Anna Maria Island Beach Florida Vacation Rentals, Hotels & Resorts

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 Island, 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 Island, 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 hundreds of Vacation Rentals, Condos and Homes in Anna Maria Island, Florida

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

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

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 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

View Rental

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

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

View Rental

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

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

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

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

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

View Rental

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

View Rental

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

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

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

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

View Rental

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 MariaĆ¢??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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

View Rental

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

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

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

View Rental

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

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

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 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

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


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.

© Reservations Direct, Inc. - Vacation Rentals, Resorts & Hotel Accommodations

About Us - Privacy - Top Destinations - Best Vacation Spots - Car Rentals