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Enjoy beautiful Anna Maria Island relaxing in a spacious ground floor condo unit with 2 bedrooms and 2 baths overlooking the heated community pool. This quiet slice of paradise has a large screened lanai off the living room with a pool view. Enjoy the amazing white sand beach and gorgeous sunsets within...
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Welcome to Flip Floppin' at Sandy Ponte by Coastal Chic VacationsProperty Highlights: - Short walk to the beach - Accommodates up to 6 guests - 2 king beds - Sleeper Sofa - Private screened balcony - Tasteful coastal décor throughout - Fully equipped kitchen - Indoor and outdoor...
Distance to beach: 350 feet to Deeded Beach Across the Street
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Breathtaking Sunsets welcome you combined with a Powder Soft Sandy Beach & Aqua Blue Water which makes AMI your memorable and desirable Vacation Destination!Your Condo is in between the Beach & the Bay! It's your ideal location for everyone including Families, Couples, Friends etc. You...
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Welcome to Mermaid Sunrise! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in *Pool heat is unavailable as of 4/7/2026...
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Bermuda Bay Club, Unit 09 Special In saving February Beautiful Condominiums located directly between the beach and the bay. Miles of sandy white beaches to walk along. Gorgeous Sunsets overlooking the Gulf of Mexico off of your front balcony. These Condominiums were recently built and nicely furnished....
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The sparkling, blue waters of the Gulf of Mexico await you at 105 Tiffany Place. Located directly on Anna Maria Island's 7-mile long beach of pure white sand, our 2-bedroom condo is the ideal location for relaxing in the sand and soaking up the sun.Our home underwent a complete renovation during...
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Welcome to Hidden Treasure Unit A! VRC18-000124.1 Miles to Holmes Beach Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Fully stocked kitchen for all your favorite home-cooked meals Shared Heated Pool High-speed Wi-Fi included Smart lock for Self Check-in...
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Welcome to Sweet Home Anna Maria! Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Private Heated Pool & Hot Tub with Plenty of Seating for the Whole Family! Game Room with Ping Pong, Dart Board, Extra Fridge & Bathroom Every Bedroom has an Ensuite Bathroom!...
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Base House on Pine Ave Anna Maria Island | Walk to Beach, Shops & Dining Wake up in the heart of Anna Maria Island, where mornings start with a short walk to grab coffee on Pine Avenue and evenings end with sunsets over the Gulf just minutes away. At Base House on Pine Ave, you're not just visiting...
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Quiet Nights of Quiet Stars on Anna Maria Island.The Vibe: Quiet, Comfortable, and Updated for 2025 Escape to "Songbird," a charming purple getaway tucked away on a peaceful side street. If you’re looking for a clean, ground-level home where the "quiet nights and quiet stars"...
Featured review
This is the place you want to stay! Clean, quiet, close to everything. Best host ever. Very friendly , kind and polite. A genuine good person, I will stay here every time I’m in AMI.
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Tiffany Place Condo - where you can experience island living at its finest and enjoy coffee on your private balcony with a calm breeze while looking out to the Gulf. Enjoy the heated pool adjacent to the beach which can be privately accessed from the property itself.TWO WEEK MINIMUM STAY. No exceptions....
Featured review
My wife and I love 114 Tiffany Place. Right in the beach. North enough on the island to be away from crowds. Comfortable, spacious apartment. We are repeaters.
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Escape to Waves, a stunning house on Anna Maria Island, offering luxurious comfort and direct beach access. Perfectly positioned just across the street from the beach, Waves offers stunning water views and the convenience of stepping from your front door to the sugar-white sands in moments.The Space The...
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Welcome to Salt and Shore by Coastal Chic Vacations!- Steps to Anna Maria Island's white sandy beaches - Community heated pool - Private putting green - 4 spacious bedrooms & 4 bathrooms - Ground level home - Close proximity to local dining, grocery store, shops... - Beach gear provided -...
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Welcome to Mermaid Sunset! VRC16-000276 Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in Pool Heat included with rental Welcome...
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Welcome to Sun Plaza West 101! *Highlighted Amenities** Location! Gulf Front Resort Condo Community! * 2 Bedrooms / 2 Bathrooms * 1 King Bed & 2 Twin Beds (Or can make 1 King upon request) * Open Air Balcony off Primary Bedroom * Screened Lanai with Patio Furniture * 3rd Balcony with view...
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28-Night Minimum Maximum capacity shall not exceed 6 personsWelcome to paradise on beautiful Anna Maria Island! Sunbow Bay 209 is a newly furnished 2-bedroom 2-bath condo with new appliances and coastal decor overlooking a peaceful, serene lagoon with kayak and canoe...
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Welcome to Flamingo Fling by Coastal Chic Vacations!- Steps to Anna Maria Island's white sandy beaches - Private heated pool - Hot tub - Private putting green - 4 spacious bedrooms & 3 bathrooms - Ground level home - Close proximity to local dining, grocery store, shops... - Beach...
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Welcome to Hidden Treasure Unit B! VRC25-000106 .1 Miles to Holmes Beach Shared Heated Pool Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Fully stocked kitchen for all your favorite home-cooked meals High-speed Wi-Fi included Smart lock for Self Check-in...
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BRAND NEW LISTING! Beautiful Gulf-front, 2 br 2ba, second-story condo directly on the beach. Our unit 216 is a 5-star listing at Tiffany Place Condominiums, with stunning sunset views from the top-floor private balcony. The master bedroom faces the brilliant Gulf of Mexico waters and includes a California...
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323 Hardin Ave | Anna Maria, FL 34216 4 Bedrooms | 3 Full Baths | Pool | Canal Front | Private DockWelcome to your slice of Old Florida paradise on Anna Maria Island's coveted north end. This beautifully renovated 4-bedroom, 3-bath ground-level home sits directly on a serene canal with a private...
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Anna Maria has moved from Snowbird Season & Summer Season to Fall Season - come visit while it is not too crowded!Peacock Place is now a three-bedroom, two-bath home and can sleep six adults. Large living room with HDTV & Roku and a big kitchen. Large master bedroom with new luxury king bed....
Featured review
My husband and I stayed in the Peacock house 2 years in a row and loved it. Denise is an excellent host and the house was amazingly roomy. The kitchen was outfitted with every item you could imagine....
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Welcome to Paradise!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 like a heated pool, private screened lanai, and easy access to the beach, dining, and...
Featured review
The property had everything we needed. It was very cozy! We loved the location and how it was within walking distance to everything we wanted to do. The pool was amazing! We hope to return!
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2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.
Featured review
Wonderful stay, quiet neighborhood, location is amazing - the beach is half a block away! Shopping including restaurants and grocery store close by, within walking distance, too. This is a great family-friendly...
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Welcome to Sea Site Unit A! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Water Views from Balcony King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWaking up to a view of the coast with your morning cup...
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Bay Dreamin By Anchor Down Vacation Rentals Wake up to open water and views of the Sunshine Skyway Bridge from your own private deck at the tip of Anna Maria Island. This fully renovated retreat pairs a heated pool and spa with a backyard putting green, so lazy mornings and playful afternoons both have...
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Beachcomber showcases spacious decking and a bright, open-concept living, dining, and kitchen area, radiating coastal luxury and charm. The main bedroom features a sumptuous king-size bed and a stylish en-suite bathroom with a soaking tub and a shower, while the second bedroom can be configured as either...
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24th St Beach House by Anchor Down Vacation RentalsTucked between the Gulf and the Bay in Bradenton Beach, 24th St Beach House puts both coastlines within a short stroll, plus a neighboring park with a kayak launch, tennis, and a playground. Recent updates keep things feeling fresh, and a full kit...
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Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self...
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Welcome to Villas by the Sea 5! .01 Miles to the World Class Beaches of Anna Maria Island .02 Miles to Bridge Street Pickleball Courts & Playground Across the Street Beach Wagon, Chairs, Umbrella, & Cooler available for use Fully stocked kitchen for all of your favorite home cooked...
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Welcome to Villas by the Sea 4! .01 Miles to the World Class Beaches of Anna Maria Island .02 Miles to Bridge Street Pickleball Courts & Playground Across the Street Beach Wagon, Chairs, Umbrella, & Cooler available for use Heated Community Pool Fully stocked kitchen for all of...
Featured review
Our stay was very nice. Found it odd that Kleenex weren't furnished, as well a basic bathroom supplies, shampoo and body wash. I just assumed they would be there. At the price point of over $400 daily,...
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Welcome to Hammock Hideaway! .02 Miles to Pine Ave. Shopping, Restaurants, and more! .03 Miles to AMI Beaches 8 Hole Mini Golf Course Private Heated Pool, Jacuzzi, BBQ Grill, Sun Loungers Beach chairs, wagon, and a cooler available Family friendly with pack'n'play and highchair ...
Featured review
We absolutely loved our stay in Holmes Beach! The location was perfect — so central and convenient to everything, which made exploring the area incredibly easy. The house itself was beautifully remodeled:...
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Welcome to Sea Site Unit B! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Private Patio for Beach Equipment and Grilling King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWelcome, too Sea Site Retreat Unit...
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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