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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

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

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

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

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

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

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

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 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 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

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 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 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

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

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

Sunrise Shore

Beautiful Home 2 Blocks From Pine Avenue. Close to it all. Come see for yourself

Welcome to Sunrise Shore; a unique waterfront property featuring 5 bedrooms, 3 bathrooms and a private heated salt water pool just one block to Pine Avenue! This home sleeps up to 13 guests in total. It is located on a secluded pond on the prestigio ....

5 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 13
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

Retro Retreat

Back In Time On Pine (3/1 Anna Maria Pine Ave Cottage)

Step back in time & relax on Island Time in the middle of Pine! 3bedroom /1bath restored cottage in the heart of it all. Short walk or bike to beaches, shops, restaurants and more. Bikes, golf cart, beach toys, beach cart all included. 2 Kings & ....

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

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

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

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 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

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

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

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 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

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 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

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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