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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 Island, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.
Newer Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK
Anna Maria Private vacation home
- 
4.7 Star Review
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.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
BEAUTIFUL BEAN POINT LOCATION 200 FEET TO ROD AND REEL PIER! EVERYTHING INCLUDED
Anna Maria Cottage
- 4.9 Star Review
The Ballyhoo is a ground floor rental on historic Bean Point in Anna Maria City. 200 feet to the beach, the Rod & Reel Pier/restaurant/bar and its great food and world class fishing . Enjoy panoramic views of Tampa Bay, the Skyway Bridge, historic Egmont Key and lighthouse, and Passage Key. Our beach offers beautiful blue water, with soft white san.......read more
2 Bedroom(s)
Sleeps 6
Cottage
Nov 11 - Dec 9 2023 Deals! - Waterfront/HotTub/ Pool/Dock/PuttGreen/Beach
Anna Maria Private vacation home
- 4.9 Star Review
Last Minute Deals
Nov 11 - 18, 2023 now $290/nt or $2,030/wk*
Dec 2 - 9, 2023 now $290/nt or $2,030/wk*
Dec 9 - 16, 2023 now $290/nt or $2,030/wk*
*plus fees and taxes.
Hurry Book Now!
Recently Renovated!
- putting green
- master bathroom upstairs
- master balcony enlarged and with seating
- metal roof
- ex.......read more
4 Bedroom(s)
Sleeps 10
Private vacation home
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
ANNA MARIA Private vacation home
- 4.8 Star Review
Welcome to Sea Waves, our newly renovated home with 3 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, free access to Netflix, washer/dryer, and a full kitchen with cooking essentials. Sea Waves cottage is located at the North End of Anna Maria Island, sailboat direct to Bimini Bay, walking di.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Nov 11 - Dec 16 Deals -Putting Green/Waterfront/Dock//Pool/ Hot Tub/StepstoBeach
Anna Maria Private vacation home
- 4.9 Star Review
Last Minute Deals
- Nov 11 - 18, 2023 now $350/nt*
- Nov 26 - Dec 1, 2023 now $350/nt*
- Dec 2 - 9, 2023 now $350/nt*
- Dec 9 - 16, 2023 now $350/nt*
*plus fees and taxes.
Hurry Book Now!
Newly Renovated 2023!
- New putting green
- New kitchen including coffee bar and wine fridge
- All 5 new bathrooms
- New .......read more
5 Bedroom(s)
Sleeps 12
Private vacation home
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria Cottage
- 4.7 Star Review
Welcome to Sea Breeze, our newly renovated home with 2 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, free access to Netflix, washer/dryer, and a full kitchen with cooking essentials. Sea Breeze cottage is located at the North End of Anna Maria Island, sailboat direct to Bimini Bay, walking .......read more
2 Bedroom(s)
Sleeps 6
Cottage
Bean Point Cottage: North End Pool Home, Close to Beach & Bay by Anna Maria Life Vacation Rentals
Anna Maria Private vacation home
- 4.6 Star Review
709 North Bay Blvd., Anna Maria, FL 34216
What You'll Love About This Home:
Location! North End of AMI and 500 Steps To The Beach!
3 Bedrooms / 2 Bathrooms
1 King ,1 Queen, & 2 Twins
Private Heated Pool
Outdoor Shower
Fully Equipped Kitchen
Gas BBQ Grill
Washer & Dryer & Complimentary WIFI
Beach Chairs & Beach .......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Unique beach house near Bean Point, heated pool and just 2 min to beach.
Anna Maria Private vacation home
- 5.0 Star Review
Beautiful elevated Beach House with a private heated pool situated in the sought after residential north end of Anna Maria Island. Superbly located, only 2 minutes walk to the best beaches, only in the north end do you have access to the Gulf and Bay beaches, watch the dolphins, see the huge variety of birds and watch the glorious sunsets. The loca.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Seahorse Cottage: Heated pool, north of Pine Ave, close to Bean Point
Anna Maria Private vacation home
- 4.9 Star Review
Welcome to Seahorse Cottage, your cozy 2-bedroom, 2-bathroom vacation rental on Anna Maria Island! Located north of Pine Avenue, this cottage offers the perfect combination of privacy and convenience. With a 2-minute walk to the beach access, you can spend your days soaking up the sun and surf at the Gulf of Mexico.
But that's not all – Seah.......read more
2 Bedroom(s)
Sleeps 4
Private vacation home
Breathtaking Views and Lasting Memories - Beachfront Fun & Relaxation
Anna Maria Private vacation home
- 4.8 Star Review
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 20 years now and have made so many wonderful memories!
THE BEACH has changed due to the storm. The last picture is the beach from the last time I was there.
Whe.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Beautiful, decorated and furnished, spacious Great Room family & kid friendly,
Anna Maria Private vacation home
- 5.0 Star Review
Beautifully decorated and furnished home located an easy walk from Gulf beaches and Tampa bay. Includes a master suite with king size bed, two additional queen bedrooms, lower level playroom off the pool, porch off of kitchen, large heated pool, Weber Gas grill, Smart HDTV, High Speed Wireless Internet, phone service with free calls to US and Cana.......read more
3 Bedroom(s)
Sleeps 6
Private vacation home
Nirvana:Pool & Hot Tub, Dock, On Canal with Gorgeous Water Views by Anna Maria Life Vacation Rentals
Anna Maria Private vacation home
- 4.9 Star Review
235 Oak Ave, Anna Maria, FL 34216
What You'll Love About This Home:
Location! On a Canal! 2 Blocks to the Beach!
4 Bedrooms / 3 Bathrooms
California King, King, Queen & Twin, Twin over Full Bunkbeds
Private Heated Pool & Spa
Pool Loungers & Umbrellas
Outdoor Shower
Private Dock with Canal Access
Gas Grill
Pool Tabl.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
Nov 11 - Dec 9 Deals! -Canal /Hot Tub/Htd Pool/ Dock/Backyard Beach Sirenia Cove
Anna Maria Private vacation home
- 4.9 Star Review
Last Minute Deals
Nov 11 - 18, 2023 now $250/nt or $1,750/wk*
Nov 25 - Dec 2 now $250/nt or $1,750/wk*
Dec 2 - 9, 2023 now $250/nt or $1,750/wk*
plus fees and taxes.
Hurry Book Now!
Many new items not shown in photos;
- New exterior Polywood dining table
- New interior dining table set
- New screened lanai conve.......read more
4 Bedroom(s)
Sleeps 12
Private vacation home
Luxury waterfront home with private pool and putting green!
Anna Maria Private vacation home
- 4.6 Star Review
Bay View Beauty by AMI Locals
Home in Anna Maria, FL
Highlights:
• Ocean Front with Private Beach Access
• Private Pool
• 4 Bicycles are Provided for Guest Use
• Putting Green
• Dog Friendly with Host Approval and $250 Fee
Room Details
-Primary Bedroom: King bed with ensuite bathroom that has a walk-in shower, s.......read more
7 Bedroom(s)
Sleeps 16
Private vacation home
Perfect Family Vacation Home with Putting Green & Waterslide! Close to Beach!
Anna Maria Private vacation home
- 4.7 Star Review
Island Pearl Oasis by Anna Maria Island Locals
Home in Holmes Beach, FL
Just steps away from the beautiful beaches of Anna Maria Island!
Highlights:
• Heated pool with waterslide and Splash n' Shoot Basketball Hoop
• Pop-a-Shot Basketball Game, Foosball, Ping Pong and Xbox Gaming System
• Keurig Coffee and Cappuccino Maker.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
Hear The Surf/Feel The Breeze... Steps To The Gulf Beach From This 4 Bd/4Ba
Anna Maria Private vacation home
- 4.9 Star Review
Just 5 houses from the white sandy beach of the Gulf. Near the heart of Anna Maria village sits this spacious home with a relaxed island feel. This ideal location allows you to walk to the beach, restaurants, bars, pier, trolley stop and Pine Avenue shopping. There's plenty of room to sit back and enjoy your surroundings in this 4 bedroom, 3.5 ba.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
On the BEACH block! Luxury home, Pool and Spa, stay and relax with your friends!
Anna Maria Private vacation home
- 4.8 Star Review
Villa La Concha by Anna Maria Island Accommodations
Home in Anna Maria, FL
Welcome to Villa La Concha, a marvelous vacation home with a private pool, hot tub, game room, and a fabulous outdoor area, all steps away from one of the most beautiful beaches in the world! This exciting rental has six bedrooms and four and a half bathrooms, .......read more
6 Bedroom(s)
Sleeps 12
Private vacation home
Bungalow On The Bayou (Best Location on the Island)
Anna Maria Private vacation home
- 5.0 Star Review
Located on the "best" street on Anna Maria Island, this two-bedroom, one-bath second floor vacation rental with a spectacular view was completely renovated at the end of 2015. The renovation included basically everything from floor to ceiling. Notice the pictures and reviews, they speak for themselves.
Growing up about 15 minutes off the i.......read more
2 Bedroom(s)
Sleeps 5
Private vacation home
Once Upon A Time managed by Beach Retreats
Anna Maria Private vacation home
- 5.0 Star Review
Welcome to Once Upon a Tide!
Once Upon A Tide is a fabulous custom design home located on the prestigious North end of Anna Maria Island. Featuring 4 bedrooms and 3.5 bathrooms. Guest will feel relaxed under the palms and mature landscaping. With private heated pool, ping-pong table, bikes and tons of beach gear, Once Upon a Tide is the idea.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
Anna Belle by Beach Boutique Rentals
Anna Maria Private vacation home
- 4.9 Star Review
Slip into "island time" immediately and surround yourself with elegance and luxury in this waterfront beauty. This stunning one-level home is situated on the island's coveted north end, on a quiet cul-de-sac and canal with one of the widest open water views on the island.
*Features include*
* Private tropical yard with sparkling wat.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Luxury home close to beach! Pool & putting green
Anna Maria Private vacation home
- 4.8 Star Review
Seaside Magnolia by Anna Maria Island Locals
Home in Anna Maria, FL
Features:
• Private pool and spa
• newly installed Putting Green
• large backyard area great for your family to get together
• a short 3 block stroll to the gorgeous Anna Maria Island beach
• Beach chairs and a beach cart for guest use
• Washer + Dryer<.......read more
7 Bedroom(s)
Sleeps 16
Private vacation home
Beautiful Anna Maria Island beach house with waterslide, pool, and rooftop deck
Anna Maria Private vacation home
- 4.7 Star Review
Harbor Haven by Anna Maria Island Locals
Home in Holmes Beach, FL
Just steps away from the beautiful beaches of Anna Maria Island!
Highlights:
• Large heated pool with spa and a waterslide
• Gas grill for BBQs
• Dog friendly with host approval and $250 pet fee
Home Layout
• Bedroom 1: King Bed, balcony, shared J.......read more
4 Bedroom(s)
Sleeps 14
Private vacation home
Soulshine: Dog Friendly! Pool, On a Canal with Dock by Anna Maria Life Vacation Rentals
Anna Maria Private vacation home
- 4.5 Star Review
322 Tarpon Ave, Anna Maria FL, 34216
What You'll Love About This Home:
Location! On a Canal. 4 Blocks to the Beach! 2 Blocks to Bay!
3 Bedrooms / 2.5 Bathrooms
California King, 2 Kings, 1 Set of Twin over Queen Bunkbeds
Private Heated Pool
Pool Loungers
Outdoor Shower
Covered Poolside Lounge with Bar & Seating & TV
Pr.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Luxury home close to beach! Private pool, spa, and putting green!
Anna Maria Private vacation home
- 4.9 Star Review
Anna Maria Beach House by AMI Locals
Home in Anna Maria, Florida
VR19-000061
Welcome to Anna Maria Beach House, a breathtaking five-bedroom and six and half-bathroom vacation home that is just a quick walk from the shimmering sands and warm waters of the Gulf of Mexico! This ultimate beach vacation house has a private pool that is sur.......read more
5 Bedroom(s)
Sleeps 8
Private vacation home
Sandy Rose: Putting green, heated pool, outdoor living spaces
Anna Maria Private vacation home
- 5.0 Star Review
Situated on the north end of Anna Maria Island, The Sandy Rose is the perfect location for your next getaway! This 4 bedroom 3 bath property is a beautiful escape from the daily grind. The gorgeous pool, large patio with tv and sectional, and putting green create a picturesque outdoor space for the entire family to enjoy. The open concept design br.......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
Blue Heron Cottage - Anna Maria Island
Anna Maria Cottage
- 5.0 Star Review
Great 1 bedroom, 1.5 bathroom cottage on the quiet north end of island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Fern Street/Alamanda Road. This great getaway sleeps up to 4.
The cottage has an open floor plan and it is about 900 sq ft. There is a bedroom .......read more
Studio
Sleeps 4
Cottage
HUGE SALE: 299/NIGHT SEPT - DEC ! 3 blocks to beach! Heated pool/20 ft dock.
Anna Maria Private vacation home
- 4.9 Star Review
3 short blocks to the sugar sand beaches of the Gulf of Mexico and 5 blocks to Tampa Bay. This traditional Florida home is on a canal, with bikes and kayaks for your recreational use. 2 bedrooms, 3 bathrooms, living room, kitchen and traditional Florida room overlooking a large patio and pool and our dock on the canal. We also have a screened porc.......read more
2 Bedroom(s)
Sleeps 5
Private vacation home
La Buena Vida - Bright Beachy & Canal Front! Steps to Beach, Pool/Spa, Dock, Beach Gear, Dogs OK
Anna Maria Private vacation home
- 4.8 Star Review
Welcome to La Buena Vida!
On Anna Maria Island (Anna Maria, FL)
The waterfront 3-bedroom home has a private heated pool, spa, and dock! This home's location is second to none, just steps to the bayside beaches and easy walking distance to Bean Point gulf side beaches & Pine Avenue.
We invite you to explore this well taken care of c.......read more
3 Bedroom(s)
Sleeps 8
Private vacation home
Luxe Island Escape by Beach Boutique Rentals
Anna Maria Private vacation home
- 5.0 Star Review
Welcome to Luxe Island Escape! A next-level, brand new construction tropical retreat.
*Features include*
* Huge heated pool and spa
* Swim up bar seating
* Rooftop deck with sweeping water views
* 4 bedrooms, 4 ½ baths
* 3 king master suites with attached baths
* Indoor/outdoor living on all 3 levels
* Patio .......read more
4 Bedroom(s)
Sleeps 8
Private vacation home
3 BR, 2 BA Home with Private Pool and Spa on the North End of Anna Maria Island
Anna Maria Private vacation home
- 4.9 Star Review
Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the famous Bean Point beach is right by the house. This 3 bedroom 2 bathroom home is situated on a corner lot on a quiet street and is located just steps to the beaches of the Gulf of Mexico. The main level of the home has an open kitchen and dining room, a larg.......read more
3 Bedroom(s)
Sleeps 6
Private 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.
Rentals in Anna Maria Island, FL
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