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My wood-frame beach cottage was built in 1936, and was originally part of 6-8 cottages and a lodge house. It is the only surviving cottage, many having been taken by hurricanes. (Forward of the cottage’s beach, a street and an entire city block of the old subdivision are submerged beneath the...
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We are so fortunate, and grateful, that we had the opportunity to stay at The Walker Family Cottage. I definitely have to say that the pictures online do not do it justice. The location is absolute paradise,...
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Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 3 has garden views and is just a few steps to the beach.It features 1 bedroom with king size...
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Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 4 has garden views and is just a few steps to the beach.It features 1 bedroom with king size...
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Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 1 has direct views of the Gulf of Mexico and is just a few steps to the beach.It features 1...
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This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...
Featured review
Loved this rental. Close to beach and has a pool. Pet friendly too. Roomy and well stocked with kitchen items as well as towels.
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Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. PLEASE INQUIRE AS TO AVAILABILITY OF UNIT TYPE, AS WE ARE UNABLE TO DELINEATE ON WEBSITE, THANKS! Each studio unit sleeps two with a queen-size bed and has a full kitchen. One-bedroom units sleep...
Featured review
We recently stayed in one of the bay side units for vacation. This place is the best of both worlds. We had a view of water from our balcony but the private beach for the ocean was right across the road....
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Welcome to Sailfish Nest A, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax...
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This well appointed condo on Anna Maria is ready for rent! Everything you need is here for you. Pack some clothes and come to the beach! The condo is fully stocked with pots and pans and virtually any kitchen appliance you will need. We include house towels, beach towels, a washer and dryer and two TV's....
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Welcome to paradise- AMI VILLA! When you come to Anna Maria Island for vacation, make this charming Mediterranean beach 3 bedroom & 3 bath villa your home away from home! With much to offer, this home will have your family wanting to return to Anna Maria Island year after year.Features include: -3...
Featured review
This house is perfect for a large family. 3 bedrooms and 3 full baths. Close to the beach and provides everything you need! Chairs, umbrellas and a wagon to use to transport everything. Even an ice...
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This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island!As you step through the front door, you enter a bright and...
Featured review
I’d give it a 10 star! Absolutely perfect vacation rental! About a block and a half from beach no busy road to cross to get there! We could see the ocean from the front porch. The home is clean, fully...
Distance to beach: 0.1 miles to 30 seconds to your left
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Temp Promo: Book 7 nights or more with us by September 30, get a free 6P Bintelli Golf Cart for your stay! Normally $1225! Mention "Free Golf Cart" to have it added onto your reservation.This newly redesigned elevated pet friendly 3 Bedroom, 2 Bathroom home is beautifully appointed throughout,...
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Located on 5th Avenue in Holmes Beach this unit is out of the way on a dead end street. Seaduction offers a heated pool, and every amenity to make your stay here a comfortable one. There are only 4 units in the complex so to pool is "semi private".This beautiful unit sleeps six with a king...
Featured review
Wir haben eine Woche in der Wohnung auf Anna Maria Island verbracht. Es war traumhaft schön. Die Wohnung ist sehr gut ausgestattet: vom Eiswürfelspender bis zur Waschmaschine, vom Strandwegen mit Stühlen...
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This spacious 2 bedroom condo is close to the beach and in the heart of it all. This stunning condo offers everything you want in a beach retreat. The unit has ample space your family. The open concept living area is perfect for entertaining, with a kitchen featuring all new appliances. You can also open...
Featured review
Location was perfect! Condo had everything we needed, nicely decorated and clean. Morgan was wonderful to work with. Thanks Morgan!
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This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...
Featured review
We spent a wonderful month in this unit. You can see the beach from the front balcony as it's just across the street. It's very spacious with an open concept living room, kitchen and dining area. It...
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Welcome to Sailfish Nest B, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax...
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Have the best of both worlds with the bay & the gulf beaches at this new 4 bed/3.5 bath luxury home. Enjoy the quiet, laid back way of life on the north end of the island being only steps to the gorgeous bayside beach with city park or a 5 minute walk to the world renowned Bean Point! You are also...
Featured review
The entire stay was above all expectations. It was my wife's birthday. We invited friends from out of town to celebrate with us. The place was roomy and very comfortable. The kitchen is fantastic with the...
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Welcome to Flirty Flamingo — a tranquil retreat on beautiful Anna Maria Island. This inviting duplex home is the ideal spot for couples, families, or friends looking to enjoy the island’s sun-soaked charm and relaxed pace.Each level of the duplex are full floor units (lower and upper...
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New Paint, Furniture and Decor as part of our mini makeover! King in primary bedroom and queen in second bedroom!When you come to Anna Maria Island for vacation, make this charming and inviting two-bedroom condo your home away from home! You're sure to love the relaxed island attitude with amenities...
Featured review
Sandy Point condo was the perfect spot for our getaway! It was clean, comfortable, and in a great location—close to everything but still nice and quiet. We loved the easy beach access and relaxing by...
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Shady Palms is a cozy secluded beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a white, sugar-sand beach and the sparkling Gulf waters. Shady Palms is the most perfect spot you'll ever find on the beach - have the best of both worlds - the sun and the shade.Beach...
Featured review
What a special place. The memories of years line the walls with incredible family. The views simply can’t be captured with a camera even though we tried many times. The sunsets can’t be described and...
Distance to beach: 45 feet to Gulf of Mexico
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Enjoy breathtaking views of Egmont Key, Tampa Bay, and the Gulf of Mexico right from your doorstep! Walk straight ahead and you are on North Bay Boulevard Beach. Walk 4 more lots to the left and you are on Bean Point! Or walk 5 lots further left and you are on the Gulf of Mexico. Perfectly situated next...
Featured review
Review Serenity by the SeaThe Good 1. Location by the ocean is definitely the big draw- - can hear waves from 2 bedrooms- 1 on second and 1 on 3rd floor. No TVs in ocean view bedrooms in case that...
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I try to work with your budget!- please inquire!!! If our cottage is booked, I help people with other cottages- you will love it!Welcome to paradise.....This updated cottage is within a small resort, just steps from a beautiful private gulf beach. Drive into the Tradewinds Resort, and you will find...
Featured review
Everything was so laid back and easy at this adorable little place. It had everything your could want or need. Very clean and the bed and bedding was of very good quality. The location was perfect for the...
Distance to beach: 100 yards to Manatee Beach
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Welcome to our home away from home on the breathtaking Anna Maria Island in the charming town of Holmes Beach Florida. Anna Maria is a barrier island on the Gulf of Mexico with an old time feel.Its only 7 miles long by 3 miles wide.Our condo is on the beach roughly 200 yds from the Gulf.We...
Featured review
The condo faced the water and lovely beach with a nice covered outside area on the second floor. This made our stay enjoyable no matter the weather. Manatee Beach was next door making easy access to food...
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One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO!Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...
Featured review
We truly enjoyed our stay at Kathleen’s house. We had a 11 month and a 3 yr old and it was so nice to have so much baby and kid stuff supplied. We rented a Golf cart which was great to have for transporting...
Distance to beach: 0.1 miles to Bayside Beach
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Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms and 3 Bathrooms...
Featured review
Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was...
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Welcome to "Lazy Manatee" at Bradenton Beach Club, where even the manatees envy the level of relaxation we offer! This spiffy condo boasts three bedrooms and two full baths, giving you more space than a hermit crab's dream home. New decor, furniture and paint!At Bradenton Beach Club,...
Featured review
This spacious condo appears to have been very recently completely renovated and extremely nicely updated. The large space was perfect for our group and we could have easily and comfortably added a couple...
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Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white sandy beaches.The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything...
Featured review
The beach is our happy place and this condo had a beautiful ocean view, lots of windows in the living room. Totally remodeled and very spacious. Beds were very comfortable. Pool was great! And it was a...
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Turtle Tales is your private Anna Maria Island retreat—made for slow mornings, sunny days, and unforgettable sunsets.Step out to your own bay-view sunrise moments, sip coffee in a private outdoor space, and spend your afternoons at sugar-white beaches just steps away. In the evening, enjoy Gulf...
Featured review
What a great stay! The location is perfect, not far from bridge street, restaurants, shops, the bay and the beach!! Anna Maria Island is beautiful and turtle tales is perfect!
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Welcome to Mermaid Manor — a tranquil retreat on beautiful Anna Maria Island. This inviting duplex home is the ideal spot for couples, families, or friends looking to enjoy the island’s sun-soaked charm and relaxed pace.Each level of the duplex are full floor units (lower and upper level...
Distance to beach: 0.1 miles to Beach Access 45th St
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Address of Manatee Watch: 205 N Harbor Drive, Holmes Beach, FL 34217MANATEE WATCH - A marvelous waterfront 3 bedroom/ 2 bath home just a short walk away from an astonishing white sand beach. Heated pool, hot tub and a spacious dock with beautiful views of the canal. Many months each year you can watch...
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Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 2 has direct views of the Gulf of Mexico and is just a few steps to the beach.It features 1...
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Escape to this beautifully decorated beachfront retreat, a 3-bedroom, 2-bathroom vacation rental just steps from the pristine white sands.The living area invites you to unwind after a day at the beach, with comfortable seating and coastal decor that soothes the senses.The fully equipped kitchen has...
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Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 Guests Pricing is for one villaDuring January February & March you can only rent 1 villa. During June & July you must rent both villas. Pricing on our site here is for only 1 villa.The...
Featured review
We had a great time and our kids loved the pool! We rented bikes and used them everyday. We had a party of 12 and it was big enough for all. We would love to stay again!
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Discover Your Perfect Beach Retreat at Bimini Breeze!Pack your bags (and some sunscreen) because you’re about to dive into an unforgettable getaway at Bimini Breeze! This stunning elevated home is just steps away from the pristine beaches of Anna Maria Island. With four bedrooms and three and...
Featured review
What a great home to visit on your Anna Maria Island vacation! Everything was exceptional and we made tons of great family memories together here. Highly recommend!
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Welcome to "Blue Skies" at Bradenton Beach Club!Discover your perfect getaway in this beautifully updated three-bedroom, two-bath condo, designed for families and friends looking to unwind in style. With coastal decor and modern furnishings, you’ll feel right at home from the moment...
Featured review
We absolutely loved Blue Skies at Bradenton Beach! The location was perfect, the condo was spacious and it had everything we needed. We loved the storage closet in the parking area, this made trips to and...
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Less than a minute's walk to the beach!Watch the sunset from the house!King sized bed in every bedroom.PARKING FOR ALL...Bring your boat or RV...Invite guests... There's room for everyone!Shell House is a two-story, 3-bedroom, 2-bath, multi-level fun-house on a extra large...
Featured review
I lived in Holmes Beach for many years. It was always my favorite place to be. When I needed to move I promised myself I would rent and come as often as I could. SunPlaza West has always been my go to...
Distance to beach: 0.1 miles to Beach Access 45th St
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Address of Areca Cove: 206 N Harbor Drive, Holmes Beach, FL 34217ARECA COVE - A bright and wonderful 4 bedroom/ 3.5 bath home just a 3-minute walk away from an astonishing white sand beach. With a heated pool in tropical and private surroundings, a covered patio by the pool area and multiple balconies...
Featured review
Olaf and Marissa were wonderful hosts - welcoming and responsive. Their home was absolutely perfect for a family get together with mixed ages. They have everything you need for a beach stay and the space...
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Palm Cay unit 10 is a two bedroom , one bath condo just 50 steps from the pristine Gulf waters of Homes Beach. There is a shared pool centered in a courtyard surrounded by lush , tropical vegetation. There is a double sofa bed in the living room. The kitchen is fully equipped , including a coffee...
Featured review
The unit was lovely. Well equipped and very clean. The pool area is very nice and a 1 minute walk to a beautiful beach.
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This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island!The decor is a perfect blend of coastal elegance and comfort, featuring...
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Welcome to Tiffany Place 205 on beautiful Holmes Beach on Anna Maria Island! This spacious 2 bedroom, 2 full bath condo has been totally remodeled in a coastal inspired décor, is meticulously clean and well organized and has everything you need to enjoy your vacation directly on the beach.Tiffany...
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Description Escape to Salt + Sol, a stunning 4-bedroom canal-front home on Anna Maria Island. This bright and airy retreat offers a perfect blend of coastal elegance and modern comfort. Enjoy easy access to sugar-white beaches, charming boutiques, and delicious dining options. Relax in the sun-filled...
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PLEASE EXCUSE THE CURRENT PICTURES. We are just finishing the condo and we don't have the bedding or the tvs yet. Just remodeled and ready to go starting February 1st, 2026! Everything you need is here for you. This well appointed condo on Anna Maria is ready for rent! Pack some clothes and come...
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KEY FEATURES:Everything You Need for a Perfect Beach Day Chairs, toys, cooler, wagon, umbrella—you’re covered! Just bring your swimsuit.3 Plush Bedrooms with Smart TVs King, queen, and a twin-over-full bunk room—all with luxe mattresses and streaming-ready TVs.Just a...
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Buckeye Haven is situated in one of the most sought after communities on Anna Maria Island. Playa Encantada is a tropical beach front community with the white sandy beaches of Anna Maria Island! This popular destination is sure to please beach goers, as well as tennis and pickleball enthusiasts. The...
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Shell Game has been transformed into a fun and stunning tropical retreat that offers 1,154 sq. ft. of spacious living area with a newly upgraded kitchen.Located in the sought after complex of Playa Encantada; Shell Game is a tropical beach front community on the white sandy beaches of Anna Maria...
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We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island! 100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7...
Featured review
Love this property, loved the location and could not have had a better experience. Owner as great to work with and the communication was outstanding.
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Description Escape to paradise in this newly remodeled 4-bedroom, 4-bathroom Anna Maria Island vacation rental on North Shore Drive. Enjoy your own private heated pool, plus a golf cart, bikes, paddle boards, and kayak for endless fun. This luxury coastal beach house is steps from the Gulf, perfect for...
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Escape the Madness to the serenity of Anna Maria's north end. This single family, two bedroom, 2 bathroom, ground level house is located on the far north end of Anna Maria Island near Bean Point. The property is only 250 feet from the sugar sand beaches where you can walk for hours or sit and...
Featured review
My family and I stayed at the cottage. House was perfect. It was nice that beach chairs and towels, etc. were available. We also enjoyed using the backyard and grill. The house is literally across the street...
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Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for...
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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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Welcome to your perfect beach getaway! This beautifully renovated 2-bedroom, 2-bathroom condo comfortably sleeps up to 4 guests and offers everything you need for a relaxing coastal escape.The primary bedroom features a luxurious king-size bed and a private ensuite bathroom with a spacious walk-in...
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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