Anna Maria Island Vacation Rentals

(117 rentals)
Dolphin Cottage - Pet-friendly and very close to beach!

$228

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

It is always summer on Anna Maria Island!We have one of the most pristine, un-crowded beaches you will ever visit. Enjoy a champagne breakfast, Duffy's burgers for lunch, or cocktails at sunset! In addition, there are many other fabulous things to do here - Busch Gardens, Universal Studios and ...

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Property Type

Anna Maria Island House

"Love the Dolphin Cottage!"
Reviewed April 23, 2019

This is where you want to stay at the beach for a quiet old Florida experience. A beautiful beach is less than a block away where you can enjoy shade under the old Australian pines. The cottage is clean, ...

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Anna Maria Paradise - Private Pool & Canal front home

$217

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Beautiful 4 bedroom, 2.5 bathroom home with direct access to Anna Maria Canal and private heated pool overlooking the water. Take a kayak ride right off your private dock area or cast a fishing pole and catch dinner. This home has lots of space and is ready for you to come enjoy all of what the island ...

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Property Type

Anna Maria Island House

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Relax at The Ulmer House...Right on the Beach...Gulf Views Everywhere!

$300

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

As you drive up to The Ulmer House, the landscape is natural, graceful and compliments the house in an authentic way. It feels like a compound from the street looking through the mature trees that surround a very large property and shield it from the view of the public. There is a very private and spacious ...

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Property Type

Anna Maria Island House

"wonderful home in a beautiful location!"
Reviewed July 23, 2019

This home was beautiful and had everything we needed for a wonderful week at the beach. The shaded lot and views of the beach from the house were outstanding!

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Bay View Dream

4 BR | 3.5 BA | Sleeps 8 | Quick View

$242

per night

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Key Amenities

  • Air Conditioning

About this property

Ah, Bay View Dream! This lovely 4 bedroom, 3.5 bath home is located in the heart of Historic Anna Maria City. It sits right on an expansive waterway leading into Tampa Bay and has been lavishly decorated with all the creature comforts and more. Stunning water views from living room, dining room, kitchen ...

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Property Type

Anna Maria Island House

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Turtle Cottage - Anna Maria Island

$220

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. This great getaway sleeps up to 4.The space:The cottage has an ...

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Property Type

Anna Maria Island Cottage

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Long Term Rental Only - 100 steps to beach!

5 BR | 4.5 BA | Sleeps 10 | Quick View

Distance to beach: 100 yards to Anna maria

$333

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Our Anna Maria home is one of the most beautifully finished private homes available for rent in Anna Maria. It was built with an eye to detail and includes all custom cabinetry, hard wood floors, marble baths, marble counter tops and a completely stocked top of the line kitchen. Our home is really ...

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Property Type

Anna Maria Island House

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Jacaranda

3 BR | 2 BA | Sleeps 8 | Quick View

$199

per night

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Key Amenities

  • Air Conditioning
  • Pet Friendly
  • Private Pool

About this property

766 Jacaranda Road - Anna Maria- fl -34218 Unique 3 bedroom 2 baths with an upstairs bonus room close to the beautiful beaches if Bean Point and the Amazing Pine Ave.This beautiful 3 bedrooms 2 bathroom single family home is minutes from the white sands beach of Anna Maria Island. Only a short walk ...

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Property Type

Anna Maria Island House

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Peacock Place - Pet-friendly and very close to beach!

$242

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

It is always summer on Anna Maria Island!We have one of the most pristine, un-crowded beaches you will ever visit. Enjoy a champagne breakfast, Duffy's burgers for lunch, or cocktails at sunset! In addition, there are many other fabulous things to do here - Busch Gardens, Universal Studios and Disney ...

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Property Type

Anna Maria Island House

"Family visit"
Reviewed July 3, 2019

Peacock Place is a great place for family reunions. Plenty of space. Close to the beach. We loved it.

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Palm Perch Newly Renovated Unit in the Heart of AMI!

$225

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Nestled on a quiet street in Holmes Beach, this newly renovated 2 bedroom(1queen 2twins) 1 bath vacation rental provides everything you will need for a great vacation! Relax on the beautiful beach just a short walk away or spend some time by the sparkling salt water pool and hot tub.The island offers ...

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Property Type

Anna Maria Island House

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Casita Marina - 11103

2 BR | 2 BA | Sleeps 6 | Quick View

1

$164

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

This classic home located on the North End of Anna Maria Island is the perfect home for your tropical beach vacation. The beautiful Anna Maria beach is across the street about 100 steps away! The home is a legal duplex (11101+11102 Gulf Drive). This unit has two bedrooms and two bathrooms. The Kitchen ...

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Property Type

Anna Maria Island Condo

"This is a Charming Beach Cottage"
Reviewed February 28, 2019

This duplex has been completely renovated inside with a nice kitchen and bathrooms. It is a perfect location in the quiet northern end of AMI. It is within walking distance to restaurants and the beach ...

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Shell Cove 4

2 BR | 1 BA | Sleeps 4 | Quick View

$144

per night

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Key Amenities

  • Air Conditioning

About this property

Shell Cove Condominium #4, is a direct Gulf front condo located at 2310 Gulf Drive in Bradenton Beach. Completely renovated in 2016 with high end features. Relax on the sugar sand beaches and cool off in the emerald green waters. This complex is conveniently located within walking distance to shopping ...

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Property Type

Anna Maria Island Condo

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Angelinos Sea Lodge

1 BR | 1 BA | Sleeps 4 | Quick View

$245

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Kid Friendly
  • Oceanfront
  • Private Pool

About this property

Angelinos Sea Lodge offers four unique vacation rentals right on the beach of Florida Gulf Coast, Anna Maria Island, Holmes Beach. Hidden in a quiet residential street, these beachfront cottages are quaint, charming, and just a few steps to the white sand and blue sea. All sea lodges have direct ocean ...

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Property Type

Anna Maria Island Cottage

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Good Time and Tan Lines

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Don't miss the opportunity to one of the first to stay in this Stunning 3 bedroom 3 bathroom with bonus den area that has been completely renovated from bottom to top. This property is a new hidden gem of Holmes Beach.   The open concept floor plan is warm and inviting making you feel at home ...

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Property Type

Anna Maria Island Townhome

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Copacabana

3 BR | 2 BA | Sleeps 8 | Quick View

$213

per night

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Key Amenities

  • Air Conditioning

About this property

Copacabana is newly remodeled 3 bedroom, 2 bath private home that sits right on the canal in Anna Maria in a very quiet neighborhood. There is now a brand new kitchen for entertaining and new tile floors flow throughout and with a designer’s stylish touch, you will feel you have found your home ...

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Property Type

Anna Maria Island House

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Fantastic Beach View - Convenience & Comfort at Beach House for Family Fun.

$214

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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 8 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

"Review of an Excellent Rental"
Reviewed April 19, 2019

The house is in a great location and is well equipped. Beach is only a few minutes away. The free trolley, which serves the entire island, is about a 5 minute walk.Supermarket and drug stores are nearby. ...

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Gulf "Beach Bungalow"

1 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.1 miles to Gulf of Mexico

$93

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This cute spacious beach bungalow is arguably one of the best values on the island for immediate beach access located at the northern end of this barrier island of Anna Maria only steps away from the secluded sugar sand beaches fronting emerald waters of the Gulf Of Mexico. From honeymooners to Hollywood ...

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Property Type

Anna Maria Island Bungalow

"Bungalow visit"
Reviewed July 29, 2019

We loved this place and Lisa was an angel with booking and answering our questions. Our only negative would be that it doesn’t have central air and the units were so noisy it was hard to hear the tv. ...

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Osprey Roost - Pet-friendly and very close to beach!

$199

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

It is always summer on Anna Maria Island!We have one of the most pristine, un-crowded beaches you will ever visit. Enjoy a champagne breakfast, Duffy's burgers for lunch, or cocktails at sunset! In addition, there are many other fabulous things to do here - Busch Gardens, Universal Studios and Disney ...

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Property Type

Anna Maria Island House

"Ideal home away from home"
Reviewed April 15, 2019

We can't stop talking about how much we miss "our" Osprey Roost. The car rarely leaves the driveway, as everything we need and want is within walking distance. The gulf is a very short walk, as are the ...

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ALECASSANDRA VACATION VILLAS

11 BR | 10 BA | Sleeps 32 | Quick View

$229

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Ideal Location - Family Reunion Accommodation 1 Property - 2 - Buildings - 6 Individual Villas - Sleeping for 32

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Property Type

Anna Maria Island Villa

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Bare Feet Retreat

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

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Key Amenities

  • Full Kitchen

About this property

Stunning beach front resort with gated covered parking.

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Property Type

Anna Maria Island House

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The Merry Mermaid on Beautiful Anna Maria Island is ready for you!

$100

per night

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Key Amenities

  • Air Conditioning

About this property

The Merry Mermaid is a complete 1 bedroom addition to the main house. The amenities are first rate with love and thoughtfulness put into the finishing touches of this charming property. The beach is only 100 feet away from your front door which also leads to your private patio! The patio has your private ...

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Property Type

Anna Maria Island House

"Great price/location"
Reviewed July 3, 2019

Always great to stay here!! Very friendly and very accommodating!! Will definitely stay here again!!!

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Villa Del Mar

4 BR | 4 BA | Sleeps 10 | Quick View

$504

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama feel. We know how exhausting and stressful traveling can be so don’t feel an ounce of guilt if the second thing you do is plop down on the living room’s couch and switch ...

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Property Type

Anna Maria Island House

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Sunset Beach

2 BR | 2 BA | Sleeps 4 | Quick View

$282

per night

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Key Amenities

  • Air Conditioning
  • Pool

About this property

Lovely, beachfront 2 bedroom, 2 bath condo with a screened porch overlooking the beautiful sand beaches of the Gulf of Mexico!! Situated in a small complex with lush landscaping, private pool and covered parking.Sunset Beach 101 offers newly renovated bathrooms and kitchen with new tile throughout ...

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Property Type

Anna Maria Island Condo

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A Shore Thing

3 BR | 2 BA | Sleeps 8 | Quick View

$213

per night

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Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

This beach house is “A Shore Thing” for creating fantastic vacation memories. This newly furnished ground level home is decorated in coastal living motif and has no stairs to climb. The open floor plan is ideal for one or two families to have a fantastic vacation. The living room, Florida ...

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Property Type

Anna Maria Island House

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Stunning Luxury Beachfront House W/Pool &Spa

$643

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

An outstanding luxury beach house furnished as our home to a very high standard. With a stunning beach coastal theme. It is located on the north end of Anna Maria island The house has 4 bedrooms and 4 bathrooms it was constructed in 2011 has been designed to accommodate a single family group. Please ...

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Property Type

Anna Maria Island House

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Lower Pricing for the Fall Season! THIS PLACE ROCKS!

$121

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

This amazing 1 bedroom house is directly across from the beach and offers full beach views from your huge deck, the living room and kitchen. Heck, you can even see the beach from your bed! We offer a clean house will all of the amenities you need and more! All linens, towels, dishes, washer and dryer, ...

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Property Type

Anna Maria Island Cottage

"Paradise Found!"
Reviewed July 25, 2019

This place is AMAZING! Couldn't have been more pleased. Exactly as pictured and described. Cozy, yet spacious with an open floorplan. Extra clean. Outstanding sea views from every room and located just ...

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Palm Haven

2 BR | 1 BA | Sleeps 6 | Quick View

$98

per night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

This quaint 2 bedroom, 1 bath grond level villa is just a short half block from the white sand beaches of Anna Maria Island. Quiet neighborhood on the beach side of Gulf Drive! Amenities include: Full kitchen with all your utensils and supplies needed, microwave, coffee maker, toaster, oven, cental ...

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Property Type

Anna Maria Island Villa

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Tradewinds Resort-Vacation Cottage Rental

$126

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Condo-cottage with Old Florida charm..... Welcome to paradise.....This 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. This is ...

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Property Type

Anna Maria Island Cottage

"Wonderful"
Reviewed March 22, 2019

Loved loved loved our stay. Very clean and felt safe. Pool was great and relaxing with plenty of amenities. Plan on returning.

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AquaBella

3 BR | 2 BA | Sleeps 6 | Quick View

$255

per night

View Details

Key Amenities

  • Air Conditioning

About this property

AquaBella is a delightful architecturally designed canal front home that offers 3 bedrooms and 2 full bathrooms. This U-shaped home was constructed to take full advantage of the many tranquil views of the deep water canal and lush tropical landscaping. As you sit with your morning tea or coffee all your ...

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Property Type

Anna Maria Island House

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Summer House Upstairs

2 BR | 2 BA | Sleeps 6 | Quick View

$197

per night

View Details

Key Amenities

  • Air Conditioning
  • Pool

About this property

This beautiful villa has two bedrooms and two bathrooms, lots of storage space, laundry room, spacious kitchen and open and light living room. In the living room there is a sleepers sofa. The unit is bright and light, is fully furnished and gives its guests the feel of home. Kitchen is fully equipped. ...

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Property Type

Anna Maria Island Villa

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Saturday to Saturday Special-$2,000/Wk+Taxes+Fees! Write For Details!

4 BR | 3 BA | Sleeps 10 | Quick View

1
LAST MINUTE DEAL 9/12 - 10/23: September-October Special Last-Minute Deal - $2,100 Inclusive - $2,100 covers rent, taxes and fees!

$350

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

PRIVATE HEATED SALTWATER POOL + PRIVATE ELEVATOR + STEPS TO GULF BEACH! SLEEPS 10 - FULLY EQUIPPED - ULTRA-CLEAN! WALKING DISTANCE TO SHOPS, RESTAURANTS, AND NIGHT SPOTS!This is a fully-equipped vacation rental. We even have a baby changing station, and for sanitary reasons suggest guests bring or ...

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Property Type

Anna Maria Island Townhome

"Great home away from home!"
Reviewed October 6, 2018

My friends and I came to Anna Maria Island to get some much needed rest and relaxation, and this rental was the perfect place. The location is awesome, as it is walking distance from the beach. But who ...

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DEAL
Sea Glass Cottage

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Adorable and completely updated 3 Bedroom 2 Bath home on Anna Maria Island! It's just 3 houses to the beach at Bean Point which is known as one of the most beautiful beaches in the US. Newly renovated and features a lovely private fenced yard and private heated pool. Amenities also include, Washer/Dryer, ...

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Property Type

Anna Maria Island House

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Sandcastle 4

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

About this property

Sandcastle is a beautiful beach front property offering all of the conveniences you would want in an island stay. You will find the furnishings & facilities very accommodating to make your vacation one to remember. This condo is a quaint 3 bedroom 2 bath beach front condo located in the heart of ...

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Property Type

Anna Maria Island Condo

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Sea Salt

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Sea Salt is a beautiful recently updated home nestled in the heart of Holmes Beach-just a short 5-minute walk to the world-renowned beaches of Anna Maria Island. This 3 bedroom 2.5 bath home offers everything you need for an unforgettable vacation. Enjoy the private heated pool with sand area, covered ...

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Property Type

Anna Maria Island House

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Anna Maria Island Club Unit 22

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This amazing beach front 2 bedroom / 2 bathroom condo is perfect for an island vacation. This unit features a fully equipped kitchen, elevator, washer & dryer, cable TV / wifi, shaded assigned parking and a shared heated pool & spa. But, it doesn’t stop there, this unit has stunning views ...

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Property Type

Anna Maria Island Condo

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Coconut Breeze Estate

4 BR | 4 BA | Sleeps 12 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious heated pool, gourmet ...

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Property Type

Anna Maria Island House

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Southern Comfort

3 BR | 2 BA | Sleeps 6 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Southern Comfort is a private, single family home centrally located in Holmes Beach. This gorgeous 3 bedroom 2.5 bath vacation rental offers a private heated pool, front and rear balconies, gas BBQ grill, tropical landscaping, one car garage and much more! Just a brief 4 minute stroll to the pristine ...

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Property Type

Anna Maria Island House

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Manna-Tee Beach House

3 BR | 2 BA | Sleeps 8 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom, 2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line finishes ...

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Property Type

Anna Maria Island House

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Walker Beach Cottage/Pet Friendly

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 ...

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Property Type

Anna Maria Island Cottage

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Casa Amiga

4 BR | 4 BA | Sleeps 10 | Quick View

$449

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

CASA AMIGOS is a brand new construction home that features 4 bedrooms and 4.5 bathrooms and a fantastic location-just a 10 minute stroll to the White sandy beaches of BEAN POINT on the coveted north end of Anna Maria. Less than 5 minutes walk to Pine Ave where you can grab your morning coffee, take the ...

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Property Type

Anna Maria Island House

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Oasis By The Beach

5 BR | 4 BA | Sleeps 12 | Quick View

1

$299

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This amazing rental is a favorite for all that stay. 5 bedroom, 4 bathroom beach home just a one minute walk to the famous Anna Maria Island beach. The beach stretches for miles in each directions. Feel the powdery sand between your toes and enjoy the warm Gulf waters. This home has all the style ...

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Property Type

Anna Maria Island House

"Lovely stay"
Reviewed May 6, 2019

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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Emerald Bay

3 BR | 3 BA | Sleeps 6 | Quick View

$279

per night

View Details

About this property

This brand new 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, ...

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Property Type

Anna Maria Island House

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Sand Dollar Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$75

per night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly

About this property

This 2 bedroom, 2 bath villa is in the heart of Anna Maria Island. It is located 300 feet to the beach in a residential neighborhood, west of Gulf Drive, which is the beach side of the main road. Decorated with simplicity, yet fully equipped this ground level villa is conveniently located in the center ...

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Property Type

Anna Maria Island Villa

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A Hart of the Gulf

3 BR | 2 BA | Sleeps 8 | Quick View

$75

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Quaint 3 bedroom, 2 bath private home in a quiet area of Holmes Beach only a short walk from the beach. A Hart of the Gulf is ground level and spacious with all the comforts of home included. Close to the free trolley, shops and restaurants. Accommodates up to 8 guests Amenities include: Linens, central ...

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Property Type

Anna Maria Island House

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Dans Florida Condos - 1 bedroom 1 bath (Private Beach Access) Runaway Bay

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

This non-smoking unit is over 900 sq ft with a screened in terrace complete with a quiet, peaceful view of the lagoon that flows through the center of the complex (see the pictures). Conveniently located close to Sarasota Airport (20 minutes) and the Tampa Airport (55 minutes). Also, close to major Florida ...

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Property Type

Anna Maria Island Condo

"Heated Pool!!!"
Reviewed May 13, 2019

Loved this unit and the excellent communication I had when booking with Dan's Florida Condos. The place had everything we needed, including beach towels & beach chairs. The heated salt water pool was awesome ...

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Gone Coastal Too: Beautiful Family & Pet-Friendly Private Home

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach.Inside it has a split plan with a king sized bedroom and a second bedroom ...

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Property Type

Anna Maria Island House

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Crosswind Cottages

3 BR | 2 BA | Sleeps 6 | Quick View

$149

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

312 (B) 61st street - Holmes Beach - FL - 34217 Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind!Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy beaches where you will enjoy time with ...

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Property Type

Anna Maria Island Cottage

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Salt Air East

2 BR | 2 BA | Sleeps 6 | Quick View

$199

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything!Salt Air East villa, located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island.Not in the mood for the beach? ...

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Property Type

Anna Maria Island House

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Turtle's Bay

3 BR | 3 BA | Sleeps 6 | Quick View

1

$279

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

This brand new 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, ...

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Property Type

Anna Maria Island House

"Beautiful Property"
Reviewed September 23, 2018

Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.

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Angel Sea

6 BR | 3 BA | Sleeps 12 | Quick View

$299

per night

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About this property

This ideally located 6 Bedroom 3.5 Bathroom is an amazing place to escape and unwind. It is the perfect place to get away with friends or family, offering a large open floor plan and multiple outdoor sitting area. This little piece of paradise is centrally located to everything you could desire, it ...

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Property Type

Anna Maria Island House

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Island Escape

4 BR | 5.5 BA | Sleeps 10 | Quick View

$599

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

ISLAND ESCAPE is the most beautiful house you'll find on AMI ~ brand new and simply FABULOUS! The photos just can’t show exactly how special this home really is. Be one of the first to bring their family and enjoy this home that features upscale, professional décor without a detail missed. ...

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Property Type

Anna Maria Island House

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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°

Choose a vacation rental on the little island that has it all

A mere 20 minutes from Bradenton, laid-back Anna Maria Island awaits. What feels like “old” Gulf Coast Florida with strict business regulations, little to no car traffic, and a peaceful way of life. That’s right, you won’t find any chain restaurants or high-rise, view-blocking buildings here. And oh, the beaches! A seven-mile strip of beautiful white-sand beaches line the barrier island of Anna Maria Island between the turquoise Gulf of Mexico and peninsular Florida. It won’t be difficult to unwind here.

Anna Maria Island has amazing beachfront with available accommodations for you. When staying in one of our Anna Maria Island vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you, just like Anna Maria Island does.

Climate

You come to Florida for warmth and guaranteed clear skies. You’ll find all that and more in Anna Maria Island. The average year-round temperature in Anna Maria Island is a comfortable 75 degrees making it an ideal destination to visit during any month. You won’t see too much shifting of temps and precipitation here, though try to avoid hurricane season in the fall. Otherwise, you can’t go wrong whenever you visit.

Getting around

Hop around the island on the Anna Maria Trolley, as it runs north to south from the pier all the way to Coquina Beach. It stops every few blocks for riders to get on and off. Since parking is rare throughout the city, the trolley is a fan favorite. The best part? This scenic, air-conditioned ride is completely FREE!

Top activities and attractions

Your family won’t run low on things to do in Anna Maria Island. You’re visiting for the beaches, of course, and the best public one is known as Bean Point, located at the north end of the island. From here, you can walk around the entire island without leaving the sand. At the southern end of the area you’ll find Bradenton Beach which is another highly-rated, soft-sand place to spread your blanket and enjoy the sun. Of course a seaside city excels at water sports, too. Try your hand at parasailing, snorkeling, jet-ski, water ski, and many more activities on the turquoise blue waves.

Once you’re through with the surf, walk along the Anna Maria City Pier. Over 100 yrs old, the Pier offers up some great views of Tampa Bay and the Sunshine Skyway bridge at the northern end of the island. Visitors can see an array of birds and marine life, including dolphins and manatee. For more scenic and historic walking, check out Coquina Baywalk. This pleasant park is fun to explore. Winding boardwalks and trails along the water's edge, hidden in the mangroves.

The local museums and art galleries are popular attractions as well and great alternatives to outdoor activities. Spend an afternoon at the Anna Maria Island Historical Museum and Park. Visitors to the museum and park can learn about the island’s history, take part in a scavenger hunt, and tour the cottage that fell into the bay.

Shopping and dining

You’ll want to shop the day away on Pine Avenue, known as “the greenest little main street in America”. It’s lined with boutiques all the way up to the City Pier. Holmes Beach is also a populars shopping center ideal for grabbing that perfect souvenir.

Nestled alongside the storefronts are award-winning dining options. For those with a sweet tooth, The Donut Experiment serves up custom creations daily including a Fruity Pebbles inspired masterpiece. Yum! Fresh seafood abounds, like at the popular Waterfront Restaurant and upscale Blue Marlin Grill. For a taste of Europe, and German hops, visit Old Hamburg Schnitzelhaus serving up sausage, beer, and pretzels - each more delicious than the last.

Events

Although we discussed how the year-round flawless weather makes AMI an ideal choice no matter the month, time your trip to coincide with some popular area events to maximize fun. Heritage Day in February features the wares and skills of local artists and crafters, and attendees can take part in activities, enjoy lively music and participate in old-fashioned games for kids. Later in spring, the Bridge Street Merchants host the Blues, Brews & BBQ event to showcase the area’s top musical talents. Outdoor Market Sundays take place November through April with crafts and local produce for sale.

Anna Maria Island beach rentals on FloridaRentals.com

Booking Anna Maria Island rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!