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Longboat Key, FL Condos for Rent

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  • 1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
    /32

    $5,000 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228

    Beachfront Longboat Key Luxury Living. Wake up every day to sweeping **Gulf views** from this beautifully renovated **5th-floor beachfront residence**. Designed for comfort, tranquility, and effortless coastal living, this 12-month annual rental places you steps from the sand and moments from the world-class dining and boutique shopping of **St. Armands Circle**. Property Highlights*Direct

    Donna Channey WAGNER REALTY

    1050 Longboat Club Rd Unit 506, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
    /31

    $5,000 Per Month

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

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228

    AVAILABLE OFF SEASON AND SEASONAL. RENTAL MAY 1, 2026 THROUGH November 30, 2026 AT $5000 A MONTH AND SEASONAL JANUARY 1, 2027 THROUGH APRIL 30, 2027 for $7500. Located the furthest South Behind The Gates of Longboat Key Club. Privateer North Complex located o Gulf of Mexico. Only a few steps to the beach. This 2 bedroom 2 bath residence has everything you need. Beautiful full Bay from this 8th

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
    /31

    $9,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,336 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228

    Available March 2026. Experience unparalleled Gulf-front living in this beautifully renovated 2-bedroom, 2-bathroom condo at Tiffany Plaza. Spanning 1,336 sq ft, this fully furnished residence boasts luxury vinyl flooring, a modern kitchen with marble countertops, and a spacious lanai offering breathtaking views of the turquoise waters of the Gulf of Mexico . The master suite features a

    Shaun Cumston STERLING REALTY

    4325 Gulf of Mexico Dr Unit 406, Longboat Key, FL 34228
  • 914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
    /31

    $6,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,341 Sq Ft
    • Condo for Rent

    914 Spanish Dr S Unit 76, Longboat Key, FL 34228

    Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the sought-after community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bath residence features all brand-new furnishings and is ideally situated just steps from the marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning

    Geoff Scalera AUM FLORIDA REAL ESTATE LLC

    914 Spanish Dr S Unit 76, Longboat Key, FL 34228
  • 5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    /28

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Condo for Rent

    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

    Breathtaking Direct Gulf views from this second floor condo at Longboat Terrace. This two bedroom, two bath has everything you need to make this your home away from home. Both the master and guest suites have their own private baths and balconies. Enjoy the morning paper at the breakfast nook or entertain in the great room. The brand new living room furniture features a sleeper sofa, perfect for

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    5393 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
  • 655 Cedars Ct, Longboat Key, FL 34228
    655 Cedars Ct, Longboat Key, FL 34228
    655 Cedars Ct, Longboat Key, FL 34228
    /22

    $7,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,244 Sq Ft
    • Condo for Rent

    655 Cedars Ct, Longboat Key, FL 34228

    AVAILABLE. 2026 SEASON.. 90 DAY MIN. ... Kick back and relax while on vacation in this marvelous townhouse located in Cedars East. Cedars East has all the amenities you desire including tennis, fitness center, beach access, swimming, community activities, tiki bar and restaurant on site. The unit has been fully upgraded and has a full gourmet kitchen with breakfast bar. Enjoy sweeping bay views

    Brenda Cozy COLDWELL BANKER REALTY

    655 Cedars Ct, Longboat Key, FL 34228
  • 750 Bayport Way Unit 750, Longboat Key, FL 34228
    750 Bayport Way Unit 750, Longboat Key, FL 34228
    750 Bayport Way Unit 750, Longboat Key, FL 34228
    /45

    $4,250 Per Month

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

    750 Bayport Way Unit 750, Longboat Key, FL 34228

    AVAILABLE IN JUNE FOR 6-MONTHS OR MORE! Turnkey Furnished Rental at Bayport Beach and Tennis Club. You will fall in love with this wonderful Longboat Key Community, featuring one of the most beautiful beach fronts, and Bay front locations on Longboat Key. This well-appointed and tastefully furnished, updated home welcomes you with its understated elegance. Everything inside is new, from the

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    750 Bayport Way Unit 750, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /34

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    2-bed, 2-bath seasonal or annual rental paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy deeded beach access and the community’s private beach area, complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3806 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • 2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
    /30

    $8,721 Per Month

    • 2 Beds
    • 2 Baths
    • 1,461 Sq Ft
    • Condo for Rent

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228

    short stories AVAILABLE NOW... Stunning 2 bedroom 2 bath Longboat Key Gulf front condo with direct sweeping view of the Gulf of Mexico. Every evening enjoy breathtaking sunsets on your private balcony. Start your day with a leisurely stroll on the soft sand beach or take a refreshing dip in the pool. This condo is beautifully furnished and professionally decorated. King size bed in both bedrooms.

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
  • 455 Longboat Club Rd Unit 1, Longboat Key, FL 34228
    455 Longboat Club Rd Unit 1, Longboat Key, FL 34228
    455 Longboat Club Rd Unit 1, Longboat Key, FL 34228
    /75

    $25,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,780 Sq Ft
    • Condo for Rent

    455 Longboat Club Rd Unit 1, Longboat Key, FL 34228

    This EXQUISITE 3 bedroom - 3 1⁄2 bath Penthouse has everything you will ever want in a Luxury Beachfront Condo; an open floor plan with plenty of space for living, dining and entertaining and custom appointments throughout. Natural light fills the condo from the moment you enter the foyer and a large skylight is overhead. Floor to ceiling windows frame the 14’ ceiling’s perimeter creating a

    Teresa Ribaudo JENNETTE PROPERTIES INC

    455 Longboat Club Rd Unit 1, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
    /12

    $9,000 Per Month

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

    2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228

    LONGBOAT KEY, this 2 bed, 2 bath luxury condo with sweeping views of the GULF OF MEXICO, from every room, will truly capture you. Enjoy exquisite sunsets from any room or either private terrace. Interior design by award- winning international artist, with paintings & sculptures from the artist's private collection for your enjoyment. Granite counters & granite inlaid floor tiles in kitchen.

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2425 Gulf of Mexico Dr Unit 4E, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
    /25

    $5,835 Per Month

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

    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228

    Available May-December with a 90 Day minimum at $2,800 per month plus taxes and fees booked for 2024 season. Welcome to Seaside Dream! Beautifully furnished and decorated, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. If you enjoy resort-style living, then the Beach Harbor Club is for you! Situated on Sarasota Bay, you will enjoy refreshing breezes which will

    Andy Moore GULF COAST REALTY & MANAGEMENT

    3806 Gulf of Mexico Dr Unit C210, Longboat Key, FL 34228
  • 1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    /71

    $15,000 Per Month

    • 3 Beds
    • 3 Baths
    • 1,710 Sq Ft
    • Condo for Rent

    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION!!! Gorgeous beach front PENTHOUSE condo available to rent in the sought after Longboat Key community of the Players Club. Enjoy views of the Gulf of Mexico, lush grounds and sparkling sandy beaches from the expansive terrace of this light and bright, corner unit, turnkey furnished condo. The property has three bedrooms, three bathrooms, living room/dining room

    C. Alison Hunter JENNETTE PROPERTIES INC

    1465 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
  • 615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
    /20

    $12,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,293 Sq Ft
    • Condo for Rent

    615 Dream Island Rd Unit 107, Longboat Key, FL 34228

    Welcome to one of the most sought-after condo units in the Harbour Villa Club. This magnificent unit is for rent fully furnished. Opening the front door, you will enjoy a beautiful view of the serene intracoastal waterway and stunning Florida palm trees. No need to mess with an elevator, this first floor unit opens directly to the swimming pool and is only steps away from a 40’ deeded boat slip

    Jerome Henin HENIN REALTY

    615 Dream Island Rd Unit 107, Longboat Key, FL 34228
  • 360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
    /78

    $6,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,298 Sq Ft
    • Condo for Rent

    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228

    Tangerine Bay Club An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5 bath with office/den features views of Sarasota Bay. It is in close proximity to New Pass and the pristine beaches of the Gulf of Mexico. Upgraded Ergon Fall White stone ceramic tile flooring is as beautiful as it is durable. The kitchen will satisfy your

    Karl Helbig SUNREAL ESTATE INC

    360 Gulf of Mexico Dr Unit 312, Longboat Key, FL 34228
  • 3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
    /24

    $2,500 Per Month

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

    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228

    AVAILABLE FOR SEASONAL OR ANNUAL RENTAL. 3 MONTH MINIMUM. 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 comfort, convenience, and island living just steps from the Gulf of Mexico. Inside, you’ll find

    Brigette Marcus NEXTHOME EXCELLENCE

    3802 Gulf of Mexico Dr Unit 204, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
    /31

    $15,000 Per Month

    • 1 Bed
    • 2 Baths
    • 1,556 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228

    Long Term Unfurnished Rental. Experience elevated coastal living in this exceptional unfurnished annual residence at The St. Regis Longboat Key Resort. Accessed via a private elevator, this sophisticated home opens into a dramatic living space defined by soaring ceilings and walls of glass that frame breathtaking views of Sarasota Bay. The expansive living area flows seamlessly to a generous

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1591 Gulf of Mexico Dr Unit 515, Longboat Key, FL 34228
  • 2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
    /25

    $8,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,273 Sq Ft
    • Condo for Rent

    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228

    LONGBOAT KEY...SUNSET BEACH CLUB II. Nicely appointed 2 bedroom, 2 bath condo, turnkey furnished. Entertainment center in the living room with a flat screen TV. King bed in the master and twin beds in the guest room. Lovely view of the Gulf of Mexico and the pool. Capture beautiful sunsets every night from the balcony. This unit is equipped with everything you will need so you can vacation with

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2109 Gulf of Mexico Dr Unit 1402, Longboat Key, FL 34228
  • 2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
    /78

    $6,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft
    • Condo for Rent

    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228

    Now available FOR LEASE at The Islander Club on Longboat Key, this updated 2-bedroom, 2-bath residence offers exceptional value in a true beachfront community.Turnkey and move-in ready, the unit features an open layout with quality finishes, an updated kitchen with stainless steel appliances, wood flooring, refreshed bathrooms, and a spacious 38-foot terrace for outdoor living. The primary

    Richard Ivan WAGNER REALTY

    2295 Gulf of Mexico Dr Unit 54S, Longboat Key, FL 34228
  • 1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
    /32

    $11,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,503 Sq Ft
    • Condo for Rent

    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228

    Seasonal. Not available Jan - April 2025. Amazing sunsets from this fabulous 5th floor, direct Gulf beach front, 2 BD, 2 BA condo. Meticulously maintained, this condo has everything you need for a care-free beach vacation! Master suite features king size bed, private bath with Gulf view. Guest room offers twin sleeping arrangements with private entrance to bath. For your comfort, there's flat

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    1135 Gulf of Mexico Dr Unit 504, Longboat Key, FL 34228
  • 3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
    /66

    $7,200 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Condo for Rent

    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228

    Absolutely beautiful turnkey furnished condo at the sought after Portobello on Longboat Key. The meticulously maintained, light and bright two bedroom, two bathroom unit has a combination living room/dining room, separate kitchen with stainless steel appliances, split bedrooms and a washer and dryer in the unit. Newly renovated bathrooms and kitchen with high end finishes round out this fabulous

    C. Alison Hunter JENNETTE PROPERTIES INC

    3240 Gulf of Mexico Dr Unit 303, Longboat Key, FL 34228
  • 1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    /12

    $30,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,684 Sq Ft
    • Condo for Rent

    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

    Enter the unit from a private elevator which features a spacious, open-plan living area with large windows allowing natural light and incredible views of the surrounding landscape and Sarasota Bay. The lavish living space opens up onto a stunning balcony that overlooks Sarasota Bay and the St. Regis grounds and includes a gas grill. The stylish living area includes high-end furniture with a

    Larry Starr SVN COMMERCIAL ADVISORY GROUP

    1581 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
  • 1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
    /77

    $3,750 Per Month

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

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228

    AVAILABLE IMMEDIATELY PENDING HOA APPROVAL! 2 MONTH MINIMUM! BOOKED FOR JAN-MARCH 2027 SEASON! LUXURIOUS, RESORT STYLE, 2BR/2B CONDO LOCATED IN THE HIGHLY SOUGHT AFTER SEAPLACE COMMUNITY ON LONGBOAT KEY. This gorgeous 4th floor condo comes turnkey furnished and located only three miles north of St. Armand's circle. When you walk in you will be blown away by the light, bright and open feeling the

    Brigette Marcus NEXTHOME EXCELLENCE

    1945 Gulf of Mexico Dr Unit M2414, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
    /30

    $11,769 Per Month

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

    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228

    ..."' short stories. ....on the island of longboat key You are on the beach included is swimming pool...and a world class tennis courtf...looking play with others and league Town of Longboat Key tennis three blocks away...fitness gym.. . This is direct Gulf front unit with interior hallways from the balcony ,the kitchen,the living room couch...Your on the water.. Breathtaking view of the

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2425 Gulf of Mexico Dr Unit 7B, Longboat Key, FL 34228
  • 1000 Longboat Club Rd, Longboat Key, FL 34228
    1000 Longboat Club Rd, Longboat Key, FL 34228
    1000 Longboat Club Rd, Longboat Key, FL 34228
    /25

    $11,000 Per Month

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

    1000 Longboat Club Rd, Longboat Key, FL 34228

    Welcome to your elevated coastal retreat on Longboat Key, located behind the gate of the prestigious Longboat Key Club. Available annually at $9,000/month or seasonally from November through April at $11,500/month, this fully renovated upper-floor residence offers refined living with sweeping Gulf and Bay views from two private balconies. Set within one of the island’s most exclusive beachfront

    Jenna Genovese KELLER WILLIAMS ON THE WATER S

    1000 Longboat Club Rd, Longboat Key, FL 34228
  • 1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
    /48

    $4,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,080 Sq Ft
    • Condo for Rent

    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228

    Seasonal Rental – Beachfront Living at The Privateer on Longboat Key / Escape the cold and enjoy a relaxing winter retreat in this beautifully maintained 1-bedroom, 1-bathroom condo located on the 4th floor of the highly sought-after The Privateer on Longboat Key. This inviting residence offers a bright and open layout, a well-equipped kitchen, and a comfortable, spacious bedroom designed for

    Cody Smith RENT SARASOTA

    1000 Longboat Club Rd Unit 406, Longboat Key, FL 34228
  • 1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    /33

    $18,000 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,143 Sq Ft
    • Condo for Rent

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

    2027 Season Rental Rate will be $24,000. The Residences at The St. Regis Longboat Key offer an exceptional blend of ultra-luxury living and world-class resort amenities on the pristine shores of the Gulf of Mexico. This exclusive beachfront community features exquisitely designed residences with soaring ceilings, floor-to-ceiling glass doors, and panoramic sunrise-to-sunset views. The gourmet

    Melissa Gissinger MICHAEL SAUNDERS & COMPANY

    1591 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
    /35

    $6,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • Condo for Rent

    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228

    AVAILABLE Feb - Apr 2026!!! 1 month minimum. Stunning Gulf views and incredible sunsets await you from this JUST completely renovated 2 bedroom, 2 bath condo on Longboat Key. You’ll fall in love with the contemporary soft-palette, coastal style! The open layout offers a seamless blend of kitchen, dining and living space, perfect for entertaining and relaxing. The gourmet kitchen features

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 203, Longboat Key, FL 34228
  • 2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /20

    $7,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,896 Sq Ft
    • Condo for Rent

    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    Absolutely stunning waterfront turnkey furnished rental property on Longboat Key. This unit features beautiful sunsets daily from your private balcony and there is a shared seating area facing east if you prefer sunrises. This spacious 2/2 split floor plan has been fully renovated and is tastefully furnished. The property boasts amenities such as a beachfront pool, workout room, tennis court, and

    Christian Higgins ANDRE LECLAIR PROPERTIES LLC

    2675 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
  • 3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
    /75

    $7,850 Per Month

    • 3 Beds
    • 3 Baths
    • 2,250 Sq Ft
    • Condo for Rent

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228

    LOCATION AT IT'S BEST!!!!! LUXURY RENTAL in Paradise on LONGBOAT KEY at GRAND BAY. This STUNNING 7th floor condominium has both sweeping WATER VIEWS of SARASOTA BAY and of the spectacular SUNSETS ON THE GULF of MEXICO. Open for a three month or longer stay July through November. Like NEW, this beautifully designed and remodeled this three bedroom luxury residence has recently completed a major

    Patrice Ivan WAGNER REALTY

    3060 Grand Bay Blvd Unit 172, Longboat Key, FL 34228
  • 5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
    /23

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,561 Sq Ft
    • Condo for Rent

    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    Pristine Gulf Beachfront on Longboat Key Welcome to this beautifully updated 2-bedroom, 2-bathroom luxury beachside retreat located in The Shore on mid-Longboat Key. This inviting second-floor condo offers stunning Gulf views and is just steps from the powdery white sand and crystal-clear waters—an ideal setting for a relaxed island getaway. Highlights-Sweeping Gulf views from living room and

    Matt Darak DARAK GROUP INCORPORATED

    5757 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • 1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228
    /25

    $8,000 Per Month

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

    1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228

    Beautiful Beachfront at SEAPLACE Condominium on LONGBOAT KEY. THREE bedroom turnkey FURNISHED READY FOR YOUR THRE MONTH OR LONGER STAY. Primary Bedroom has two full beds, queen in second bedroom, and two twins in the third bedroom. Spacious lanai with beautiful beach views. The Seaplace amenities include two large beachfront pools, fitness center, clubhouse, tennis courts and a great expansive

    Jane Hunter JENNETTE PROPERTIES INC

    1925 Gulf of Mexico Dr Unit G8208, Longboat Key, FL 34228
  • 1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    /83

    $15,000 Per Month

    • 1 Bed
    • 1.5 Baths
    • 1,721 Sq Ft
    • Condo for Rent

    1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

    Annual Furnished Rental Available at The Residences at The St. Regis Longboat Key mark the debut of a truly iconic address — the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico. Welcome home to the legendary service and sophistication of St. Regis, paired with the tranquil allure of a seaside retreat on the exclusive barrier island of Longboat Key,

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    1581 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
  • 455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
    455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
    455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
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    $9,000 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,780 Sq Ft
    • Condo for Rent

    455 Longboat Club Rd Unit 401, Longboat Key, FL 34228

    Welcome to Paradise! Beautiful 3 bedroom 3.5 baths, luxury split floor plan condo on LONGBOAT KEY. Behind the gates of Longboat Key Club, known for its privacy and yet close to St. Armand's Circle for dining, shopping, entertainment & cultural offerings of downtown Sarasota. Located on the south end of Longboat Key, this tastefully furnished 4th floor updated unit offers a partial view of the

    Deserea Hardy ROSSI & COMPANY INC

    455 Longboat Club Rd Unit 401, Longboat Key, FL 34228
  • 2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
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    $6,950 Per Month

    • 2 Beds
    • 2.5 Baths
    • 2,369 Sq Ft
    • Condo for Rent

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228

    Luxury Furnished Longboat Key Retreat with Private Beach Club Access & Golf Course Views. Remodeled 2BR Residence with Elevator, Designer Finishes & Resort-Style Living. Step into elevated coastal living at 2013 Harbour Links Drive, a recently remodeled and beautifully curated 2-bedroom, 2-bathroom residence offering 2,369 square feet of beautifully designed living space on Longboat Key. Offered

    Andrew Clark SECURE DOOR PROPERTY MANAGEMENT

    2013 Harbour Links Dr Unit 2013, Longboat Key, FL 34228
  • 2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
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    $16,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,235 Sq Ft
    • Condo for Rent

    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228

    Wake up to breathtaking Gulf of Mexico views from this beautifully remodeled 2-bedroom, 2-bath oceanfront residence at The Islander Club. Spanning approximately 1,233 sq ft, this turnkey condo offers sweeping panoramic views of the Gulf from the spacious living room and both bedrooms. Step inside to find a thoughtfully updated interior featuring modern finishes, a fully equipped kitchen with

    Michele Conn PREFERRED SHORE LLC

    2301 Gulf of Mexico Dr Unit 102N, Longboat Key, FL 34228
  • 1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
    /23

    $5,000 Per Month

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

    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228

    Turnkey Townhouse on Longboat Key – Resort-Style Living!Live the island dream in this beautifully furnished 2-bedroom, 2.5-bathroom townhouse in the exclusive gated community of Fairway Bay. Located on picturesque Longboat Key, this bright and spacious home offers two ensuite bedrooms for ultimate comfort and privacy.Enjoy private beach access to the stunning Gulf of Mexico, take

    Victoria Campbell LPT REALTY LLC

    1922 Harbourside Dr Unit 1102, Longboat Key, FL 34228
  • 4420 Exeter Dr Unit 208, Longboat Key, FL 34228
    4420 Exeter Dr Unit 208, Longboat Key, FL 34228
    4420 Exeter Dr Unit 208, Longboat Key, FL 34228
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    $5,000 Per Month

    • 2 Beds
    • 2 Baths
    • 1,168 Sq Ft
    • Condo for Rent

    4420 Exeter Dr Unit 208, Longboat Key, FL 34228

    Must read entirely. 2026 RENTAL- Not Available until Nov 2026. Talk about the perfect beach place. Intercoastal view and private easy access to the beach with a private beach house! Longboat Harbour Condominium Association has tennis courts, a fitness center, Kayak launching pads, docks, fishing areas, many pools, private access to the beach on the Gulf of Mexico. Marina slips MAY be available so

    Armando Gonzalez AG REALTY SERVICES LLC

    4420 Exeter Dr Unit 208, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228
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    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228

    2 bed, 2 bath paradise on the stunning Longboat Key, where every amenity you could dream of is at your fingertips! Nestled in the fabulous Beach Harbor Club, this beach-to-bay community is packed with perks. Enjoy the community’s private beach access complete with grills, showers, and comfy beach chairs and lounges. Swim in the heated pool, paddle around on community kayaks, socialize with

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    3806 Gulf of Mexico Dr Unit C211, Longboat Key, FL 34228
  • 3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228
    /22

    $5,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • Condo for Rent

    3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

    Stunning Portobello Vacation 2/2 Condo on Longboat Key. Season rate is $8000 (Jan-Apr) and off season rate is $5500 (May-Dec). Minimum 2 month rental and full months only. This beautiful condo provides easy and relaxed living with gorgeous direct gulf views. Full length screened lanai to enjoy the view. This totally renovated condo features luxurious and relaxed beach style décor, new windows and

    Terri Lindsay LINDSAY LEASING LLC

    3235 Gulf of Mexico Dr Unit 302, Longboat Key, FL 34228

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Florida Manatee County Longboat Key

Condos for Rent in Longboat Key, FL

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