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!

Unwind at Casa Blu: Sun, fun, pool, close to Beach

Your next retreat to Florida paradise should be Casa Blu with it's private pool and serene backyard. It's just minutes to area beaches, restaurants and parks. Let the stresses of daily life melt away as you float in the salt water pool, sipping margaritas, listening to Jimmy Buffett singing "It's Five O' Clock Somewhere" The single-floor layout, comfy bedrooms with private baths await. Fast WiFi, Smart TVs, and fully equipped kitchen. Everything's covered, from beach gear to a pack 'n play.

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.

Private Heated Pool/Spa, 4bed/2bath, Pets Welcome

Welcome to Paradise! This 4 bed/ 2 bath dog friendly, heated pool & spa home features a large fenced in yard and oversized lanai area. It sleeps up to 6 guests & offers plenty of gathering space. Located within 15 minutes to Warm Mineral Springs, Atlanta Braves Spring Training and 30 minutes to Englewood/ Venice beaches. Located 5 miles off I75 & close to all the attractions of beautiful southwest FL. This home provides the perfect combination of a country home while being close to everything.

Sleeps 2-Close to Downtown, Beaches & Airport

This small but quaint one-bedroom condo is a perfect blend of charm and modern convenience, featuring a series of thoughtful upgrades. The kitchen and bathrooms have been meticulously renovated with sleek countertops and contemporary fixtures, adding a touch of luxury. Modern ceiling fans and bed-side reading lights enhance comfort and functionality, while flat-screen televisions in both rooms provide ample entertainment options. And let’s not forget the built-in device-charging capabilities!

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

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

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!

New Luxury 3/3 Condo in Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features wonderful unobstructed water views of Anna Maria Sound and Tampa Bay. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.