124

Longboat Key, FL Homes for Rent with Pool

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  • 1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
    /46

    $11,250 per month

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Condo for Rent

    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228

    Available May-rest of 2025. Direct Beachfront, Longboat Key remodeled 2/2 Condo in Beachplace. Beautiful Beachplace is a gated community located on the southern end of Longboat Key, FL. Our unit is located in building nine, 4th floor, with a green belt area just to the north, the beach to the west, tennis courts to the East and few steps to the pool/library,rec and workout room. It is one of four

    Jennifer LeBlanc PRECISE REALTY CORP

    1045 Gulf of Mexico Dr Unit 402, Longboat Key, FL 34228
  • 1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228
    /37

    $14,000 per month

    • 2 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • Condo for Rent

    1211 Gulf of Mexico Dr Unit 405, Longboat Key, FL 34228

    Gulf Front Longboat Key Seasonal Rental! Located at the luxurious Promenade on Longboat Key, this sleek and modern 4th floor condo offers stunning gulf views, has two bedrooms, two baths, and is a true split plan. You will love the updated kitchen, with stainless appliances, granite counters, and sparkling tile backsplash. The living and dining areas have wood flooring, a nice contrast to the

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1211 Gulf of Mexico Dr Unit 405, 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

    $9,721 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

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    2105 Gulf of Mexico Dr Unit 3404, Longboat Key, FL 34228
  • 5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
    5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
    5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
    /48

    $11,900 per month

    • 3 Beds
    • 2 Baths
    • 1,731 Sq Ft
    • Condo for Rent

    5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228

    Available February 2025. Looking for a vacation in warm sunny Florida in a condo where you walk directly out onto the deck directly onto the beach? Stay in this 3 bedroom (2 king beds/1 queen), 2 bath condo in Salty Acres with 2 covered parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and recently remodeled. It must be a monthly rental. $6,950 a month April -

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5621 Gulf of Mexico Dr Unit 103, Longboat Key, FL 34228
  • 2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
    /63

    $10,000 per month

    • 2 Beds
    • 2 Baths
    • 1,463 Sq Ft
    • Condo for Rent

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228

    ***NEW VACATION RENTAL LISTING** Rented for Season 2025 February through April 20th.* Booked Dec1st-March 31st. Welcome to your amazing beachfront Longboat Key at Sunset Beach vacation. Sunset Beach is a 3 building complex located directly on Gulf of Mexico and it's powdery sandy beach and perfect sunset views. Guests will find a large gulf front pool, spa, community room for social gatherings,

    Jennifer LeBlanc PRECISE REALTY CORP

    2109 Gulf of Mexico Dr Unit 1203, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
    /40

    $5,500 per month

    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228

    Longboat Key vacation rental, rarely available Tiffany Plaza direct Gulf Front condo with amazing views! As you enter your gaze will be drawn to the turquoise waters of the Gulf of Mexico and the serene beach frontage. This lovely home offers 2 beds & 2 baths, plus a bonus office space with a twin Murphy bed! The kitchen and the baths have been updated, the primary bedroom offers a King bed, walk

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 208, Longboat Key, FL 34228
  • Unlisted Address
    Unlisted Address
    Unlisted Address
    /16

    $6,000 per month

    • 2 Beds
    • 2 Baths
    • 1,257 Sq Ft
    • Condo for Rent

    Unlisted Address

    SEAPLACE on LONGBOAT KEY. Relax and spend your winter days at this tropical seaside paradise. This pretty two bedroom condominium is well appointed with a king size bed in the primary suite. Primary bathroom has a walk in shower. SEAPLACE has all the amenities. to enjoy your stay: Two swimming pools, tennis courts, fitness center, clubhouse, and the most amazing beach on LBK. Just minutes to ST

    Jane Hunter JENNETTE PROPERTIES INC

    Unlisted Address
  • 3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
    /47

    $4,800 per month

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

    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228

    VACATION RENTAL!!! AVAILABLE JAN - MARCH 2026! Spacious 6th floor condo awaits your arrival! This lovely 2 Bedroom, 2 Bath condo is inviting and warm and features an updated kitchen with granite counter tops and appliances. Stunning views await you from most rooms! This bright and airy unit provides views of Buttonwood Bayou and Sarasota Bay whether you're sitting inside or relaxing on your

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    3240 Gulf of Mexico Dr Unit 603, Longboat Key, FL 34228
  • 2369 Harbour Oaks Dr, Longboat Key, FL 34228
    2369 Harbour Oaks Dr, Longboat Key, FL 34228
    2369 Harbour Oaks Dr, Longboat Key, FL 34228
    /99

    $7,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,424 Sq Ft
    • House for Rent

    2369 Harbour Oaks Dr, Longboat Key, FL 34228

    LIVE THE LIFE ON LONGBOAT KEY...in this three bedroom, two-and-a-half bathroom villa in the BAY ISLES gated community. Open floor plan, with vaulted ceilings, hardwood floors throughout. Private screened in pool with a view of the golf course and evening sunsets with plenty of space for entertaining. Kitchen is equipped with everything a cook would need including a separate wet bar with a

    Teresa Ribaudo JENNETTE PROPERTIES INC

    2369 Harbour Oaks Dr, 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 RENTAL JULY 1, 2025 THROUGH NOVEMBER 30, 2025 AT $5000 A MONTH AND SEASONAL JANUARY 2026 THROUGH APRIL 30, 2026 through MAY 30, 2026 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 floor

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 804, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
    /24

    $5,000 per month

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • Condo for Rent

    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228

    Available 07/15/2025 through 12/30/2025. LEASED SEASON JAN, 2026 THROUGH MARCH, 2026. This residence is gulf and bay views through your hurricane sliding doors and a view from every room. Pristine sandy beaches from a luxurious direct front gulf complex. Located in the gated Longboat Key club and Resort. A spacious 2 bedroom, 2 bathroom unit turn-key furnished. Both bedrooms have private lanais,

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 502, Longboat Key, FL 34228
  • 1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
    /42

    $12,000 per month

    • 3 Beds
    • 3 Baths
    • 2,698 Sq Ft
    • Condo for Rent

    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228

    LONGBOAT KEY'S SEAPLACE Enjoy the tropical sea breezes and the magical Water Views from this custom designed THREE BEDROOM spacious corner unit. Beautiful wrap around Lanai terraces with panoramic scenery of the GULF OF MEXICO. Primary Suite-King Bed, Bedroom #2 Suite-King Bed, Bedroom #3- two twin beds. Seaplace is located close to shopping and restaurants and just minutes to ST Armand's Circle

    Jane Hunter JENNETTE PROPERTIES INC

    1925 Gulf of Mexico Dr Unit 309, Longboat Key, FL 34228
  • 500 Schooner Ln, Longboat Key, FL 34228
    500 Schooner Ln, Longboat Key, FL 34228
    500 Schooner Ln, Longboat Key, FL 34228
    /75

    $17,000 per month

    • 2 Beds
    • 2 Baths
    • 1,657 Sq Ft
    • House for Rent

    500 Schooner Ln, Longboat Key, FL 34228

    Booked May 1st- June 16th, July13th-July 27th, Nov 14th-rest of 2025. Must be a one month minimum stay during seasonal months and 2 week minimum stay out of season. Charming, waterfront Longboat Key surprise! This 2 bedroom 2 bath house is sure to impress. Total renovation will bring you delight upon entering. Every detail was thought out from kitchen to bathrooms. Fun, chic, beach inspired

    Jennifer LeBlanc PRECISE REALTY CORP

    500 Schooner Ln, Longboat Key, FL 34228
  • 2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
    /55

    $12,000 per month

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

    2425 Gulf of Mexico Dr Unit 14B, 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,

    Andrey markov ANMARK REALTY LLC

    2425 Gulf of Mexico Dr Unit 14B, Longboat Key, FL 34228
  • 3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
    /55

    $7,000 per month

    • 2 Beds
    • 2 Baths
    • 1,133 Sq Ft
    • Condo for Rent

    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228

    Welcome to Sunset On The Gulf! This gorgeous 2-bedroom, 2-bathroom, third-floor, corner condo offers the perfect location. Located between the bay and the beach, you are bound to have endless adventures. The community of Beach Harbor Club offers resort-style living at its finest. There is a large community pool, a clubhouse with a bar, and a fitness center to get in your morning exercises! You

    Andy Moore GULF COAST REALTY & MANAGEMENT

    3804 Gulf of Mexico Dr Unit 307, Longboat Key, FL 34228
  • 6925 Longboat Dr S, Longboat Key, FL 34228
    6925 Longboat Dr S, Longboat Key, FL 34228
    6925 Longboat Dr S, Longboat Key, FL 34228
    /39

    $30,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,230 Sq Ft
    • House for Rent

    6925 Longboat Dr S, Longboat Key, FL 34228

    Available May-December with a 90 Day minimum at $15,550 per month plus taxes and fees booked for 2024 season. Welcome to The Captain's Quarters! This newly built Luxury Rental Home on Longboat Key has everything for you and your family to enjoy your home away from home! This three-story 3-bedroom, 3.5-bath home boasts top of the line features, Smart Home technology, and beautiful décor

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    6925 Longboat Dr S, Longboat Key, FL 34228
  • 1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
    /41

    $6,000 per month

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

    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228

    Available 07/01/2025 THROUGH 12/30/2025 RENTED SEASON JAN, 2026 THROUGH APRIL, 2026(POSSIBLE ANNUAL)Privateer North PH located Behind the Gates of Longboat Key. GULF VIEWS FROM EVERY ROOM. A top of the line remodel with 2 spacious bedrooms with walk-in closets. The master bedroom ensuite has a king size bed and guest bedroom is a queen size. 2 updated bathrooms with walk-in closets and views of

    Marni Hayden CHROME REALTY LLC

    1050 Longboat Club Rd Unit 1006, Longboat Key, FL 34228
  • 2089 Gulf of Mexico Dr Unit G1204, Longboat Key, FL 34228
    2089 Gulf of Mexico Dr Unit G1204, Longboat Key, FL 34228
    2089 Gulf of Mexico Dr Unit G1204, Longboat Key, FL 34228
    /69

    $12,369 per month

    • 2 Beds
    • 2.5 Baths
    • 1,214 Sq Ft
    • Condo for Rent

    2089 Gulf of Mexico Dr Unit G1204, Longboat Key, FL 34228

    Welcome to Beachfront Paradise! This stunning waterfront second-floor, 2-bedroom, 2.5 bath two-story condo is located in the exclusive community of Seaplace in Longboat Key. The location is everything! This condo is located just 4 miles from St. Armand’s Circle, where you can find various restaurants and boutique shopping. The community of Seaplace is a popular Gulfside community on the Southern

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    2089 Gulf of Mexico Dr Unit G1204, Longboat Key, FL 34228
  • 1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228
    /72

    $11,000 per month

    • 2 Beds
    • 2 Baths
    • 1,839 Sq Ft
    • Condo for Rent

    1485 Gulf of Mexico Dr Unit 109, Longboat Key, FL 34228

    LOCATION, LOCATION, LOCATION!!!!! Gorgeous beach front condo in the sought after Longboat Key community of the Players Club. This light and bright turnkey furnished condo has two bedrooms, two bathrooms, living room/dining room combination, sitting area off the living room, separate sitting room at the front entrance, three lanais with ocean views and a laundry closet with full sized washer and

    C. Alison Hunter JENNETTE PROPERTIES INC

    1485 Gulf of Mexico Dr Unit 109, 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
    /34

    $11,500 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
  • 4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
    /37

    $5,500 per month

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

    4325 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

    Gorgeous Gulf front, turnkey furnished rental in Tiffany Plaza. Walk out to the beach from this lovely updated and exquisitely furnished 2 bed/2 bath condo. Coastal inspired décor, king bed in the primary bedroom, full bed and day bed with trundle in the second bedroom. Smart TV's and Wi Fi make this the perfect winter retreat! Tiffany Plaza offers a sparkling heated pool, club room with sauna,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 102, 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

    $5,000 per month

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

    750 Bayport Way Unit 750, Longboat Key, FL 34228

    Seasonal 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 flooring to the kitchen and baths,

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    750 Bayport Way Unit 750, Longboat Key, FL 34228
  • 4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228
    /23

    $9,587 per month

    • 3 Beds
    • 2.5 Baths
    • 1,336 Sq Ft
    • Condo for Rent

    4325 Gulf of Mexico Dr Unit 507, Longboat Key, FL 34228

    AVAILABLE FEBRUARY, MARCH 2025!!!" short stories'...THIS WONDERFUL PROPERTY IS FOR RENT...NOT FOR SALE...short stories inc...be careful of 3rd party web sites. Stunning direct Gulf front 3 bedroom condo on the quaint island of Longboat Key on Florida's tranquil Gulf Coast. Sunny days and uncompromising beauty awaits you. Experience the island lifestyle of relaxation and escape. Warm ocean

    Gerald Cunningham KELLER WILLIAMS ON THE WATER S

    4325 Gulf of Mexico Dr Unit 507, 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
    /24

    $5,000 per month

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

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

    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 king-sized bed, while the guest

    Shaun Cumston STERLING REALTY

    4325 Gulf of Mexico Dr Unit 406, 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
  • 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
    /43

    $7,500 per month

    • 2 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • Condo for Rent

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

    OPEN FOR SEASON 2026. Also available off season @$3300 per month. Rarely available tranquil 2 bed/2 bath corner unit condo with full bay views at desirable Windward Bay! This light and bright condo is the perfect place to spend your season in the sun in a quiet community directly across the street from the sparkling Gulf of Mexico waters and white sandy beaches of Longboat Key. Walk or bike along

    Bridget Gennett JENNETTE PROPERTIES INC

    4540 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
  • 2045 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    2045 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    2045 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228
    /30

    $8,000 per month

    • 2 Beds
    • 2 Baths
    • 1,265 Sq Ft
    • Condo for Rent

    2045 Gulf of Mexico Dr Unit 313, Longboat Key, FL 34228

    OPEN FOR 2026 SEASON. Live your Florida Dream in this 2 bed/2 bath condo on beautiful Longboat Key! Just steps away from the soft sandy beaches and sparkling waters of the Gulf of Mexico, this unit is one of the closest to the beach of all the Seaplace condos, directly across from the large resort style pool and the beach. Relax on the lanai, have a cocktail, and watch one of our spectacular

    Bridget Gennett JENNETTE PROPERTIES INC

    2045 Gulf of Mexico Dr Unit 313, 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 ½ 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

    $8,000 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
  • 775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
    /37

    $9,000 per month

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

    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228

    AVAILABLE 2025 SEASON. Enjoy beautiful sunsets or sunrises from this spacious 4th floor condo with partial gulf and bay views. This 1600 sq. ft. two bedroom two bath condo is located directly on the sugary beach of Longboat Key with lounge chairs and umbrellas provided. Wrap around balcony with partial Gulf of Mexico and Longboat Key Club golf views. Washer/dryer in the unit, pool, fitness

    Brenda Cozy COLDWELL BANKER REALTY

    775 Longboat Club Rd Unit 405, Longboat Key, FL 34228
  • 1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228
    /51

    $11,000 per month

    • 2 Beds
    • 2 Baths
    • 1,642 Sq Ft
    • Condo for Rent

    1125 Gulf of Mexico Dr Unit 403, Longboat Key, FL 34228

    Rented February and March 2026. New beautiful renovated kitchen with quartz countertops. SEASONAL or ANNUAL Call for Annual rate. BEACHPLACE is one of Longboat Key's most popular vacation rental resorts on the Island. The condo views from this unit look onto the Gulf of Mexico and the well manicured grounds of the community. Relax on the lanai and take in the beautiful gulf views at sunset. The

    Margaret Young JENNETTE PROPERTIES, INC.

    1125 Gulf of Mexico Dr Unit 403, 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. 2025 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

    Brenda Cozy COLDWELL BANKER REALTY

    655 Cedars Ct, Longboat Key, FL 34228
  • 501 Channel Ln, Longboat Key, FL 34228
    501 Channel Ln, Longboat Key, FL 34228
    501 Channel Ln, Longboat Key, FL 34228
    /56

    $17,850 per month

    • 4 Beds
    • 3 Baths
    • 2,349 Sq Ft
    • House for Rent

    501 Channel Ln, Longboat Key, FL 34228

    Booked March through Sep 3rd 2025. Looking for a 3 month renter for January, February, and March or the month of January 2026. This fabulous newly constructed 4 bedroom 3 bath pool home is located on the south end of Longboat Key. Spacious with an open floorplan, the kitchen and family room are perfect to entertain your friends and family. From the stainless steel appliances to the gorgeous

    Jennifer LeBlanc PRECISE REALTY CORP

    501 Channel Ln, Longboat Key, FL 34228
  • 3806 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
    3806 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
    /25

    $6,000 per month

    • 2 Beds
    • 2 Baths
    • 1,027 Sq Ft
    • Condo for Rent

    3806 Gulf of Mexico Dr Unit 111, 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. Seasonal, furnished, 2 bedrooms, 2 bath condo located in Beach Harbor Club on Longboat Key. This ground floor unit is centrally located and minutes away from urban activities with in-unit washer and dryer. The master bedroom features a queen bed, walk-in closet and ensuite

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    3806 Gulf of Mexico Dr Unit 111, Longboat Key, FL 34228
  • 4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228
    /34

    $7,200 per month

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

    4825 Gulf of Mexico Dr Unit 605, Longboat Key, FL 34228

    This magnificent Gulf front vacation retreat sits on the 6th floor of the beautiful Westchester of Longboat Key, boasting expansive full Gulf views. This is a stunning property situated on a 7-acre stretch of white, powdery beaches and meticulously manicured landscape. The amenities can’t be beat and include 2 heated pools, tennis court, Clubhouse, shuffleboard, private Tiki-huts, & covered

    Jaime Barcelo GULF COAST REALTY & MANAGEMENT

    4825 Gulf of Mexico Dr Unit 605, 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
  • 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
    /28

    $10,000 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
  • 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
  • 2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    2425 Gulf of Mexico Dr Unit 7C, Longboat Key, FL 34228
    /25

    $11,900 per month

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

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

    SEASONAL; NOW AVAILABLE Jan - Mar 2026!!! Call now, won't last! From floor to ceiling – you’ll just love the magnificent views from every room plus the 85 inch TV in this direct Gulf front residence. Perched on the seventh floor of Sea Gate, this Southern Longboat community offers gorgeous sand beaches, great location and amazing sunsets! This two bedroom, two bath condominium is beautifully

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    2425 Gulf of Mexico Dr Unit 7C, 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

    $8,000 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. 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 sliding glass doors, new laminate flooring and carpet, new kitchen appliances, three flat screen TVs with HD boxes

    Terri Lindsay LINDSAY LEASING LLC

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

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Homes for Rent with Pool in Longboat Key, FL

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