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Indulge in the ultimate beach escape to “Oceans Blue” located on the *premier corner* of Coconut & Los Cedros in Anna Maria. Oceans Blue is a very short walk (only 0.15 miles) to the gorgeous, white sandy beaches of Anna Maria Island, just north of Pine Ave. This *ultimate beach house*...
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Welcome to West O’ Gulf. This property suffered minimal damage from hurricanes Helene and Milton and is better than ever! If you are ready for a relaxing stay on beautiful Anna Maria Island, then this is the beach house for you! This exceptional custom-built 4 Bedroom 3-bathroom house makes it easy...
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Casa Amiga by Beach Retreats Vacation Rentals 144 Crescent Dr. Anna Maria, FL 34216 City of Anna Maria | 4 Bedrooms | 4.5 Bathrooms | Sleeps 10 | Heated Pool + Jacuzzi | Rooftop Deck | Shared DockLuxury Island Living Near Bean Point Welcome to Casa Amiga, a beautifully designed 4-bedroom, 4.5-bath...
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VRC16-000901Anna Maria Beach House | Beach House Rental on Anna Maria Island | Steps to the Beach* Special promotion! Receive 10% off the rental fee when you book your stay with us! This exclusive offer is available for all remaining 2026 dates. To take advantage of this promotion, please call...
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Bradenton Beach Club is a beautiful Gulf to Bay property that is 1/2 a block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. This beautiful townhouse sleeps up to eight people with 3 bedrooms/2.5 bathrooms, full laundry, elevator, garage, and large...
Featured review
My family and I travel every year for the 4th of July, this year we decided to visit Anna Maria Island. WE LOVED IT! Everything was great, the weather, the relaxed atmosphere, the water temperature and...
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Approximately 40 steps and you'll be at the beach entrance to Anna Maria's sandy, white beach. This property offers convenient access to one of the island's main attractions. As the upper level of a two-unit home, Bean Point Residence Unit A boasts 3 bedrooms/3 bathrooms, providing ample...
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Welcome to Dune Our Thing, your relaxing beachside getaway on Anna Maria Island. This thoughtfully designed unit is all about comfort, convenience, and making lasting memories—just steps from the sand and full of amenities that make your stay easy and enjoyable.The Space: - End unit in a quiet...
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Description Escape to Sandcastle, a stunning Anna Maria Island house with breathtaking beach and water views! This family-friendly retreat boasts a private pool, is steps from the beach, and offers luxurious amenities like a complimentary 6-passenger Golf Cart, BBQ grill, and bikes. Enjoy the perfect...
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35 Steps to the Beach at Runaway Bay 104 is a 1 bedroom/1 bath, ground floor condo that can sleep 4. Featuring the largest heated pool on the island, private beach access, gym, and an array of amazing amenities, this ground-floor condo is your perfect home base on the Gulf Coast. The fully-equipped kitchen...
Featured review
We had a great time on the island. The condo seemed to be completely remodeled. It was comfortable and convenient to the beach, grocery store and restaurants. We like the bottom floor and ready access...
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*This property is formerly known as "Mia Bella" and has been renamed to "Hidden Hammock"Create unforgettable memories at “Hidden Hammock” located on Hammock Road, just north of Pine Avenue, in a *premier deep water canal location* in Anna Maria. Hidden Hammock is a...
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Salty Mermaid Vacation Rental in Anna Maria Island- Even before arriving to Mia Bella, the communication with both Bella and David was incredible. They both go above and beyond to make you feel comfortable...
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Turtle's Bay by Beach Retreats Vacation Rentals 306 Clark Dr Unit B, Holmes Beach, Anna Maria Island VRC17-000006 3 Bedrooms | 3.5 Bathrooms | Sleeps 6 | Heated Pool Pet Friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsDog...
Featured review
Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.
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This 1 BR, four-guest, condo strategically placed within short walks to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) will keep you CHEERFUL your entire stay! Coastal amenities: new King Bed (not pictured), front screened lanai, heated...
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Welcome to your perfect Anna Maria Island getaway. This charming 3-bedroom, 2-bath beach retreat offers a relaxed and comfortable space just steps from everything you come to the island to enjoy.From the moment you arrive, you’ll feel right at home. Leave your car parked and enjoy the convenience...
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Need a GREAT AMI GETAWAY? Just steps from the bayfront park in the City of Anna Maria is a charming island beach house called “La Cocolia” lovingly translated as the "little crab". This property is ready to host you and your family as you enjoy this newly renovated and decorated...
Featured review
The property is centrally located on the island which makes it very convenient. It has everything you need, and was very clean. We would definitely rent it again.
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A few things that make Martinique South Unit 207 special: Gulf-front location in Holmes Beach on Anna Maria Island Heated community pool and relaxing spa Convenient elevator access plus shared gas grills and picnic areas Laundry facilities available on every floor Fresh, professionally cleaned linens...
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Welcome to “Barefoot Mermaid 1” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...
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A few things that make Sunset Penthouse special: Concierge Collection Property Bradenton Beach on Anna Maria Island - Beachfront Top floor of Bradenton Beach Club Community beachfront pool, private elevator Professional Linen Services Complimentary WiFi Beach chairs, beach wagon, & beach umbrella Parking...
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NEW MANAGEMENT! Spend your days at the beach, your afternoons by the pool, and your evenings unwinding at Cheerful North Beach Getaway — a peaceful island villa just a three-minute walk from the soft white sands of the Gulf in Holmes Beach on Anna Maria Island.This freshly renovated 2-bedroom,...
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Crosswind Cottage 312 A 61st Street, Holmes Beach, FL 34217 VRC19-000277 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | Elevator This home can park up to 3 vehicles Elevator Quiet hours at 10p-7a: please respect neighborsWelcome to Crosswind Cottage, a spacious island...
Featured review
Very nice house, everything worked. Two things that were not so wonderful- The pool gets barely any sun coverage daily. There is NO easy way to walk to the ocean. Houses block off and no entry unless...
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Recently Renovated!Welcome to your perfect beach retreat! This beautifully renovated 2 bedroom/2 bathroom condo offers fresh charm with brand new stainless steel appliances, new flooring, and stylish new furniture and decor throughout. Every detail has been thoughtfully updated, and you get to be...
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6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....
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Description Escape to Beach Escape, a charming 3-bedroom, 3-bathroom Mediterranean-style house in the heart of Holmes Beach, Florida. Enjoy easy access to the pristine beach, walkable dining and shopping, and a free trolley stop. This home offers a private outdoor oasis with a heated pool, outdoor dining,...
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Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds and sunsets you'll remember for the rest of your life. This beautifully remodeled 1 bedroom/1 bathroom condo has everything you will need to make everlasting memories of adventure...
Featured review
Everything you would need for a beach vacation. The beach front cafe had live entertainment nightly, a perfect place for sunsets.
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Escape to Beach Bliss, a stunning 4-bedroom, 3-bath waterfront home on Anna Maria Island. Enjoy the perfect blend of luxury and relaxation with a private pool and spa, ideal for soaking up the Florida sun. With beach access and water activities nearby, your dream island getaway awaits.The Space Backyard...
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Top Reasons to Book The Cranes Nest: - Prime Holmes Beach Location on Anna Maria Island - 3 Bedrooms · 3 Bathrooms · 3 Stories - Community Pool Access (Heated Nov–April) - Bikes, Beach Gear & Golf Cart Rental Available - Dog Friendly! (2 Max & Additional Fees Apply) -...
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Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will make preparing meals easy. Spend time grilling on the private patio after a day of fun on the beach.You are just a seashell's throw from the white sands of the Gulf of Mexico, it...
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35 Steps to the Sea at Runaway Bay 112 is a 1 bedroom/1 bath, ground floor condo that can sleep 4. Featuring the largest heated pool on the island, private beach access, gym, and an array of amazing amenities, this ground-floor condo is your perfect home base on the Gulf Coast. The fully-equipped kitchen...
Featured review
This was a very nice condo. Clean and well kept. Very close to the beach and to the pool. Location was everything we wanted. Walking distance to restaurants and the heart of town. Great food, great people....
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Caribbean Surf by Beach Retreats Vacation Rentals VRC 306 67th Street Unit B Holmes Beach, Anna Maria Island 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-Friendly Your Anna Maria Island Bungalow Retreat Welcome to Caribbean Surf, a bright and inviting 3-bedroom, 2-bath bungalow...
Featured review
The home has recently been redone, very comfortable and accomodating with a nice sitting deck and new pool. We had a short walk to a beach access and the location allowed us to visit the north island area...
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A few things that make It's Miller Time special: Concierge Collection Property Golf cart included! Holmes Beach on Anna Maria Island - 7 min walk to Gulf Beaches Spacious heated pool / spa with an in-water dining table Ping pong table, foosball table, EV charger Outdoor seating Gas grill...
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Recently renovated! Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk...
Featured review
Love, Love, Love this beach house. I had reserved it a year in advance and was concerned about coming here during a pandemic but as soon as I arrived I was so happy and relieved to be here. The first...
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This cozy and beautifully updated 2-bedroom, 2-bath condo offers a bright, open floor plan and all the comforts of home - plus a few extras to make your stay unforgettable. After a sun-soaked day at the beach, unwind on the private lanai, the perfect spot to relax and enjoy time with loved ones. Runaway...
Featured review
Location in a gated community. Pretty much had the elevator to our selves. Down side was the elevator broke the day we were leaving and had to haul everything down 4 flights of stairs. But had a nice beach.
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Indulge in the ultimate beach escape to “Mary’s Place” located on Los Cedros, a *premier location* just north of Pine Avenue in the city of Anna Maria. Mary’s Place is a very short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *ultimate beach house* has been...
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Welcome to "Barefoot Mermaid 2" a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft, to white powder sand beaches of the Gulf of Mexico and less than a few flip flop...
Featured review
We booked last minute for a long weekend to get out of the COLD Midwest. Location was exceptional! Literally STEPS to the beach where Pine Avenue dead ends at the GULF. Beach chairs and towels provided....
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Costa Lotta is "home away from home”. All the amenities you will need in this 2,100 sq.ft. home. Costa Lotta is the perfect vacation spot for relaxation on Anna Maria Island! Just 200 steps and you are on a gorgeous, white sandy beach looking at the spectacular Gulf of Mexico! Walking distance...
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Welcome to Bella Luna, where you'll find a beachfront condo boasting two bedrooms and two bathrooms, complete with access to a heated community pool and spa. Whether you prefer basking in the sun on the beach or enjoying the breathtaking Gulf views from indoors, this is the perfect retreat. And don't...
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Beautiful 3 bedrooms/2 baths condo is in the highly sought out Bradenton Beach Club community. It has quality finishes including wood cabinets, solid granite surfaces, stainless steel appliances and quality tile in the living and bathroom areas. So well-appointed with comfortable furniture, fishing dock,...
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Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 8 people with the add-on of the sleeper sofas. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV Charger. Upon entry in both...
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Welcome to Stillpoint, a beautifully designed single-level home just one block from the beach in the heart of Holmes Beach, where island ease meets modern comfort. Thoughtfully laid out and ideal for families or multiple guests, this 3-bedroom, 2-bath getaway is perfectly positioned so you can park the...
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Step into island luxury at this beautifully renovated 2-bedroom, 2-bath vacation retreat, perfectly situated just across the street from the white-sandy shores of Bradenton Beach on Anna Maria Island. Located on the lower level for easy access, Margaritaville at Runaway Bay 137 is a light, bright, and...
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Looking for the perfect beach destination? Well, it doesn't get better than this! This 2 bedroom/2 bath condo, recently updated, is centrally located on Holmes Beach and is only steps from the sparkling gulf waters and white sandy beaches. New floors, new furnishings and decor - this place is your...
Featured review
Location is where it's at! Close to everything, yet on a quiet street. We had a great time celebrating 5 years post cancer! Loved the Island and everyone on it. We didn't want to leave! Loved the way...
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A few things that make Bimini Sunrise special: - Concierge Collection Property - Golf cart included! - Anna Maria on Anna Maria Island - A short walk to Pine Avenue - Spacious heated pool / spa - Rooftop deck, elevator, private dock - Gas grill (propane included) - Professional Linen Service -...
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Welcome to your perfect coastal getaway on beautiful Holmes Beach, just one block from the shimmering Gulf of Mexico with its turquoise-blue waters and powdery white sand. This charming 3-bedroom, 2.5-bath single-family home captures the essence of Anna Maria Island living, featuring soft pastel interiors...
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Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group needs for an unforgettable island escape — from elegant interiors...
Featured review
This home was perfect for our family vacation- great views, clean, well stocked, we will definitely be back! Thank you!
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Wake up to the sound of waves and step straight onto the sugar-white sands of Anna Maria Island. Serendipity Gulf is your private beachfront sanctuary on the coveted north end—where relaxed bohemian style meets unforgettable Gulf views.Just completed: a stunning beachside heated pool, perfectly...
Distance to beach: 250 feet to About a 50 second walk
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We have last minute openings available at 50% off! Act fast! Won't last! To qualify, you must have 6 or less in your group. Person booking must be no less than 25 years old. NO PETS. Act FAST because this sale ends soon!This home was great before but now it's undergone a 3+ year no expense...
Featured review
We’ve been traveling to Anna Maria Island multiple times a year for the past few years, and this was easily our favorite stay. The location is unbeatable—walkable to the beach with quick access to...
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If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedroom oasis. Located on the idyllic north end, Anchor Splash is a short stroll from the white sandy beaches and warm, aquamarine gulf waters. It's also within walking distance...
Featured review
House is bigger then it looks with the main bedroom/bathroom feeling like its a whole other unit. Had 10 quests 6 being kids under 12. With the pool right there and the beach and bridge street within a...
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Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath duplex is located on the north end of desirable Holmes Beach. This home offers all the comforts of home and is just steps to the beautiful white sandy beach. The kitchen is fully equipped...
Featured review
Overall, I was happy with this place. We stayed there two years ago. It is located a block from the gulf. The beach is nice and quiet. The house is very nice with two walk in showers.Area for improvement...
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Please reach out for a quote or if you have any questions, we respond quickly. Welcome to Sol Y Mar! This bright, newly refreshed 3 Bedroom beach house oasis features the perfect mix of modern decor mixed with touches of mid-century inspired furnishings and original terrazzo floors. Guest will love the...
Featured review
This house had everything we needed! The host and company was very accommodating and worked with us with everything we need. Pool was warm and the backyard was awesome! Plenty of space.
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Perfectly located 2 bedroom/2 bathroom condo is directly across the street from the gulf beaches. Pelican Cove is located in a small, private complex on a very unique part of the Island. It is one of the few condos with views of both the Gulf and the Bay. Pelican Cove is just 40 yards from one of the...
Featured review
Our stay at Pelican Cove 3 couldn't have been better. The condo was clean, steps away from the beach, and check in was a charm. We truly enjoyed our evening view of the beach and the sunsets from our balcony....
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Sunset Landings Unit 5 is a spacious 2 bedroom/2.5 bath townhome with amazing views of the Gulf of Mexico. With just a few steps across the street, you can enjoy the white sandy beaches and numerous fishing piers. There are no buildings to obstruct your view of the beach!This beautiful townhouse sleeps...
You book directly with the owner, so FloridaRentals charges no booking fee or service fee, unlike larger online travel agencies. Here approximately based on the length of your stay.
SHORT STAY
3 nights
all in
$391/night
| $391 × 3 nights | $1173 |
| Cleaning + damage waiver | $250 |
| Tax (13%) | $185 |
| Booking fee | $0 |
| Total | $1,608 |
WEEKLY STAY
7 nights
all in
$292/night
| $292 × 7 nights | $2044 |
| Cleaning + damage waiver | $250 |
| Tax (13%) | $298 |
| Booking fee | $0 |
| Total | $2,592 |
MONTHLY STAY
30 nights
all in
$268/night
| $268 × 30 nights | $8040 |
| Cleaning + damage waiver | $250 |
| Tax (13%) | $1078 |
| Booking fee | $0 |
| Total | $9,368 |
The shoulder months in late spring and early fall bring warm water and lower rates. Anna Maria Island is also popular among snowbirds in the winter because it offers mild temperatures and a relaxed lifestyle.
| Month | Median nightly | Difference from annual | High / low gulf temp | Avg. gulf temp | What’s going on |
|---|---|---|---|---|---|
| January | $337 | -10% | 74° / 52° | 65° | Calm, uncrowded beaches |
| February | $485 | +29% | 76° / 54° | 65° | Cortez Fishing Festival |
| March | $560 | +49% | 79° / 57° | 68° | Springfest arts festival in late February or early March |
| April | $450 | +20% | 83° / 61° | 74° | Sea-turtle patrols begin; temperatures begin to rise |
| May | $369 | -2% | 88° / 67° | 79° | Sea-turtle nesting begins |
| June | $438 | +17% | 91° / 72° | 83° | Ideal beach weather; morning wildlife sightingss |
| July | $450 | +20% | 91° / 73° | 85° | 4th of July Parade and fireworks show |
| August | $323 | -14% | 92° / 74° | 87° | Warmest Gulf water |
| September | $285 | -24% | 90° / 73° | 85° | Peak hurricane season |
| October | $250 | -33% | 86° / 67° | 82° | Bayfest; nesting season ends |
| November | $274 | -27% | 81° / 60° | 76° | Symphony on the Sand; cooler, drier days begin |
| December | $300 | -20% | 76° / 54° | 70° | Tree lighting and holiday boat parade |
Based on the median Anna Maria Island nightly rate on FloridaRentals.com.
For something quieter and more upscale, Longboat Key, the next island south, is a good option.
SRQ is the closest, about 18 miles and 30 minutes from mid-island. Tampa International (TPA) is farther, roughly 50 to 55 miles, but flies more routes, and St. Pete–Clearwater (PIE) falls between the two.
The fare-free island trolley runs Gulf Drive end to end, roughly every 20 minutes, about 6 a.m. to 10:30 p.m. It's all you need to move up and down the island, but if you want to explore the mainland, you’ll need a car.
The lots at Coquina Beach and at Manatee Public Beach in Holmes Beach are free but they close in the evening. Each town writes its own parking ordinance, and tickets or towing are common on private lots, so make sure to read the signs.
Hurricane season runs June through November, peaking in September. Red tide, a Gulf algae bloom, surfaces along this coast
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