luxury real estate for rent Osprey, United States

ANNUAL FURNISHED CONDO RIGHT ACROSS THE STREET FROM SIESTA KEY BEACH! Experience the perfect blend of nature and culture with this stunning, fully renovated two-bedroom, two-bath corner unit condo, available for annual lease! This light-filled, spacious 4th-floor residence features two walls of glass sliders opening to two large, furnished balconies, offering seamless indoor/outdoor luxury living. Just steps from world-renowned Siesta Beach, consistently rated among the best beaches globally, this condo is situated in a meticulously maintained building with resort-style amenities, including tennis courts, a heated swimming pool, and a large covered picnic pavilion with a grill. Enjoy expansive windows in every room, in-unit laundry, air conditioning, three new flat-screen smart TVs, linens, and all essentials for a comfortable, stylish home. The beautifully landscaped gardens enhance the serene atmosphere. Conveniently located, you're a short drive from downtown Sarasota, where you'll find fine dining, shopping, museums, theaters, and art galleries. There is even a complimentary trolley to take you to Siesta Village shopping and restaurants. Embrace comfort, style, and the ultimate coastal lifestyle in this exceptional rental! One covered parking spot included as well as additional guest parking. Water, basic cable, and internet are included.

SEASONAL OR ANNUAL RENTAL AVAILABLE AT BEACH TERRACE ON SIESTA KEY! Experience Siesta Key beachfront living at it's best in this beautifully renovated, fifth-floor corner condo directly on world-renowned Siesta Beach, ranked #1 in the U.S. This turnkey furnished 1-bedroom, 1.5-bath retreat features floor-to-ceiling impact sliding glass doors opening to three private balconies, creating over 1,280 sq ft of indoor-outdoor space with sweeping Gulf views and stunning sunsets. The open-concept living area includes a chef's kitchen with Quartzite countertops, custom European cabinetry, premium stainless appliances, and a large island, plus a custom Murphy bed for guests. The serene primary suite offers a spa-like bath with glass walk-in shower and elegant finishes, while recent upgrades like a new A/C system ensure year-round comfort. Residents enjoy a heated saltwater Gulf-view pool, fitness center, community lounge, and controlled-access security, all just steps from the beach and a short walk to Siesta Key Village's shops, cafés, and dining—with downtown Sarasota's arts and culture only minutes away. Perfect for seasonal or annual stays. High season rates are $14000/month. Off season rates are $9000/month. The annual rate is $6000/month.

AVAILABLE FOR 2024 SEASON STARTING NOV 15TH--TURNKEY FURNISHED TOWNHOUSE IN PAYNE PARK VILLAGE! This beautiful 3 story townhouse has a first-floor bedroom with en suite bathroom—excellent privacy. The second floor is an open concept living room, dining room, large kitchen, powder room, and balcony. The third floor has a primary bedroom/bathroom suite and third bedroom. The kitchen has quartz countertops, stainless steel appliances, and range hood. The home also has a two car attached garage. The location in downtown Sarasota is just across the street from 29-acre Payne Park with tennis courts, auditorium, playground, and more. Payne Park Village has a community pool and spa and direct access to the Legacy Trail. The location is convenient to downtown Sarasota shopping, dining, and entertainment. Or you can hop on the Bay Runner which stops nearby Payne Park for a trip to St. Armand's Circle and Lido Beach. 6 month+ rental considered at $4500 per month. 3 month high season rental rate is $7000.

Lido Key dream vacation rental! Newly remodeled and tastefully furnished, two-bedroom, two-bath condominium at the desired Kingston Arms. No need for a car, close to the sparkling sands of Lido Beach and all the wonderful locally owned restaurants and shops on the historic St. Armands Key, or hop on the BayRunner Trolley to downtown Sarasota. No expense was spared for renovation, all tile throughout, a gorgeous new kitchen with all new appliances, cabinets and lovely granite countertops. The main living area has comfortable seating, a smart TV, dining for four or more and overlooks a quiet residential street. The primary bedroom has a king bed, walk-in closet, a smart TV, a full bath and expansive windows, so light and bright. The guest bedroom has a queen bed, a desk and the bath is en suite. You will enjoy your morning coffee on the screened lanai and go to the beach for gorgeous sunsets. Welcome to paradise. Weekly rates are available for off-season bookings too.

A stay in paradise deserves a stay in luxury! This beautiful two-bedroom (sleeps six maximum) home's primary suite features king bed, upgraded mattress, and the secondary bedroom features two full beds, and upgraded mattresses. Each bedroom features its renovated full bath, both with step-in showers. This fully furnished ground-level property is in Sarasota's premier location 1.5 blocks from the soft, crystal white sand of Lido beach, one block from renowned St. Armands Circle where you can enjoy morning coffee, ice cream, gelato or other specialty treats. Whether you're looking for casual or elegant dining, it's on the circle. If you enjoy the ability to go freely to Lido Beach, dining and the best shopping in Sarasota, this location is for you! And you're only a short five-minute drive or a free open-air trolley ride to downtown Sarasota and the fabulous boutiques, restaurants, clubs and festivals on Main Street. The community pool and hot tub are a short distance from the front door. The condominium has been fully renovated featuring luxury upgrades and updated new furnishings, fast Wi-Fi for streaming and downloading, expanded channels featuring high definition cable TV (two TVs), all new kitchen cabinets, plumbing and appliances, new step-in showers, new flooring, freshly painted, new area rugs and more. A carport for covered parking. Open for weekly rentals all summer and fall, call for availability!

St. Armands Circle/Lido Key dream vacation rental! Welcome to your completely remodeled favorite vacation spot, this exceptional location offers the combination of comfortable living, convenience and proximity to three of this vibrant area's sought-after attractions, St. Armands Circle, Lido Beach and of course, downtown Sarasota. This lovely two-bedroom, two-bath first-floor condominium has just been renovated and features a gorgeous open floor plan in the main living area, the kitchen has all new stainless appliances, a center island with breakfast bar, the baths all have new vanities and showers! This gorgeous reno is turnkey furnished and ready for you. You won't need a car, the BayRunner Trolley takes you where you want to go, you are just a short distance to the beach and the many fine shops and restaurants. Take a bike ride or book a guided kayak tour of the mangrove tunnels. This condominium offers a king-size bed in the primary bedroom, and two full beds in the second bedroom, both bedrooms are en suite. This charming residence is fully equipped with all you need, walkable to everything including the sparkling sands of Lido Beach! After a day of fun and sun, take the free trolley downtown where you will find a variety of shops and restaurants and many options for arts and culture. Make sure you are back in time for a dazzling sunset! Hurry to book your visit to our lovely city now! This lovely property is available for weekly rentals April through November, rates vary by time of year, call for a quote. Available for weekly rentals in the off season, rates vary by month.

ANNUAL UNFURNISHED CONDO AVAILABLE IN SARASOTA HARBOR EAST, 55+ COMMUNITY! This tastefully remodeled condo is located directly on Sarasota Bay and features amazing views. The community offers a heated pool, kayak storage, clubhouse, and shuffleboard. The excellent location is minutes from St. Armand's Circle, Lido Beach, and downtown Sarasota. Boat slips may be available on a first come first serve basis.

Location, Location, Location! Annual Unfurnished 3rd floor condo available NOW! Located on the corner of Gulfsteam and Ringling Avenue, this charming boutique style condo is ready for occupancy. You will love this spacious and private condo, from the gleaming wood flooring to the wonderfully updated kitchen and baths! Offering 2 bedrooms and 2 baths, and both bedrooms are carpeted for comfort. Walk to the bayfront and all the great shops and fabulous local cuisine the vibrant Downtown has to offer. Call today for your private tour!

Location, Location! Live, work and play in the heart of downtown Sarasota! You will love living in this fabulous location, this furnished annual, one bed, one bath condo is ready for you to call home. Just bring your toothbrush. There is a secure parking space in the garage for your convenience. Walkable to all the great local restaurants, shops and the beautiful bay front, and minutes form the thriving arts and cultural activities this growing city offers. Take the day and visit the many beautiful local beaches, just minutes away or book a guided kayak tour. No need for a car, electric scooters are available on just about every corner. Welcome to paradise! Please note there is a $100 transfer fee and a $200 deposit for utilities.

Experience modern and stylish living at The Mark in this beautiful two-bedroom, 2.5-bath plus den unfurnished condominium available for annual lease. The location in downtown Sarasota is a short distance from shops, restaurants, Whole Foods, theaters and the waterfront, with easy access to the airport and beaches. This elegant unit features porcelain plank floors, a gourmet kitchen with European cabinetry, Calacatta quartz counters, JennAir stainless steel appliances, including an induction stovetop and wine chiller, and a chic island with bronze pendant lighting. Enjoy pool and partial bay views through floor-to-ceiling windows with automated shades. The primary suite offers a private balcony, 10-foot ceilings, custom walk-in closets, and a luxurious bath with a white oak vanity, dual sinks and a tiled shower. A guest bedroom with en-suite bath and a versatile den with a Murphy bed complete the layout. Includes two parking spaces and a climate-controlled storage unit. Residents benefit from 24-hour concierge support, a secure entry lobby, and exceptional community facilities on the fifth-floor deck, including a 65-foot heated saltwater infinity pool with Jacuzzi, relaxation zones, a cozy fire pit, barbecue areas, a state-of-the-art gym with spin studio, and a social lounge equipped with a fireplace, bar, pool table, full catering kitchen and media room.

Enjoy amazing views in The VUE! This stunning 2-bedroom, 2.5-bath condo + office offers breathtaking, floor-to-ceiling views of sparkling Sarasota Bay. You will fall in love with the expansive windows and large terrace overlooking the resort-style pool, Sarasota Bay, and Marina Jack's. Beautiful modern design elements and contemporary furnishings create an elegant, move-in-ready retreat. The primary suite features a king bed, bay views, a spacious walk-in closet, and a spa-like bath. The guest bedroom offers a queen bed and private ensuite. In addition, this unit has TWO parking spaces! The VUE sets the standard for luxury living with valet parking, concierge services, 24/7 security, a heated resort-style pool and spa, and a state-of-the-art fitness center. All just moments from Sarasota's vibrant arts scene, culture, and award-winning dining.

ANNUAL FURNISHED CONDO AVAILABLE FOR LEASE AT THE VUE SARASOTA! This highly desirable, downtown waterfront condominium overlooking the Sarasota bayfront, barrier islands, and marina has been meticulously styled and features high end finishes throughout. Upon entering through your semi-private elevator entrance, you are welcomed by an open and bright space with 10 foot floor-to ceiling windows and sliders that allow you to enjoy the panoramic views overlooking the motor yachts, moored sailboats, Ringling Causeway Bridge, downtown Sarasota and the waterfront park. Additional features include two VIP parking spaces, a climate-controlled storage unit, a spacious walk-in laundry room with stackable washer/dryer, utility sink, and storage cabinetry, designer light fixtures and fans throughout, plus Crestron motorized solar shades with blackout shades in the bedrooms for seamless comfort and privacy at the touch of a button. Amenities for this extraordinary residence include a state-of-the-art fitness center, 24/7 concierge service, a club lounge, resort-style pool and spa, and outdoor kitchen. And there's even a social committee that organizes casual events all year-round.

ANNUAL FURNISHED CONDO AVAILABLE FOR LEASE AT THE VUE SARASOTA! This highly desirable, downtown waterfront condominium overlooking the Sarasota bayfront and marina has been meticulously styled and features high end finishes throughout. Upon entering through your semi-private elevator entrance, you are welcomed by an open and bright space with 10 foot floor-to ceiling windows and sliders that allow you to enjoy the panoramic views overlooking the motor yachts, moored sailboats, Ringling Causeway Bridge, downtown Sarasota and the waterfront park. Amenities for this extraordinary residence include a state-of-the-art fitness center, 24/7 concierge service, a club lounge, resort-style pool and spa, and outdoor kitchen. And there's even a social committee that organizes casual events all year-round.

Located in the heart of Downtown Sarasota, this beautifully designed 2 bed, 2.5 bath, two story townhome in Library Mews offers exceptional urban living with rare private outdoor spaces, including a rooftop deck and two private parking spaces! The main level features an open living, dining, and kitchen layout with multiple sliders that create a seamless indoor outdoor flow and overlook the private courtyard, ideal for al fresco dining or quiet relaxation. The chef inspired kitchen includes high end appliances, a large center island, Cambria quartz countertops, a mother of pearl backsplash, and solid wood cabinetry. A dedicated den/office with custom mahogany built ins provides a refined workspace, and a convenient powder room completes the first floor. Upstairs, the owner's suite is light and bright, featuring triple sliders, Brazilian cherry hardwood flooring, and a walk in closet with built in storage. The en suite bath offers a soaking tub, separate shower, dual quartz vanity with undermount sinks, and a TOTO commode. The guest suite is thoughtfully split from the primary and includes its own en suite bath with a skylight and a spacious closet. A private rooftop deck provides an additional outdoor retreat perfect for enjoying Sarasota's warm breezes and skyline views. With its prime location, thoughtful layout, and distinctive architectural style, this villa delivers an exceptional downtown lifestyle. Library Mews is a world apart. Just two blocks to Whole Foods and Starbucks, across the street from Selby Library, the Opera House, and Florida Studio Theater, Library Mews is only a few minutes walk to Main Street restaurants and shops, the Saturday morning Farmers Market, as well as the Bayfront.

One or more photo(s) has been virtually staged. Annual unfurnished rental in sought-after Bayso Sarasota luxury complex with gorgeous views from every window. You will love this light and bright two-bedroom plus den, three-bath home. As you enter the condominium, your eyes will be drawn to the floor-to-ceiling windows and sliders overlooking the bayfront and the city. The interior space is well defined and offers a gorgeous designer kitchen with stainless appliances, European cabinetry, a center island and quartz countertops. Just off the kitchen is the laundry room with tons of storage. The main living area has 10-foot ceilings and sliders that open to a 10-foot deep terrace with glass railings that showcase the stunning views. The primary bedroom has stunning views, ample room for a king bed, two closets and a spa-like bath. The guest bedroom has equally stunning views, great closet space and a luxurious bath. The den can be used as an office or combination office/guest flex space. The Bayso community offers a state-of-the-art fitness room with a movement studio for personal and group classes, and a business center on the first level. The fifth floor is where you will find the gorgeous heated pool and spa, the outdoor grilling area, dog park and entertainment area. You will have access to a climatized storage area as well and one conveniently located parking space. Just down Quay Commons you will find the new Ocean Prime restaurant for fine dining as well as The Bay Sarasota with 53 acres for recreation, biking, kayaking and yoga.

Annual unfurnished condominium available at Condo on the Bay! Final repairs to the docks are being made, and there is a rare opportunity for tenants to lease a boat slip while availability lasts. On a private 9-acre gated peninsula where downtown Sarasota meets the bay, this 14th-floor corner/end unit features stunning panoramic views of the Bay, the Gulf, Lido and Longboat Key from every room. Spanning 1,642 square feet, the home is filled with natural light and water views from every room along with two balconies. The open combination living and dining area flows seamlessly into a gourmet kitchen featuring custom Italian solid maple cabinets, new Italian quartzite countertops, a breakfast bar, Kenmore Elite French-door refrigerator with double freezer drawers, Kenmore Elite range and a new dishwasher installed in October 2024. New 55-inch Smart TVs were recently installed in the living room and bedrooms, and the entire home was just freshly painted. Additional features include tinted windows with Duette shades for glare reduction and a reverse-osmosis water filtration system at the kitchen sink. Residents enjoy an unmatched waterfront lifestyle with two pools, two new fitness centers, four pickleball courts, a tennis court, private boat docks, and kayak storage and access near the building. The community is guarded 24 hours a day and sits directly beside the new Sarasota Bay Park, offering trails, playgrounds, performance spaces, and just a short distance away Ritz-Carlton, Ocean Prime, Van Weisel Performing Arts Center, Bay Park and downtown Sarasota. Concierge services are available with groceries and packages brought to your door. The assigned parking spot is ideally in the first row in front of the building entrance and extra storage is available. Internet, basic cable and water included. Available furnished for an additional fee.

Virtually Staged. Virtually Staged. This beautifully updated/unfurnished two-bedroom, two-bath Spanish Main standalone villa with beach access is available for annual lease! The fully remodeled home features neutral tile plank flooring throughout, a spacious chef's kitchen with 42-inch wood cabinets, quartz island that seats seven, slow-close drawers, and new appliances—all opening to a bright living area. The primary suite offers an en-suite bath with frameless glass shower and double sinks, plus a large walk-in closet. Step through new double doors to a generous screened lanai overlooking lush wetlands and Bay views, perfect for relaxing, dining, or using as a flexible third space, complete with retractable awning, brick paver patio, hurricane-rated windows and doors, motion lights, and electric blinds. In the vibrant 55+ Spanish Main Yacht Club community enjoy a pool, shuffleboard, private deeded beach access on Longboat Key, and easy boating, fishing, and cycling, all just minutes from St. Armands Circle, downtown Sarasota, dining, shopping, and the airport. Basic cable and water included. Move-in ready and waiting—call for details on this piece of paradise.