Anna Maria Island Vacation Rentals

(227 rentals)
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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

$759

avg/night

$759
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Create unforgettable memories at “Mia Bella” located on Hammock Road, just north of Pine Avenue, in a *premier deep water canal location* in Anna Maria. Mia Bella is a short walk to the gorgeous, white sandy beaches of Anna Maria Island. This *very spacious beach house* has been fully renovated ...

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Property Type

Anna Maria Island House

Featured review

"Delight in Anna Maria Island"

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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Anna Maria Island House
1 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 2 bathrooms

$253

avg/night

$253
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use the link provided below to check availability on Unit B.Unit B: Visit Unit BWelcome to “The Magic Dolphin A” an elevated vacation rental located on the northern section ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$546

avg/night

$546
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Escape to this Anna Maria Island vacation rental “Katmandu” just 0.15 miles or 300 steps to the wonderful white sandy beaches of the Gulf of Mexico. This property is west of Gulf Drive, with no busy roads for beach access. This property suffered minimal damage from Hurricanes Helene and Milton ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$314

avg/night

$314
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2024, new photos coming soon!*Welcome to Sea'Esta on gorgeous Anna Maria Island! Sea'Esta is a ground level Home that offers all the luxuries and comfort you will come to expect from staying at one of our vacation rentals on Anna ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
4.8 rating on other travel sites

$414

avg/night

$414
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

312 A 61st Street Holmes Beach, FL 34217 VRC Welcome!Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind! Get ready to make memories at Crosswinds Cottage!Your home away from homeThis home has been professionally decorated and ...

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Property Type

Anna Maria Island House

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Anna Maria Island Apartment
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$542

avg/night

$542
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This 3 bedroom condo sits close to the Gulf Beaches at Gulf Place Condominium. Sit on the lanai and drink your coffee looking out onto the Gulf.

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Property Type

Anna Maria Island Apartment

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
2 reviews

$1228

avg/night

$1,228
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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 ...

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Property Type

Anna Maria Island House

Featured review

"Best Place On Anna Maria"

Hosts are fabulous! very responsive and caring! House is amazing! our friends and family were blown away by how much attention to detail they put in to the furnishings and the home itself! A true paradise!

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Anna Maria Island Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
2 reviews

$286

avg/night

$286
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to “Barefoot Mermaid 3” 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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Property Type

Anna Maria Island Apartment

Featured review

"Lovely Accomodation"

We were so pleased with Barefoot Mermaid 3. Everything was so clean and well cared for. The kitchen was stocked with the things we might need. We were so close to all our favorites like The Sandbar, Mademoiselles ...

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$647

avg/night

$647
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

North End Escape is a 2,300 sq. ft. Custom Built 3 bedroom 2 ½ bathroom Home featuring a 400 sq. ft. Rooftop Covered Gazebo; 750 sq. ft. of Covered Outdoor Living Area with Travertine flooring and a Heated Pool.This spacious home has wide plank hardwood flooring throughout; open concept living ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

Distance to beach: 0.1 miles to Bayside Beach

$957

avg/night

$957
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Just updated 2021, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep many with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for smaller ...

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Property Type

Anna Maria Island House

Featured review

"Family holiday"

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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Anna Maria Island Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
3 reviews

$305

avg/night

$305
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Vacations can be exciting and so overwhelming. Don’t worry, we’re here to help. Pack your bags and get ready to enjoy our beautiful island. This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
4 BR | 2 BA | Sleeps 9 | Quick View
Sleeps 9, 4 bedrooms, 2 bathrooms
2 reviews

$522

avg/night

$522
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to the “Blue Pearl”. This gorgeous beach house offers all the charm and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island.Find ease and relaxation the moment you arrive …” Blue Pearl” is the perfect vacation rental ...

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Property Type

Anna Maria Island House

Featured review

"Family vacation"

The house was great! Close proximity to the trolly, which made exploring the island very easy!The beach is just a few minute walk, and was so convenient. Everyone loved the pool and hot tub, even though ...

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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

$581

avg/night

$581
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

New pictures coming by early February!Discover island paradise at “North Shore” located on the *premier corner* of North Shore & Palmetto in Anna Maria, only 2 blocks from the gorgeous, white sandy beaches of Anna Maria Island and a few steps from very popular Slim’s Place restaurant ...

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Property Type

Anna Maria Island House

Featured review

"Amazing house!!"

This house was great we have been coming to the island for about 10 years! This was the best house and so close to the beach!! We will be back

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms

$559

avg/night

$559
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This stylish 3 bedroom, 2 and a half bath vacation home is located just a short walk from Anna Maria Island's sugar white beach. Gone Coastal 3 is amazingly updated and chic!*Features include** Super close to the beach * Heated private pool * Outdoor shower * Tiki Bar with games and ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$553

avg/night

$553
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

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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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

$429

avg/night

$429
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Less than a minute's walk to the beach!Watch the sunset from the house!PARKING FOR ALL...Bring your boat or RV...Invite guests... There's room for everyone!Shell House is a two-story, 3-bed, 2-bath, multi-level fun-house on a large shady lot in a quiet residential neighborhood ...

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Property Type

Anna Maria Island House

Featured review

"Great Two Weeks in Holmes Beach"

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 ...

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$660

avg/night

$660
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

$404

avg/night

$404
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

306 67th Street Unit B Holmes Beach, FL 34217 VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations ...

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Property Type

Anna Maria Island House

Featured review

"Cozy & Comfy"

This home was exactly what we were looking for. It was a minute walk to the beach, 1 1/2 blocks. The home was equipped with everything we needed, including beach, chairs, umbrellas, and a cart to lug everything ...

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Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$513

avg/night

$513
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

*This home is being rebuilt after the Major Hurricanes of 2024, new photos coming soon!*Welcome to Sunrise Vista on gorgeous Anna Maria Island. Pack up the family car and head to Anna Maria Island's perfectly located beach house. Find one of the last-remaining generations owned single-family ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms
5 reviews

$770

avg/night

$770
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

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 ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
7 reviews

$454

avg/night

$454
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Longing for an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
5 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 2 bathrooms
2 reviews
last minute deal
LAST MINUTE DEAL 5/3 - 5/17: May Special - $375 per nt plus taxes/cleaning. Saturday to Saturday bookings, min 7 nights.

$756

avg/night

$756
avg per night
Offer for: May 3 - May 17:
May Special - $375 per nt plus taxes/cleaning. Saturday to Saturday bookings, min 7 nights.

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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 ...

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Property Type

Anna Maria Island House

Featured review

"Hidden paradise"

We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...

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DEAL
Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews
last minute deal
LAST MINUTE DEAL 4/14 - 5/26: April 30th - May 9th open and only $105 per night!! Book Now

$197

avg/night

$197
avg per night
Offer for: Apr 14 - May 26:
April 30th - May 9th open and only $105 per night!! Book Now

View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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 ...

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Property Type

Anna Maria Island Condo

Featured review

"Enjoyed our stay at Sand & Surf"

Cute condo in a GREAT location. Clean with a coastal vibe. Well stocked kitchen with great appliances. Beach is walkable but we drove as there usually was parking available. The pool at this complex is ...

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DEAL
Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1126

avg/night

$1,126
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Right across the street from the beach and the Beach Bistro! Gulf Views available from this beautiful home.This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen with gas stove, wine bar, roof top deck with sweeping views ...

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Property Type

Anna Maria Island House

Featured review

"Ideal family vacation home!"

The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally ...

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
owner special
Owner special: Enjoy the views at discounted rates!

$534

avg/night

$534
avg per night
Owner special:
Enjoy the views at discounted rates!

View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just steps away to the bay beach access located directly across the street; walking distance to Bean Point Beach, Bay Front Park and the historic Pine Avenue. Enjoy shopping at ...

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Property Type

Anna Maria Island House

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Anna Maria Island Apartment
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$293

avg/night

$293
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Welcome to “Sand Dollar Villa”, one of our newest luxury properties at Salty Mermaid Vacation Rentals. This elevated condo offers all the luxury and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island. Find ease, relaxation, and luxury the moment ...

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Property Type

Anna Maria Island Apartment

Featured review

"Sand dollar"

Great location. Comfortable. Looks bed it. Great weather. Adequate furnishings Elevator to First condo was working and appreciated Will rent again if on market.

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Anna Maria Island Apartment
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$361

avg/night

$361
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

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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Property Type

Anna Maria Island Apartment

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Anna Maria Island Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

$163

avg/night

$163
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

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 ...

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Property Type

Anna Maria Island Condo

Featured review

"Great place to stay"

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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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

$199

avg/night

$199
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Click on calendar for available 2024 dates. Book now before they are gone! CALL FOR UNBELIEVABLE SAVINGS. ONLY PHONE CALLS GET DISCOUNTS.TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry.20 STEPS TO THE SAND - GREAT VIEW Last minute deals don’t last long, we price to rent. We are ...

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Property Type

Anna Maria Island Condo

Featured review

"Ok"

️ love this area one of my favorite places to stay AnnaMaria island.. love it .. can’t wait to go o back

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$678

avg/night

$678
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

*New photos are coming soon!*Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida.This ground level beach house ...

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Property Type

Anna Maria Island House

Featured review

"A True Retreat"

This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing. ...

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Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$273

avg/night

$273
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

VRC 107 78th street Holmes Beach 34217To Book Directly please visit: /chasing-wavesIf you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team:“You are vacationing in ...

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Property Type

Anna Maria Island House

Featured review

"Great Location and Clean"

We had a great week in this unit and were pleased with many things it had. I would stay there again without hesitation. A FEW issues though with the unit. A fee of $69 for linens. We rented for 10 days ...

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$848

avg/night

$848
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

128 49th St Holmes Beach VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on or less ...

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Property Type

Anna Maria Island House

Featured review

"Great Thanksgiving Vacation!"

We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its ...

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

$755

avg/night

$755
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to “Pineapple Cottage” – a beautifully updated ground-level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants, and fun on Pine Avenue. This charming cottage has been completely restored after hurricanes Helene and Milton. This ...

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Property Type

Anna Maria Island House

Featured review

"Great Property"

This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay ...

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

*30 Day min rental @ $500/night rate + taxes and fees.Welcome to Pink Pearl – your perfect coastal escape! This stunningly renovated 4-bedroom, 3-bathroom oasis is ready to make your dream getaway a reality.Designed with both comfort and luxury in mind, this one-story home boasts a seamless ...

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Property Type

Anna Maria Island House

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Anna Maria Island Cottage
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
21 reviews

$190

avg/night

$190
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

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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Property Type

Anna Maria Island Cottage

Featured review

"Old Florida Gem"

Loved the old Florida vibe! A hop and skip to the beach - just what we were looking forward to! Sure beats a condo high rise!

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$659

avg/night

$659
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

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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Property Type

Anna Maria Island House

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Anna Maria Island Townhome
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

$800

avg/night

$800
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

202 69 th Street - Holmes Beach - FL 34217 VRCBook with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that ...

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Property Type

Anna Maria Island Townhome

Featured review

"Lovely stay"

Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were ...

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$1186

avg/night

$1,186
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to “Salty Sunsets” on beautiful Anna Maria Island. This luxurious property is located north of Pine Ave with easy access to Bean Point. Property suffered minimal damage from the hurricanes and is better than ever. This Anna Maria Island vacation rental home offers all the goodies to ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
23 reviews

$228

avg/night

$228
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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 ...

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Property Type

Anna Maria Island Condo

Featured review

"5 star experience"

My family enjoyed this vacation rental for a glorious week. The place was so comfy and inviting. They really thought of everything when it came to the overall experience. The property offers a nice peaceful ...

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$302

avg/night

$302
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Come experience Unit 204 at Sun Plaza West on beautiful Anna Maria Island. This 2-bedroom 2-bathroom Condo is in the heart of Holmes Beach within walking distance to restaurants, shopping, and the Islands Free Trolley. Sun Plaza West complex offers secure entry, an elevator, heated pool, and an On-Site ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Cottage
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
54 reviews

$251

avg/night

$251
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Condo-cottage with Old Florida charm..... 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 quaint, pastel colored cottages on both sides of you hidden behind lush tropical foliage. ...

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Property Type

Anna Maria Island Cottage

Featured review

"AMI’s the Best!"

Love Anna Marie Island, it’s food, shopping, beaches and wonderful places to stay! The family enjoyed staying at the Tradewinds, the location is great. The cottages fit our needs perfectly. We enjoyed ...

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Distance to beach: 0.1 miles to Bean Point

$909

avg/night

$909
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling home named for its spectacular porches and outdoor space.*Features include** Private heated pool and backyard oasis * Poolside lounge, bar and dining area * 85" Outdoor tv and gas ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms

$785

avg/night

$785
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

To Book Directly please visit: /its-miller-time If you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team: This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Come experience Unit 201 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated pool and an ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

$457

avg/night

$457
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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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Property Type

Anna Maria Island House

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Anna Maria Island House
6 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5.5 bathrooms
14 reviews

$923

avg/night

$923
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access!This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...

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Property Type

Anna Maria Island House

Featured review

"Perfect!"

This place was perfect for our family! The 4 bedrooms with King size beds and en suite baths made it so convenient for each couple. The bunk beds were perfect for the kids. The children (and adults) loved ...

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Need a getaway? We have the perfect spot for you. Welcome to "Sun & Surf", a direct gulf front condominium on beautiful Anna Maria Island. This 2-bedroom, 2-bathroom condominium offers all the charm and comforts you will come to expect from a Salty Mermaid Vacation Rental. This unit has ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
13 reviews

$363

avg/night

$363
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

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 ...

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Property Type

Anna Maria Island House

Featured review

"Great Location and Spacious Condo"

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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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

$175

avg/night

$175
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided- sleeps 4, 2 bedroom/2 bath, very private- On second floor with covered stairs. No elevator.- all linens provided, washer/dryer in unit- stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin ...

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Property Type

Anna Maria Island Condo

Featured review

"Great condo!"

We enjoyed our stay! The condo was clean, spacious & inviting! The location was wonderful. We will definitely stay again. The owner was very quick to reply to my emails.

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
owner special
Owner special: Playa Encantada Free Day Giveaway! Book 14 pay for 12

$229

avg/night

$229
avg per night
Owner special:
Playa Encantada Free Day Giveaway! Book 14 pay for 12

View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

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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Property Type

Anna Maria Island Condo

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Anna Maria Island Vacation Rentals

Anna Maria Island Weather

 | 

7423°  5211°
JANUARY
Ocean 6518°
7624°  5412°
FEBRUARY
Ocean 6518°
7926°  5714°
MARCH
Ocean 6820°
8328°  6116°
APRIL
Ocean 7423°
8831°  6719°
MAY
Ocean 7926°
9133°  7222°
JUNE
Ocean 8328°
9133°  7323°
JULY
Ocean 8529°
9233°  7423°
AUGUST
Ocean 8731°
9032°  7323°
SEPTEMBER
Ocean 8529°
8630°  6719°
OCTOBER
Ocean 8228°
8127°  6016°
NOVEMBER
Ocean 7624°
7624°  5412°
DECEMBER
Ocean 7021°

Enjoy the Perfect Anna Maria Island Getaway


Looking for a gorgeous and relaxing Anna Maria Island vacation rental without leaving the Florida coast? Anna Maria Island is the perfect vacation spot for you. Anna Maria Island is located on Florida’s western shore, just a few miles south of St. Petersburg.

This small, quaint island is separated from mainland Florida by the waters of Palma Sola Bay and Anna Maria Sound. However, the coast is connected to the island by way of U.S. Highways 64 and 684, making it easy to travel between the two. Despite its size, Anna Maria Island is packed with activities to enjoy and many gorgeous rental homes.

With FloridaRentals.com, you can live like a local while on your vacation by enjoying authentic architecture from the inside out within Anna Maria Island’s residential neighborhoods.

Hotel stays can be enjoyable, but there’s nothing quite like a high-quality rental home while on vacation. Not only will your trip feel more immersive within Anna Maria Island’s unique energy, but you will also be able to truly relax while on your trip.

There is no worrying about sharing a wall with strangers or lacking privacy. Additionally, you’ll be able to relax in a private backyard with some much-needed peace and quiet. Many Anna Maria rentals with FloridaRentals.com even feature unique amenities like pools, hot tubs, entertainment centers, walkable beach access, and much more.

Anna Maria Island Travel Tips


If you’re planning a trip to Anna Maria Island, you should keep a few key details in mind. The first is which airport you plan on flying into. Anna Maria Island is reachable by car from many of Florida’s largest cities, including St. Petersburg, Clearwater, Tampa, and Sarasota. However, depending on where you live, traveling to Anna Maria Island by plane might be easier.

There is no airport on the island, so you will have to fly into a nearby city and rent a car or take public transport from there. The closest commercial airport to Anna Maria Island is the Sarasota Bradenton International Airport, which is about 16 miles south of the island.

The St. Pete-Clearwater International Airport can also connect to Anna Maria Island via I-275 across Tampa Bay. This option is less convenient as this airport is about 45 miles north of the island. However, by flying into St. Pete–Clearwater, you could bundle multiple popular Florida destinations into one trip by taking the “long way.”

Another detail to keep in mind is the climate. Though many Florida cities experience warm weather throughout the year, the best time to enjoy the outdoors with warm yet pleasant temperatures on Anna Maria Island is mid-spring or fall. During these times of the year, average temperatures are between 80 and 85 degrees Fahrenheit, and chances of precipitation are low.


Best Eats on Anna Maria Island


There are many incredible restaurants and bars on Anna Maria Island, many featuring beachfront views. Rod and Reel Pier is a great example. Located on the northernmost tip of Anna Maria Island with a full menu of seafood and cocktails.

City Pier Grill and Bait, located on the end of Anna Maria Pier, is another great local spot for a meal with family, drinks with friends, or a romantic date. The delicious globally-inspired seafood dishes are complemented by the gorgeous view of Tampa Bay, which is especially breathtaking at sunset.

As you travel farther south down the island, there are many more eateries to explore during your visit to Anna Maria Island. Scott’s Deli is a great choice for fresh and delicious sandwiches if you’re looking to grab something quick to take for a picnic lunch on the beach.

Nearby are Duffy’s Tavern and Freckled Fin Irish Pub, two local bars that serve their own unique menus of American favorites and ice-cold drinks. If you’re looking for a more upscale after-dinner drinks experience, The Doctor’s Office is a hip cocktail bar in central Anna Maria with plenty of imaginative cocktails and light bites to enjoy. And yes, the building used to be a real doctor’s office!


Things to Do Near Anna Maria Island Vacation Rentals


Despite its small size, there is a huge variety of beaches to explore near Anna Maria Island rentals. Manatee Public Beach, located on the southwestern side of the island, is a popular destination for white sand, warm waters, and plenty of fun in the sun.

As you travel even farther south to the neighborhood of Bradenton Beach on Anna Maria Island, you’ll find spots like Coquina Beach, which wraps around the southern tip of the island. For prime beach access on the island’s northernmost tip, Bean Point Beach and Bayfront Park are two of the most popular. Many of the island’s beaches have a variety of amenities, such as playgrounds, volleyball nets, picnic tables, and concession stands.

The many Anna Maria Island piers are a special way to experience the beauty of the area from the water (without getting wet!). Some of these include Rod and Reel Pier, the Anna Maria City Pier, and Bridge Street Pier. Visitors can find local art and culture, gift shops, restaurants, and stunning views at any of the island’s piers.

Aside from taking a stroll along a pier, there are many other ways to experience the shimmering waters of Tampa Bay or the Gulf of Mexico. One popular activity for vacationers is to rent a boat or kayak from one of the many vendors along the island’s shores.

One of Anna Maria Island’s most popular rental shops is Beach Bums. At Beach Bums, you can rent kayaks and paddle boards for the whole family or even book a special kayak tour led by an experienced local. Need a break from the water? You can also rent bicycles or golf carts to explore Anna Maria Island by land!

Experience Bliss on Anna Maria Island


Adventure is waiting for you on Anna Maria Island. Make the most out of your adventure by vacationing at a luxurious private home, courtesy of FloridaRentals.com.


FAQ

How many vacation rentals are there in/around Anna Maria Island?

There are 227 Anna Maria Island vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Anna Maria Island?

There are vacation rentals available in Anna Maria Island for as low as $127 per night with an average price per night of $423.

Can I find a vacation rental in Anna Maria Island?

Yes, you can find vacation rentals in Anna Maria Island close to Holmes Beach, Coquina Beach, and Bradenton Beach. Don't forget to stop in to Bean Point or Manatee Public Beach.

Do any vacation rentals in Anna Maria Island have a pool?

Yes, there are 163 vacation rentals with a pool in Anna Maria Island on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Anna Maria Island vacation rentals on the ocean?

There are 18 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!