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.

If you’re looking for a simple, by the bay, relaxing place, this is your place! Jeff was very responsive when communicating. Some complimentary food and drink items in the room were super helpful after a day of travel and awaiting our groceries. We had WalMart+ delivery right to our building. The pool is clean with beach towels provided and large enough to spread out when a large crowd is there. This place is in a hotel, so having hotel perks was great! The gym was small, but perfect for a treadmill walk to wait out the rain. The Tiki bar/restaurant on the property was very nice. Highly recommend their tacos and mango cart beer! There was a band or dj every night we were there with great music. For the price of our stay, we have zero complaints!

Totally enjoyed our 10 days at McGill's condo. The lanai was huge and very comfortable. Everything was clean and organized with a kitchen that included all we needed for cooking in. Access to the beach was easy and there was a well stocked cabinet next to the elevator with beach chairs and accessories. Transportation via free shuttles was convenient but we were also able to walk to the village in 15-20 minutes. If you are here on Sunday evening be sure to join the drum circle across the street on the beach. Finally, McGill was always quick to answer questions and make our stay as smooth as possible. We will return.

The condo is very conveniently located, has a cute kitchen, spacious bedrooms, and super comfortable beds. 15 to 20-minute drive to some of the most beautiful beaches I've ever seen. The host is quick to respond to any concerns, and she hopes to correct them and make sure her place is well taken care of for guests in the future. Our family enjoyed making memories here and hope to be back soon. Thank you ❤️

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!

This place and the community was fabulous! We have young kids and it was perfect. The condo was in great shape- nice and comfortable furniture, spacious bedrooms, nice kitchen with appropriate amount of kitchen fixtures. Our kids loved the pool, a little too much! The community was quiet and everyone was friendly. It is a little bit of a hike, about 15 minutes to get to the beach, but the place had a big beach cart to use so that helped to lug everything. We will keep this place in mind if we venture down to Siesta again!

Brenda’s place was just as listed. Great location, clean, great space to call home for the week. Within walking or short drive to many restaurants and shopping areas. Walk to the beach was easy especially with all the beach supplies in the condo. Brenda was also very responsive when I reached out with clarifying questions.

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 is our 5th time staying here, and the place and location speak for itself. The one thing that takes this place over the top in our opinion is the amazing and friendly hosts, Honestly they have treated us like family and made sure our stay has been amazing and safe. We were there for hurricane Helene and they made sure we were taken care of the whole time. I can’t thank them enough, including Vince who is always on top of everything. Thank you from the bottom of my heart.

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!

David’s home exceeded our expectations and was an excellent choice for our stay. It was conveniently located near all the beaches, restaurants, groceries, and shops, but not in the midst of the bustling city center. David even provided us with a variety of beach essentials and even bikes for our convenience. The home was spotlessly clean and well-stocked with blankets, towels, and cookware and dishes. We thoroughly enjoyed our stay and will definitely be returning in the future.

Extremely proactive and responsive host. Very nice condo which was very clean and had everything we needed. Nice pool, hot tub, and workout facility. Location was close to downtown, restaurants, beaches, golf, and shopping.

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!

We had a great stay in Siesta Key. The grounds were beautifully kept. Pool right out the back door. Quick walk to one of the most beautiful beaches in the US. Great week, can’t wait to go back.

An excellent and spacious property for a family get-away! Ample bedrooms with private bathrooms to accommodate extended family members. Peaceful and beautiful setting on the IMG golf course. Pool, outdoor seating, and back deck were perfect to unwind with family after dinner. We loved our stay in this quiet neighborhood!

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.

Your home is beautiful and very comfortable. We truly enjoyed our stay at your home. Would recommend it to to others and would stay again when we come to Florida.

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

I can’t begin to express how happy I was! The house was spotless!!! I’ve stayed in places that were incredibly disappointing. They are wonderful hosts. I highly recommend staying there!

We had a great stay at this beautiful and spacious home in Bradenton. It was perfect for our group, with comfortable bedrooms and a well-equipped kitchen. The pool area was very enjoyable refreshing after hot beach days. The location is excellent, just under 15 minutes from the beach and close to stores, restaurants, and markets. The house also includes beach gear, which was super convenient. There’s a grill area and a yard with games for everyone to enjoy. The lake view made our morning coffee even better. My family and I were very happy with our stay and would definitely book again!

We truly enjoyed this place! Lynn and Matt were very nice and helpful throughout our stay. We will absolutely be returning next year, this was the perfect house and area. They don’t have this on the listing but they had several pool floats, noodles, googles, small pool toys, a beach wagon, beach chairs adult and kids, kids life jackets, a cooler, shark teeth scooper, and several other things! The kitchen was also well quipped! Our two dogs had a blast in the very large fenced in yard. Great hosts, 10/10 would recommend! We can’t wait to return!

Thank yall for allowing us to stay in yalls beautiful home. We couldn’t have asked for anything better!! This home is so beautiful and exceeded all of our expectations and some!! We felt right at home and loved that the house had everything we needed. Check in and out was a breeze. Jeffery and Ammie were excellent at communicating and fast with responses with any questions we had. Top hosts for sure! If I could give a 10 star rating I wouldn’t think twice about it!! Highly recommend!