Featured Properties

Some or all of the listings below are provided by the Sarasota Downtown office.
$15,000 / mo (USD)
Active

Sarasota Area Rental

Active

1850 Webber Street Sarasota, FL 34239

6 Bed
4 Baths
4755 sqft
MLS# A4693021
Virtual Tour
One or more photo(s) has been virtually staged. West of trail, 2026 Custom Build, Exquisite Modern Mediterranean estate with a seamless blend of classic architecture and contemporary finishes. This exceptional 5-bedroom, 4-bathroom residence is thoughtfully designed for both everyday living and effortless entertaining. The main level features a luxurious first-floor primary suite with a walk-in closet and spa-inspired bathroom with dual vanities, along with two first-floor guest bedrooms and a private office. Wide-plank oak hardwood floors, custom built-ins and maple wood cabinetry with inset doors , and a warm, inviting electric fireplace enhance the home’s elegant yet comfortable ambiance. A fully integrated surround sound system extends throughout the living room, kitchen, and outdoor entertaining areas. The chef’s kitchen is beautifully appointed with premium Viking appliances, Taj Mahal quartzite countertops, custom cabinetry, elevated fixtures and designer lighting, along with a stylish bar featuring Cristallo quartzite and a beverage center—perfect for hosting and entertaining. The second level offers a spacious bonus room ideal for a media lounge or game room, along with two additional bedrooms and a gallery-style hallway with an open balcony, adding architectural interest and natural light. Additional highlights include natural gas, a gas-on-demand water heater, enhanced exterior insulation for energy efficiency, a concrete tile roof, irrigation system, and abundant storage throughout. Architecturally, the home embraces classic Mediterranean elements with a modern sensibility. Arched doorways, windows, and passageways create a sense of flow and understated grandeur, while intricate wrought iron detailing and extensive millwork add depth and craftsmanship. Statement chandeliers and curated designer lighting elevate each space, enhancing the home’s refined aesthetic. A detached guest home, complete with a private bedroom, full bathroom, and living area, offers ideal accommodations for guests or extended stays. Outdoors, a custom-designed oversized pool showcases timeless Mediterranean blue tile, complemented by elegant fire bowls and a cascading waterfall spa—creating a true resort-style setting. The property is complete with a 2-car attached garage in the main home, 2 car covered parking under the guesthouse, and an additional two-car garage, offering both functionality and flexibility. Ideally situated in Southside Village, this residence offers a highly walkable lifestyle just moments from Southside Elementary, Morton's Gourmet Market, local restaurants, and boutique shopping.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Dyrk Dahl, Coldwell Banker Realty
$7,000 / mo (USD)
Active

Longboat Key Area Rental

Active

4780 Gulf Of Mexico Dr. Villa 5 Longboat Key, FL 34228

2 Bed
2 Baths
1325 sqft
MLS# A4668115
Virtual Tour
Booking Now for Summer 2027! Booked for January-June 30, 2027. Looking for the perfect vacation getaway? Lucky you! This stunning, light-filled end-unit beach and bay villa is now available for January 2027! Enjoy views of unforgettable morning sunrises on Sarasota Bay and breathtaking Gulf Sunsets directly across the street, with three beach access points — including private deeded beach access. Appreciate the convenience of pulling directly into your private carport with no steps or elevators and relish the peace and privacy of having no neighbors above or below during your stay. This beautifully appointed coastal villa features two bedrooms, two bathrooms, a spacious open concept living area, and an opulent interior design that is soaked in sunlight. The brand new remodeled and fully equipped kitchen is ideal for preparing meals with fresh local ingredients from nearby farmers' markets or head out to dine at one of the delectable nearby restaurants. Windward Bay is a low-density, wildlife-rich community nestled mid-Longboat Key on 26 acres, offering resort-style amenities including two heated pools, two tennis/pickleball courts, two marinas, kayak racks, shuffleboard, a clubhouse with kitchen, library, fitness room, two saunas, and multiple fire pits and barbecue areas throughout the property. Enjoy half a mile of scenic waterfront trails and direct access to the Gulf or Bay for boating, fishing, or simply soaking up the sun. Located just minutes from Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and vibrant cultural attractions. This is a rare opportunity to create lasting memories in a home that guests return to year after year. This villa is more than a vacation rental — it’s a tradition. One couple has returned every March and April for over a decade, drawn by the comfort, beauty, and unbeatable location.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Deborah "Debby" McCaig, Coldwell Banker Realty
$6,500 / mo (USD)
Active

Longboat Key Area Rental

Active

3330 Gulf Of Mexico Drive 104D Longboat Key, FL 34228

2 Bed
2 Baths
1106 sqft
MLS# A4690993
Virtual Tour
Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease. Groceries are carried in with ease, morning coffee is enjoyed on your lanai, and just beyond, a nearly private lawn stretches out like your own backyard retreat. Only sixty feet away, the tranquil waters of Cranes Bayou create a breathtaking backdrop along with the Sarasota Bay. From your windows and lanai, the view feels intimate and serene as dolphins surface in the distance, manatees glide through calm waters, and coastal birds fill the sky. Just outside, an eagle’s nest tucked within a Spanish pine offers a daily reminder that nature is not something you visit here; it’s something you live beside. The lifestyle extends beyond the view. A deeded private walkway leads you directly to the soft sands of the beach, inviting spontaneous sunset strolls, morning shell hunts, and afternoons spent with your toes in the sand. For boaters, a private slip just steps from your front door makes life on the water feel effortless, ready for quiet cruises or sunset rides along the coast. Recently refreshed with a 2025 community pool upgrade and lush landscaping, the setting feels nature-filled with peacefulness. Inside, the residence reflects a thoughtful balance of high-end furnishings, warm textures, and a blend of contemporary design and classic Old-Florida charm, creating a space that feels both elevated and inviting. Carefully curated lighting, including modern fixtures and Frank Lloyd Wright–inspired sconces, lets you shape the atmosphere, whether you're hosting friends, unwinding with a book, or enjoying a quiet evening at home. This is more than a seasonal escape; it’s a place where mornings feel slower, evenings feel softer, and everyday moments carry the calm of island living. For those looking for a coastal rental that blends privacy, tranquility, and a seamless connection to the water, this inviting retreat delivers an island lifestyle you’ll appreciate the moment you step inside. ANNUAL RATE $4,000 / month. SEASONAL RATE $6,500 / month.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: John Schafer, Coldwell Banker Realty
$4,250 / mo (USD)
Active

Sarasota Area Rental

Active

988 Blvd Of The Arts 115 Sarasota, FL 34236

2 Bed
2 Baths
1555 sqft
MLS# A4674014
Virtual Tour
Newly renovated baths, newly tiled lanai. Spacious first-floor 2-bedroom, 2-bath condo featuring soaring 10-foot ceilings and stunning views of the bay and private boat docks. Enjoy an open layout filled with natural light, all with the convenience of ground-floor living — no elevator needed. Relax on your private patio while taking in the waterfront scenery and peaceful marina atmosphere. Perfect for easy coastal living with effortless access in and out of the home . Annual rental available at this spectacular bayfront property...where downtown Sarasota meets the bay, Tenants pay only the electric bill. Brand new hurricane sliders were just installed giving you a wall to wall 10 ft high view. New blinds were installed. The condo was recently painted. Located on a gated 9 acre peninsula, it is direct waterfront. No one will ever build in front of it and block your views of the bay & sunsets. The open floor plan extends from the kitchen to the large lanai with floor to ceiling sliders; this unit feels much larger than its sq footage and is laid out perfect for entertaining. The kitchen has plenty of storage, SS appliances and a stackable full size washer/dryer. The split bedroom floor plan offers you maximum privacy. This unit has tons of storage. The primary ensuite has a walk in closet and 3 other closets. the bath has a shower/tub and dual sinks. The large guest bedroom has a good size closet and is directly adjacent to the bath. The guest bedroom furniture can be included. The guest bath has dual sinks and a walkin shower. At Condo on the Bay you can have it all....enjoy the conveniences of downtown living and the perks of living waterfront. Walk out your front door to jump on your boat or kayak, fish off the dock or lounge at one of our two resort style heated pools. Take a walk or bike to downtown to enjoy our many restaurants, theatres, art galleries, music, festivals, farmers market...Next door is the Bay Park Sarasota a 53 acre world class park with walking paths, playground, snack bar, music events and a performing arts center.. Behind the building across the canal is the Ritz Carlton/Hyatt yacht basin which is undergoing a transformation into a shopping/entertaining area. 24 hour security is provided and a concierge is on duty everyday from 8-6. Looking to make friends? There are a variety of organized social activities in this friendly community, from yoga, water aerobics, walking groups, card clubs, get togethers on the sky decks for no reason, etc. Underground assigned parking for one vehicle and lots of open parking on top deck. Condo on the Bay is located 4 miles from the airport, 2 miles from Lido Beach and Armands Circle & 6 miles from Siesta beach. If you are looking to buy a home in Sarasota or waiting for your home to be built this is a great location to rent and explore the area. Or just rent long term and not worry about home ownership. Minimum lease 1 year. This condo can be a longer term rental if you are looking for a forever home as the condo will never be sold.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Debbie Huffman, Coldwell Banker Realty
$4,000 / mo (USD)
Active

Longboat Key Area Rental

Active

3330 Gulf Of Mexico Drive 104D Longboat Key, FL 34228

2 Bed
2 Baths
1106 sqft
MLS# A4683575
Virtual Tour
Tucked along the quiet edge of the key, where the water gently meets the shoreline and wildlife drifts by with the tide, this easily accessible residence offers something increasingly hard to find: effortless coastal living with the comfort and privacy of a home. Here, your day begins without elevators or long corridors. You simply pull up, step inside, and settle into a space designed for ease. Groceries are carried in with ease, morning coffee is enjoyed on your lanai, and just beyond, a nearly private lawn stretches out like your own backyard retreat. Only sixty feet away, the tranquil waters of Cranes Bayou create a breathtaking backdrop along with the Sarasota Bay. From your windows and lanai, the view feels intimate and serene as dolphins surface in the distance, manatees glide through calm waters, and coastal birds fill the sky. Just outside, an eagle’s nest tucked within a Spanish pine offers a daily reminder that nature is not something you visit here; it’s something you live beside. The lifestyle extends beyond the view. A deeded private walkway leads you directly to the soft sands of the beach, inviting spontaneous sunset strolls, morning shell hunts, and afternoons spent with your toes in the sand. For boaters, a private slip just steps from your front door makes life on the water feel effortless, ready for quiet cruises or sunset rides along the coast. Recently refreshed with a 2025 community pool upgrade and lush landscaping, the setting feels nature-filled with peacefulness. Inside, the residence reflects a thoughtful balance of high-end furnishings, warm textures, and a blend of contemporary design and classic Old-Florida charm, creating a space that feels both elevated and inviting. Carefully curated lighting, including modern fixtures and Frank Lloyd Wright–inspired sconces, lets you shape the atmosphere, whether you're hosting friends, unwinding with a book, or enjoying a quiet evening at home. This is more than a seasonal escape; it’s a place where mornings feel slower, evenings feel softer, and everyday moments carry the calm of island living. For those looking for a coastal rental that blends privacy, tranquility, and a seamless connection to the water, this inviting retreat delivers an island lifestyle you’ll appreciate the moment you step inside. ANNUAL RATE $4,000 / month. SEASONAL RATE $6,500 / month.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Janette Schafer, Coldwell Banker Realty
$3,975 / mo (USD)
Active

Longboat Key Area Rental

Active

842 Bayport Way Longboat Key, FL 34228

2 Bed
2 Baths
1260 sqft
MLS# A4689796
Virtual Tour
Available June through December. This first-floor corner condo means extra privacy, added natural light and the convenience of a walk-out patio. Nicely furnished and move-in ready for a comfortable stay. A spacious dining and living area opens out to a screened lanai and large west facing outdoor patio overlooking landscaped grounds. A patio gate allows easy access to a path out to the beach access road plus it makes dog walking a breeze. Yes, Bayport is small pet friendly- a rarity in island condo communities. The primary bedroom has a king bed, large walk-in closet, and an alcove with a desk overlooking the garden. The guest bedroom can be configured as a king or two twins. There is under building parking for one car, outside locked storage and plenty of guest parking. Bayport Beach and Tennis Club is a true Gulf to Bay community, with a fishing pier and kayak launch out to Sarasota Bay, and access to 1200 feet of private beach with beach chairs and umbrellas, just 2-3 minutes from your front door. Enjoy a swim in the Jr Olympic pool, tennis on 4 har-tru courts, a club house, a well equipped gym, and shelled walking paths along tropical landscaped grounds. Groceries, parks and conveniences are within 2 miles, with shopping and terrific dining dotted along the Key. Sarasota's entertainment and cultural attractions are a short drive away.
Listing Courtesy of STELLAR as distributed by MLS GRID / Listed By: Rosemarie McKee, Coldwell Banker Realty