Fitness-friendly holiday 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!

Early Chkin, Elevator-4th fl 2mins-DT, 7mins-Airpt

Beach ready Apt!! Echo/white noise machine Beside Ringling College! 2 minutes from downtown Sarasota 7 mins - Airport Corner Apt Steps to the elevator 2 bicycles & 2 escooters Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb that's on a main road . 60+ amenities from a secure room safe to a luxurious, indulgent bed. Essential amenities such as grocery stores/pharmacies/ & CVS. less than a mile away. Send me a message if you have any questions .

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.

Plant Lovers Tranquil Paradise

A newly renovated, fully furnished studio in a house, with own private entrance, surrounded by a tropical garden in a safe and quiet neighborhood. Private bathroom with shower and oversized bathtub, walk-in closet with additional folding bed. Kitchenette comes equipped with a small fridge, microwave,hot plate,coffee maker, teapot,toaster,slow cooker,dishes,pots and pans. At the screened lanai there is a table with chairs where you can have a cup of coffee in the early morning with birdsongs.

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

Lovely large one+ in the heart of downtown Venice

Large, quaint, quiet condo in the heart of downtown Venice Island. Short walking distance to all the idyllic downtown shops, restaurants, entertainment, bars, arts & a quick bike ride to an amazing beach. Bikes included. Very spacious & well equipped rental suitable for short or long-term visits. Large fully equipped kitchen. Lots of amenities & beach gear! Comfy king bed. Free parking. Venice Beach 1.1 miles / Sharkey's Restaurant & Pier 1.7 miles / Coffee shop & downtown just 3 blocks away.

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.

The Palm Bay Club on Siesta key Beach

Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

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.

Downtown Apartment w/ Pool, Gym, & Coworking 329

This 2/2 apartment features an oversized kitchen with island, slider with views of Downtown. Primary has a king bed and en-suite bathroom. 2nd bedroom has a twin bed with twin trundle. Shared amenities include: gym; sunset deck; massive roof deck with heated pool; gazebo with big-screen TV, fireplace, wet bar, dog run and access to the adjacent Cowork office space building. Also on-site is a full service cafe.