Skip to content

Florida Vacation Rentals by Owner

Search by Destination or Property Name

           

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+ homes, apartments, condo rentals, hotels and more....

Best Prices in Anna Maria Island

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

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!

Book Your Anna Maria Island Vacation Rentals Directly Online Here and Save!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Anna Maria Island, Florida.

We have partnered with a major provider for Vacation Rentals by Owner, directly through Florida Vacation Rental Homes. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida.


Anna Maria House

Diamond Surf - Anna Maria House

AMI North End Private Heated Saltwater Pool. Great location to beach. You'll fall in love with Diamond Surf's “Old Florida” charm and feel. Our private ground level home means no stairs to climb. Diamond Surf is perfect for families, couples or a small group of friends. The house is located with an easy 3-minute stroll down Beach Avenue to the gorgeous white sand beaches of the Gulf of Mexico or steps to a F....

3 Bedrooms 2 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria House

Aquaville A - Anna Maria House

Aquaville A - 2/1 beauty with private pool in the heart of Anna Maria. Pets!. The location of Aquaville A is just fantastic: Enjoy a short walk away from everything at the prestigious North End of Anna Maria Island: From the famous beach, from the stop of the free Island trolley, from well known Ginny's and Jane E's Cafe and Gift Store, from Harry's Grill or The Sign of the Mermaid restaurant and some others and of course ju....

2 Bedrooms 1 Baths - Sleeps 4
Anna Maria, FL

View Rental

Anna Maria House

Lay-by at the Point - 305 Poinsettia - Anna Maria House

Dog Friendly Private Pool Home on the North End of Anna Maria. A Short Walk To The Beach And Bay!. Welcome to Lay-by at the Point, located on the coveted north end of Anna Maria Island! What You'll Love About This Home: Location! 2 blocks to Bean Point- Anna Maria's most legendary Beach 3 Bedrooms / 2 Bathrooms 1 King, 1 Queen, 2 Twins Fully Equipped Kitchen Private, Heated Saltwater Pool Outdoor Shower Professional Linen Service, Washer &....

3 Bedrooms 2 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria House

Starfish Cottage - Anna Maria House

Heated Pool FREE WiFi & Trolley Close to Gulf & Bay Beach Dog Friendly!. You'll be right at home in this tastefully designed 4-bedroom 3-bath ground floor cottage, nestled at the corner of Alamanda and North Bay Boulevard, just half a block from the Rod and Reel Pier. The home's backyard oasis is sure to be your favorite place to relax. The patio extends the length of the yard, with areas to grill, picnic and loun....

4 Bedrooms 3 Baths - Sleeps 8
Anna Maria, FL

View Rental

Anna Maria House

Mary Ann of Anna Maria - 213 Periwinkle - Anna Maria House

Funky & Fun Pool & Spa Home 2 Blocks to Beach - on AMI North End. Welcome to Mary Ann of Anna Maria! What You'll Love About This Home: Location! Two blocks to the Gulf of Mexico Beaches! 3 Bedrooms / 2 Bathrooms 2 King Beds, 1 Full Bed, Sofa Sleeper Private, Heated Pool & Spa Fully Equipped Kitchen Gas BBQ Grill Professional Linen Service, Washer & Dryer, Complimentary WIFI, Beach Towels Details: Mary Ann of ....

3 Bedrooms 2 Baths - Sleeps 8
Anna Maria, FL

View Rental

Anna Maria House

Coconut Bayou - Anna Maria House

Coconut Bayou - a gem with heated pool on a fantastic location in Anna Maria. Coconut Bayou is a 3 bedroom, 3.5 bath Key West style beauty with all the comforts you may think of. The kitchen is gorgeous and spacious - a dream for every chef who likes to cook. All rooms are equipped with TV's and high speed internet. The house is fully stocked with everything you need. Enjoy the front and back porch, the spacious pool with a ....

3 Bedrooms 4 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria House

Sunshine & Serenity - Anna Maria House

Breathtaking Views and Lasting Memories - Beachfront Fun & Relaxation. We welcome you to stay in our family beach house located on beautiful "Bean Point"; the most beautiful spot on Anna Maria Island, Florida. We have owned this beach house for 15 years+ and have made so many wonderful memories! When you walk up the stairs to the front door entrance (located on a huge wrap around balcony) you immediately see the spar....

3 Bedrooms 2 Baths - Sleeps 9
Anna Maria, FL

View Rental

Anna Maria House

Coconut Bayou Pool Home AMI - Anna Maria House

Best Waterfront Pool Home with Great Views in Anna Maria. 2 Bedroom 2 full Bathrooms sleeps 8 has large Patio and pool and spa Great WiFi and entertainment with split floor plan gives this property a unique advantage as it gives each couple unbeatable privacy. The master bed room has a comfy King Tropical sleigh bed with and an en-suit bath. The second bedroom is a Tropical themed shutter Queen bed with....

3 Bedrooms 3 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria House

Island Time - 426 Spring - Anna Maria House

Charming North End Home with Private, Heated Pool - 2 blocks to the Bay. Welcome to Island Time! What You'll Love About This Home Location! In the heart of Anna Maria, and within walking distance to restaurants and shopping on historic Pine avenue! Steps to Tampa Bay & 4 blocks to the beautiful powder-soft, white sand beach & turquoise water of the Gulf of Mexico! 2 Bedrooms / 2 Bathrooms & and a Den - 2 Queen & 1 ....

2 Bedrooms 2 Baths - Sleeps 4
Anna Maria, FL

View Rental

Anna Maria House

Dreamscape - 773 Jacaranda - Anna Maria House

Private Pool Home - 2 Blocks From Pristine Beaches On the North End of Anna Maria!. Welcome to Dreamscape! What You'll Love About This Home: Location! Just two blocks from the most pristine beaches of the north end of Anna Maria Island. 2 Bedrooms / 2 Bathrooms 1 King Bed & 2 Twin Beds Private Heated Pool Outdoor Shower Screened Balcony Professional Linen Service, Washer & Dryer, Complimentary WIFI 2 Parking Spaces Details: A ....

2 Bedrooms 2 Baths - Sleeps 4
Anna Maria, FL

View Rental

Anna Maria House

Pirates Bay - Anna Maria House

Beachfront with stunning views, heated pool, golf cart, bikes and water toys. Start your day waking to stunning views of the Bay and Egmont Key; end your night looking out at the moonlight on the bay and the Sunshine Skyway bridge glowing in the distance. The expansive waterfront pool deck fronts a sandy beach and calm sea water that is ideal for swimming, kayaking and paddling. This vintage seaside home on the coveted Nort....

2 Bedrooms 2 Baths - Sleeps 4
Anna Maria, FL

View Rental

Anna Maria House

415 Alamanda - Anna Maria House

Island Living, refreshing outdoor shower and pool , pet friendly if approved . Our vacation home is 1 1/2 blocks to either the Gulf of Mexico or Tampa Bay. We have remodeled the kitchen and added a beautiful pool with a table in the water to enjoy cocktails while you soak up the sun. Our home has an outdoor shower, bikes, kayaks and a charcoal and gas grill. We are located on a large corner lot and we are completely fenced....

3 Bedrooms 3 Baths - Sleeps 4
Anna Maria, FL

View Rental

Anna Maria House

BON AMI - 804 N Bay - Anna Maria House

Beautiful Family-Friendly Private Pool Home Just a Short Walk To Bean Point!. Welcome to Bon Ami! What You'll Love About This Home: Location! Located just 1 block from Bean Point, Anna Maria's most pristine white sand beach!! 3 Bedroom / 2 Bathroom 2 Queen Beds, 1 Twin over Full Bunk Bed Fully Equipped Kitchen Private Heated Pool Tropical Backyard Professional Linen Service, Washer & Dryer, Complimentary WIFI, Beach To....

3 Bedrooms 2 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria Condo

Tucked Away - Anna Maria Condo

Tucked Away in Anna Maria. Tucked Away is a newly renovated custom home with everything you could possibly need for the vacation of a life time. The incredibly private setting includes a 38’ X 15’ heated and cooled pool with spa and sun shelf as well as a 16’ dock! If Beach-style living is what you long for this beautiful vacation rental has it all. From the mo....

3 Bedrooms 2 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria House

Big Seader - Anna Maria House

FREE WiFi & Trolley ONLY STEPS to Pristine Sandy Beach NO Roads to cross!. Enjoy a simple, old fashioned seaside vacation in this adorable duplex west of Gulf Drive and just two houses from the beach in the quaint village of Anna Maria. Walk up the shell path and enter through a shared screened in porch to a newly remodeled haven. With 4 parking spaces you have plenty of space for golf carts and guests. "Big S....

Studio 0 Baths - Sleeps 8
Anna Maria, FL

View Rental

Anna Maria House

Pelican Bay - Anna Maria House

Heated Pool FREE WiFi & Trolley Close to Beach Dock your Boat Dog Friendly!. A contemporary aesthetic combined with a top-notch location is sure to make Pelican Bay a favorite part of your Anna Maria vacation! Tucked away at the north end of the Island just a bit beyond the shops and restaurants of Pine Avenue, this lovely two bedroom, two bath home is nestled on the banks of Lake LaVista and sports a new dock ready f....

2 Bedrooms 2 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria House

SEA WHISPER - Anna Maria House

Sea Whisper in Anna Maria with private dock and pool. Sea Whisper is located at north end of Anna Maria island. Brand new renovation, 3 bedrooms with 3 bath rooms, with swimming pool, private dock, sailboat direct to Bimini bay, 2 block to Pine Ave, walking distance to gulf side beach and the city pier. (The two floor building next to the swimming pool is part of the house and only is used for owne....

3 Bedrooms 3 Baths - Sleeps 7
Anna Maria, FL

View Rental

Anna Maria House

The Beach House on Pine Avenue - Anna Maria House

THE BEACHHOUSE ON PINE AVENUE HI SPEED INT SLEEPS 10 CLEANLINESS POLICY. 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 decorated in "Old Style Florida" decor--bright, cheerful and tropical. Recently renovated, the house ....

4 Bedrooms 4 Baths - Sleeps 10
Anna Maria, FL

View Rental

anna Maria House

303 North Bay Blvd LLC - anna Maria House

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 minutes to trendy Sarasota (St Armands Circle for great shopping!) Newly decorated three bedroom, t....

3 Bedrooms 2 Baths - Sleeps 6
anna Maria, FL

View Rental

Anna Maria House

Azure Seas - Anna Maria House

Beach Front and Close to Bean Point Azure Seas. This property is thoroughly cleaned and sanitized prior to your arrival. We pay special attention to high touch areas like remotes, light switches and doorknobs, etc... All bedding is professionally laundered and sanitized with fresh clean comforters or duvets. This property also features contact less check in with key less access. The Azure S....

3 Bedrooms 2 Baths - Sleeps 8
Anna Maria, FL

View Rental

Anna Maria House

OakView - Anna Maria House

Newer Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK . This large home was constructed in 2009. It is a decorator furnished, pool home and considered top of the line in vacation rental homes. With approximately 3200 square feet of conditioned space and over 2000 square feet of covered balconies, poolside dining and lounging areas, there is plenty of room for a family to spread out and relax in this Fl....

5 Bedrooms 3 Baths - Sleeps 14
Anna Maria, FL

View Rental

Anna Maria House

Twin Dolphins Cottage - Anna Maria House

FREE Wi-Fi & Trolley Close to Gulf & Bay Beach Stroll the Village of Anna Maria!. This absolutely charming cottage can be yours for an affordable vacation in the sun! Nestled in an alcove of cottages tucked away by the bay in the village of Anna Maria, this adorable two-bedroom, one-bath cottage is filled with Old Florida charm! Twin Dolphins Cottage was recently remodeled with an eye to maximizing charm and comfort, inclu....

Studio 0 Baths - Sleeps 4
Anna Maria, FL

View Rental

Anna Maria House

Whispering Pines - 213 Spruce - Anna Maria House

Dog Friendly Classic 1920's Island Cottage, 3 Houses To The Beach!. Welcome to Whispering Pines! What you'll love about this home: Location! On the North End of Anna Maria & 3 houses From The Beach 2 Bedrooms / 2 Bathrooms 1 Queen, 2 Twins & 1 Queen Sofa Bed Fully Equipped Kitchen Dog Friendly (see notes below) Outdoor Dining for 4 Professional Linen Service, Washer & Dryer, Complimentary WIFI Beach Chairs Beach ....

2 Bedrooms 2 Baths - Sleeps 6
Anna Maria, FL

View Rental

Anna Maria House

Enchanted Cottage - 520 A Spring - Anna Maria House

Charming & Cozy Cottage steps to Tampa Bay. Dog Friendly!. Welcome to Enchanted Cottage What You'll Love About This Home Location! In the heart of Anna Maria, and within walking distance to restaurants and shopping on historic Pine avenue! Steps to Tampa Bay & 5 blocks to the beautiful powder-soft, white sand beach & turquoise water of the Gulf of Mexico! 2 bedrooms / 1 Bathroom 1 King & 1 Twin trundle b....

2 Bedrooms 1 Baths - Sleeps 4
Anna Maria, FL

View Rental

Scroll To Top