Home > Vacation Rentals > Anna Maria Island

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.


Search for Vacation Rental Homes or Hotels

           
Best Prices Booking


Vacation Places To Stay We have chosen to partner with Booking.com to offer travelers the best choices for vacation properties - No Booking Fees, Last Minute Room Availability, 2,146,000+ hotels, apartments, villas, condo rentals and more....

Best Rental Prices in Anna Maria, FL

Don't know Where To Stay? Select your destination and search for discount accommodations.

If you don't see your travel destination, just type it in the box and search for hundreds of Hotels, Resorts, Motels, Homes, Villas or Condos and more!

Cheap Hotels Anna Maria, FL

Trying to save money on your vacation? VacationPlacesToStay.com has great deals and low prices on hotels, Best Price Guaranteed.

Save when you book directly online for last minute deals with 3 to 5 Star Resorts, Inns, Hotels and more!


Search many beachfront Vacation Rentals & Cottages on Anna Maria Island

Book Your Vacation Homes Directly Online Here and Save!

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

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

Anna Maria house

Buttonwood Cottage

Book NOW for 2017! Exquisite Designer Beach Cottage, 3BR, 2BA

Welcome to Buttonwood Cottage. This elegant nautically inspired single family beach home sleeps 8 comfortably. We have 3 nicely appointed bedrooms and 2 full baths. The master BR has a king bed, the second BR a queen, and the third BR has 2 twin trun ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
Anna Maria, FL

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

Anna Maria cottage

Eureka

Eureka by Duncan Real Estate.

Soak up the rays, play in the waves, and watch the beautiful Florida sunsets from the North end beaches of Anna Maria Island. Eureka is so close to the beach you will not miss a single sunset! This light and airy 2 bedroom and 2 bath cottage has been ....

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

anna Maria house

303 North Bay Blvd LLC

Beach front/pool house, quiet, private,

Come and enjoy our tropical paradise on the quiet North End of Anna Maria Island - located at the south end of Tampa Bay, within 40 minutes of Tampa Airport. One-and-one-half hours to Disney and all the Central Florida theme parks and thirty minut ....

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

Anna Maria house

Paradise on Pine

WOW! Reduced 25% for open dates now - 4/27/19 at Paradise on Pine: Private Pool!

Paradise on Pine 410 Pine Avenue Anna Maria, FL 34216 The name says it all for this gorgeous 4 bedroom and 3.5 bathroom home with private heated pool, boat dock, canal access and so much more! This gorgeous home is located in the heart of Pine Ave ....

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

View Rental

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

View Rental

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

View Rental


© Reservations Direct, Inc. - Tampa Bay Vacation Rentals, Hotels & Places To Stay

About Us - Privacy - Popular Destinations - Top Florida Getaways