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....

Rentals 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 vacation rentals & 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

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

View Vacation Home

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 Vacation Home

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 Vacation Home

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 Vacation Home

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 Vacation Home

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

View Vacation Home

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 Vacation Home

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 Vacation Home

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

View Vacation Home

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 Vacation Home

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 Vacation Home

Anna Maria house

Anna's Cottage

Perfect Island Location! Heated pool and plenty of room for the entire family.

AnnaĆ¢??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

View Vacation Home

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 Vacation Home

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 Vacation Home

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 Vacation Home

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

View Vacation Home

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 Vacation Home

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 Vacation Home

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 Vacation Home

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

View Vacation Home

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 Vacation Home

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

View Vacation Home

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 Vacation Home

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 Vacation Home

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

View Vacation Home

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 Vacation Home

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 Vacation Home

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

View Vacation Home

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 Vacation Home

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 Vacation Home


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