into the village was so easy. The beach accessories were so nice to use. All we had to do was cross the street and we were on the beach. The pool area was also very nice! Grilling area was nice and clean and a small smoking area so my husband could enjoy a few cigars. Great communication! Thank you! Was a fantastic vacation!

My wife and I spontaneously booked a last-minute getaway at Colin’s condo, and we couldn’t be happier with our decision. The condo was beautiful—just steps from the beach—and the view from the porch was absolutely stunning. We loved that beach chairs and umbrellas were included, which made our three days of relaxing by the ocean even more enjoyable. The location was great, with restaurants just a short drive away. I also took advantage of a well-equipped workout area just down the street, which was a nice bonus. The bed was very comfortable, and we made good use of the full-sized fridge during our stay. Colin was incredibly responsive and proactive in his communication, checking in frequently to ensure everything was going smoothly. The resort itself was spotless, and the staff were all warm and welcoming. It was the perfect short escape—we’d definitely come back!

Thank you Judy! We really enjoyed our stay it was delightful sitting out looking at the Marina watching the boats and the Sunset! Cass Cay is a great place to get dinner, drinks and listen to great music! Met your neighbor Mark and his friends Jim and Debby very nice to meet and talk with them. If we come to the area again we would definitely stay with you again! Thank you!

Our stay at Ten35 was great! Great location with direct access to the beach. If you plan to stay around the area while visiting, you most likely will not need a vehicle as this is close walking distance to most of the restaurants and shops near by. The condo was overall very nice, comfortable, clean, and very spacious.

We had a group of 9 adults and 2 babies and really enjoyed our stay. Plenty of room and loved having so many bathrooms. Place was very clean and we appreciated that there were beach towels, beach chairs and etc. The pool was nice and clean and someone came by to clean twice a week. Loved the open floor plan in the living room too. Leslie was super helpful and responsive. The stay pretty much had everything we needed.

Wow!! Jeff & Lyn’s home was perfect for our stay of 3 adults, 2 kids & 1 infant! Very kid friendly! Everything was extremely clean, organized, all cabinets were labeled. The house was fully stocked with everything you could need including items for baby/child. Garage had plenty of beach toys, wagon, chairs, baby pool float, baby beach tent. Beds were very comfortable & nice linens! The home looks recently upgraded and everything is in great condition. Home is conveniently located to downtown Sarasota, restaurants and local beaches. Jeff & Lyn thought of everything! I can’t think of anything that could be changed or added! Highly recommend this property & will definitely return for a future stay.

Amazing place! Perfect for our large group that came and stayed for a week. Plenty of sleeping spaces. Great AC! Plenty of towels and beach gear to take. Overall very satisfied. Would definitely stay here again.

Ester and David’s home was exactly as listed. The photos were spot on. The house is absolutely adorable, comfortable and impeccably clean and organized. One of the best airbnbs we have stayed in. The backyard was so inviting, we k my wish we could have spent more time outside! Hoping next time we come to Sarasota this home will be available!

This home is well- maintained and has lovely outdoor spaces. The artwork in the home was unique and fun, not cookie-cutter or generic. I loved that. The amenities were just what was needed to prepare meals or enjoy ourselves. The neighborhood is quiet and walkable, with friendly neighbors. Overall, this is a great location and property.

Wanted to thank you for having us in your house. My family were happy and we had a great time at the pool and beaches around. House was good organized and clean. Liz Choe’s was really nice and friendly all the time, she let us check out later because of our flight was later in the day. We recommend Liz Choe as host and her house as a vacation spot. Thanks

Really enjoyed the backyard with the pool/hot tub and gazebo. A little oasis in the middle of town.

Wonderful island getaway home! Me and my wife were searching for a quiet and relaxing weekend away and Debbie’s place sure delivered! We enjoyed the closeness of food options and the location of the home on the island. Debbie was super responsive and helpful with any needs or questions that we had, and they made us feel right at home. So look no further for your next stop on Longboat Key!