155

Homes for Rent in ZIP Code 34228

Section Image Section Image
  • 6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
    /38

    $5,696

    Total Monthly Price

    • 1 Bed
    • 2 Baths
    • 1,076 Sq Ft
    • Condo for Rent

    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228

    The advertised rate of $5,696/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 28, 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

    6701 Gulf of Mexico Dr Unit SI ID1591482P, Longboat Key, FL 34228
  • 4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
    /20

    $20,804

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,065 Sq Ft
    • Condo for Rent

    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228

    The advertised rate of $20,804/month is the lowest available price, based on a 30 day(s) stay with a move-in date of December 31, 2028. 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

    4330 Falmouth Dr Unit SI ID1578356P, Longboat Key, FL 34228
  • 1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
    /20

    $9,841

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,894 Sq Ft
    • Condo for Rent

    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228

    The advertised rate of $9,842/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 30, 2027. 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

    1922 Harbourside Dr Unit SI FL1-ID1590867P, Longboat Key, FL 34228
  • 6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
    /20

    $4,567

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft
    • Condo for Rent

    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228

    The advertised rate of $4,568/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 13, 2027. 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

    6997 Longboat Dr S Unit SI ID1591477P, Longboat Key, FL 34228
  • 5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
    /20

    $27,987

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,184 Sq Ft
    • Condo for Rent

    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228

    The advertised rate of $27,987/month is the lowest available price, based on a 30 day(s) stay with a move-in date of March 18, 2027. 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

    5201 Gulf of Mexico Dr Unit SI ID1578376P, Longboat Key, FL 34228
  • 807 Bayport Way, Longboat Key, FL 34228
    807 Bayport Way, Longboat Key, FL 34228
    807 Bayport Way, Longboat Key, FL 34228
    /20

    $11,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,370 Sq Ft
    • Condo for Rent

    807 Bayport Way, Longboat Key, FL 34228

    Welcome to your dream condo in beautiful Longboat Key! This spacious 2-bedroom, 2-bathroom gem offers 1,370 square feet of modern living, perfect for those who appreciate both comfort and style. With a host of amenities and a vibrant community atmosphere, this property is sure to impress. RARELY AVAILABLE FOR 2027 SEASON. LESING NOW FOR DECEMBER 2026 AND JANUARY TRHOUGH APRIL 30TH 2027. MINIMUM

    807 Bayport Way, Longboat Key, FL 34228
  • 1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
    /26

    $4,434

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,388 Sq Ft
    • Condo for Rent

    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228

    The advertised rate of $4,434/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 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

    1109 Gulf of Mexico Dr Unit SI ID1591491P, Longboat Key, FL 34228
  • 6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
    /15

    $3,149

    Total Monthly Price

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

    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228

    The advertised rate of $3,149/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 25, 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

    6750 Gulf of Mexico Dr Unit SI ID1591465P, Longboat Key, FL 34228
  • 1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
    /20

    $3,472

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,388 Sq Ft
    • Condo for Rent

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228

    The advertised rate of $3,472/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 25, 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

    1145 Gulf of Mexico Dr Unit SI ID1591375P, Longboat Key, FL 34228
  • 320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
    /20

    $6,345

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 2,131 Sq Ft
    • Condo for Rent

    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228

    The advertised rate of $6,345/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 4, 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

    320 N Shore Rd Unit SI ID1591451P, Longboat Key, FL 34228
  • 5275 Gulf of Mexico Dr Unit SI FL2-ID1623889P, Longboat Key, FL 34228
    5275 Gulf of Mexico Dr Unit SI FL2-ID1623889P, Longboat Key, FL 34228
    5275 Gulf of Mexico Dr Unit SI FL2-ID1623889P, Longboat Key, FL 34228
    /20

    $8,640 Per Month

    • 3 Beds
    • 3 Baths
    • Condo for Rent

    5275 Gulf of Mexico Dr Unit SI FL2-ID1623889P, Longboat Key, FL 34228

    The advertised rate of $8,640/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 10, 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

    5275 Gulf of Mexico Dr Unit SI FL2-ID1623889P, Longboat Key, FL 34228
  • 5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
    /20

    $6,358

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,474 Sq Ft
    • Condo for Rent

    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228

    The advertised rate of $6,358/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 27, 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

    5055 Gulf of Mexico Dr Unit SI FL1-ID1590856P, Longboat Key, FL 34228
  • 605 Sutton Place Unit SI FL2-ID1626830P, Longboat Key, FL 34228
    605 Sutton Place Unit SI FL2-ID1626830P, Longboat Key, FL 34228
    605 Sutton Place Unit SI FL2-ID1626830P, Longboat Key, FL 34228
    /17

    $3,810 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    605 Sutton Place Unit SI FL2-ID1626830P, Longboat Key, FL 34228

    The advertised rate of $3,810/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 7, 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

    605 Sutton Place Unit SI FL2-ID1626830P, Longboat Key, FL 34228
  • 1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
    /20

    $25,403

    Total Monthly Price

    • 3 Beds
    • 4 Baths
    • 3,272 Sq Ft
    • Condo for Rent

    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228

    The advertised rate of $25,403/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 28, 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

    1281 Gulf of Mexico Dr Unit SI FL1-ID1594589P, Longboat Key, FL 34228
  • 779 St Judes Dr N Unit SI FL2-ID1604522P, Longboat Key, FL 34228
    779 St Judes Dr N Unit SI FL2-ID1604522P, Longboat Key, FL 34228
    779 St Judes Dr N Unit SI FL2-ID1604522P, Longboat Key, FL 34228
    /20

    $4,500

    Total Monthly Price

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

    779 St Judes Dr N Unit SI FL2-ID1604522P, Longboat Key, FL 34228

    The advertised rate of $4,500/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 2, 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

    779 St Judes Dr N Unit SI FL2-ID1604522P, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /67

    $8,000 Per Month

    • 3 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    Prime location... This absolutely gorgeous fully furnished condo located in the Promenade Longboat Key with breathtaking water views from every room. It offers 2 bedroom/den/2 bathroom. The master bedroom features a king-size bed, elegant master bath separate bathtub, shower and a vidette for your convenience. For your guests the second bedroom offers 2 twin beds that can convert into a king-size

    Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 4401 Gulf of Mexico Dr Unit 705, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 705, Longboat Key, FL 34228
    4401 Gulf of Mexico Dr Unit 705, Longboat Key, FL 34228
    /43

    $10,500 Per Month

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

    4401 Gulf of Mexico Dr Unit 705, Longboat Key, FL 34228

    Welcome to this stunning property located just steps away from a private deeded beach, offering an unparalleled lifestyle of coastal living. This spacious residence features an open layout that maximizes natural light, creating a bright and airy atmosphere.The heart of the home is undoubtedly the kitchen, equipped with elegant quartz countertops and high-quality wood cabinetry. The modern

    Agent Photo

    Antonietta Car

    KELLER WILLIAMS SUBURBAN TAMPA

    4401 Gulf of Mexico Dr Unit 705, Longboat Key, FL 34228
  • 691 Russell St, Longboat Key, FL 34228
    691 Russell St, Longboat Key, FL 34228
    691 Russell St, Longboat Key, FL 34228
    /38

    $8,900 Per Month

    • 3 Beds
    • 2 Baths
    • 2,140 Sq Ft
    • House for Rent

    691 Russell St, Longboat Key, FL 34228

    Experience luxury coastal living in this completely renovated annual rental on the desirable north end of Longboat Key. Situated on an oversized double lot just minutes from the pristine Gulf beaches, this exceptional pool home offers the perfect blend of style, comfort, and convenience.Thoughtfully redesigned from top to bottom, the home features a bright, open-concept floor plan with

    691 Russell St, Longboat Key, FL 34228
  • 3808 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
    3808 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
    /35

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,085 Sq Ft
    • Condo for Rent

    3808 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228

    Completely updated first-floor 2-bedroom, 2-bath condo, just steps from the Gulf of Mexico and Sarasota Bay.Beach Harbor Club offers an array of amenities, including a heated pool, clubhouse, fitness center, bayside dock, community kayaks, kayak lift, and private beach access with beach chairs, lounge chairs, outdoor showers, and gas grills.Enjoy a fun and active social calendar with

    Kathleen Magnus FLORIDA GALLERY REAL ESTATE

    3808 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
  • 510 Golf Links Ln, Longboat Key, FL 34228
    510 Golf Links Ln, Longboat Key, FL 34228
    510 Golf Links Ln, Longboat Key, FL 34228
    /87

    $34,000 Per Month

    • 5 Beds
    • 7 Baths
    • 4,290 Sq Ft
    • House for Rent

    510 Golf Links Ln, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION!! STUNNING LIGHT AND BRIGHT single family home in the very sought after Country Club Shores community of Longboat Key is available for your winter rental. This home has all the bells and whistles and the location can't be beat. Walking in the front door your met with an expansive living room/kitchen/dining room/wine room combination with fabulous floor to ceiling

    C. Alison Hunter JENNETTE PROPERTIES INC

    510 Golf Links Ln, Longboat Key, FL 34228
  • 4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
    4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
    4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
    /78

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Condo for Rent

    4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

    RARE LATE-FALL OPPORTUNITY: NOVEMBER & DECEMBER 2026 AVAILABLE FOR A TWO-MONTH MINIMUM STAY AT $10,000, OFFERING A $8,000 SAVINGS. START EVERY DAY ON VACATION WITH A SUNRISE AND END IT WITH A SUNSET. From the first light of sunrise dancing across Sarasota Bay to the breathtaking sunsets over the Gulf of Mexico, this penthouse offers the best of both worlds, and the very essence of Longboat Key

    Debby McCaig COLDWELL BANKER REALTY

    4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
    /24

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,046 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228

    This charming turnkey 2-bedroom, 2-bath condo is perfectly positioned between the Gulf of Mexico and Sarasota Bay, offering breathtaking sunrise and sunset views. Enjoy deeded beach access complete with lounge chairs, picnic tables, charcoal grills, and outdoor showers. On the bayside, recent upgrades include a new dock, community kayaks, an electric kayak launch, and a fishing pier with a

    Kathleen Magnus FLORIDA GALLERY REAL ESTATE

    3806 Gulf of Mexico Dr Unit 209, Longboat Key, FL 34228
  • 561 Tarawitt Dr, Longboat Key, FL 34228
    561 Tarawitt Dr, Longboat Key, FL 34228
    561 Tarawitt Dr, Longboat Key, FL 34228
    /56

    $4,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • House for Rent

    561 Tarawitt Dr, Longboat Key, FL 34228

    Welcome to this beautiful waterfront property in Longboat Key, freshly renovated and ready for its next occupant. Upgrades include a hurricane-proof front door, fresh paint, and a kitchen with brand-new appliances. A washer and dryer are also included. Both bedrooms have their own bathrooms, and a bonus room off the living room with pocket doors could serve as a third bedroom or office. The

    Edward Holloway INTEGRITY REAL ESTATE SERVICES LLC

    561 Tarawitt Dr, Longboat Key, FL 34228
  • 3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    /45

    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,175 Sq Ft
    • Condo for Rent

    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

    LONGBOAT KEY...Lovely 2 bedroom 2 bath penthouse located on the top floor in Building B directly across from the private beach. Updated kitchen with stainless steel appliances and master and guest bathrooms with ceramic tile and marble. Split floor plan, master suite with a king size bed and the guest room can be used as an office, den or bedroom with its king size murphy bed and a private

    Teresa Ribaudo JENNETTE PROPERTIES INC

    3804 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
  • 3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
    /57

    $10,500 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228

    Luxury Seasonal or Annual Rental in Grand Bay– Longboat KeyExperience unparalleled luxury and breathtaking views from this stunning 9th-floor condominium at Grand Bay. From sunrise to sunset, enjoy panoramic vistas from your private wraparound balcony or through the floor-to-ceiling sliding glass doors that frame the living room. Designed for both relaxation and sophistication, this residence

    Desiree Doggett NEXTHOME EXCELLENCE

    3040 Grand Bay Blvd Unit 292, Longboat Key, FL 34228
  • 5801 Gulf of Mexico Dr, Longboat Key, FL 34228
    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
    /56

    $19,975 Per Month

    • 4 Beds
    • 3 Baths
    • 4,000 Sq Ft
    • House for Rent

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228

    Welcome to your own Gulf-front retreat on Longboat Key!This expansive 4-bedroom, 3-bath home offers over 4,200 square feet of living space designed for relaxation, entertaining, and soaking in stunning beach views.Inside, you’ll find an open living and dining area with vaulted ceilings and multi-level walls of windows that bring in natural light and frame the Gulf.The

    5801 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 2934 Gulf of Mexico Dr, Longboat Key, FL 34228
    2934 Gulf of Mexico Dr, Longboat Key, FL 34228
    2934 Gulf of Mexico Dr, Longboat Key, FL 34228
    /39

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,433 Sq Ft
    • Condo for Rent

    2934 Gulf of Mexico Dr, Longboat Key, FL 34228

    Spend your season in the sun in this unique treehouse condo at Seaside Gardens on beautiful Longboat Key! This 2 bed/2 bath totally remodeled condo is a true island retreat situated to capture coastal breezes and brilliant light defining the true meaning of light and airy. Literally a stone’s throw away from the shoreline, it’s wrap-around decks extend indoor/outdoor living nearly to the lush

    Bridget Gennett JENNETTE PROPERTIES INC

    2934 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 714 Norton St, Longboat Key, FL 34228
    714 Norton St, Longboat Key, FL 34228
    714 Norton St, Longboat Key, FL 34228
    /39

    $12,000 Per Month

    • 3 Beds
    • 3 Baths
    • 1,518 Sq Ft
    • House for Rent

    714 Norton St, Longboat Key, FL 34228

    Offered fully furnished and turnkey for lease terms from 6 to 12 months, this private Longboat Key canal-front retreat captures a dreamy beach lifestyle while blending original mid-century character with elevated coastal charm. The bright, open interior is thoughtfully furnished for comfort and entertaining, with ceiling fans throughout, a fully stocked kitchen and a brand-new appliance package.

    Traci de Wid RESIDENTIAL WEALTH PARTNERS

    714 Norton St, Longboat Key, FL 34228
  • 2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
    /19

    $2,700 Per Month

    • 2 Beds
    • 1 Bath
    • 695 Sq Ft
    • Condo for Rent

    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228

    Enjoy the best of the Longboat Key lifestyle from this charming fully furnished, turnkey 2-bedroom, 1-bath condo. Ideally located along Gulf of Mexico Drive with beach access directly across the street within walking distance! It offers a warm, inviting space with everything you need for a relaxing extended stay. The open living and dining area features comfortable seating, a dining table, plenty

    Deserea Hardy ROSSI & COMPANY INC

    2850 Gulf of Mexico Dr Unit 2, Longboat Key, FL 34228
  • 537 Outrigger Ln, Longboat Key, FL 34228
    537 Outrigger Ln, Longboat Key, FL 34228
    537 Outrigger Ln, Longboat Key, FL 34228
    /12

    $7,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,305 Sq Ft
    • House for Rent

    537 Outrigger Ln, Longboat Key, FL 34228

    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

    537 Outrigger Ln, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
    /26

    $2,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 761 Sq Ft
    • House for Rent

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228

    AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. $2000 PRICE LISTED IS FOR SEPTEMBER-DECEMBER ONLY. REACH OUT FOR SEASONAL RENTAL PRICE. Beach Harbor Club – Turnkey Furnished Gulf-View Condo. Welcome to your seasonal coastal retreat at the highly desirable Beach Harbor Club on Longboat Key. This beautifully appointed 1-bedroom, 1.5-bath furnished condo offers the perfect blend of

    3802 Gulf of Mexico Dr, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /52

    $14,500 Per Month

    • 3 Beds
    • 3 Baths
    • 1,498 Sq Ft
    • Condo for Rent

    Unlisted Address

    Pricing: In-Season: $14,500/month (60 Day Minimum) | Off-Season: $9,450/month | All rates include taxes and feesSunset at Banyan Bay is a beautifully appointed 2nd-floor Gulf-front condominium in the coveted Banyan Bay community on Longboat Key — one of Florida's most serene Gulf Coast barrier islands. This 3-bedroom, 3-bathroom residence sleeps up to 8 and offers sweeping views of the

    Dave Holt PMI SOUTHWEST FLORIDA

    Unlisted Address
  • 6700 Gulf of Mexico Dr Unit 117, Longboat Key, FL 34228
    6700 Gulf of Mexico Dr Unit 117, Longboat Key, FL 34228
    6700 Gulf of Mexico Dr Unit 117, Longboat Key, FL 34228
    /51

    $4,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,449 Sq Ft
    • Condo for Rent

    6700 Gulf of Mexico Dr Unit 117, Longboat Key, FL 34228

    RARE UNFURNISHED ANNUAL Longboat Key Whitney Beach 2-bedroom, 2 full bath 1st floor end-unit located on the serene north end of Longboat Key. This waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou from Livingroom, master bedroom, dining area and kitchen. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout,

    Kim Blakeney JENNETTE PROPERTIES, INC.

    6700 Gulf of Mexico Dr Unit 117, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
    /44

    $12,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,470 Sq Ft
    • Condo for Rent

    2425 Gulf of Mexico Dr, Longboat Key, FL 34228

    Escape to the beauty of Southern Longboat Key with this stunning direct Gulf front vacation rental. From the moment you step into this fourteen-floor residence at Sea Gate, you will be captivated by the breathtaking views from every room. Relax on the lanai with new glass railings and enjoy your morning coffee while you plan your daily adventures. This beautifully renovated two-bedroom, two-bath

    2425 Gulf of Mexico Dr, Longboat Key, FL 34228
  • 6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
    /50

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,367 Sq Ft
    • Condo for Rent

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228

    Available September 1, 2026 through January 31, 2027 with a one-month minimum rental. Experience the best of Longboat Key in this beautifully renovated and newly furnished 2-bedroom, 2-bathroom condo. Simply pack your flip-flops and beachwear and settle into the relaxed island lifestyle. Residents enjoy an impressive array of resort-style amenities, including two heated swimming pools, tennis and

    Kelly Baldwin COLDWELL BANKER REALTY

    6750 Gulf of Mexico Dr Unit 171, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /41

    $11,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,409 Sq Ft
    • Condo for Rent

    Unlisted Address

    Experience the best of Longboat Key living in this beautifully updated, turnkey furnished 2-bedroom, 2-bath residence located behind the gates of the sought after Longboat Key Club. This light-filled condominium features brand-new countertops, new appliances, and an open, inviting floor plan designed for effortless coastal living. Enjoy partial Gulf views and beautiful bay vistas from two private

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    Unlisted Address
  • 706 Spanish Dr S, Longboat Key, FL 34228
    706 Spanish Dr S, Longboat Key, FL 34228
    706 Spanish Dr S, Longboat Key, FL 34228
    /34

    $4,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,423 Sq Ft
    • Condo for Rent

    706 Spanish Dr S, Longboat Key, FL 34228

    Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after, active 55+ community of Spanish Main Yacht Club! Ideally situated just steps from the marina, this 2-bedroom, 2-bathroom villa features a bright Florida room and a fully stocked kitchen, providing a refined yet comfortable living experience from the moment you arrive. It is

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    706 Spanish Dr S, Longboat Key, FL 34228
  • 2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
    /34

    $3,500 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,590 Sq Ft
    • Condo for Rent

    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228

    Welcome to 2012 Harbourside Dr, a beautifully located home within the Bay Isles community on Longboat Key. This spacious residence provides access to the best of Florida’s coastal lifestyle, including a nearby marina, private golf course, pool, and spa. Enjoy the serenity of this gated community, which offers privacy and proximity to the scenic Sarasota Bay. Just a short drive from the cultural

    Alex Larchenko KELLER WILLIAMS ON THE WATER S

    2012 Harbourside Dr Unit 2102, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /67

    $13,500 Per Month

    • 2 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    **Prime Location – Luxurious Waterfront Living at Promenade, Longboat Key**This absolutely gorgeous condo is located in the prestigious Promenade on Longboat Key, offering breathtaking water views from every room. The residence features 2 bedrooms plus a den and 2 bathrooms. The spacious master suite includes a king-size bed and an elegant en-suite bathroom with a separate bathtub, walk-in

    Elsie Salazar BERKSHIRE HATHAWAY HOMESERVICE

    1211 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228
    /36

    $11,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,602 Sq Ft
    • Condo for Rent

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228

    AVAILABLE DEC. '26 THROUGH FEB.'27. Beautiful 9th floor, 1600 sq. ft. 2 bedroom 2 bath at the sort after Beaches condominium which is within the gates of the Longboat Key Club. Updated kitchen and bathrooms. Fabulous bay, and Longboat Key Club golf views. Wrap around balcony with partial Gulf view. Washer/dryer in the unit, pool, fitness center and tennis courts plus 24 hr. Concierge and garage

    Brenda Cozy COLDWELL BANKER REALTY

    775 Longboat Club Rd Unit 904, Longboat Key, FL 34228

Showing Results 1 - 40, Page 1 of 4

Florida Sarasota County Longboat Key

Newest Homes for Rent in ZIP Code 34228

How to Rent a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group