Anna Maria Island Vacation Rentals

(238 rentals)
booking message booking message Save search

3 BR | 2 BA | Sleeps 6 | Quick View

1

$346

avg/night

View Details

About this property

If you are travelling with another family or have a larger party than 6 people, we also offer the sister property to this unit at “BBC #246”Welcome to “Bradenton Beach Club #234” on beautiful Anna Maria Island!Need something close to the beach that offers a pool – ...

View all property information

Property Type

Anna Maria Island Apartment

"Great place"

We were happy staying at the sandpiper. The proximity to the beach is excellent. It is also easy to get to other areas. Having never been to Ana Maria Island before it was a great experience. Condo is clean ...

See all reviews

Show less

4 BR | 2 BA | Sleeps 9 | Quick View

2

$480

avg/night

View Details

About this property

Welcome to the “Blue Pearl” one of our newest properties at Salty Mermaid Vacation Rentals. BIG NEWS: a brand new, full sized pool and spa was installed this fall and is ready for your use. This gorgeous beach house offers all the charm and comfort you will come to expect from staying at one ...

View all property information

Property Type

Anna Maria Island House

"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 ...

See all reviews

Show less

6 BR | 4 BA | Sleeps 17 | Quick View

$1108

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to Coastal Cove, your ultimate Anna Maria Island vacation rental experience! Discover the luxurious charm of this 6-bedroom, 4.5-bathroom beach home located in the heart of Bradenton Beach. This stunning property features a private heated pool and spa, along with a rooftop deck offering breathtaking ...

View all property information

Property Type

Anna Maria Island House

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$322

avg/night

View Details

About this property

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 Maria Island. This 2 Bed/2 Bath sweet and cozy beach home is located on North Shore Drive right ...

View all property information

Property Type

Anna Maria Island House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

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 ...

View all property information

Property Type

Anna Maria Island House

"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!

See all reviews

Show less

$251

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool

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. ...

View all property information

Property Type

Anna Maria Island Cottage

"Deluxe cottage"

We found the cottage cute comfortable and clean. The kitchen was well stocked with plates, bowls and utensils. The Tradewinds was an awesome spot and everyone was so friendly. The location was awesome. ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive ...

View all property information

Property Type

Anna Maria Island House

"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 ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

1

$478

avg/night

View Details

About this property

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 ...

View all property information

Property Type

Anna Maria Island House

"Spectacular"

We have rented many properties on Anna Maria Island and this one was my favorite! The home is wonderful with every amenity you can imagine and immaculate as far as cleanliness! It is completely updated ...

See all reviews

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

$671

avg/night

View Details

About this property

Welcome to “Oceans Blue” on beautiful Anna Maria Island. Enjoy Luxury Living all on one floor. There are no stairs to climb at this ground level home.Peace, tranquility and the ultimate in privacy are yours at this completely renovated beach house with brand new private pool and spa and ...

View all property information

Property Type

Anna Maria Island House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

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 ...

View all property information

Property Type

Anna Maria Island Villa

"Beautiful, peaceful and serene."

Unbelievable location with state of the art appliances throughout. Views of the ocean and the beach that were priceless.

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$551

avg/night

View Details

About this property

WELCOME to “Island in the Sun” ...this newly renovated home on AMI offers charm, comfort, and luxury. Island in the Sun is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach and the popular restaurant - The Waterfront. The City Pier Bay ...

View all property information

Property Type

Anna Maria Island House

Show less

3 BR | 3 BA | Sleeps 8 | Quick View

2

$571

avg/night

View Details

About this property

*A Brand new Pool/Spa has been installed and is ready for guest use! New Pool pictures are at the end of the photo list*Come Relax and Unwind at the "North Shore" on gorgeous Anna Maria Island. This ground level, newly renovated and professionally decorated 3 bedroom, 3 bath beach house ...

View all property information

Property Type

Anna Maria Island House

"Gertie's East"

We stayed at Gertie's East and had a great vacation. Perfect duplex for 2. Very clean and cute. Very close to Publix and to the beach. Pool was very clean and a perfect size. Patio with a propane grill ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

2
last minute deal
LAST MINUTE DEAL 2/21 - 4/3: Book your summer vacation today! Lots of availability!

$242

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

For a quote or to book please visit - our website or send inquiry and we will send you quote.Welcome to Sand & Surf! 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 for ...

View all property information

Property Type

Anna Maria Island Condo

"Great vacation rental!"

My husband and I rented this condo, Sand & Surf, from Owner, Morgan Henderson, and we were completely pleased with the accommodations. Morgan was wonderful about replying immediately to any questions we ...

See all reviews

Show less

DEAL

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

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 ...

View all property information

Property Type

Anna Maria Island Condo

"Ok"

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

See all reviews

Show less

4 BR | 5 BA | Sleeps 8 | Quick View

$1144

avg/night

View Details

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. This Anna Maria Island vacation rental home offers all the goodies to make sure your vacation does not skip a beat. This beautiful property offers ...

View all property information

Property Type

Anna Maria Island House

Show less

3 BR | 2 BA | Sleeps 6 | Quick View

1
last minute deal
LAST MINUTE DEAL 2/21 - 4/3: Book your summer vacation today!

$499

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool

About this property

Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white sandy beaches of Holmes Beach, FL. This stunning property can accommodate up to 6 guests and features a community heated pool, outdoor shower, and a fully equipped kitchen.The spacious ...

View all property information

Property Type

Anna Maria Island Condo

"Relaxing and fun"

What an amazingly spacious, comfortable and fun place to stay in Anna Maria Island Fla. Steps from Gulf and beach with beautiful sunsets from the place. Amenities galore making many options for daily activities ...

See all reviews

Show less

DEAL

2 BR | 2 BA | Sleeps 4 | Quick View

$289

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool

About this property

Come experience Unit 204 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 ...

View all property information

Property Type

Anna Maria Island Condo

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

VRC This stunningly built and decorated 4 bedroom + Bunk Den 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico with crystal clear blue waters. Located in prime Holmes Beach, you are within walking distance to the award winning Beach Bistro and many other restaurants, ...

View all property information

Property Type

Anna Maria Island House

"Pleasantly surprised"

We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

$233

avg/night

View Details

Key Amenities

  • Air conditioning

About this property

Welcome to “Barefoot Mermaid 4” 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 ...

View all property information

Property Type

Anna Maria Island Apartment

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. Each studio unit sleeps two with a queen-size bed and has a full kitchen. One-bedroom units sleep four and offer a king size bed in the bedroom and a queen sleeper sofa in the living area. There ...

View all property information

Property Type

Anna Maria Island Condo

"Great stay!"

We really enjoyed our suite. Our balcony faced the bay and the ocean was just across the street. We loved having a full kitchen and living area to make our vacation feel more like home. Thank yo for a ...

See all reviews

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

$711

avg/night

View Details

About this property

Welcome to West O’ Gulf, one of our brand-new luxury rentals at Salty Mermaid Vacation Rentals. If you are ready for a relaxing stay on beautiful Anna Maria Island, then this unit is for you! This exceptional custom-built 4 Bedroom 3 bathroom beach house makes it easy to perfect the art of vacationing. ...

View all property information

Property Type

Anna Maria Island House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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 ...

View all property information

Property Type

Anna Maria Island House

"Friends Get Away"

We had a lot of criteria for our vacation home. Four Kings Size Beds minimum as most rentals have maybe 1 king and the balance queens or smaller, At least 4 bathrooms. Heated pool and hot tub and close ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

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 ...

View all property information

Property Type

Anna Maria Island House

"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 ...

See all reviews

Show less

5 BR | 4 BA | Sleeps 8 | Quick View

$671

avg/night

View Details

About this property

Mia BellaMia Bella has been completely restored and updated, creating one of the most unique and spacious residential properties on Anna Maria Island. The property is located on a deep water canal with over 80 feet of private patio running alongside mature mangroves. A new heated swimming pool is ...

View all property information

Property Type

Anna Maria Island House

Show less

4 BR | 4 BA | Sleeps 8 | Quick View

$658

avg/night

View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

*Under new owners, and new property management*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 located west of Gulf drive, with no busy roads to cross for beach access. ...

View all property information

Property Type

Anna Maria Island House

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

2

$728

avg/night

View Details

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 professionally decorated and offers all the luxuries you will ...

View all property information

Property Type

Anna Maria Island House

"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 ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

19
last minute deal
LAST MINUTE DEAL 2/21 - 4/3: Last week in July open, August and Sep openings! March 2025 openings

$291

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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. After a day at the beach, you can relax by the pool or in the private, nicely landscaped picnic area. There are only 4 units ...

View all property information

Property Type

Anna Maria Island Condo

"Home :)"

We love our stays at Seaduction. It has become our 3rd home! Morgan and Dan have created a home for their guests not a rental. They are responsive and very helpful. It is well stocked, great location, ...

See all reviews

Show less

DEAL

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

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 ...

View all property information

Property Type

Anna Maria Island House

"AMAZING!!!"

This house is the best rental we have ever stayed in! The scenery out back is incredibly relaxing.. trees, Adirondack chairs, the OCEAN!! It is so private, and also the best equipped kitchen I’ve ever ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

20

$209

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

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 ...

View all property information

Property Type

Anna Maria Island Cottage

"Beach cabin"

So close to the water for someone with gait issues. We always enjoy our stay here. So close to restaurants and beach. Best of both worlds

See all reviews

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

$295

avg/night

View Details

Key Amenities

  • Air conditioning

About this property

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 ...

View all property information

Property Type

Anna Maria Island Apartment

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$190

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Welcome 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 access directly to the intercoastal waterway.Enjoy stunning sunrises with a cup of coffee on ...

View all property information

Property Type

Anna Maria Island Condo

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$334

avg/night

View Details

About this property

Welcome to “Beachcomber” a cozy villa reminiscent of days past on Anna Maria. This charming villa is only 3 houses (300 Ft) TO DIRECT BEACH ACCESS in the City of Holmes Beach on Anna Maria Island!!! When arriving at “Beachcomber” you will get excited with how close you are ...

View all property information

Property Type

Anna Maria Island Villa

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Welcome to MANATEE HARBOUR, our spacious 2 Bed / 2 Bath home with backyard canal, and lanai covered heated pool.At the serene North End, this private oasis has everything you need for a perfect beach vacation. Beach chairs, carts, toys, and umbrellas. Kitchen stocked with supplies. Linens and towels ...

View all property information

Property Type

Anna Maria Island House

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

1

$524

avg/night

View Details

About this property

Treat yourself to “Crescent Palms” on the north end of Anna Maria Island. This ground level, newly renovated and professionally decorated 3 bedroom, 2 bath beach house offers comfort, luxury, and relaxation. Crescent Palms is located on a quiet street- north of Pine Ave and just a few flip ...

View all property information

Property Type

Anna Maria Island House

"Peaceful and relaxing family trip"

We were looking for a quiet spot for the family and hit the bullseye at Max and Denise's place on Northern Anna Maria island. Centrally located, 3 blocks either way, between the Gulf of Mexico or Tampa ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 150 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 ...

View all property information

Property Type

Anna Maria Island House

"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. ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$289

avg/night

View Details

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 ...

View all property information

Property Type

Anna Maria Island Apartment

Show less

3 BR | 3 BA | Sleeps 6 | Quick View

$472

avg/night

View Details

About this property

Welcome to "Beach Escape" on beautiful Anna Maria Island. Appropriately named, this Mediterranean-inspired beach house offers all the charm and luxury you expect from a memorable vacation on AMI.Find ease and relaxation the moment you arrive, this charming multi-level home is nestled among ...

View all property information

Property Type

Anna Maria Island House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the grand total.Be one of the very first ...

View all property information

Property Type

Anna Maria Island House

"Holmes beach"

This is an amazing property! Location and pool and lanai were awesome! Private and close to everything! There was a Publix right up the road also. We rented golf carts from zoom around and we could easily ...

See all reviews

Show less

Key Amenities

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

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 ...

View all property information

Property Type

Anna Maria Island House

"Great Vacation Spot. Great Owner. Awesome Location"

What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...

See all reviews

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

1

$756

avg/night

View Details

About this property

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 offers 4 bedrooms, 3 bathrooms ...

View all property information

Property Type

Anna Maria Island House

"Immaculate"

My family loved the Orca. It was newly renovated and meticulously appointed. The owners have put alot of thought into what you might need and they nailed it. We brought our small boat and had an amazing ...

See all reviews

Show less

2 BR | 2.5 BA | Sleeps 4 | Quick View

$543

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront

About this property

The Beach House is a charming beach bungalow nestled among numerous Australian pines and sea grapes. A unique setting directly on the Gulf of Mexico shaded among the trees. Walk out the back door on your private path to a white sugar-sand beach. Best of both worlds, you have the shade and sunny beach. The ...

View all property information

Property Type

Anna Maria Island House

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

$675

avg/night

View Details

About this property

Welcome to Zen Gardens on beautiful AMI. BIG NEWS: a brand new, full sized pool and spa was installed and is ready for your use. Zen Gardens is located just north of Pine Ave - and 1 house from the beach - in the City of Anna Maria. This property offers a beachy bohemian vibe and has all you need for ...

View all property information

Property Type

Anna Maria Island House

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

$621

avg/night

View Details

About this property

*3 Night Minimum stays are allowed during low season, please refer to the rate table for the specific date ranges* Magnolia Location, Location, Location! Magnolia is situated on a quiet residential street, 2 blocks from the gorgeous white sand beaches of the Gulf of Mexico and 2 blocks from ...

View all property information

Property Type

Anna Maria Island House

Show less

3 BR | 2.5 BA | Sleeps 6 | Quick View

4.8 rating on other travel sites

$540

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

312 A 61st Street Holmes Beach, FL 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% ...

View all property information

Property Type

Anna Maria Island House

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

306 67th Street Unit B Holmes Beach, FL 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive ...

View all property information

Property Type

Anna Maria Island House

"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 ...

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

We have developed a comprehensive Safety / Cleaning / Sanitation Plan and work with an amazing team to ensure the home & pool are sparkling clean for all of our guests. Our home goes through rigorous cleaning per CDC guidelines using only EPA approved detergent and highest MERV 13 A/C filters changed ...

View all property information

Property Type

Anna Maria Island House

"Great house"

We had a remarkable time at this house. The location, pool and house exceeded our expectations. We'll come back.

See all reviews

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

$295

avg/night

View Details

Key Amenities

  • Air conditioning

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 ...

View all property information

Property Type

Anna Maria Island Apartment

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

4
last minute deal
LAST MINUTE DEAL 2/21 - 4/3: Book your summer vacation today!

$181

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Endless Summer is two bedroom, two bath condo located on Anna Maria Island. Specifically, located in Runaway Bay on Bradenton Beach. The condominium complex beautifully maintained and consists of 186 one- and two-bedroom units nestled uniquely between Palma Sola Bay to the east and the Gulf of Mexico ...

View all property information

Property Type

Anna Maria Island Condo

"Great Place, Perfect Location"

My husband and I recently stayed at this condo while visiting family and friends. This was the perfect condo and perfect location for us. Unfortunately, the pool was down for repairs of some sort but we ...

See all reviews

Show less

DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

202 69 th Street - Holmes Beach - FL 34217 VRCBook with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive ...

View all property information

Property Type

Anna Maria Island Townhome

"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 ...

See all reviews

Show less

$609

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

306 Clark drive (B) Holmes Beach, FL 34217 VRC Book with confidence: Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive ...

View all property information

Property Type

Anna Maria Island Townhome

"Beautiful Property"

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.

See all reviews

Show less

Map
Expand map Close map
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 238 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 $160 per night with an average price per night of $463.

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 109 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 15 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!