248

Siesta Key, FL Homes for Rent

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  • /65

    $22,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,788 Sq Ft
    • House for Rent

    3939 Higel Ave, Sarasota, FL 34242

    Arrive. Unwind. Experience Siesta Key at its finest.Welcome to your private luxury retreat on Siesta Key, a modern sophisticated 4-bedroom, 4-bathroom home designed for elevated coastal living. Tucked away in one of the island’s most desirable locations, this residence offers the perfect blend of privacy, comfort, and effortless elegance.From the moment you step inside, you’re welcomed by

    Agent Photo

    Raffilena Hamilton

    GOOD LIFE REALTY LLC

    3939 Higel Ave, Sarasota, FL 34242
  • /17

    $5,564

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,496 Sq Ft
    • Condo for Rent

    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242

    The advertised rate of $5,564/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6265 Midnight Pass Rd Unit SI FL2-ID1545741P, Siesta Key, FL 34242
  • /56

    $17,000 Per Month

    • 5 Beds
    • 5 Baths
    • 3,126 Sq Ft
    • House for Rent

    5624 Cape Leyte Dr, Sarasota, FL 34242

    Prime Siesta Key Waterfront Retreat – Fully Furnished & Walk to the Beach Welcome to 5624 Cape Leyte Drive, a fully furnished luxury beach retreat just a short walk to world-famous Siesta Key Beach. This turnkey property showcases refined coastal elegance with designer furnishings, Italian tile and quartz finishes throughout, and spa-inspired bathrooms featuring rainfall showers. Every detail

    Agent Photo

    Wally Sabrii

    SARASOTA INTERNATIONAL REALTY

    5624 Cape Leyte Dr, Sarasota, FL 34242
  • /15

    $7,015

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 1,797 Sq Ft
    • Condo for Rent

    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242

    The advertised rate of $7,016/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 6, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    5885 Midnight Pass Rd Unit SI FL2-ID1546103P, Siesta Key, FL 34242
  • /27

    $9,975 Per Month

    • 3 Beds
    • 2 Baths
    • 1,794 Sq Ft
    • House for Rent

    1232 Northport Dr, Sarasota, FL 34242

    Annual Rental: Waterfront 3BD/2BA home with private pool and sailboat water with boat slip. Looking for a laid-back Siesta Key flip-flop lifestyle with urban conveniences? Discover 1232 Northport Drive, a secluded, peaceful setting less than one mile from world-famous Siesta Key beach. This updated island one-story home awaits your annual escape from daily demands, but not too far, as high-speed

    Agent Photo

    Lynn Brock

    BROCK REALTY INC.

    1232 Northport Dr, Sarasota, FL 34242
  • /20

    $5,773

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,593 Sq Ft
    • Condo for Rent

    1037 W Peppertree Dr Unit SI FL3-ID1546456P, Sarasota, FL 34242

    The advertised rate of $5,774/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 11, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1037 W Peppertree Dr Unit SI FL3-ID1546456P, Sarasota, FL 34242
  • /50

    $6,300 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,260 Sq Ft
    • Condo for Rent

    5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242

    RARE OPPORTUNITY to RENT THE PENTHOUSE. 3 BEDS/2.5 BATHS full size washer/dryer and a roof top deck with panoramic views available September 2025 stay for a year, 2 or 3+ owner wants this beautiful turnkey home with a BOAT DOCK (no lift yet)RENTED LONG TERM. Owner open to lift discussion. You will enjoy Penthouse end unit in Boca Siesta is located in the heart of Siesta Key the #1 Beach in the

    Agent Photo

    Marianne LeBar

    ROSEBAY INTERNATIONAL REALTY, INC

    5911 Midnight Pass Rd Unit 601, Sarasota, FL 34242
  • /20

    $8,532

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Condo for Rent

    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242

    The advertised rate of $8,533/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 5, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    324 Avenida Madera Unit SI ID1578359P, Siesta Key, FL 34242
  • /49

    $9,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,489 Sq Ft
    • Condo for Rent

    6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242

    ***AVAILABLE MAY 2026 THRU DECEMBER 2026. BOOKED FOR SEASON AND THEN AVAILABLE AGAIN APRIL 2027*** Welcome to the Beach! Prime Siesta Key location. This large, spacious 2 Bedroom/2 Bath split floor plan condo comes with a full-length balcony with views of the gulf and intracoastal waterway, as well as the beautiful sunsets. Available as a monthly rental, the interior boasts a decorative

    Agent Photo

    Anthony DeLuca

    AUDREY RAIN RENTALS, INC

    6415 Midnight Pass Rd Unit 602, Sarasota, FL 34242
  • /20

    $4,327

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,054 Sq Ft
    • Condo for Rent

    5830 Jamaica Royale Unit SI ID1578366P, Siesta Key, FL 34242

    The advertised rate of $4,327/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 19, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    5830 Jamaica Royale Unit SI ID1578366P, Siesta Key, FL 34242
  • /27

    $8,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,455 Sq Ft
    • Condo for Rent

    1195 Coquille St Unit 309, Sarasota, FL 34242

    Beautiful 2 Bedroom 2 Bathroom Townhome available! Come see this gorgeous home ready for you to call home! Large living spaces including full kitchen, living room and dining room, 3 seasons room and loft area. Loft area ideal for office space or second floor den. Two large bedrooms including plenty of closet and storage space. Nice patio with grill to enjoy evenings and entertaining. Large full

    Agent Photo

    Anna Fattore

    COMPASS FLORIDA LLC

    1195 Coquille St Unit 309, Sarasota, FL 34242
  • /20

    $9,091

    Total Monthly Price

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

    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242

    The advertised rate of $9,092/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 14, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1179 Lake House Cir Unit SI ID1578383P, Siesta Key, FL 34242
  • /63

    $15,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 3,524 Sq Ft
    • Condo for Rent

    1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242

    AVAILABLE 1/4/27 Experience the pinnacle of coastal living in this exceptional penthouse at Marina Del Sol with PRIVATE 52 FT BOAT SLIP. Perfectly positioned moments from the #1-rated Siesta Key Beach. This rare residence offers panoramic Gulf of Mexico sunsets on one side and serene Bay views on the other—an unmatched indoor-outdoor lifestyle framed by water in every direction.****Designed for

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    Tracy Srodes

    FINE PROPERTIES

    1308 Old Stickney Point Rd Unit WP3, Sarasota, FL 34242
  • /20

    $14,253

    Total Monthly Price

    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft
    • Condo for Rent

    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242

    The advertised rate of $14,253/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 21, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    5165 Sandy Cove Ave Unit SI ID1578384P, Siesta Key, FL 34242
  • /20

    $6,506

    Total Monthly Price

    • 2 Beds
    • 1.5 Baths
    • 850 Sq Ft
    • Condo for Rent

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242

    The advertised rate of $6,507/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 11, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1400 Cove II Place Unit SI FL2-ID1578373P, Sarasota, FL 34242
  • /20

    $9,237

    Total Monthly Price

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

    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242

    The advertised rate of $9,238/month is the lowest available price, based on a 30 day(s) stay with a move-in date of July 21, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    6327 Midnight Cove Rd Unit SI ID1578382P, Siesta Key, FL 34242
  • /16

    $9,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Condo for Rent

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242

    Just steps from Crescent Beach, this unit has 2 bedrooms and 2 full bathrooms. Complete with a full kitchen supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and has a Keurig.The formal dining area has seating for 6. This flows into the living area that has comfortable couch seating, a fan, access to the lanai and a 55"

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 603AA, Sarasota, FL 34242
  • /27

    $9,819

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 2,055 Sq Ft
    • Condo for Rent

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242

    The advertised rate of $9,819/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 23, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    349 Avenida Madera Unit SI ID1578360P, Siesta Key, FL 34242
  • /35

    $7,400 Per Month

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

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242

    Indulge in the ultimate coastal lifestyle with this charming 2-bedroom, 2-bathroom first-level condo in the heart of Gulf & Bay Club Bayside on Siesta Key, Florida. As you enter, the coastal vibes welcome you into a thoughtfully designed space adorned with beach-inspired decor and sunlit interiors. Step through the sliding glass doors onto your private screened-in lanai, where the gentle

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1338 Siesta Bayside Dr Unit 1338C, Sarasota, FL 34242
  • /17

    $5,368

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • Condo for Rent

    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242

    The advertised rate of $5,369/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    5760 Midnight Pass Rd Unit SI ID1545688P, Siesta Key, FL 34242
  • /36

    $7,500 Per Month

    • 1 Bed
    • 1 Bath
    • 728 Sq Ft
    • Condo for Rent

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242

    Discover your own slice of paradise at Jamaica Royale! This beautifully updated and tastefully decorated 1-bedroom, 1-bathroom condo is just steps from the refreshing waters of heated Pool #1 and a short stroll to the world-famous, powdery whit e sands of Siesta Key Beach. Enjoy the convenience of your assigned covered parking space located right outside your door.Inside, the condo is

    Robert Bevington SHOWTIME REALTY

    5830 Midnight Pass Rd Unit 54, Sarasota, FL 34242
  • /73

    $5,995 Per Month

    • 3 Beds
    • 2 Baths
    • 1,595 Sq Ft
    • ALL THE CHARM! - Siesta Key 1+ acre on the Bay - 3 bed/ 2 bath pool home

    4237 Higel Ave, Siesta Key, FL 34242

    Charming 3 bed/2 bath waterfront estate located on the coveted north end of Siesta Key. This parcel is one of the last of its kind, featuring 1.3 acres of prime waterfront property overlooking Cocoanut Bayou. Completely private by its original growth of lush tropical landscaping, this property is captivating for all your senses.  This 1,500 sqft home was built in 1946 and will wow you from the

    4237 Higel Ave, Siesta Key, FL 34242
  • /18

    $5,970 Per Month

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

    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242

    This beautifully updated Villa 12 at Aloha Kai is ready to give the perfect beach getaway. Just steps from the villa, you can stroll along the beach with your morning coffee and return in time for a breathtaking sunset. The screened porch provides a lovely spot to enjoy the balmy afternoon breezes in comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 12, Sarasota, FL 34242
  • /20

    $6,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,288 Sq Ft
    • Key West style home on Siesta Key minutes to village and beaches

    5157 Sandy Beach Ave, Siesta Key, FL 34242

    ANNUAL RENTAL. Stay at this large Key West style Siesta Key home minutes to Siesta Key village and beaches. The property offers a private backyard with heated pool. Located on a quite street just 1 mile from Siesta Key village puts it at a perfect distance for a easy bicycle ride in the mornings to grab some breakfast or a coffee. 4 bedrooms and 2.5 baths brings you back inside with a large open

    5157 Sandy Beach Ave, Siesta Key, FL 34242
  • /80

    $8,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • House for Rent

    5216 Calle de Costa Rica, Sarasota, FL 34242

    Listing reflects peak season rate. Available months: July 2026, August 2026, October 2026, November 2026 December 2026, January 2027, March 2027 and April 2027. Imagine a place where the warm sunshine beckons you to relax, unwind, and truly escape the everyday. Welcome to House of the Sun, a delightful 3-bedroom, 2-bathroom island bungalow meticulously designed for your ultimate Siesta Key

    Beth Dilley ASCENDIA REAL ESTATE

    5216 Calle de Costa Rica, Sarasota, FL 34242
  • /21

    $2,200 Per Month

    • 1 Bed
    • 1 Bath
    • 800 Sq Ft
    • Condo for Rent

    212 Pass Key Rd, Sarasota, FL 34242

    Oceanview unit in Siesta Key

    212 Pass Key Rd, Sarasota, FL 34242
  • /49

    $4,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,438 Sq Ft
    • House for Rent

    5253 Avenida Del Mare, Sarasota, FL 34242

    This is a short-term rental. Listing price reflects off season rate, in season rates will be higher. Escape to paradise at this beautiful vacation retreat located on the coveted north end of Siesta Key. Nestled in a quiet residential neighborhood, this spacious and elegantly appointed home offers the perfect blend of privacy, comfort, and convenience—just minutes from world-famous Siesta Key

    Beth Dilley ASCENDIA REAL ESTATE

    5253 Avenida Del Mare, Sarasota, FL 34242
  • /36

    $2,595 Per Month

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Condo for Rent

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242

    5649 Midnight Pass Rd Unit 803, Siesta Key, FL 34242
  • /54

    $9,500 Per Month

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

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242

    Indulge in opulent coastal living with this luxurious 3-bedroom, 2-bathroom second-floor, two-level condo in the prestigious Gulf & Bay Club Bayside on Siesta Key, Florida. This impeccably designed residence offers a unique and spacious layout, with the primary bedroom occupying its own private floor for the utmost in privacy and elegance.As you enter, the living room, dining room, and

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1389 Siesta Bayside Dr Unit 1389F, Sarasota, FL 34242
  • /42

    Call for Price

    • 1 Bed
    • 1 Bath
    • 820 Sq Ft
    • Condo for Rent

    797 Beach Rd Unit 305, Sarasota, FL 34242

    Welcome to Your Slice of Paradise – Crescent Royale 3053D Tour URL: AVAILABILITY, PRICING and BOOKING HERE: Note: 7 day minimum required booking.Fully remodeled and infused with a modern coastal flair, this deluxe one-bedroom, one-bath condo is the ultimate Siesta Key escape. With over 820 square feet of bright, open living space, you’ll find all the bells and

    797 Beach Rd Unit 305, Sarasota, FL 34242
  • /28

    $7,050 Per Month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • Condo for Rent

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242

    This luxurious condo is in a Gulf-side High-rise and is located on the 7th floor. This condo has 2 bedrooms and 2 full bathrooms.A fully equipped kitchen awaits you with cabinet lighting, a ceiling fan and a breakfast bar for 3. It is supplied with the necessary items you need for cooking (pots/pans, dishes, utensils) and a 12-cup standard coffee maker and a Keurig.The formal dining room

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    1055 W Peppertree Dr Unit 703AA, Sarasota, FL 34242
  • /51

    $3,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • Annual UNfurnished Siesta Key Gulf front 2/2 condo with water views!

    4822 Ocean Blvd, Sarasota, FL 34242

    Annual – Unfurnished | Gulffront Living on Siesta Key Live on the water and enjoy breathtaking Gulf views from this beautiful condo in Siesta Towers. This luxury 11-story, 65-unit beachfront building sits directly on the Gulf of Mexico, offering spectacular panoramic views and an unbeatable island lifestyle. The condo features an open floor plan filled with natural light from large sliding glass

    4822 Ocean Blvd, Sarasota, FL 34242
  • /45

    $9,500 Per Month

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

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242

    Welcome to this beautifully designed 2-bedroom, 2-bathroom first floor condo located in the sought-after Gulf and Bayside Bay Club, offers breathtaking views of the boat harbor and Intracoastal Waterway.The kitchen is a chef's delight, boasting stainless steel appliances and sleek countertops. The living room is the perfect place to kick back and relax after a day of adventure, with

    Andy Moore GULF COAST REALTY & MANAGEMENT

    1335 Siesta Bayside Dr Unit 1335C, Sarasota, FL 34242
  • /19

    $2,200 Per Month

    • 1 Bed
    • 1 Bath
    • 656 Sq Ft
    • 1 Bedroom 1 Bath Condo Sandy Cove II Short Term Rental/Annual Rental

    111 Pass Key Rd, Siesta Key, FL 34242

    Available off season till 10/31/26 for $2200 per month!!! Welcome to your perfect beach getaway with this 1 Bedroom 1 Bath Condo in Sandy Cove II, located in beautiful Sarasota, FL. This cozy condo offers a serene escape with a partial ocean view, private beach access, and a fishing pier for those who love to cast a line. Enjoy the convenience of in-unit laundry and make use of the outdoor BBQ

    111 Pass Key Rd, Siesta Key, FL 34242
  • /30

    $5,370 Per Month

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

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242

    Starting at $179/night! Welcome to your vibrant beachside retreat—a newly renovated 1-bedroom, 1-bathroom escape thoughtfully designed for modern comfort and coastal style. Featuring a luxurious king bed and a fully equipped kitchen with a cozy nearby dining space, this inviting getaway is your perfect base for both relaxation and adventure. Convenience begins with your own private carport just

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6006 Midnight Pass Rd Unit 14, Sarasota, FL 34242
  • /16

    $7,470 Per Month

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

    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242

    Villa 4 at Aloha Kai is the perfect beach getaway—light, bright, and designed to help you rest and relax. Spend your days lounging by the pool, soaking up the sun on the beach, or getting lost in a good book—the choice is yours. All you need is a willingness to unwind; everything else is provided for your comfort. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 4, Sarasota, FL 34242
  • /40

    $6,500 Per Month

    • 3 Beds
    • 4 Baths
    • 2,168 Sq Ft
    • House for Rent

    1256 Riegels Landing Dr, Sarasota, FL 34242

    This newly renovated (March, 2025) 3 bed, 4 full bath home with a deep water dock just down the street is located within walking distance of the famous Siesta Key Beach. The one of a kind house was design by the Sarasota School of Architecture. The master and main guest bedroom are located on the main level along with the kitchen, living, laundry and dining rooms. An additional bedroom and full

    Christopher Davenport STARLINK REALTY INC

    1256 Riegels Landing Dr, Sarasota, FL 34242
  • /60

    $15,000 Per Month

    • 3 Beds
    • 2 Baths
    • 2,259 Sq Ft
    • House for Rent

    5516 Avenida Del Mare, Sarasota, FL 34242

    This is a short term rental. Listing reflects peak season rate. Unwind and Explore Siesta Key from Stylish Surf's Up! Discover the ease of being just a short walk from the renowned Siesta Key Beach while enjoying the ample space and thoughtful design of this fantastic home. Picture your family enjoying separate living areas – a fun zone for the kids downstairs and a relaxing haven for adults

    Beth Dilley ASCENDIA REAL ESTATE

    5516 Avenida Del Mare, Sarasota, FL 34242
  • /16

    $9,000 Per Month

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

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242

    Beach or pool today? Or perhaps you'd rather stay in and enjoy a good book on the charming porch of Villa 53 at Aloha Kai. This beautifully remodeled retreat features an updated kitchen and bath, paired perfectly with coastal-inspired furnishings that create a relaxing home away from home. The spacious bedroom offers generous closet space, ensuring comfort and convenience during your stay.

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6020 Midnight Pass Rd Unit 53, Sarasota, FL 34242
  • /25

    $12,296 Per Month

    • 2 Beds
    • 2 Baths
    • 1,319 Sq Ft
    • House for Rent

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

    Welcome to your luxurious retreat nestled by the poolside! This stunning 2-bedroom, 2-bathroom condo on the 1st floor offers a perfect blend of comfort, style, and convenience. Step into the beautifully renovated living space, where every detail has been carefully curated to create an inviting atmosphere. The open-concept layout seamlessly connects the living, dining, and kitchen areas, making it

    Heather Sutter DESTINATION FLORIDA RENTALS & REAL ESTATE

    6046 W Peppertree Way Unit 223B, Sarasota, FL 34242

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Why Live in Siesta Key

Siesta Key, located on a barrier island off the coast of Sarasota, Florida, is renowned for its pristine Siesta Beach, which boasts white quartz sand and was ranked the No. 2 beach in the United States by TripAdvisor in 2023. The island spans 8 miles, with most homes and activities concentrated on the north end, particularly around the downtown area and the quaint village district. This area features a variety of unique shops, restaurants, and nightclubs, enhancing the island's vibrant local flavor. Residents enjoy great walkability and a convenient trolley service that traverses the island. Housing options on Siesta Key include modern styles, Spanish Mediterraneans, ranch-style homes, cozy cottages, coastal-style homes, and several condominium complexes with amenities like pools and tennis courts. Dining highlights include the Toasted Mango Café, Miguel’s, and Captain Curt’s Crab & Oyster Bar, located roughly 3 miles south along the Midnight Pass corridor. The island also offers attractions such as Crescent Beach and Turtle Beach, with facilities for tennis, volleyball, and fishing. Education is served by the highly rated Out-of-Door Academy on the island and top-rated Sarasota County Schools, including Southside Elementary, Brookside Middle, and Riverview High. Siesta Key is accessible via the Siesta Key North Bridge and the Stickney Point Bascule Bridge, with the Sarasota Bradenton International Airport just 10 miles away.

Frequently Asked Questions

How much does it cost to rent a home in Siesta Key, FL?
The median rent for a home in Siesta Key, FL is $4,500 per month, though prices vary by neighborhood, size, and property type. As of July 2026, condos tend to be the most affordable option.
How much do you need to make to afford rent in Siesta Key, FL?
To comfortably afford the median rent in Siesta Key, FL, a household needs to earn roughly $180,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $4,500 per month in Siesta Key, FL, renters typically need to show $13,500 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Siesta Key, FL?
In Siesta Key, FL, the price-to-rent ratio is 49.6, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.
What neighborhoods in Siesta Key, FL are best for renting a home?
The best neighborhood for renting in Siesta Key, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a home include South Sarasota, Coral Cove/Holiday Harbor, Southside, Ridge Wood Heights and Lido Key, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
248
Median Rent
$4,500
Median Condo Rent
$4,500
How to Rent a Home