Homes for Rent near Anna Maria Elementary School

FULL WATER FRONT NEWLY RENOVATED (internal photos coming soon) and TURNKEY FURNISHED VILLA for SEASONAL LEASE -3 MONTH MINUMUM RENTAL. AVAILABLE STARTING DECEMBER 1, 2025. Seasonal Lease January-April is $7,000 per month (OR inquire about annual or off season option at $5,500/month). Utilities, Cable and Tax included! Waterfront Villa with Full Bay Views in Spanish Main Yacht Club – Experience

Norma Mladineo COLDWELL BANKER REALTY

Available for immediate occupancy! GULF BEACH and BAY ACCESS! This single story end unit is the perfect place to escape the cold winter months and experience Island living on Longboat Key. This 2 bedroom, 2 bathroom condo has a spacious living and dining room combo, which opens to a bright and airy Florida room, perfect for relaxing or entertaining. The Florida room is fully enclosed, and windows

Tanner Frey KELLER WILLIAMS ON THE WATER S

2025 Hurricane-Rebuild! Longboat Key Retreat: Serene 2-Bed, 2-Bath with Home Office! Discover tranquility in this fully rebuilt 2-bedroom, 2-bath Longboat Key home with a built-in home office that may be utilized as a guest bedroom. Nestled on a peaceful corner lot surrounded by lush tropical foliage. Enjoy an open-concept layout featuring a modern kitchen, brand new bathrooms, and a spacious

Keith Gordon ADDVANTAGE

Centrally located on Longboat Key, FL 2bed/2bath stand-alone villa in Spanish Main Yacht Club. Spacious lanai is suitable year-round. Queen bed in guest room and King bed in primary. Villa is FULLY REMOMDELED, with new kitchen appliances and washer/dryer. Deeded beach access is just steps across to Gulf of Mexico Drive. Community pool, Close to many restaurants, Durante Park, and Bayfront Park,

Shawna Baker JENNETTE PROPERTIES INC

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

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

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

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.

Don’t miss this rare chance to rent this Remodeled home on beautiful Anna Maria Island. Inside you will find wonderful designer touches in every room including a gorgeous kitchen perfect for meals with the family. Home Features washer and dryer hook up. Walk down the street for breathtaking views of the Gulf of Mexico and the intercostal waterway. This house is just steps from the beach or

Robert Louloudes STARZ REAL ESTATE, LLC

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

2025 Hurricane-Rebuild! Longboat Key Retreat: Serene 2-Bed, 2-Bath with Home Office! Discover tranquility in this fully rebuilt 2-bedroom, 2-bath Longboat Key home with a built-in home office that may be utilized as a guest bedroom. Nestled on a peaceful corner lot surrounded by lush tropical foliage. Enjoy an open-concept layout featuring a modern kitchen, brand new bathrooms, and a spacious

Keith Gordon GETMOREOFFERS

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

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

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.

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

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

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,

Nataliya Fillers FUTURE HOME REALTY INC

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

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

Rented January-April 2026. 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

Joseph Stephens ONE STEP AHEAD REALTY INC

**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

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

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

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

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

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

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 decor, 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

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 breezes flow through the unit and the peaceful sound of

Gerald Cunningham KELLER WILLIAMS ON THE WATER S

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

Available for immediate move in. Available for 2026 season. The rental rates are as follows: Off Season (May through December): $3,500 per week or $6,500 per month. In Season (January through April): $3,500 per week or $9,500 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

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

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

Brenda Cozy COLDWELL BANKER REALTY

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

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