Anna Maria Island Beach Florida Vacation Rentals, Hotels & Resorts

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We have partnered with a major provider for Vacation Rentals by Owner, directly through Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Anna Maria Island, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Anna Maria cottage

Serendipity Deux

2019 New Construction 4 bed/4.5 bath

Brand New 2019 4 bedroom 4.5 bath Beach Front Home with a Beach Front Pool and Spa Gourmet Kitchen, high end finishes and one of a kind features. Look for updated progress photos or give us a call and we are happy to update you. Professionally Des ....

4 Bedroom(s) 5 Bath(s) Cottage - Sleeps 6
Anna Maria, FL

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Anna Maria house

The Beach House

WOW!! Reduced 25% on open dates now - 4/27/19 at The Beach House: 3 BR / 2.5 BA

The Beach House 9308 Gulf Drive Anna Maria, Fl. 34216 Totally updated 3 bedroom 2.5 bath elevated home just six houses from the Gulf of Mexico. French doors and sliders open to your covered wrap-around porches. Listen to the sounds of rustling ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 7
Anna Maria, FL

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Anna Maria house

Moon Shadow South - 1381834-9

Newly Built! Spectacular Location Desirable North End w/Water Views Heated Pool!

Moon Shadow South is a custom built home that was just completed in July of 2015 by Kimball Construction the premier builder on Anna Maria Island. With its unparalleled views of Tampa Bay it's the perfect place to relax and get away from it all! The ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Anna Maria, FL

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Anna Maria house

Sea La Vie Beach House

SPECTACULAR LUXURY NEW WATERFRONT HOME w/Pool & Spa on Canal, Close to Pine Ave

Words and photos can not even begin to do this home justice. This two story canal front home just finished completion in 2018 and is brand new! This 4 bedroom, 4 1/2 bath, extremely spacious and meticulously designed and decorated home will take yo ....

4 Bedroom(s) 6 Bath(s) Vacation Rental - Sleeps 8
Anna Maria, FL

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Anna Maria house

Southern Breeze 6

WOW! REDUCED 25% on open dates now until 4/27/19 at Southern Breeze 6!

Southern Breeze #6 610 Rose Street #6 Anna Maria, Fl. 34216 ISLAND 6-PLEX! These are 2 bedroom, 1 bath ground level units located at the tip of Anna Maria Island just steps from the Bay. Heated pool with nicely landscaped surroundings. Each is ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Anna Maria, FL

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Anna Maria house

Angel Fish Cottage

Angel Fish Cottage - North End - Steps to Gulf and Bay with Heated Pool-

NEWLY REMODELED BATHROOM (pics not up yet on site) - Situated at the quiet north end of Anna Maria Island. Removed from the condos, hotels, and crowds. We are one short block (12 houses) from sunrises on the bay, and 6 houses from the historic Rod ....

2 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 6
Anna Maria, FL

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Anna Maria house

Beach Escape

BRAND NEW HOME - 5 BEDROOM, PRIVATE HEATED POOL/SPA, LESS THAN 1 BLOCK TO BEACH

Fabulous new construction 5-bedroom coastal home with 4 baths located on the highly desirable northern end of Anna Maria Island. The home has upscale finishes and an amazing floor plan with open concept kitchen, dining and living area. In addition, t ....

5 Bedroom(s) 4 Bath(s) Vacation Rental
Anna Maria, FL

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Anna Maria house

The Big Yellow House

WOW!! REDUCED 20% ON OPEN DATES NOW UNTIL 4/27/19 at The Big Yellow House!

The Big Yellow House on Pine 104 Pine Avenue Anna Maria Fl. 34216 This home is direct Gulf front with a private heated pool! It has all the perfect ingredients for a wonderful vacation. Enjoy your front row seat to spectacular sunsets from this ....

5 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 14
Anna Maria, FL

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Anna Maria house

Starboard Sea-renity

Starboard Sea-renity - Brand new house 4 King bedrooms - Spring Break Deals

Welcome to the Starboard Sea-renity, a beautiful New Construction Home perfectly located 10 houses off the beach! PLEASE NOTE- this is a BRAND NEW property. All pictures shown are for illustration purpose only. Check back soon for actual photos an ....

4 Bedroom(s) 7 Bath(s) Vacation Rental
Anna Maria, FL

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Anna Maria house

Anna's Cottage

Perfect Island Location! Heated pool and plenty of room for the entire family.

Annaâ??s Cottage is a completely renovated island home that is perfectly located on Spring Avenue in the city of Anna Maria. Only 2 blocks west is the beautiful Gulf of Mexico and the Sandbar restaurant. Only 3 blocks east is the historic Anna Maria ....

4 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Anna Maria, FL

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Anna Maria house

Beachhouse, Bring your dog

Private Beachfront Paradise, Dogs R Free, Walking Beach, Military disc

This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The home has a private beach right in the backyard. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the ....

4 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Anna Maria, FL

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Anna Maria house

Family Beach House Sleeps 10

4 Bedroom Sleeps 10 Large Family Pool Home Steps to Beach Located on North End

This is a 4 bedroom 3 bath home 2600 sq ft with large lanai out door living area. Let the sea breezes blow! If you need additional space there is a 2 bedroom 1 bath attached apt attached to this property that shares the beautiful pool area that is ....

5 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 10
Anna Maria, FL

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Anna Maria house

Buttonwood Cottage

Book NOW for 2017! Exquisite Designer Beach Cottage, 3BR, 2BA

Welcome to Buttonwood Cottage. This elegant nautically inspired single family beach home sleeps 8 comfortably. We have 3 nicely appointed bedrooms and 2 full baths. The master BR has a king bed, the second BR a queen, and the third BR has 2 twin trun ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Anna Maria, FL

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Anna Maria house

Limelight

WOW! REDUCED 25% on open dates now - 4/27/19 at Limelight with Private Pool!

Limelight 771 Jacaranda Rd. Anna Maria, Fl. 34216 Limelight is a gorgeous and well-maintained beach house, conveniently located on the prestigious North End of Anna Maria Island. With only a brisk 3 minute walk away from the sandy white beaches, ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 6
Anna Maria, FL

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Anna Maria house

AMI Life

WOW!! REDUCED 20% ON OPEN DATES NOW UNTIL 4/27/19 at AMI Life: 5 BR / 3.5 BA!

AMI Life 520 Bayview Place Anna Maria, FL 34216 AMI Life is a gorgeous custom luxury direct canal front home tucked away on the prestigious North end of Anna Maria Island. This beautiful 5 bedroom and 3 bathroom home includes a private heated p ....

5 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 10
Anna Maria, FL

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Anna Maria cottage

Emma's Cottage

Oceanfront dog-friendly home w/private pool & ocean view - right on the beach!

Emma's Cottage Vacasa is proud to partner with HomeAway to offer you the ability to instantly book this property! Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now! ....

3 Bedroom(s) 2 Bath(s) Cottage
Anna Maria, FL

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Anna Maria house

Sea Mist

Sea Mist by Duncan Real Estate

Welcome to Sea Mist! This beautiful 3 bedroom, 2 bathroom property has 1,742 square feet of elevated living space and the ability to accommodate 6 guests very comfortably inside and out. From the quality quilts and linens on the beds, to TVs in th ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Anna Maria, FL

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Anna Maria house

Paradise on Pine

WOW! Reduced 25% for open dates now - 4/27/19 at Paradise on Pine: Private Pool!

Paradise on Pine 410 Pine Avenue Anna Maria, FL 34216 The name says it all for this gorgeous 4 bedroom and 3.5 bathroom home with private heated pool, boat dock, canal access and so much more! This gorgeous home is located in the heart of Pine Ave ....

4 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 12
Anna Maria, FL

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Anna Maria house

Paradise Cottage

Paradise Cottage by Duncan Real Estate

Come discover "Paradise Cottage" with all it's old Florida charm as well as newly updated appliances and decor. This lovely and colorful two bedroom, two bath home feels brand new. You'll enjoy tile floors throughout, a large eat-in kichen, comfort ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Anna Maria, FL

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anna maria house

Shoreline Cottage

Waterfront Dream - Private beach 70 feet from backdoor!! **FEBRUARY SPECIAL**

**REAL Vacation Rental by Owner** - talk directly with the owner - not a company! Ignore VRBO fees in pricing :) Beautiful waterfront home located on the north end of Anna Maria Island. Located on North Shore Drive, approx 9 houses east of the Rod ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 8
anna maria, fl

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Anna Maria cottage

Minnow 1

Minnow 1 by Duncan Real Estate

Vacation bliss at Minnow 1! This property is a ground level duplex and will enlighten your stay no matter if a week or a month long! The beautiful and tastefully decorated one bedroom, one bathroom bungalow has polished terrazzo throughout and offers ....

1 Bedroom(s) 1 Bath(s) Cottage - Sleeps 2
Anna Maria, FL

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Anna Maria house

Parakeet Properties

Fabulous Home with Outstanding Location and HEATED POOL!

Lovely, 2 story home with large, elevated screened-in porch. En-suite master-bath. Second bedroom and bath on main living floor. Third bedroom is a spacious loft, ideal for children. Recent interior renovations and brand-new heated pool. Newly renova ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Anna Maria, FL

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Anna Maria cottage

Blue Heron Cottage

Blue Heron Cottage - Anna Maria Island

Great 1 bedroom, 1.5 bathroom cottage on the quiet north end of island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Fern Street/Alamanda Road. This great getaway slee ....

1 Bedroom(s) 2 Bath(s) Cottage - Sleeps 4
Anna Maria, FL

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Anna Maria hotel

Blue Dolphin Inn

Beautiful 2B/2B unit w/ freestyle heated pool, fountains & nearby tiki table

The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units sur ....

2 Bedroom(s) 2 Bath(s) Resort Hotel
Anna Maria, FL

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Anna Maria house

Coconut Breeze Estate

Family Fun Vacation Home, Huge Outdoor Kitchen, Pool,Roof Top Deck with Amazing Views

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 I ....

4 Bedroom(s) 4 Bath(s) Vacation Rental
Anna Maria, FL

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Anna Maria cottage

Pine Ave Hide-Away 797442

Newly Built Pine Ave 2/2 Steps To Beach, Bay, Shops, Restaurants & Free Trolley!

Newly built â??Pine Ave Hide-Awayâ?? is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and Tampa Bay on the desirable North End. Walk to all your favorite restaurants, shops, City Pier and all the other great ....

2 Bedroom(s) 3 Bath(s) Cottage - Sleeps 4
Anna Maria, FL

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Anna Maria house

OHasis Getaway

Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!

OHasis Getaway is a true oasis on both the outside and inside! When you step into our vacation rental, your eyes are immediately drawn to one of a kind woven bamboo vaulted ceiling and then down to the beautiful Italian travertine tile. Your eye co ....

2 Bedroom(s) 1 Bath(s) Vacation Rental - Sleeps 4
Anna Maria, FL

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Anna Maria house

ANGEL'S ENVY

Anna Maria Island Rentals - Beach Front - "Angels Envy"

First, Anna Maria Island is broken up into 3 cities, Anna Maria, Holmes Beach and Bradenton Beach. The City of Anna Maria is the most northern part of the Island and the most popular. When searching for Beach front rentals, be careful. A standard ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Anna Maria, FL

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Anna Maria house

Beach Breeze

UPDATED GROUND LEVEL HOME, NEW HEATED POOL/SPA, BLOCK TO BEACH

Beach Breeze ~ Ideal location, southern exposure pool/spa and completely renovated inside! Just 1 BLOCK to the beach and just 1 BLOCK to Pine Ave, which has quaint beach shops, restaurants and make your own donuts! From the moment you arrival you'll ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
Anna Maria, FL

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Anna Maria house

Bay Bungalow

NEW LISTING! Bay side family-home w/pool, 2 blocks from Bean Point beaches

Bay Bungalow Vacasa is proud to partner with HomeAway to offer you the ability to instantly book this property! Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!' ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Anna Maria, FL

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Find Affordable Anna Maria Island Hotels & Vacation Rentals

Plan your Anna Maria Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Anna Maria, Florida. Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Tampa Bay Area.


Vacation Rentals Nearby Tampa Bay Destinations

Find nearby vacation rentals and some of the Best Hotels with cheap rates in Anna Maria Island, FL for you visit to the area, all a short drive to Anna Maria, Florida. Spend quality time with your family and friends with cheap hotel rates you can afford, visit the nearby beaches for nightlife, entertainment and a wide variety of beach activities. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.

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