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Anna Maria Vacation Rentals, Hotels, Motels and Small Inns

Find the best prices for Small Inn and Hotel Accomodations on Anna Maria Island

The award winning Gulf Coast beaches of Anna Maria Island are popular vacation spots for relaxing, laid back family getaways. The waterfront small inns and cottages of Anna Maria Island offer an affordable holiday in the Tampa Bay area. This is a favorite Florida destination for people that travel with Pets.


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Rentals in Anna Maria, FL

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Cheap Hotels Anna Maria, FL

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Search many beachfront Vacation Rentals & Cottages on Anna Maria Island

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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, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Anna Maria house

Bodacious Oasis

Bodacious Oasis by Duncan Real Estate

Welcome to Bodacious Oasis! This beautiful 4 bedroom 2 and 1/2 bath property can accommodate 8 guests very comfortably inside and out. Larger families will enjoy the open floor plan, providing plenty of room to spread out and enjoy comfortable island ....

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

Your Home Away From Home

Anna Marie Hideaway!

2013 is the first year we have rented our family beach house on Anna Maria Island. Our kids are in school and it is harder to get down to FL. We love this quaint and charming area of Florida. The house sits on a canal at the end of a cul de sac off ....

4 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

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

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

Sunshine Reef

WOW! REDUCED 25% ON OPEN DATES NOW UNTIL 4/27/19 at Sunshine Reef: Private Pool!

Sunshine Reef 308 Palm Avenue Anna Maria Island, Fl 34216 Sunshine Reef is a gorgeous 4 bedroom and 4 bathroom ground level private home that offers an incredible location on top of wonderful amenities that the whole family will enjoy. Located on ....

4 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 10
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

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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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 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 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

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

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

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

Sea Song

Incredible beachfront bungalow with deck, grill, outdoor shower, and more

Sea Song 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!'Get r ....

2 Bedroom(s) 1 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

Ahh Sea Breeze

Gulf Front Vacation in Paradise

SEA BREEZE Gulf Front vacation home is located on Anna Maria's North Shore Drive with magnificent panoramic views of the Gulf of Mexico. This spacious 3 bedroom 2 bath home is tastefully furnished and well maintained for your comfort and with all co ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
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

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

Gulf Front Paradise

WOW!! Reduced 25% for open dates now - 4/27/19 at Gulf Front Paradise!

Gulf Front Paradise 101 Palmetto Avenue Anna Maria, FL 34216 Wow- look at this brand new rental!! Gulf Front Paradise provides everything you could possibly dream of from an Anna Maria Island vacation home. This 4 bedroom and 4.5 bathroom with a ....

4 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 10
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 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

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

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 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 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 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

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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