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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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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

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

The Sassy Seahorse

Top-rated Anna Maria Florida Vacation Rental

Our Sassy Seahorse has been rated as one of the top 15 out of 260 vacation rentals by Island Real Estate, the largest real estate agency on Anna Maria Island. Our 5-Star rated vacation rental home is private, immaculately clean, whimsically decorated ....

3 Bedroom(s) 3 Bath(s) Vacation Rental - 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 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

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

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

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 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

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 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

Paradise Pointe

Breezy canalfront home w/ pool & dock - 3 blocks to Bean Point Beach!

Paradise Pointe 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

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

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 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 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

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 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

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 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

Rose Street Retreat

Casual, relaxing island home w/ a private pool - walk to dining & the beach!

Rose Street Retreat 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 ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
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

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

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

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 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

Casa Mariposa

LUXURY Florida Charm w/Pool, Spa, Lanais,Gardens. Steps to BEST Beach & Pine Ave

Immerse yourself in luxurious 'Old-Florida' feel in this STUNNING one-of-a kind gem of an island home, Casa Mariposa! You truly won't find a more unique and sacred home with its lush landscaping and butterfly sanctuary gardens that is in a better loc ....

4 Bedroom(s) 5 Bath(s) Vacation Rental - Sleeps 8
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

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 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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