Anna Maria Island Beach Florida Vacation Rentals, Hotels & Resorts

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Cheap Hotels Anna Maria Island, FL

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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

The Seashell Cottage

Sunny, dog-friendly cottage w/ a spacious patio and grill, steps from the beach!

The Seashell 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 'Boo ....

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

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Anna Maria house

Sandy's Getaway

Dog-friendly condo w/ beautiful upstairs deck and grill, steps from the beach

Sandy's Getaway 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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Anna Maria house

The Beach House

THE BEACH HOUSE ON PINE AVENUE

This 4 bedroom/3 bath home is situated in the perfect location on the most desirable street on Anna Maria Island. It is located a short 1.5 block walk to the pristine 7 miiles of the white sandy beaches of the Gulf of Mexico. Interior tastefully de ....

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

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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 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

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 house

Heavenly Holly

Canalfront home w/ pool, dock & lanai - 2 blocks to the beach, dogs OK!

Heavenly Holly 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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Anna Maria house

Anna Maria Escape

Peaceful and Relaxing 2BR/2BA Gulf Front Home Steps from the Beach, w/ Free Wifi

The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! Itâ??s a perfect Anna Maria Island vacation home! ....

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

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Anna Maria house

Pesky Pelican

~Spectacular Sunrises~Bayfront w/Dock for Fishing, Manatee & Dolphin Watching!

Direct Bay front estate with dazzling panoramic views of the bay. Spectacular Sunrises with Awesome views and only blocks from the White Sandy Beaches! What more could you ask for...the best of both sides of the island! Dolphin, manatee and great ....

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

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Anna Maria cottage

Bay Breeze Cottage #1

Bay Breeze Cottages on Beautiful Anna Maria Island

Charming re-modeled Anna Maria Cottage one block to the beach & Rod & Reel Pier. 1.5 blocks to Bean Point Park on the North End of Anna Maria Island. Relax in a resort style pool surrounded by Palms and luscious landscaping. End your day with a frien ....

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

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Anna Maria house

Palm Beach House

Dog-friendly home w/ private pool - blocks from the beach - near shopping/dining

Palm Beach House 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 No ....

4 Bedroom(s) 3 Bath(s) Vacation Rental
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 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 cottage

The Lime Door

Beautiful Beach Cottage In Anna Maria

�� �� �� �� �� Everyone LOVES the Lime Door! Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine i ....

2 Bedroom(s) 2 Bath(s) Cottage - Sleeps 6
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

Diamond Surf

Anna Maria-Private Backyard, Heated Saltwater Pool, 1 block to beach.

Diamond Surf is a 2Bedroom/2Bath, Ground Level Cottage on Anna Mariaâ??s North End. This cottage is one block walking distance to the beach access on Beach Avenue. Master suite with a King bed, a guest bedroom with a Queen bed, and Twin Trundle bed ....

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

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Anna Maria house

Hidden Oasis

WOW!! REDUCED 20% ON OPEN DATES NOW UNTIL 4/27/19 at Hidden Oasis: 1 BR / 1 BA!

Hidden Oasis 777A North Shore Anna Maria, Fl. 24216 This lovely 1 bedroom, 1 bathroom gulf front hideaway has just been completely renovated from top to bottom! This second level location has a private balcony with large southern views of the beau ....

1 Bedroom(s) 1 Bath(s) Vacation Rental - 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

Pineapple Breeze

Steps to Bean Point, Pineapple Breeze is a quaint home with private pool

Pineapple Breeze is a beach oasis offering a small luxury vacation home with the finest furnishings and fixtures. Anna Maria Island was voted in the top ten of the â??Happiest Seaside Townsâ?? in 2018 by Coastal Living Magazine. The island is a uniqu ....

2 Bedroom(s) 2 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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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 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

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 house

Lighthouse Lagoon

WOW! REDUCED 20% ON OPEN DATES NOW UNTIL 4/27/19 at Lighthouse Lagoon!

Lighthouse Lagoon 508 Spring Avenue Anna Maria, Fl. 34216 "LIGHTHOUSE LAGOON" IS KNOWN FOR ITS GREAT LOCATION, EXTREMELY GENEROUS LIVING AREAS, AND TROPICAL LAGOON POOL. "Lighthouse Lagoon" is a beautifully updated 5 bedroom, 4 full bathroom pool ....

5 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 14
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

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 cottage

Mangrove Cottage

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

Mangrove 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 No ....

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

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Anna Maria house

Azure Seas

Spacious 3B/2B Gulf Front Home on the tranquil north end of Anna Maria Island

The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and ....

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

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Anna Maria condo

Paradise at the Bayou

Waterfront Views - North End Anna Maria Island

Great north end location on historic Pine Avenue - this beautifully appointed, 2BR/1BA upstairs condo is picture perfect. A palette of colors meets the eye upon entry - complimented by tasteful furnishings, an updated kitchen and bath with granite c ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
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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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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