Houses for Rent in City Island, Sarasota, FL

Property Status: Active ANNUAL UNFURNISHED. Welcome to Alinari at Rosemary Place, a unique, luxury condominium development set on 11 acres in Downtown Sarasota. Experience this exclusive blend of privacy, space and style in this unique multilevel end-unit remodeled townhome with your own private entrance. Enjoy 1,734 sq. ft. of remodeled interior living space and your very own private 942 sq. ft. Rooftop Deck with sweeping views of Sarasota Bay, the Sarasota city skyline, resort-style pool & spa deck, and unforgettable sunsets. 1 of only 6 private townhomes located just of

Move-in ready, custom Home- your Sarasota Bay view home is awaiting your arrival. Introducing 1156 Cocoanut Avenue, a newly built modern residence that delivers bold architecture, refined finishes, and effortless urban living in the heart of Sarasota. Designed for today’s lifestyle, this striking home blends clean lines, open spaces, and elevated craftsmanship into a seamless expression of contemporary luxury. The home features five bedrooms and four bathrooms across 2,882 square feet. You are greeted by large-format, marble-look tile throughout the first floor for a seam

Property Status: Active SARASOTA DOWNTOWN LIVING!!! This stylish 4 story townhome offers 2-bedrooms, 3.5-bathroom and a 2 CAR GARAGE and is perfectly situated in Downtown. The complex is an easy pedestrian distance to shopping, many dining options, and nearby open spaces. On-site features include pool and fitness center. On the first floor there is a roomy office space provided for you. You can take the stairs or the elevator to the amazing second floor where you will have your living room area and an AMAZING kitchen with top of the line finishes. Worthy of a photo-op, the

Come explore this beautifully updated 988 sq. ft. home, thoughtfully designed for both relaxation and entertaining. This cozy yet spacious cottage offers 2 bedrooms and 1.5 bathrooms, ideal for a year-round retreat or comfortable living. The open-concept layout features a main bedroom with a king-size bed, a second bedroom with a queen bed, and a bright sunroom with a full-size pull-out sofa, desk, and direct access to the patio. Enjoy your morning coffee or evening meals on one of two private patios overlooking the inviting pool. Set on a lush, fully fenced 1/3-acre lot

Property Status: Active Located in the highly sought-after community of Bird Key, this immaculate 3-bedroom, 3-bath home plus dedicated office offers the perfect blend of classic Florida charm and modern comfort. Ideally positioned between downtown Sarasota and Lido Key, you’re just minutes from St. Armands Circle, world-class beaches, dining, and cultural attractions. The light-filled open floor plan is designed for effortless living and entertaining, with expansive sliding glass doors leading to a private backyard oasis. The split-bedroom layout provides privacy, with e

Welcome boating enthusiasts to this exceptional waterfront residence located in the highly desirable Country Club Shores community on Longboat Key. Situated on a deep-water canal with direct access to the Gulf of America, this beautifully updated two-bedroom, two-bath home with a den offers the ultimate island lifestyle for boaters and beach lovers alike. The property features a brand-new 20,000-pound boat lift and a newly constructed seawall, ideal for accommodating larger vessels and frequent boating excursions. Available for long-term annual lease at rate of $7,000 per

Property Status: Active West of N Tamiami Trail and the bay (US-41) in a private and quiet neighborhood.- Walk 2 blocks to watch the sunsets on the bay or exercise or stroll through the beautiful neighborhood on the Sarasota Recreational Trail. Duplex in Ind. Beach/Sapphire Shores neighborhood. Fully remodeled unit with new roof, impact windows, updated plumbing/electrical, and central cooling/heating. Updated kitchen with shaker cabinets, quartz counter tops, and stainless steel appliances. Beautiful bathroom with modern plumbing fixtures. Shared covered laundry. 1-1/2 mi

Property Status: Active West of N Tamiami Trail and the bay (US-41) in a private and quiet neighborhood. - Walk 2 blocks to watch the sunsets on the bay or exercise or stroll through the beautiful neighborhood on the Sarasota Recreational Trail. Duplex in Ind. Beach/Sapphire Shores neighborhood. Fully remodeled unit with new roof, impact windows, updated plumbing/electrical, and central cooling/heating. Updated kitchen with shaker cabinets, quartz counter tops, and stainless steel appliances. Beautiful bathroom with modern plumbing fixtures. Shared covered laundry. 1-1/2 m

SEASONAL VACATION RENTAL IN THE BROADWAY PROMENADE! AVAILABLE DEC-APRIL 2027. Enjoy the best of Sarasota living in this spacious two-bedroom, two-bath residence at Broadway Promenade. The well-appointed galley kitchen features granite countertops, a convenient pass-through, and a breakfast bar, along with stainless steel appliances and a pantry—perfect for both everyday living and entertaining. The open living and dining areas overlook the tranquil courtyard, creating a bright and inviting atmosphere. The primary suite offers a private balcony, a walk-in closet, and an en-

Property Status: Active Welcome to Beach & Boaters Paradise located on Longboat Key. Enjoy immediate access access to beautiful Sarasota Bay, the Gulf of Mexico and Longboat Key's sugar white sand beaches and emerald green waters. Fish off the dock or walk to the beach! Or enjoy the large heated pool in this 4 bedroom, 3.5 bath luxury waterfront home designed to provide you and your family a lifetime of vacation memories to cherish. The deeded beach access is a short walk across Gulf of Mexico Drive. The dock-side screened patio has a large family-friendly heated pool and

Short-Term Waterfront Home in Bird Key. Enjoy the ultimate Florida waterfront lifestyle in this comfortable and inviting 4-bedroom, 3-bathroom pool home, perfectly situated on a canal with no bridges to the bay and able to accommodate up to a 26' boat. This beautifully positioned home offers effortless boating access and relaxed coastal living in one of Sarasota’s most prestigious neighborhoods. The open floor plan is filled with natural light and features a spacious living room that opens directly onto an expansive covered lanai—ideal for indoor-outdoor living and enterta

Amazing 3 bedroom, 3 bathroom house in Country Club Shores on Longboat Key. Amenities included: central air, central heat, deck, dishwasher, pool, washer dryer, yard, and garage. Utilities included: cable, electricity, heat, internet, air conditioning and water. Is not pet friendly. Date Available: November 1, 2026 to December 13, 2026 at $12,000 per month plus tax and fees. Then again starting March 13, 2027 to April 15, 2027 . $18,000/month rent. $2,000 security deposit required. Please submit the form on this page or contact Jeff Merckle at 941-302-1009 to learn more. M

Annual Furnished Rental Available at The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key, Florida. Step inside to beautifully designed interiors featuring soaring ceilings and expansive floor-to-ceiling sliding glass doors that wrap around the living, dining, and kitchen s

Property Status: Active STUNNING UNFURNISHED SINGLE FAMILY HOME IN THE SOUGHT AFTER COMMUNITY OF HARBOR ACRES IS AVAILABLE TO RENT!!! This is the one you've been looking for! Renovated from top to bottom this home has all the bells and whistles with a contemporary design, spacious floor plan, two stories, split bedrooms and a private second floor primary bedroom. The kitchen is truly the heart of this home with two islands, stainless appliances, double ovens, drawer microwave, counter and cabinet space for all your needs, open dining room space, coffee bar and large floor

Property Status: Active LONGBOAT KEY...If you're looking for a Luxury winter vacation home, stop searching. You have just found the perfect house located on a private & peaceful cul-de-sac. This beautiful 5 bedroom, 5.1 bathrooms has everything you would want and more with all the comforts of home. All new furniture throughout in every room. Primary, 1st & 2nd bedrooms all have king size beds. Bedrooms 3 & 4 have twin beds. Kitchen is a chef's delight with, state of the art appliances, granite countertops, solid wood cabinets, double wall oven, generous amount of counter s

Discover the epitome of living at this beautifully renovated 3-bedroom, 2.5-bath home located directly across from the street from waterfront of Sarasota Bay. Recently updated, the open and inviting layout offers approximately 1,775 square feet of living space designed for both comfort and style. Features include a spacious living area with a cozy fireplace, hurricane-rated windows and doors, an upgraded kitchen and baths, and a screened lanai perfect for enjoying refreshing breezes and serene water views. The oversized one-car garage includes built-in workbenches, provid

Property Status: Active Lido Towers Unit 108 has a beautiful renovated interior and is perfect for your escape to Sarasota Florida. This 1 bedroom/1.5 bath is open and bright and has a cozy lanai lending itself to you enjoying the warmth of your coffee each morning before you stroll out to the beach (which is footsteps away). You won’t see any snowflakes here! The master bedroom has a huge king sized bed and a beautiful renovated bathroom. Open living room, dining room, and kitchen. New flooring that is classy to say the least! After you wrap up Christmas, hop on a

Property Status: Active Annual Rental – Stunning Waterfront Home in Country Club Shores on Longboat Key. Experience the best of waterfront living in this beautiful 4-bedroom, 3.5-bathroom home located in the sought-after Country Club Shores community on Longboat Key. This spacious and elegant residence offers breathtaking canal views, luxurious amenities, and direct boating access and boat lift. This exceptional home features four bedrooms, a spacious bonus room, and a dedicated office, providing plenty of space for both relaxation and productivity. The private heated pool

Real Property Management Horizons are delighted to offer for rent this stunning, recently re-modelled 2-bed / 2-bath furnished condo located at the coveted, landmark building at 101 S Gulfstream Ave in Sarasota, FL. Situated in a waterfront position in downtown Sarasota, this condo offers stunning views of the marina & Sarasota Bay from the swimming pool and sun deck. The block has gated secure parking and the entrance is secure with a 24 hour concierge in the lobby. Spanning a generous 1320sq ft, the open plan concept and extended kitchen, is ideal for those who love t

Property Status: Active THIS HOME WILL BE AVAILABLE ON APRIL 1, 2026 - MONTH-TO-MONTH lease This is a 2,100 Sq Ft home, 5 Bdrm, 2 full baths home in walking distance to Downtown! Description: BD#1: king, BD#2: queen, BD#3: queen, BD #4 two twin. Office and Large living room. Kitchen. Front porch with outdoor furniture. Perfect location in Sarasota's cultural arts district. Walk to "By The Bay" Park, free Friday night concerts, dining, shopping. Use our bicycle for Fresh Market and Farmers Market. Enjoy Sunday-Funday at Modern hotel. Gas grill. Fenced-in yard is fully fur