Fitness-friendly vacation rentals in Osprey

5 minutes to private Siesta Key Beach + 2 pools

Escape to this luxurious 1st-floor condo on Siesta Key, just 5 minutes from the award-winning Siesta Key Beach. Enjoy private access to its soft, white sand and turquoise waters. Perfect for families, the condo offers two heated pools, lighted tennis and pickleball courts, a fishing pier, gym, and sauna for endless fun and relaxation. Nestled in a tropical setting, it’s the ideal spot for your beach vacation, staycation, or a peaceful getaway. Everything you need for an unforgettable experience!

Garage to a Tiny House Studio Near Shopping Center

Experience comfort and style in this charming, pet-friendly space, perfect for short getaways. Enjoy the privacy of your own entrance, along with a full shower, cozy living room, dining area, and bedroom, all within one convenient layout. The fully fenced backyard, shared with other tenants, features a grill and fire pit—ideal for relaxing evenings outdoors. While the space includes a kitchenette, access to the main shared house may be available if you need a full kitchen or laundry facilities.

Heated Pool - Just 1 mile to Beach! Updated/Fun!

Fun for the whole family!! Only 1 mile to the Beach! This newly updated home comes fully furnished with 4 bedrooms and 3 bathrooms. With a total of 6 beds, the home sleeps 10 comfortably. The Heated Pool is perfect for swimming, and being only 1 mile to the world famous Siesta Key Beach Access 12, this home also makes beach going easy and convenient. Inside, the home is clean, spacious and newly updated and equipped with smart tvs, air hockey table, pool table foose-ball, Pac-Man - fun for all

Lake View, 6 Miles From Beach

-Located inToscana Isles (gated community with heated infinity pool, gym, tennis/pickleball/bocce ball courts, playground, dog park, billiard room, and monthly events) -Backs up to 1 of 3 lakes (kayaking and fishing allowed, 2 kayaks, 2 fishing poles and tackle box included) -6 Miles from Nokomis Beach, 6.8 miles to Venice and dog beach, the only pet friendly beach in the area (4 beach chairs, umbrella, cooler, wagon and beach bags included) -Close to Legacy Trail and Oscar Scherer State Park

Halo cottage pool, hot tub ,Myakka River

Reconnect with nature at this unforgettable escape. In the beautiful Ramblers Rest RV resort park that offers a resort style swimming pool and hot tub, fully equipped exercise gym, pickle ball, tennis courts, billiards room and so much more. Halo cottage is fully remodeled mobile home. The kitchen in stocked with basic needs, dishwasher, fridge and a washer/dryer. Enjoy the Myakka River view and head out and enjoy coffee in the morning at the dock, or launch a kayak. Absolutely no smoking.

Free Early Chk-in, Near-Ringling College Van Wezel

Beach ready Apt!! Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on a main road 1 mile from downtown Sarasota. Beside ARTS&DESIGN COLLEGE!! Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. This cornerr apartment has a dazzling wrap-around patio .and 2 Bicycles. Send me a message if you have any questions .

A Home on the golf course W/Hot tub near Downtown

Modern style with new floor!Located in Burnt Store Isles, a privileged canal&golf community. Close to downtown, restaurants, Fisherman ‘s village, beach parks, groceries-Publix ,accesses to highways 41 &75. Sitting on the 18th green of Twin Isles Contry Club. 2BRS&2BAS&a queen size Italian dove sleeper provide a rejuvenating retreat for 6 people; complete with a hot tub, enclosed lanai/patio and fully equipped modern Kitchen! Walk to TICC club house, 2 sets of golf clubs provided.

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking!

The Sandpiper House

Our unit includes all the amenities of a hotel stay combined with the comfort of home, located inside The Royal Coachman Resort. Our unit has beds for up to 5, in unit washer/dryer, and outdoor patio! You won't want to miss the beautiful pool area, ping pong, and plenty of chairs for sun bathing. Near the pool are sand volleyball courts, and a playground. You also have access to a library, a full gym, and more!! Feel free to bring your furry friend with you.

Palm Bay Club! Resort Style Living on Siesta Key!

Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

2BR Beachfront Condo Steps To Turtle Beach | Pool

Beachfront 2 BR condo on Siesta Key with stunning Gulf views, short walk to Turtle beach, and resort-style amenities including pool, tennis courts, and marina. Enjoy a modern kitchen, open layout, and private balcony perfect for relaxing or entertaining. Located near Turtle Beach, waterfront dining, kayaking, and nature trails. Just minutes from Siesta Key Village and downtown Sarasota. Ideal for short or long-term stays in a true coastal paradise.