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 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

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 cottage

Turtle Cottage

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 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 Gladiolus Street/Alamanda Road. This great getaway s ....

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

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Anna Maria apartment

Vacation Home

Waterfront apartment in Anna Maria Village

Second floor contemporary apartment with views over the canal on Anna Maria s lovely north end. A block from City Pier and Tampa Bay and only four blocks to the white sand beaches of the Gulf of Mexico. Anna Maria is noted for its relaxed way of life ....

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

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Anna Maria house

C-view Florida

Best Location on Island/Ideal for 2 families/Canal/Dock/Heated Pool/Near Gulf

Do not run the risk of being disappointed by your vacation rental. Read our reviews. Be sure to look at the Total Cost of booking before deciding. A lower Daily Rate does not mean a lower total cost. C-view Florida is ONE of ONLY TWO 5-bedroom home ....

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

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Anna Maria villa

Northshore Beach Home

ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa

Quaint and quiet Northshore Villa nestled in the heart of the village of Anna Maria, on Anna Maria Island. Our 2 bedroom 1 bath home has been recently updated for our guests enjoyment. Sit out on our deck in the morning and enjoy a peaceful quiet c ....

2 Bedroom(s) 1 Bath(s) Villa - Sleeps 5
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

Vacation Home

New listing! Bay -Canal Waterfront, Tiki Bar 5 BR 5 BA Heated Pool, 2 Kitchens

Just remodeled December 2018, with state of the art finishes! 5 BR 5 BA Duplex with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! A few blocks down from the 5 Star Waterfront Res ....

5 Bedroom(s) 6 Bath(s) Vacation Rental - Sleeps 14
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

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 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 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

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

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

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 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

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

Beach Escape

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

Beach Escape 236 Gladiolus Street Anna Maria, FL 34216 The Beach Escape is a completely renovated, charming, beautiful elevated cottage nestled in the desirable North End of Anna Maria Island, in the center of island shopping, the piers, restaura ....

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

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Anna Maria house

Beach Cay

ONLY 1 HOUSE AWAY from Nicest GULF Beach, LARGE Heated Pool

Location, location, location. If you are looking to be close to the GULF beach, this is the one. Beach Cay (www.BeachCay.com) is perfectly situated at the very desirable North End of Anna Maria Island, just steps to the Gulf of Mexico's white sugar ....

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

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Anna Maria hotel

Blue Dolphin Inn

4 Units w/ Tropical Heated Pool, Rooftop Observation Decks & loads of charm!

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 ....

9 Bedroom(s) 6 Bath(s) Resort Hotel
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 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

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 house

Beach To Bay Getaway

Beach to Bay Getaway by Duncan Real Estate

Welcome to Beach to Bay Getaway! This newly renovated 3 bedroom/2 bath heated pool/spa home feels like you're living in a private resort. The living area and 2 bedrooms are elevated. Spread out in the living room includes that features a 48" flat sc ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
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

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

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 cottage

Sundance Cottage

Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!

Sundance 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 ....

3 Bedroom(s) 2 Bath(s) Cottage
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

Spoonbill Hideaway

Spoonbill Hideaway -Huge Pool/Spa/Private Tropical Oasis/Across from Gulf Beach

Our house is located on North Shore Drive in Anna Maria Florida across the street from one of the widest and finest beaches on the island near Bean Point on the very desirable north end, in the city of Anna Maria. Come visit our house most appropria ....

3 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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