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Homes for Rent near Anna Maria Elementary School

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  • /11

    $3,200 per month

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

    600 Sutton Place Unit 201, Longboat Key, FL 34228

    Available 6/1/25 **** Sarasota Bay view. 1 Bedroom x 1 1/2 Bathroom Condo. Living Room looks out over the pool that sits on Sarasota Bay. Fully furnished. 90 day minimum rental period. Prefer 6 mo.- 1 year rental. Sutton Place has many amenities including two heated pools, bicycle storage, outdoor grills, Gulf beach access with beach house, 1 assigned parking spot and several shared

    Agent Photo

    Tracy Srodes

    FINE PROPERTIES

    (941) 335-6064

    600 Sutton Place Unit 201, Longboat Key, FL 34228
  • /15

    $2,700 per month

    • 2 Beds
    • 2 Baths
    • 1,023 Sq Ft
    • Condo for Rent

    6300 Flotilla Dr Unit 71, Holmes Beach, FL 34217

    Shellpoint is an active AMI community with pool and tennis courts. This unit is a great rental for someone working on the island who doesn't want the commute on and off every day, or for the new full-time Florida resident who wants to experience Island living. Renovated from top to bottom, this unfurnished condo has warm coastal tones and well-proportioned living spaces. Living on the ground

    Agent Photo

    Stephen Arters

    FINE PROPERTIES

    (941) 206-2079

    6300 Flotilla Dr Unit 71, Holmes Beach, FL 34217
  • /16

    $4,500 per month

    • 2 Beds
    • 2 Baths
    • 1,057 Sq Ft
    • Condo for Rent

    4307 Gulf Dr Unit 103, Holmes Beach, FL 34217

    Property Id: 2004411Cayman Cay is a small boutique condominium located in the most perfect spot of Holmes Beach. Just a 3 min walk to the beautiful white sands, a block from the public beach and the Anna Maria Island Beach Cafe. Two blocks from Publix and shops for gear and restaurants. Half a mile to the Center of Holmes Beach where you will find famous restaurants and small beach gift

    4307 Gulf Dr Unit 103, Holmes Beach, FL 34217
  • /74

    $17,000 per month

    • 4 Beds
    • 3 Baths
    • 2,447 Sq Ft
    • House for Rent

    830 Tarawitt Dr, Longboat Key, FL 34228

    Luxury and Coastal Elegance! This Stunning Turnkey Canal-Front Pool Home was Built in 2015. Situated on the Highly Desired North End of Longboat Key. Featuring 120 Feet of Beautiful Canal Frontage, A 10,000lbs Boat Lift and Deeded Beach Access only Steps Away! Truly A Boater's Paradise! At Almost 2500 Sq. Ft. of Interior Living, The Home Offers 4 Bedrooms, 3 Full Washrooms, 2 Balconies and

    Ian Greenberg BRISTA REALTY LLC

    830 Tarawitt Dr, Longboat Key, FL 34228
  • /7

    $4,500 per month

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

    2601 Gulf Dr N, Bradenton Beach, FL 34217

    Property Id: 1760224Taking applicants now for 2025-26 season. Rent reflects months of Jan-Apr.55+ community with some flexibility on age. This property won't last long due to its high-demand location. Just 50 steps to the beach and free trolley, enjoy all the beauty Anna Maria Island has to offer. ESA pets permitted.

    2601 Gulf Dr N, Bradenton Beach, FL 34217
  • /25

    $10,000 per month

    • 3 Beds
    • 2 Baths
    • 1,454 Sq Ft
    • House for Rent

    6979 Longboat Dr S, Longboat Key, FL 34228

    Escape to your own private garden oasis on beautiful Longboat Key. This home features lush tropical landscaping, a sparkling heated pool, and a spacious screened lanai perfect for outdoor dining and relaxation. Inside, enjoy a chef’s kitchen with premium appliances, including a Wolf range, and newly updated bedrooms and baths — the primary suite offers a brand-new king bed, while the kid’s room

    Rinat Sikdar COLDWELL BANKER REALTY

    6979 Longboat Dr S, Longboat Key, FL 34228
  • /20

    $4,900 per month

    • 2 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    561 Tarawitt Dr, Longboat Key, FL 34228

    Bring your boat and walk to the beach from this beautiful 2 bedroom/2 bath home that sits on a canal to the intercoastal. There is a dock and plenty of seawall with 2 whips on this double lot home for other water toys as well. The home has just had a kitchen renovation with brand new cabinets and appliances. With 1800 square feet inside, there is room to spread out. The back of the property has

    561 Tarawitt Dr, Longboat Key, FL 34228
  • /10

    $3,000 per month

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft
    • Townhouse for Rent

    209 83rd St Unit A, Holmes Beach, FL 34217

    This spacious ground level duplex is approximately 2-3 blocks to gulf beach. Private pool for the enjoyment of B side only. New kitchen, appliances, ready for a new resident!This is an unfurnished annual rental. It includes water, trash, lawn care and pool maintenance.Don't miss this one!!

    Jo Anne Curtan A PARADISE INC REALTOR

    209 83rd St Unit A, Holmes Beach, FL 34217
  • /13

    $2,500 per month

    • 2 Beds
    • 2 Baths
    • 1,760 Sq Ft
    • Townhouse for Rent

    208 Magnolia Ave Unit A, Anna Maria, FL 34216

    Annual Rental – Newly Renovated Island Duplex!Live the dream with this newly renovated 2 Bedroom / 2 Bath Duplex, just steps from the stunning beaches of Anna Maria Island.Unfurnished12-month leaseTenant pays utilitiesPets allowed$2,500/monthEnjoy modern updates, island charm, and unbeatable proximity to the beach. Experience the best of island living—schedule

    Joshua Sato SATO REAL ESTATE INC.

    208 Magnolia Ave Unit A, Anna Maria, FL 34216
  • /20

    $3,200 per month

    • 3 Beds
    • 2 Baths
    • 2,752 Sq Ft
    • Townhouse for Rent

    306 63rd St Unit B, Holmes Beach, FL 34217

    ANNUAL RENTAL. Nice spacious 3bdrm 2bath raised Duplex just blocks to the beach. Extra bonus rooms off the dining area and in the lower level. Primary bedroom with its own bath and private covered deck. Open kitchen in to dinning/ family room area. Large garage space with extra storage for all your beach toys. Application approval required.

    Paige Rogers DUNCAN REAL ESTATE, INC.

    306 63rd St Unit B, Holmes Beach, FL 34217
  • /22

    $2,600 per month

    • 2 Beds
    • 1 Bath
    • 760 Sq Ft
    • Townhouse for Rent

    2909 Gulf Dr Unit A, Holmes Beach, FL 34217

    Newly remodeled Home On Anna Maria Island. Blocks from the beach access.

    Robert Louloudes STARZ REAL ESTATE, LLC

    2909 Gulf Dr Unit A, Holmes Beach, FL 34217
  • /47

    $6,000 per month

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

    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    Furnished beachfront vacation rental! This spacious (1336 sq ft + balcony) condo is a luxurious living space that offers breathtaking panoramic views of the beach, sunset, and Gulf of Mexico. It is located in a smaller building, on an uncrowded segment of beach that can often be enjoyed in complete solitude. The unit was recently upgraded with a new washer/dryer, luxury vinyl flooring in the

    Daniel Goldman COMPASS FLORIDA LLC

    4325 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • /18

    $4,450 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    640 Broadway St, Longboat Key, FL 34228

    Hurricane rebuild completed in 2025. Discover tranquility and comfort at our serene 3-bedroom, 2-bath home, nestled among lush tropical foliage on a peaceful corner lot in Longboat Key. Inside, experience a welcoming open floor plan with a brand-new living room, modern kitchen, and clean-cut updated bathrooms. Master bedroom features wet bar with mini fridge & windowed ensuite bath. The backyard

    Keith Gordon GETMOREOFFERS

    640 Broadway St, Longboat Key, FL 34228
  • /60

    $6,900 per month

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • House for Rent

    535 Forest Way, Longboat Key, FL 34228

    Welcome to your perfect coastal escape in the heart of Cedars East on Longboat Key, Florida! Professionally managed by Gulf Coast Vacation Rentals, this chic, playful, and stylish 3-story, 2-bedroom, 2-bathroom townhome is nestled in one of the island’s most sought-after communities—offering a unique blend of tropical charm, resort-style amenities, and a peaceful coastal atmosphere.Step into

    Andy Moore GULF COAST REALTY & MANAGEMENT

    535 Forest Way, Longboat Key, FL 34228
  • /33

    $2,950 per month

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

    3607 E Bay Dr Unit 206, Holmes Beach, FL 34217

    Furnished Annual Rental Available July 1, 2025. Close distance to Holmes Beach! Spacious and bright 2 bedroom, 2 bath condo with Water Views. This amazing unit features a carport and two storage areas. Updated Kitchen & Baths, Laminate floors, and lovely furnishings. Relax and enjoy the Gulf, Preserve & Intercoastal views from the screened balcony. High Ceilings, Granite counters, Stacking washer

    Kathy Liga RE/MAX ALLIANCE GROUP

    3607 E Bay Dr Unit 206, Holmes Beach, FL 34217
  • /28

    $5,500 per month

    • 3 Beds
    • 3 Baths
    • 2,154 Sq Ft
    • House for Rent

    606 N Point Dr, Holmes Beach, FL 34217

    Annual rental. Great for boaters. Beautiful single-family home on North Point of Key Royal. This 3 bdrm 3 full bath home sits on a quiet canal in Holmes Beach. Features include a large updated eat-in kitchen, vaulted ceilings, arches, columns, 2-sided fireplace, wet bar and a large screened in lanai. Great master suite with jacuzzi and fireplace. A heated community pool and tennis courts. Pet

    Paige Rogers DUNCAN REAL ESTATE, INC.

    606 N Point Dr, Holmes Beach, FL 34217
  • /17

    $5,500 per month

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

    Unlisted Address

    Merging classic elegance with modern luxury featuring high vaulted ceilings, a state-of-the-art kitchen, high-speed internet, and a cutting-edge reverse osmosis water system. Enjoy the convenience of an in-closet washer/dryer and UV air filtration for pristine air quality. Perfect for romantic getaways or peaceful solitude, with boat parking & public launch nearby. The property offers a furnished

    Keith Gordon GETMOREOFFERS

    Unlisted Address
  • /18

    $7,850 per month

    • 2 Beds
    • 2 Baths
    • 2,331 Sq Ft
    • House for Rent

    701 Broadway St, Longboat Key, FL 34228

    Newly remodeled bungalow blocks from Whitney Beach & a block from bay. Historic home was once a post office in the 1920's. Open layout w/high ceilings, stainless appliances w/ gas stove. Heated swimming pool & hot tub. Relax & listen to breezy palms smack up against each other in this gorgeous landscaping! Sleep tight in a quiet neighborhood that allows zero public parking. Very serene, private

    Keith Gordon GETMOREOFFERS

    701 Broadway St, Longboat Key, FL 34228
  • /26

    $2,300 per month

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

    2315 Avenue C Unit 7, Bradenton Beach, FL 34217

    Welcome to your slice of paradise! This delightful 1-bedroom, 1-bathroom condo is located just steps from the breathtaking beaches of Anna Maria Island, offering you the perfect coastal retreat. Situated in the charming town of Bradenton Beach, this fully furnished unit provides convenient access to a community pool, ensuring you can enjoy both the beach and poolside relaxation.Just two blocks

    Dakota Magnus FLORIDA GALLERY REAL ESTATE

    2315 Avenue C Unit 7, Bradenton Beach, FL 34217
  • /42

    $7,800 per month

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

    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228

    SEASONAL: Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, in unit washer/dryer, large walk-in closets and covered parking. The Master suite

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 201, Longboat Key, FL 34228
  • /63

    $9,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,048 Sq Ft
    • House for Rent

    4808 Gulf Dr Unit B, Holmes Beach, FL 34217

    Beachside Luxury Rental – 3BR, 2.5BA with PoolLive just steps from the sand at 4808 Gulf Drive Unit B, an upscale and fully furnished 3-bedroom, 2.5-bath home located in the heart of Holmes Beach. Available for starting July 19th, this multi-level coastal retreat blends modern comfort with laid-back island living—perfect for a long vacation or seasonal stay.Step into a bright, open-concept

    Nataliya Fillers FUTURE HOME REALTY INC

    4808 Gulf Dr Unit B, Holmes Beach, FL 34217
  • /30

    $23,000 per month

    • 6 Beds
    • 4 Baths
    • 3,735 Sq Ft
    • House for Rent

    405 28th St, Holmes Beach, FL 34217

    This newly renovated waterfront home has 80 feet of canal frontage including a dock and boat lift for up to 10,000 lbs. Perfect for easy access directly into the bay and located just a short stroll from the beach. Inside you will find a kitchen with high-end appliances overlooking the pool. The open concept living and dining area are perfect for both relaxation and living the island life,

    Amanda Cornett PINEYWOODS REALTY LLC

    405 28th St, Holmes Beach, FL 34217
  • /46

    $3,750 per month

    • 2 Beds
    • 2 Baths
    • 1,169 Sq Ft
    • Condo for Rent

    5200 Gulf Dr Unit 504, Holmes Beach, FL 34217

    Gulf front condo at the Martinique, with two bedrooms, two bathrooms, amazing views of the Gulf through the recently installed floor to ceiling windows in the living area. A unique opportunity to look out over the island from the fifth floor as this is the only high-rise complex around. A heated pool and tennis courts are available as well as elevators for your convenience. Walking distance to

    William Alexander, IV A PARADISE INC REALTOR

    5200 Gulf Dr Unit 504, Holmes Beach, FL 34217
  • /22

    $9,500 per month

    • 2 Beds
    • 2 Baths
    • 1,346 Sq Ft
    • Condo for Rent

    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228

    AVAILABLE MARCH 2025 - APRIL 10 $7,000 30 day lease. Looking for a Beach front vacation in warm sunny Florida in a condo where you walk out onto the deck and directly onto the beach? Stay in this 2 bedroom , 2 bath condo in Salty Acres with 2 parking spaces. It is on the Gulf Side beach with amazing views. Condo is beautiful and is in excellent condition. It must be a monthly rental. $6,950 a

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5621 Gulf of Mexico Dr Unit 102, Longboat Key, FL 34228
  • /30

    $7,000 per month

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

    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228

    SEASONAL/VACATION RENTAL! AVAILABLE FOR 2026 SEASON! CALL TODAY! Stunning Gulf views and beautiful sunsets from this spacious, immaculate turnkey furnished 2-bedroom, 2 bath split plan corner unit. Featuring 2 tiled screen enclosed lanais that overlooking lush garden, pools and, of course, serene beach views. This turnkey residence comes complete with cable & wifi, large walk-in closets and

    Diann Thelen GULF COAST RENTAL HOMES&CONDOS

    4825 Gulf of Mexico Dr Unit 202, Longboat Key, FL 34228
  • /38

    $4,500 per month

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

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228

    This immaculate 2-bedroom, 2-bath ground-floor villa located in the highly sought-out community of Windward Bay has peek-a-boo views of the Gulf. Turnkey furnished with one carport at your front door. The community of Windward Bay is pristine. There is private deeded beach access just across the street, two public beach access, two marinas BBQ grills, 1/2 mile of walking trails, two heated pools,

    Joseph Stephens ONE STEP AHEAD REALTY INC

    4780 Gulf of Mexico Dr, Longboat Key, FL 34228
  • /39

    $10,500 per month

    • 3 Beds
    • 2 Baths
    • 1,576 Sq Ft
    • Condo for Rent

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228

    **BEST WATER VIEWS - Enjoy a warm Winter Escape at this expansive 3 bed 2 bath LONGBOAT KEY PENTHOUSE BEACHFRONT CONDO!** **AVAILABLE to lease JANUARY and FEBRUARY 2026 with the option to include APRIL 2026** Welcome to your dream winter retreat, where you can bask in the beauty of the Gulf of Mexico right from your living room. This pristine, 2-bedrooms +Den/Office with Sleeper Sofa and 2-bath

    Norma Mladineo COLDWELL BANKER REALTY

    4485 Gulf of Mexico Dr Unit PH2, Longboat Key, FL 34228
  • /35

    $8,500 per month

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

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

    BEAUTIFULLY RENOVATED VACATION RENTAL: 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
  • /51

    $5,500 per month

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

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228

    Available rental for July 15, 2025-October 2025 ONLY! 60 Day Minimum Lease. Fully remodeled and impeccably furnished with Gulf views on Longboat. Situated on the top floor, this 2 bedroom, and 2 bath residence presents coveted views of the beach and Gulf of Mexico! Take note, that the clear, Caribbean blue waters and white sand beaches are not upstaged by the finishes in this redesigned floor

    Scott Nold TNG PROPERTY MANAGEMENT

    5757 Gulf of Mexico Dr Unit 305, Longboat Key, FL 34228
  • /39

    $14,000 per month

    • 3 Beds
    • 2 Baths
    • 1,675 Sq Ft
    • Condo for Rent

    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228

    DIRECTLY on the GULF. WITH PRIVATE BEACH .Be Prepared for style, relaxation and Longboat luxury. This stunning boutique condominium renovated in 2024 and located on Longboat Key's Gulf of Mexico Beach. Its newly designed layout emphasizes the magnificent ocean view throughout its open floor plan that is visible from the time you walk in the door, through the beautiful dining area, upscale

    William Glade WILLIAM GLADE LIC. REAL ESTATE BROKER

    5611 Gulf of Mexico Dr Unit 1, Longboat Key, FL 34228
  • /39

    $12,000 per month

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

    4325 Gulf of Mexico Dr Unit 408, Longboat Key, FL 34228

    Longboat Key Gulf Front Vacation Rental! Gorgeous views from every window, 2 beds, 2 baths, fourth floor end unit in the wonderful boutique-style community of Tiffany Plaza. Look no further for your perfect vacation retreat, located directly on the Gulf of Mexico, this lovely condo has all you need. The updated kitchen has a center Island with breakfast bar, farm-style sink, and stainless steel

    Stephanie Deshaies PREMIER SOTHEBY'S INTERNATIONAL REALTY

    4325 Gulf of Mexico Dr Unit 408, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /68

    $7,000 per month

    • 3 Beds
    • 2 Baths
    • 1,673 Sq Ft
    • Townhouse for Rent

    305 57th St Unit A, Holmes Beach, FL 34217

    Available starting 8.4.25. Available for 2026 season. The rental rates are as follows: Off Season (May through December): $3,500 per week or $7,000 per month. In Season (January through April): $3,500 per week or $10,000 per month. The vacation home is beautifully renovated and elevated, with three bedrooms and two bathrooms. It features a large pool and spa in a tropical backyard oasis. The

    Jonathan OSteen O'STEEN GROUP INC

    305 57th St Unit A, Holmes Beach, FL 34217
  • /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
  • /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

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