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Sarasota, FL Homes for Rent in a Gated Community

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  • 9611 Castle Point Dr Unit 915, Sarasota, FL 34238
    9611 Castle Point Dr Unit 915, Sarasota, FL 34238
    9611 Castle Point Dr Unit 915, Sarasota, FL 34238
    /44

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,333 Sq Ft
    • Condo for Rent

    9611 Castle Point Dr Unit 915, Sarasota, FL 34238

    AVAILABLE FOR SEASON 2027 - MULTIPLE MONTHS ONLY - AVAILABLE OFF-SEASON: EXCEPTIONAL GROUND FLOOR UNIT, an immaculate and updated vacation condo at Stoneybrook G&CC offers all the amenities you would want for a few months in the sun. The well-equipped kitchen has a breakfast nook with view of front lanai, SS appliances, and lots of cabinet space. The dining area is open to the living area and the

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    9611 Castle Point Dr Unit 915, Sarasota, FL 34238
  • 8735 Olde Hickory Ave Unit 8302, Sarasota, FL 34238
    8735 Olde Hickory Ave Unit 8302, Sarasota, FL 34238
    8735 Olde Hickory Ave Unit 8302, Sarasota, FL 34238
    /27

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • Condo for Rent

    8735 Olde Hickory Ave Unit 8302, Sarasota, FL 34238

    AVAILABLE JAN 2027 & OFF-SEASON 2026. 3rd floor vacation condo with great view of the golf course from the screened lanai, two bedrooms, two baths, king bed in the master bedroom and adjoining bathroom with walk-in shower. 2nd bedroom has queen bed and is next to the guest bathroom. Well-equipped kitchen with everything you would need for a few months in the sun. Bright and cheerful unit with

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    8735 Olde Hickory Ave Unit 8302, Sarasota, FL 34238
  • 1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
    /87

    $7,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,467 Sq Ft
    • Condo for Rent

    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242

    Waterfront Elegance at Marina Del Sol – Your Seasonal Retreat. Indulge in the ultimate Sarasota lifestyle at this stunning 3-bedroom, 2,467 sq. ft. residence in the exclusive Marina Del Sol. Thoughtfully designed and beautifully updated, this spacious condo offers the perfect balance of elegance and comfort, with three oversized porches capturing serene water views and warm coastal breezes. Step

    Olga Smith IMPERIAL PROPERTY GROUP LLC

    1308 Old Stickney Point Rd Unit W32, Sarasota, FL 34242
  • 5251 Mahogany Run Ave Unit 524, Sarasota, FL 34241
    5251 Mahogany Run Ave Unit 524, Sarasota, FL 34241
    5251 Mahogany Run Ave Unit 524, Sarasota, FL 34241
    /40

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,311 Sq Ft
    • Condo for Rent

    5251 Mahogany Run Ave Unit 524, Sarasota, FL 34241

    Comfort and Convenience at its best! Heritage Oaks Golf & Country Club a hidden golf gem in Sarasota. Rear stunning views of the water and 12th and 13th golf course. Front screened in lanai, relax with your cup of coffee or glass of wine while you watch the sun go down. Two bedroom/ two bath 2nd floor condo has been remodeled. Enjoy the updated kitchen with stainless steel appliances, dual sink

    Angela Bailey MONARCH PROPERTY GROUP LLC

    5251 Mahogany Run Ave Unit 524, Sarasota, FL 34241
  • 1677 Brookhouse Cir Unit BR223, Sarasota, FL 34231
    1677 Brookhouse Cir Unit BR223, Sarasota, FL 34231
    1677 Brookhouse Cir Unit BR223, Sarasota, FL 34231
    /29

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,077 Sq Ft
    • Condo for Rent

    1677 Brookhouse Cir Unit BR223, Sarasota, FL 34231

    **AVAILABLE NOW UNTIL 12/31/26- INCLUDES ALL UTILITIES** **BOOKED FOR JAN-MARCH 2027 SEASON**CHARMING PELICAN COVE - Newly updated 2 bed/2 bath condo in the resort community of Pelican Cove. This 2nd floor unit features decorator furnishings, vaulted ceilings, hardwood floors and everything you need to enjoy a vacation getaway or extended stay. Enjoy your morning coffee on the screened lanai

    Brigette Marcus NEXTHOME EXCELLENCE

    1677 Brookhouse Cir Unit BR223, Sarasota, FL 34231
  • 8780 Pebble Creek Ln, Sarasota, FL 34238
    8780 Pebble Creek Ln, Sarasota, FL 34238
    8780 Pebble Creek Ln, Sarasota, FL 34238
    /30

    $7,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,366 Sq Ft
    • House for Rent

    8780 Pebble Creek Ln, Sarasota, FL 34238

    RENTED, totally renovated villa at Stoneybrook G&CC. Luxurious kitchen, stunning bathrooms, master bedroom downstairs, den/office downstairs with queen hide-a-bed, spacious open floor plan, sliding glass doors lead out onto a screened lanai with crystal clear pool. Upstairs loft with lots of comfortable seating and large smart TV, guest bedroom, and full bath with beautiful tiled shower. The

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    8780 Pebble Creek Ln, Sarasota, FL 34238
  • 2110 Benjamin Franklin Dr Unit 104, Sarasota, FL 34236
    2110 Benjamin Franklin Dr Unit 104, Sarasota, FL 34236
    2110 Benjamin Franklin Dr Unit 104, Sarasota, FL 34236
    /57

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Condo for Rent

    2110 Benjamin Franklin Dr Unit 104, Sarasota, FL 34236

    Short term rental available. Immediate occupancy available. Off season rent rates and seasonal rent rates available . Experience coastal luxury in this updated residence at 2110 Benjamin Franklin Drive, Unit 104, ideally positioned on the south end of Lido Key. This spacious ground-floor condo offers the perfect blend of convenience and tranquility, with easy access and no elevators required.

    Tammy Garner COLDWELL BANKER REALTY

    2110 Benjamin Franklin Dr Unit 104, Sarasota, FL 34236
  • 8369 Wingate Dr Unit 2114, Sarasota, FL 34238
    8369 Wingate Dr Unit 2114, Sarasota, FL 34238
    8369 Wingate Dr Unit 2114, Sarasota, FL 34238
    /26

    $4,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Condo for Rent

    8369 Wingate Dr Unit 2114, Sarasota, FL 34238

    AVAILABLE DEC. 2025, JAN., FEB., MARCH, APRIL 2026 and off-season. VACATION IN STYLE IN THIS 3-BEDROOM GROUND FLOOR TOTALLY UPDATED UNIT AT PINESTONE. Quartz countertops in kitchen, new cabinets, new appliances, all new furniture throughout, smart TVs, new carpet in the living room and bedrooms, and a new washer and dryer. Lots of natural light lend to the bright and cheerful atmosphere in this

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    8369 Wingate Dr Unit 2114, Sarasota, FL 34238
  • 1703 N Tamiami Trail Unit 205, Sarasota, FL 34234
    1703 N Tamiami Trail Unit 205, Sarasota, FL 34234
    1703 N Tamiami Trail Unit 205, Sarasota, FL 34234
    /42

    $3,750 Per Month

    • 2 Beds
    • 2 Baths
    • 958 Sq Ft
    • Condo for Rent

    1703 N Tamiami Trail Unit 205, Sarasota, FL 34234

    Newer condo available for weekly or monthly rental - conveniently located on Whitaker Bayou close to Indian Beach and Downtown Sarasota. Enjoy all of the amenities including a heated pool, spa, fitness center, BBQs and firepit area. Light and bright! The second bedroom serves as a lounge space, and the sofa easily converts to a queen size bed. The primary bedroom has a king size adjustable bed.

    Philip Pisano, III MICHAEL SAUNDERS & COMPANY

    1703 N Tamiami Trail Unit 205, Sarasota, FL 34234
  • 5152 Northridge Rd Unit 204, Sarasota, FL 34238
    5152 Northridge Rd Unit 204, Sarasota, FL 34238
    5152 Northridge Rd Unit 204, Sarasota, FL 34238
    /21

    $1,595 Per Month

    • 2 Beds
    • 1 Bath
    • 1,116 Sq Ft
    • Condo for Rent

    5152 Northridge Rd Unit 204, Sarasota, FL 34238

    Nice condo located on second floor in gated community within Palmer Ranch. This is a desirable gated community with two heated pool, hot tub, fitness center, and tennis court. Close to Siesta Key Beach, I-75, restaurants and shopping. Inside unit laundry, extra vanity outside of bathroom for added convenience, screened lanai, large walk-in closet, and open kitchen/living area all make this a very

    Maureen Plichta STRINGER MANAGEMENT INC

    5152 Northridge Rd Unit 204, Sarasota, FL 34238
  • 1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242
    1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242
    1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242
    /34

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242

    Experience luxury waterfront living in this stunning 2-bedroom, 2-bathroom condo situated on the second level of Gulf & Bay Club Bayside in Siesta Key, Florida. Boasting breathtaking views of the bay, this meticulously designed residence boasts comfort. Step into a spacious living area adorned with coastal finishes and large windows that invite an abundance of natural light. The open-concept

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1382 Siesta Bayside Dr Unit 1382C, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 29, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 29, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 29, Sarasota, FL 34242
    /16

    $7,500 Per Month

    • 1 Bed
    • 1 Bath
    • 696 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 29, Sarasota, FL 34242

    If the beach is calling your name, Villa 29 at Aloha Kai is the perfect retreat. Whether you’re grabbing a towel and heading to the shore or curling up with a good book by the pool, you’ll find plenty of sunshine and tranquility to enjoy. Unwind on your screened porch or sink into the comfort of a king-size bed as you rest and recharge. For your convenience, this villa also includes a washer and

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 29, Sarasota, FL 34242
  • 4275 Castlebridge Ln Unit 1323, Sarasota, FL 34238
    4275 Castlebridge Ln Unit 1323, Sarasota, FL 34238
    4275 Castlebridge Ln Unit 1323, Sarasota, FL 34238
    /57

    $3,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft
    • Condo for Rent

    4275 Castlebridge Ln Unit 1323, Sarasota, FL 34238

    *SPACIOUS "CHATEAU" TOWNHOME STYLE CONDOMINIUM* Available 5/1/2027 - 9/30/2027. The "Chateau" model is the largest of the units in the Pinestone at Palmer Ranch community! The condo features three bedrooms or two bedrooms and a den. The primary bedroom has a Queen bed, bedroom #2 has a queen bed and bedroom#3 is set up as a bedroom or den with a desk and two bed chairs. This open floor plan condo

    Jana L. Nizny M&M PROPERTY MANAGEMENT GROUP

    4275 Castlebridge Ln Unit 1323, Sarasota, FL 34238
  • 8681 Rain Song Rd, Sarasota, FL 34238
    8681 Rain Song Rd, Sarasota, FL 34238
    8681 Rain Song Rd, Sarasota, FL 34238
    /48

    $3,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,677 Sq Ft
    • House for Rent

    8681 Rain Song Rd, Sarasota, FL 34238

    This is a spectacular FURNISHED 2 bedroom 2 bath PLUS DEN Villa in Gated, Sunrise Preserve at Palmer Ranch. This property is in "model like" condition ~ just pack you bags and move right in. This immaculate property, built in 2020, has a great open floor plan, fantastic Kitchen, nice den/office and large bedrooms. Sunrise Preserve is an amenity filled community featuring a clubhouse with

    Tony Andrews ANDREWS & ASSOCIATES REALTY

    8681 Rain Song Rd, Sarasota, FL 34238
  • 1001 Point of Rocks Rd Unit 208, Sarasota, FL 34242
    1001 Point of Rocks Rd Unit 208, Sarasota, FL 34242
    1001 Point of Rocks Rd Unit 208, Sarasota, FL 34242
    /33

    $12,630 Per Month

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    1001 Point of Rocks Rd Unit 208, Sarasota, FL 34242

    Villa 208 at Siesta Sands is a relaxing island getaway where comfort meets coastal charm. Light-filled and airy, this inviting villa features an open-concept design and a soothing beach-inspired feel that helps you settle into vacation mode right away. The kitchen is fully equipped for easy meals, while the comfortable living areas offer plenty of space to relax and reconnect. Embrace the

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1001 Point of Rocks Rd Unit 208, Sarasota, FL 34242
  • 8735 Olde Hickory Ave Unit 8104, Sarasota, FL 34238
    8735 Olde Hickory Ave Unit 8104, Sarasota, FL 34238
    8735 Olde Hickory Ave Unit 8104, Sarasota, FL 34238
    /31

    $5,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • Condo for Rent

    8735 Olde Hickory Ave Unit 8104, Sarasota, FL 34238

    RENTED JAN., FEB., MARCH, 2027: AVAILABLE OFF-SEASON AT REDUCED RATE: GROUND FLOOR - GOLF VIEW - UPDATED CONDO - Open the door and be delighted, new kitchen cabinetry, granite countertops, new bathrooms with new designer tile and granite, new flooring, new living room furniture, and so much more. This is a two-bedroom, two-bath condo with a screened lanai overlooking the golf course, internet

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    8735 Olde Hickory Ave Unit 8104, Sarasota, FL 34238
  • 1001 Benjamin Franklin Dr Unit 505, Sarasota, FL 34236
    1001 Benjamin Franklin Dr Unit 505, Sarasota, FL 34236
    1001 Benjamin Franklin Dr Unit 505, Sarasota, FL 34236
    /19

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Condo for Rent

    1001 Benjamin Franklin Dr Unit 505, Sarasota, FL 34236

    LIDO TOWERS!!! Highly sought after FIFTH Floor 2 bedroom 2 bath condo in Lido Towers. Secure Building with Lido Beach Access. Enjoy the Beautiful Sunsets from the Sparkling Sandy Beach Across the Street. Lido Towers features a Heated Pool and Jacuzzi, BBQ on the Patio, Sauna, Clubhouse, Laundry Room on Each Floor, Guest Parking, and a Secure, Gated Building. Kayaking available one block away.

    Pamala Casey CASEY REALTY CORPORATION

    1001 Benjamin Franklin Dr Unit 505, Sarasota, FL 34236
  • 6461 Baytown Dr, Sarasota, FL 34240
    6461 Baytown Dr, Sarasota, FL 34240
    6461 Baytown Dr, Sarasota, FL 34240
    /24

    $2,495 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Townhouse for Rent

    6461 Baytown Dr, Sarasota, FL 34240

    Spacious townhouse located in Baytown Square, at a great Sarasota location, is now available. The home features 3 bedrooms and 2.5 bathrooms. In this two-story, all concrete brick construction townhome, downstairs includes an open concept design with a well-equipped kitchen providing all appliances and a generously spaced living area. The appliances' package includes refrigerator, build-in

    Wojciech Suchanek EXPERTIA REALTY

    6461 Baytown Dr, Sarasota, FL 34240
  • 5655 Bentgrass Dr Unit 9117, Sarasota, FL 34235
    5655 Bentgrass Dr Unit 9117, Sarasota, FL 34235
    5655 Bentgrass Dr Unit 9117, Sarasota, FL 34235
    /20

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,378 Sq Ft
    • Condo for Rent

    5655 Bentgrass Dr Unit 9117, Sarasota, FL 34235

    Resort-Style Living in a Gated Community! AVAILABLE IMMEDIATELY, this spacious 3-bedroom, 2-bath townhouse-style condominium offers the perfect blend of comfort, convenience, and resort-style amenities. Featuring an attached 1-car garage and a desirable open floor plan, this home has been thoughtfully updated with modern kitchen cabinetry, granite countertops, stainless steel appliances, and

    Tammy Londer RE/MAX ACTION FIRST

    5655 Bentgrass Dr Unit 9117, Sarasota, FL 34235
  • 1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
    /35

    $8,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242

    Welcome to your coastal retreat at Gulf & Bay Club Bayside in Siesta Key, Florida! Nestled on the second level, this 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and breathtaking views of the bay and boat slip.As you step into this meticulously designed space, you'll immediately be drawn to the open-concept living area bathed in natural light. The coastal vibes are

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1343 Siesta Bayside Dr Unit 1343C, Sarasota, FL 34242
  • 5600 Bentgrass Dr Unit 8103, Sarasota, FL 34235
    5600 Bentgrass Dr Unit 8103, Sarasota, FL 34235
    5600 Bentgrass Dr Unit 8103, Sarasota, FL 34235
    /21

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,615 Sq Ft
    • Condo for Rent

    5600 Bentgrass Dr Unit 8103, Sarasota, FL 34235

    LOCATION - LOCATION - LOCATION -- Don't miss out on this updated townhouse style condo with 3 bedrooms, 2 bathrooms, plus a 1 car garage. Located in the gated, resort style community of Las Palmas of Sarasota. Community amenities include; 2 pools, hot tub, tennis court, playground, 2 clubhouses, full fitness center at front clubhouse and fitness room at back clubhouse and onsite RV/boat parking

    Roger Coles PRIORITY REAL ESTATE MGMT.

    5600 Bentgrass Dr Unit 8103, Sarasota, FL 34235
  • 97 Sunset Dr Unit 501, Sarasota, FL 34236
    97 Sunset Dr Unit 501, Sarasota, FL 34236
    97 Sunset Dr Unit 501, Sarasota, FL 34236
    /40

    $9,650 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,516 Sq Ft
    • Condo for Rent

    97 Sunset Dr Unit 501, Sarasota, FL 34236

    Owner is willing to lease the condo unfurnished for an annual lease. Live above it all in this rarely available penthouse at Lawrence Pointe, one of Sarasota’s premier bayfront communities beside the Ritz-Carlton. With unmatched views of Sarasota Bay and the Ringling Bridge, this 2-bedroom, 2.5-bath residence delivers the ultimate waterfront lifestyle. Inside, expansive living and dining areas

    Jomarie Alicea PREFERRED SHORE LLC

    97 Sunset Dr Unit 501, Sarasota, FL 34236
  • 1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
    1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
    1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
    /29

    $6,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242

    This two bedroom, two bath ground floor unit is steps from the pool and short distance to the beach. Enjoy all of the amenities that Gulf and Bay Club Bayside has to offer, two swimming pools, 2 pickle-ball courts, tennis, workout room, fishing dock and walking path. Washer and Dryer and one car garage sets us apart from other Siesta Key condos and makes it feel more like a home away from home.

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1328 Siesta Bayside Dr Unit 1328C, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 39, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 39, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 39, Sarasota, FL 34242
    /19

    $8,300 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 39, Sarasota, FL 34242

    Paradise is found at Villa 39 at Aloha Kai! Meticulously renovated, this villa stands out with its beamed ceilings and open floor plan, creating a cozy and inviting atmosphere from the moment you step inside this exceptional beach retreat. The primary bedroom features relaxing coastal decor and a spa-like private bath, while guests will feel equally comfortable in the thoughtfully designed living

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 39, Sarasota, FL 34242
  • 9393 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    9393 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    9393 Midnight Pass Rd Unit 605, Sarasota, FL 34242
    /12

    $2,495 Per Month

    • 2 Beds
    • 2 Baths
    • 1,029 Sq Ft
    • Condo for Rent

    9393 Midnight Pass Rd Unit 605, Sarasota, FL 34242

    Beautifully decorated 2 bedroom 2 bath condo located at The Pointe on Midnight Pass Road. Large lanai accessible from master bedroom and living room features views of the Intracoastal. Look out your kitchen window and guest bedroom for a view of the beautiful Gulf. Beautiful furnishings, full size washer/dryer. Complex amenities include heated pool, whirlpool, sauna, fitness room, tennis court &

    Pamala Casey CASEY REALTY CORPORATION

    9393 Midnight Pass Rd Unit 605, Sarasota, FL 34242
  • 6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242
    /23

    $8,550 Per Month

    • 2 Beds
    • 1 Bath
    • 1,014 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242

    Welcome to Villa #27, your home away from home on beautiful Crescent Beach, Siesta Key. As one of Aloha Kai’s closest villas to the Gulf of Mexico, you are just steps away from the top-rated beach in the United States. The villa’s décor is comfy and casual, featuring two sofas, a dining table that seats six, and an open kitchen—perfect for relaxing evenings in. Kick back and enjoy a late-night

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 27, Sarasota, FL 34242
  • 3092 Via Sienna Cir, Sarasota, FL 34243
    3092 Via Sienna Cir, Sarasota, FL 34243
    3092 Via Sienna Cir, Sarasota, FL 34243
    /61

    $2,700 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,221 Sq Ft
    • Townhouse for Rent

    3092 Via Sienna Cir, Sarasota, FL 34243

    Luxury Townhome Living with Single-Family Space in Sienna Park! Welcome to 3092 Via Sienna Circle, a beautifully designed end-unit townhome in the gated Sarasota community of Sienna Park at University. This 2022 built property offers the expansive feel of a single family home with the low maintenance convenience of townhome living, featuring 3 bedrooms, 2.5 bathrooms, and 2,221 square feet of

    Brie Bender INNOVATE REAL ESTATE

    3092 Via Sienna Cir, Sarasota, FL 34243
  • 8755 Olde Hickory Ave Unit 7109, Sarasota, FL 34238
    8755 Olde Hickory Ave Unit 7109, Sarasota, FL 34238
    8755 Olde Hickory Ave Unit 7109, Sarasota, FL 34238
    /37

    $2,095 Per Month

    • 2 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • Condo for Rent

    8755 Olde Hickory Ave Unit 7109, Sarasota, FL 34238

    Available April 22nd through November. Turnkey Furnished Condo in Stoneybrook Golf & Tennis Community.Welcome to your perfect getaway in the vibrant, amenity-rich Stoneybrook community! Available rental from May through November, this ground-floor condo offers peaceful golf course views and an unbeatable location.Relax on your private lanai overlooking the newly remodeled , challenging

    Maureen Plichta STRINGER MANAGEMENT INC

    8755 Olde Hickory Ave Unit 7109, Sarasota, FL 34238
  • 1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
    /58

    $8,000 Per Month

    • 3 Beds
    • 3 Baths
    • 1,835 Sq Ft
    • Condo for Rent

    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242

    Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside.Perched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1366 Siesta Bayside Dr Unit 1366F, Sarasota, FL 34242
  • 1001 Benjamin Franklin Dr Unit 512, Sarasota, FL 34236
    1001 Benjamin Franklin Dr Unit 512, Sarasota, FL 34236
    1001 Benjamin Franklin Dr Unit 512, Sarasota, FL 34236
    /27

    $2,850 Per Month

    • 1 Bed
    • 1.5 Baths
    • 813 Sq Ft
    • Condo for Rent

    1001 Benjamin Franklin Dr Unit 512, Sarasota, FL 34236

    Unit 512 has just been re-furbished, and is steps from the beautiful Lido Key beaches and a short walk to St. Armand's Circle. This 1 bedroom/1.5 bath is spacious and has a beautiful lanai lending itself to you enjoying the warmth of Florida in January and February. You won’t see any snowflakes here! The master bedroom has a huge king sized. Open living room, dining room, and kitchen perfect for

    Pamala Casey CASEY REALTY CORPORATION

    1001 Benjamin Franklin Dr Unit 512, Sarasota, FL 34236
  • 1708 Glenhouse Dr Unit GL313, Sarasota, FL 34231
    1708 Glenhouse Dr Unit GL313, Sarasota, FL 34231
    1708 Glenhouse Dr Unit GL313, Sarasota, FL 34231
    /32

    $2,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,330 Sq Ft
    • Condo for Rent

    1708 Glenhouse Dr Unit GL313, Sarasota, FL 34231

    Look no further. This property is located in the highly requested community of Pelican Cove which is gated with a guard present 24 hours. A beautiful renovated two bedroom two bath ground floor unit with a pool view. The kitchen is spacious and easy to work in. Living room and dining room are spacious and comfortable. All windows have privacy film. Pelican Cove is a waterfront community with

    Pat Gillum RE/MAX ALLIANCE GROUP

    1708 Glenhouse Dr Unit GL313, Sarasota, FL 34231
  • 6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
    /13

    $6,972 Per Month

    • 1 Bed
    • 1 Bath
    • 672 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242

    New photos coming soon! Villa 36 at Aloha Kai is perfectly situated on Siesta Key, a popular barrier island on Florida’s West Coast. Aloha Kai is a family-friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States. Known for its bright white quartz sand and emerald-green waters, Siesta Key ranks among Florida’s top vacation

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 36, Sarasota, FL 34242
  • 1001 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
    1001 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
    1001 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
    /21

    $5,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,224 Sq Ft
    • Condo for Rent

    1001 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236

    LIDO TOWERS!!! Highly sought after FIFTH Floor 2 bedroom 2 bath condo in Lido Towers. Condo is newly renovated and updated. This beautiful condo overlooks the gulf of Mexico. Secure Building with Lido Beach Access. Enjoy the Beautiful Sunsets from the Sparkling Sandy Beach Across the Street. Lido Towers features a Heated Pool and Jacuzzi, BBQ on the Patio, Sauna, Clubhouse, Laundry Room on Each

    Pamala Casey CASEY REALTY CORPORATION

    1001 Benjamin Franklin Dr Unit 507, Sarasota, FL 34236
  • 1111 N Gulfstream Ave Unit 4E, Sarasota, FL 34236
    1111 N Gulfstream Ave Unit 4E, Sarasota, FL 34236
    1111 N Gulfstream Ave Unit 4E, Sarasota, FL 34236
    /33

    $7,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,575 Sq Ft
    • Condo for Rent

    1111 N Gulfstream Ave Unit 4E, Sarasota, FL 34236

    Enjoy upscale bayfront living in this updated 2-bedroom, 2-bathroom condo at One Watergate. Ideal for active lifestyles, with exclusive rooftop access to 2 tennis courts with pickleball conversions (recently refreshed with new cushioned surfaces).The modern kitchen features premium quartzite waterfall countertops and elegant cabinetry. The spa-like master bath has luxurious marble tile and a

    Danielle Gladding DANIELLE GLADDING & CO. REALTY

    1111 N Gulfstream Ave Unit 4E, Sarasota, FL 34236
  • 6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242
    6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242
    /28

    $8,250 Per Month

    • 2 Beds
    • 2 Baths
    • 1,552 Sq Ft
    • House for Rent

    6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242

    Let’s all go to the beach! Villa 52S at Aloha Kai is a spacious and bright 3-bedroom, 2-bath getaway with plenty of room for everyone to relax and enjoy. The large, open kitchen is perfect for gathering with friends and family to prepare drinks, snacks, or full meals to enjoy in the dining room or on your private rooftop patio. For added convenience, this villa also includes a washer and dryer.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 52A, Sarasota, FL 34242
  • 1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
    /27

    $9,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,280 Sq Ft
    • Condo for Rent

    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242

    Come and watch the dolphins and manatees on the intercoastal waterway from our lanai! This unit has 2 large bedrooms and 2 full baths. There is a washer and dryer in the unit and a garage to park your car and store all the beach equipment you will need for the beach. It's only a short 10 min. walk down the private deeded beach access to the beautiful white sands of Siesta Key beach. We share

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1365 Siesta Bayside Dr Unit 1365C, Sarasota, FL 34242
  • 9320 Clubside Cir Unit 2208, Sarasota, FL 34238
    9320 Clubside Cir Unit 2208, Sarasota, FL 34238
    9320 Clubside Cir Unit 2208, Sarasota, FL 34238
    /42

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,106 Sq Ft
    • Condo for Rent

    9320 Clubside Cir Unit 2208, Sarasota, FL 34238

    AVAILABLE FEB., MARCH., APRIL 2026 - And off-season months. Fantastic views of the lake and golf course from the screened and glassed lanai of this CORNER UNIT picture-perfect condo decorated in a coastal theme, lots of comfortable seating, windows in well-equiped kitchen and living room not found in interior units. King bed in the master bedroom, walk-in shower in the master bath, and a queen

    Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICES FLORIDA REALTY

    9320 Clubside Cir Unit 2208, Sarasota, FL 34238
  • 5601 Bentgrass Dr Unit 102, Sarasota, FL 34235
    5601 Bentgrass Dr Unit 102, Sarasota, FL 34235
    5601 Bentgrass Dr Unit 102, Sarasota, FL 34235
    /55

    $2,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,395 Sq Ft
    • Townhouse for Rent

    5601 Bentgrass Dr Unit 102, Sarasota, FL 34235

    Gated Las Palmas townhome near UTC with 3 bedrooms, 2 baths, and an attached 1-car garage. Offered turnkey, furnished with a flexible lease option. Split floor plan with a primary suite featuring an en-suite bath and a large walk-in closet. Includes in-unit washer and dryer and a screened balcony lanai. Cable, trash, and pest control are included. Community amenities include two pools, fitness

    Tayna Vy Lilly SPECIALIZED REAL ESTATE LLC

    5601 Bentgrass Dr Unit 102, Sarasota, FL 34235
  • 9393 Midnight Pass Rd Unit 302, Sarasota, FL 34242
    9393 Midnight Pass Rd Unit 302, Sarasota, FL 34242
    9393 Midnight Pass Rd Unit 302, Sarasota, FL 34242
    /66

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,029 Sq Ft
    • Condo for Rent

    9393 Midnight Pass Rd Unit 302, Sarasota, FL 34242

    Siesta Key Resort Style Vacation Rental, you will love the fabulous renovation these owners have done, everything is brand new and the aboslute best! The kitchen has been updated with gorgeous cabinets, a stunning Quartz waterfall countertop, there is a breakfast bar as well as dining table, and stainless appliances. All new furniture throughout and amazing views of the water from almost every

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    9393 Midnight Pass Rd Unit 302, Sarasota, FL 34242
  • 6052 W Peppertree Way Unit 235B, Sarasota, FL 34242
    6052 W Peppertree Way Unit 235B, Sarasota, FL 34242
    6052 W Peppertree Way Unit 235B, Sarasota, FL 34242
    /27

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,180 Sq Ft
    • Condo for Rent

    6052 W Peppertree Way Unit 235B, Sarasota, FL 34242

    This property is a 30 night minimum. 6052 WPW is a Large Garden condo, located approximately 50 yards away from Crescent BeachOpen porch lanai with a 6 person table. Recessed lighting in both bathrooms. Master bathroom has a seat. Recessed lighting in the kitchen. This unit has access to a private garageApprox. 1250 Sq. Ft. (1375 including the lanai) Condo Summary:Bedding: Master

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6052 W Peppertree Way Unit 235B, Sarasota, FL 34242

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