Anna Maria Vacation Rentals, Private Rental Homes & Cottages.
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Vacation Rentals by Owner in Anna Maria Florida -- We have partnered directly with a major provider for By Owner Rentals, and now have the selection and value to offer our visitors searching for places to rent in Florida. Choose from Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your stay enjoyable.
Custom Home Walking Distance from the Gulf ! NOT LISTED ON FACEBOOK
Private Vacation Home in Anna Maria
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 Florida lifestyle home.
Soak in the sparkling pool after a day at the beach and then gather for dinner at the table for eight in the dining room,.......
9.6 Star Review 
The Ballyhoo on Bean Point, 200 feet to a beautiful bayside beach and views!
Cottage in Anna Maria
The Ballyhoo is a ground floor cottage located on Bean Point at the very tip of Anna Maria Island. Around the corner, (200 feet away) is the Rod and Reel Pier and beach. A classic 1940s old Florida fishing pier. The pier is an excellent place to see all our local wildlife, dolphins, herons, pelicans, and if you are lucky, maybe a manatee. The pier offers some of the best fishing on the island. A family friendly place with very good food and drink. With panoramic views of Tampa Bay, the Skyway, E.......
Sirenia Beach House - Waterfront/HotTub/ Pool/Dock/Putting/Beach AMIHomeRental
Private Vacation Home in Anna Maria
Sirenia Beach House is a Popular Vacation Home. Hurry Book Now for High Season! Our last renovation
- putting green
- master bathroom upstairs
- master balcony enlarged and with seating
- metal roof
- exterior paint, lighting, garage doors, etc..
- composite decking on all stairs, lanai and dock
- pool terrace and garage surfacing
- exterior dining table
- interior dining table set, bar stools and chandelier
- living room furnishings
- upgraded dishwasher, re.......
Water Front Sea Waves Cottage With Private Dock, Access To Bimini Bay
Private Vacation Home in ANNA MARIA
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 distance to Pine Ave, City Pier, and popular restaurants. Our private oasis has everything needed for a perfect beach vacation at the serene North End o.......
Sirenia By The Sea -Waterfront/Dock/Pool/ Hot Tub/Putting/ Beach AMIHomeRental
Private Vacation Home in Anna Maria
Recently Added in 2025
- outdoor cabana over dining table
- outdoor kitchen with bbq grill and wine fridge
- new front yard green landscaping
- new living room furniture
- new primary bedroom furniture
- new twin bedroom furniture
- new queen bedroom furniture
- Fresh and Coastal!
Book Now this home gets booked up for the high season very quickly!
Sleeps up to 12 people
7 night stays or more
Saturday turnovers only
Live in a dreamy, large and l.......
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Cottage in Anna Maria
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, 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 distance to Pine Ave, City Pier, and popular restaurants. Our private oasis has everything needed for a perfect beach vacation at the serene North End of Anna Maria Island. <.......
Bean Point Beach Cottage: North End Pool Home, Close to Beach & Bay by Anna Maria Life
Private Vacation Home in Anna Maria
Bean Point Beach Cottage by Anna Maria Life Vacation Rentals
709 North Bay Blvd., Anna Maria, FL 34216
What You'll Love About This Home:
Location! 2 Blocks to the Beach & Bean Point!
3 Bedrooms / 2 Bathrooms
King, Queen, 2 Twins
Private Heated Pool
Pool Loungers & Umbrella
Outdoor Patio Dining for 5
Gas Grill
Professional Linen Service, Washer & Dryer
Complimentary WIFI
Beach Towels, Beach Chairs, Beach Wagon
Driveway Parking for 2 Cars
Details:
W.......
Nirvana:Pool & Hot Tub, Dock, On Canal with Gorgeous Water Views by Anna Maria Life Vacation Rentals
Private Vacation Home in Anna Maria
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 Bunkbed
Private Heated Pool & Spa
Pool Loungers & Umbrellas
Outdoor Shower
Private Dock with Canal Access
Gas Grill (Please note the Green Egg is not for guest use)
Pool Table
Putting Green
Corn Hole
Multiple Furnished Outdoor Patios
Keurig & Drip Coffee Makers
Aug 8 - 15 Discounted! Lg Htd Pool/Hot Tub/CanalBackyard BeachDock AMIHomeRental
Private Vacation Home in Anna Maria
Hurry Book the last weeks available at discounted rates!
Aug 8 - 15
Sirenia Cove's pool is heated and the hot tub is bubbling!
Many new items not shown in photos;
We have upgraded many items! Waiting for Fall low season to redo photos and video.
- New Kitchen!
- New Sectional Sofa and Swivel Chairs in Main Living Room
- New Swivel Chairs in Library Loft
- Newer exterior Polywood dining table (2025)
- Newer interior dining table set
- Newer screened l.......
Island Retreat! Pool, Spa, Rooftop Views and Covered Outdoor Dining
Private Vacation Home in Anna Maria
Bay View Beauty by Exclusive Vacations
VR18-000097
Welcome to Bay View Beauty, part of our Exclusive Collection. This luxurious seven-bedroom, seven and a half bath waterfront home with unobstructed bay views. Ideally located along Anna Maria’s North Shore Drive, this luxury retreat places you steps from the white-sand Bay beaches, minutes from the Gulf beaches and Bean Point, and within walking distance of Pine Avenue’s boutique shops and restaurants. With a resort-style pool an.......
Hear The Surf/Feel The Breeze... skip to beach! Located on Anna Maria Island
Private Vacation Home in Anna Maria
Just 5 houses from the white sandy beach of the Gulf. Located in the city of Anna Maria 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 bath private home with a brand new pool and patio.
The main level includes a bedroom with a Twin trundle bed and a full bath. A separate laundry/pantry.......
Bungalow On The Bayou (Best Location on the Island)
Private Vacation Home in Anna Maria
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 island and enjoying the beach so much, my wife and I (and three kids) decided to purchase our piece of paradise. We found this "bungalow" in the Bayou.......
Once Upon A Tide managed by Beach Retreats FL Anna Maria Island
Private Vacation Home in Anna Maria
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 ideal family vacation home. For your convenience you will find an elevator making it a seamless check in.
All of the outdoor amenities are unparall.......
Anna Belle by Beach Boutique Rentals
Private Vacation Home in Anna Maria
Slip into "island time" immediately and surround yourself with elegance and style in this amazing one-level beauty. The coveted canal setting and quiet north island cul-de-sac location boast one of the widest open water views on the island. This home is simply spectacular.
*Features include*
* Private tropical yard with sparkling waterfront pool and spa!
* Canal front with boat dock
* Gorgeous master suite with walk in closet
* 3 bedrooms, 3 full bathrooms
* Fun bu.......
Soulshine: Dog Friendly! Pool, On a Canal with Dock by Anna Maria Life Vacation Rentals
Private Vacation Home in Anna Maria
Soulshine by Anna Maria Life Vacation Rentals
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
Private Dock with Canal Access
Gas Grill
Foosball
4 Balconies with Seating & Water Views
Ke.......
Sandy Rose: Putting green, heated pool, outdoor living spaces
Private Vacation Home in Anna Maria
***Photos Updated October 2025***
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 brings the whole group together when relaxing after a long day on the beach. The fully stocked kitchen has abun.......
Blue Heron Cottage - Anna Maria Island
Cottage in Anna Maria
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 with 1/2 bath inside and a laundry room. There is a full bath out of the bedroom which makes it very comfortable when there are more than 2 guests wit.......
Perfect Anna Maria. Dock on Canal. 3 blocks to sugar sand beach. Heated pool.
Private Vacation Home in Anna Maria
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 porch for relaxing on warm sunny afternoons, or you could grab your morning cup of coffee and sit out on the dock and watch the fish jump. The perfect pla.......
La Buena Vida – Canal Home w/ Pool, Spa, Dock, Pets OK & Walk To Beach
Private Vacation Home in Anna Maria
Welcome to La Buena Vida!
On Anna Maria Island (Anna Maria, FL)
The Space
Mornings begin with sunlight dancing across the canal and coffee enjoyed on the screened porch. Days unfold between the pool, the dock, and the nearby beach—each moment flowing into the next with ease. Designed for togetherness, this home combines open, airy interiors with plenty of outdoor space to connect, celebrate, and unwind. Whether you're planning a family vacation or a long weekend with friends, La B.......
Luxe Island Escape by Beach Boutique Rentals
Private Vacation Home in Anna Maria
Welcome to Luxe Island Escape, a next-level tropical retreat designed for unforgettable island getaways.
*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 dining for 6, plus lounge area
* Chaise loungers by the pool
* Garage game room with ping pong table and TV
* 2 blocks t.......
Aqua Marine on Tampa Bay
Private Vacation Home in Anna Maria
Discover an Anna Maria little secret --BAYFRONT HOME WITH A WHITE SANDY BEACH -- offering the best of both worlds. Nestled among sea oats, this newly renovated and intimate property is ideal for families or couples looking for an Island escape. Enjoy a quiet, private-like beach experience only a short walk or bike ride to Pine Avenue's shops and restaurants. The master bedroom and primary living spaces all offer picturesque vistas of majestic sailboats, splashing dolphins and soaring pelic.......
The Happy Hibiscus Island Oasis with Ocean Views
Private Vacation Home in Anna Maria
Welcome to The Happy Hibiscus! We are located in a perfect location where we can catch the sunrise and sunset, less than 100 yards to the beautiful, Passage Key Inlet and a short walk to the white sand beaches on Bean Point! Located on the north end of Anna Maria, this 4 BR home comfortably sleeps 8. With large bedrooms and a spacious floor plan, this house is perfect for gathering. Game room, Private heated salt water pool and hot tub, putting green and outdoor games all for your enjoyment!
Bella Vista: Bay front with gorgeous views and outdoor living space.
Private Vacation Home in Anna Maria
Looking for the perfect waterfront home for your next vacation? Bella Vista is a beautiful Bayfront home with gorgeous views of Tampa Bay.
Enjoy one of the many outdoor spaces where you can spot dolphins, manatees, Egmont Key, and view the Skyway Bridge light show in the evenings! Cook meals in the fully stocked kitchen and enjoy in one of the two 6 seater dining spaces. Curl up on the comfortable, oversized leather furniture in the living room while watching a movie and enjoying the beauti.......
Bellablu: A Waterfront Haven, The Ideal Retreat for Your Next Getaway!
Private Vacation Home in Anna Maria
Escape to waterfront paradise at Bellablu! This newly renovated haven offers the ideal retreat for your next vacation. With two spacious living rooms seamlessly connected by a galley-style kitchen, there's ample room for relaxation and socializing.
The ground level boasts two luxurious bedrooms with ensuite bathrooms for added privacy and comfort. Upstairs, two more bedrooms share a convenient hallway bathroom. Step onto the screened porch overlooking the pool to savor balmy summer evenin.......
AMI Stay! Family-Friendly Home with Pool, Soaking Tub and Bay Views
Private Vacation Home in Anna Maria
Bay Happy by AMI Locals
VR21-000047
Welcome to Bay Happy, a four bedroom, three bath home located across the street from Tampa Bay and Bayfront Park on Anna Maria Island. With a private pool, bay view balconies, and just a 10-minute walk to the Gulf beaches, this home is the perfect blend of island adventure and relaxation. Guests will love being close to Pine Avenue’s boutique shopping, restaurants, and the island trolley for exploring all of Anna Maria.
Highlights
•.......
Turtle Cottage - Anna Maria Island
Cottage in Anna Maria
Great 1 bedroom, 1 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 Gladiolus Street/Alamanda Road. This great getaway sleeps up to 4.
The cottage has an open floor plan and it is about 800 sq ft. The bedroom has direct access to a private patio area with washer and dryer. The living room has a sofa, which also becomes a comfortable queen bed. The property has.......
At Last: Ground-level, pool, hot tub, canalfront, dock
Private Vacation Home in Anna Maria
***Photos Updated May 2025***
Come slip away to this luxurious island retreat where all of your cares will drift away! This beautiful, professionally decorated, and newly remodeled home has every modern luxury you can think of.
The two spacious king bedrooms are sure to provide you with a great night's sleep! The also spacious third bedroom offers a 2 queen sleeper sofas, along with a couch, providing a versatile space to watch movies, practice your putting, take part in a shuffleboa.......
Northshore Beach House near Pine Ave, north end of Anna Maria Island
Villa in Anna Maria
Pine Ave and Northshore Drive adorable beach home. Recently remodeled we are open for guests . Anna Maria Island vacation beach house located at the north end of the historic village of Anna Maria, Anna Maria Island. Just steps to Pine Ave, the beach, restaurants, and shopping. Walk conveniently everywhere. We have another 2 bedroom 1 bath villa to offer as well, visit VRBO listing # 394722 for information.
Every morning with both of our villas location you can enjoy a short stroll to ea.......
Playing Hooky: On Canal, Dock, Pool & Spa, Game Room by Anna Maria Life Vacation Rentals
Private Vacation Home in Anna Maria
Playing Hooky by Anna Maria Life Vacation Rentals
513 Loquat Drive, Anna Maria, FL 34216
What You'll Love About This Home:
Location! North End Canal Home! 1 Block to Bay!
6 Bedrooms / 3 Full Bathrooms & Two Half Bathrooms
2 Kings, 3 Queens, 2 Sets of Twin over Twin Bunkbeds
Private Heated Pool & Spa
Pool Loungers & Umbrella
Poolside Covered Lounge with Patio Seating
Outdoor Shower
Gas Grill
Summer Kitchen with Mini Fridge & Outdoor Bar with Seating for Six
Charming cottage in quiet area, close to beach & bay.
Cottage in Anna Maria
Welcome to Anna Maria Island ''paradise without an attitude''. Our ground level newly renovated unit is located in the village of Anna Maria on a quiet residential street, a short stroll to the sugar white sand beach. Free trolley stop, shopping, a variety of restaurants, both fishing piers, the island community center are all within walking distance.
Many local concerts, festivals, art & craft shows and fireworks depending on the season of your visit.
With Bradenton, Sarasota .......
One block off Pine Ave w/ Amazing Rooftop Views! - AMI Memories
Private Vacation Home in Anna Maria
AMI Memories by AMI Locals
VR20-000052
Welcome to AMI Memories, a stunning five bedroom, three and a half-bath Anna Maria Island vacation home that offers luxury coastal living across three levels. Perfectly located just a four-minute walk to the Gulf beaches and close to local restaurants and boutiques, this elegant retreat features a private pool, rooftop deck with 360° Gulf and Bay views, and a spacious layout designed for families and groups to relax and make unforgettable islan.......
Villa Maria: 1 Block to Pine! 3 Blocks to Beach! Pool, Ping Pong by Anna Maria Life
Private Vacation Home in Anna Maria
307 Spring Ave, Anna Maria, FL 34216
What You'll Love About This Home:
Location! 3 Blocks to the Beach! 2 Blocks to Bay & AMI Pier!
3 Bedrooms / 2.5 Bathrooms
2 Kings, Two Sets of Twin over Twin Bunkbeds
Private Heated Pool
Pool Loungers
Outdoor Shower
Patio Dining Seating for Six
Gas Grill
Ping Pong Table
Professional Linen Service, Washer & Dryer
Complimentary WIFI
Beach Towels, Beach Chairs & Beach Wagon
Parking for 3 Cars
Details:
Villa Mar.......
Beach N Bay 204 by Duncan Real Estate
Private Vacation Home in Anna Maria
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Amenities Include:
- Bedroom 1 King
- Bedroom 2 Twins
- Bathroom 1 Walk-in Shower
- Hot Water
- Ground Level Y
- Central A C
- Central Heat
- Sqft under a c 832
- Free Parking
- Parking Spots 2
- Dogs up to 50 lbs Y
- Self Check In
- Keyless Entry
- Bath Towels
- Beach Towels
- Quality Linens
- Hair Dryer
- Hangers
- R.......
Sand Dollar Cottage - Vintage - updated - flip flop walk to Gulf Beaches
Private Vacation Home in Anna Maria
We only rent thru VRBO! Your safety is our priority.
We are writing here as the owners of this lovely cottage. If you find pictures of this cottage on other websites or in social media (e.g. Facebook) all these offerings are scam and published by people how are not our representatives or the owner of this cottage. We recommend to do bookings through VRBO, mainly for your security, so that you can be sure that you have a valid rental agreement.
Your vacation and family time on Anna M.......
Waterfront house with pool - bring boat and rod - close to Gulf and Bay Beaches
Private Vacation Home in Anna Maria
This beautifully spacious home sits on a very large waterfront lot on the northern tip of AMI. The house is embedded in a natural landscape.
The fully air-conditioned house has two air conditioners and parking spaces in front of the house. It was completely renovated in 2015. You have 4 bedrooms with 2 baths, large open kitchen, French doors from nearly all rooms to the pool area, TV in the living room and in the two master bedrooms, free WIFI and short walking distance to Bay and Gulf Beache.......
Jacaranda Gem by Beach Boutique Rentals
Private Vacation Home in Anna Maria
Take a break from the hustle and bustle, and relax in the calm and serene atmosphere of this spotless vacation home. Jacaranda Gem offers every amenity you need to have the vacation you have been dreaming of on Anna Maria Island.
*Features include*
* Beautiful and remodeled home
* Huge Saltwater heated pool plus seating ledge with jacuzzi jets
* Tropical private yard, chaise loungers, outdoor shower
* 3 bedrooms, 2 full bathrooms and powder room
* Laundry room
.......
Ocean Walk- 5 bedroom heated pool/spa and 6 houses from the white sandy beach
Private Vacation Home in Anna Maria
Ocean Walk 117 Willow Ave, Anna Maria What you will love about this property: • Southern facing private heated pool with a spa • West of Gulf Dr. direct beach access • Rooftop deck with sweeping views of the Gulf water • Part of our Professional Linen Program • Beach wagon, chairs, and toys provided Property details: Freshly updated January 2024! All new complete kitchen and freshened up bedrooms. Enjoy your vacation to the fullest when you stay at Ocean Walk on Anna Maria Island. This.......
Home just steps to BEACH! Private pool and spa - Sign of the Mermaid
Private Vacation Home in Anna Maria
Sign of the Mermaid by AMI Locals
116 Peppertree Ln, Anna Maria, Florida
Vacation Rental License: VR17-000054
Welcome to Sign of the Mermaid, a breathtaking four bedroom, four and a half bath luxury vacation home with a bonus loft, located just four houses from the white sands of Anna Maria Beach. Featuring a private pool with spa, coastal chic interiors, and multiple balconies, this home offers the perfect blend of island charm and modern elegance. With its prime location near t.......
A Wave From It All – Pool, Cabana, Putting Green & Pet-Friendly Oasis on AMI
Private Vacation Home in Anna Maria
Welcome to A Wave From It All!
On Anna Maria Island (Anna Maria, FL)
Experience A Wave From It All — a single-level island home crafted for connection and carefree living. Tucked on the quiet north end of Anna Maria Island, this pet-friendly retreat offers open living spaces, a private backyard oasis, and all the comforts you need to gather with family and friends.
Just a short 6-to-8-minute walk leads to the white sands of the Gulf, while Pine Avenue's shops and cafés are cl.......
Cozy Cottage w private Beach Access,AC&WiFi -Quiet North End AMI. Tropical Oasis
Cottage in Anna Maria
Sea Garden Cottage is a true island gem and escape. Sea Garden Cottage is located on North Shore Drive at the north end of the island. It’s charming decor and garden oasis are sure to make you lose yourself in your future get-a-way.
This home rests on a 1.23 acre lot directly on the Gulf, a rarity on the island. The lot is surrounded by mature trees, tropical vegetation, and views of the Gulf and its sandy shores. We had lost 2 very large trees since the 2 hurricanes in 2024, so there.......
South Bay Beach House: Bay Front Luxury Beach Villa with Heated Pool
Private Vacation Home in Anna Maria
Photos updated March 2025!
Newly redesigned in 2025, this stunning 4-bedroom, 3.5-bathroom beach house offers the perfect coastal escape with breathtaking views of Tampa Bay. Thoughtfully updated with high-end finishes, modern amenities, and stylish outdoor spaces, this home is designed for relaxation and comfort.
Enjoy the heated pool, new outdoor kitchen, and private beach area, or catch a game on the outdoor TV. Inside, the spacious great room offers a SMART TV and panoramic wat.......
Pure Bliss: Heated Pool, Lanai, Walk to Beach
Private Vacation Home in Anna Maria
***Photos Updated June 2025***
This newly renovated 2-bedroom, 2-bathroom cottage truly lives up to its name. Completed after the 2024 hurricane season, Pure Bliss has been thoughtfully renovated to offer the perfect blend of comfort and style for your island getaway.
Located just a 5-minute walk from the beach on the quiet, sought-after North End of Anna Maria Island, this charming home features a private, heated pool and a screened-in lanai—ideal for relaxing afternoons after a day.......
LOCATION, COMPLETE REHAB 1/1. Great pool, close to beaches, twin family rooms!
Private Vacation Home in Anna Maria
Location, Location, Location.... recently remodeled and improved after storms... surrounded by multi million dollar homes.....and three great beaches......this house contains 4 bedrooms, 2 baths. This four bedroom house - boasts 3 king bedrooms, one queen and a pull out couch-. Large heated pool w/sun shelf- large hot tub spa. TWIN FAMILY ROOMS, perfect for spreading the families out, washer & dryer, outdoor grill- all this is just steps from the northern most point on Anna Maria Island.
.......
Canal front pool home on the north end of Anna Maria Island
Private Vacation Home in Anna Maria
What more could you want from a vacation rental then a beautiful Mediterranean inspired canal home nestled into the private North End of Anna Maria Island? Mediterranean Canal Retreat is the perfect escape for those looking to relax enveloped in the simplicity and peacefulness that is Anna Maria. This four bedroom, two bathroom home has a spacious and fully equipped kitchen and large area for entertaining or relaxing, a heated pool and dock with gorgeous views of our luscious mangrove landscape........
Mermaid Cove: Updated Forida Cottage w/pool, hot tub
Private Vacation Home in Anna Maria
You'll fall in love with Mermaid Cove the second you step inside. This beautifully refurbished property boasts all the modern updates without sacrificing any of its original charm. This three bedroom, three bathroom home has a comfortable living space, huge master suite, a gourmet kitchen and is decorated impeccably. Step out back to the pool area and you will not be disappointed. The pool is large and the outdoor living space is perfect for entertaining or relaxing and enjoying the sun. Mermaid.......
BEST LOCATION! NORTH END OF ANNA MARIA, FL STEPS TO BEACH & DINING - LOWER UNIT
Private Vacation Home in Anna Maria
Blue Jacaranda Unit A (Downstairs Unit) - 2 bedroom/1 bath Duplex on the North End of Anna Maria , Bean Point Beach less than 5 min walk
Set on the desired North End of Anna Maria Island, this fully remodeled coastal retreat is just steps from the pristine shoreline of Bean Point Beach—one of the island’s most exclusive and serene beaches.
The duplex property features fully remodeled units thoughtfully arranged around a freestyle heated pool, creating a private, resort.......
Hawaiian Punch -3 Blocks to Beach, Pool, Dock on Canal, Dog Friendly by Anna Maria Life
Private Vacation Home in Anna Maria
Hawaiian Punch by Anna Maria Life Vacation Rentals
125 Crescent Drive, Anna Maria, FL 34216
What You'll Love About This Home:
Location! AMI North End Canal Home! 3 Blocks to Beach!
4 Bedroom / 2 Bathroom
3 King Beds / 2 Twin Beds
Private, Heated Pool
Pool Loungers & Hammock
Outdoor Shower
Tropically Landscaped Fenced Backyard
Dock on Canal with Ladder Access for (guest supplied) Paddleboats & Kayaks
Patio Dining for 6
Professional Linen Service, Washer & D.......
SPOIL YOURSELVES! Located direct Gulf front, pool, hot tub, 5 masters, SUNSETS!
Private Vacation Home in Anna Maria
If sugar-white sand between your toes, waves that sing you to sleep, and sunsets that look like they were painted just for you sound good… this is your chance.
It’s one of those spots where time slows down, the views are endless, and the only real question is sunrise swim or sunset toast? Safely swim right outside your door! Bean Point is a leisurely 15 minute walk away.
Built on sand, designed for joy, beachfront, modern and ready for you and your crew! Nest on the Beach did not get .......
Yellowbird: AMI North End, Gulf Views, Pool, Tiki Hut, Elevator by Anna Maria Life Vacation Rentals
Private Vacation Home in Anna Maria
Yellowbird by Anna Maria Life Vacation Rentals
705 North Shore Dr., Anna Maria, FL 34216
What You'll Love About This Home:
Location! North End of AMI - Quick Walk to Beach.
4 Bedrooms / 3.5 Bathrooms
2 Kings, 1 Queen, 1 Queen Murphy, 1 Full, 1 Twin Trundle
Smart TVs in each Bedroom
New Tile Flooring - Main Level
Resurfaced Private Heated Pool with LED Night Light
New Limestone Pool Pavers
Outdoor Shower
New Outdoor Game Room Area with Ping Pong Table
Bac.......
Glory Days: AMI North End, Backyard Oasis, Pool, 1.5 Bocks to Beach by Anna Maria Life
Private Vacation Home in Anna Maria
Glory Days by Anna Maria Life Vacation Rentals
206 Archer Way, Anna Maria, FL 34216
What You'll Love About This Home:
Location! 1.25 Blocks to the Beach!
3 Bedrooms / 2 Bathrooms
1 King, 1 Queen, 2 Twins, and Queen Sofa Sleeper
Master Bedroom with Private Deck - 2nd Floor
Private Heated Oversized Lagoon Shaped Pool & Spa
Pool Loungers & Umbrellas
Outdoor Hot Water Shower
Screened Lanai with Patio Dining for 8
Amazing Oversized Private Backyard Perfect for Fam.......
75 ft Canal Front Anna Maria House, Great for Boaters, Newly Renovated
Private Vacation Home in Anna Maria
This Anna Maria Island waterfront house newly renovated. The house is located on a large 75 ft wide deep water canal and is within a short walking distance to the beautiful white sand beaches that the island is known for. Bring your boat and moor it to the 56 ft seawall that is behind the house and enjoy deep water access to Tampa Bay and nearby Gulf of Mexico. If you do not have a boat that is OK, there are several places you can fish from land including the canal behind the house.
Wit.......
Beautiful brand new guest house, steps to Pine, 5 minutes to beach, heated pool
Guest House in Anna Maria
We don't want to waste your time so please carefully read the listing details before you request to stay.
A few points before you go any further -
1. The Boathouse is for a maximum of 2 guests aged 25 or over. No children, no infants, no exceptions.
2. When arranging your travel plans please note that our checkout time is 11 am. We strive to keep the Boathouse in pristine condition which requires time on a changeover day. It is therefore unlikely that we can accommodate a.......
Luxury AMI Home - Heated Pool & Spa - Steps to Beach - Ocean Views
Private Vacation Home in Anna Maria
• Custom-built 5BR/4.5BA retreat on Anna Maria Island’s quiet North Shore—just one house from the beach!
• Gorgeous ocean views from the porch—perfect for morning coffee or sunset cocktails
• Private heated pool & spa in a shaded backyard oasis
• Spacious 3,200 sq. ft. layout—ideal for families and groups
• Professionally decorated with wood floors, marble countertops, stainless appliances, and custom cabinetry
• Dining table seats 10 .......
? LOCAL LANDMARK. The BLUE HOUSE on PINE ?Casa Caliente?
Private Vacation Home in Anna Maria
Newly Renovated. 🌀CASA CALIENTE 🌀
A spectacular and truly MAGICAL place to experience.🐬
AMI,fl This 2 bed , 2 bath home is a spectacular, and truly a special place to experience. Along with a queen size pull out couch. This local landmark, 🛏sleeps 6 very comfortably . Owner is willing to book less than 7 nights, upon request. ( if able )..
CASA CALIENTE Talk about detail 🌞 This perfectly located, blue 💙 beach cottage, was built for entertai.......
Cloud 9 - BeachFront Splendor
Private Vacation Home in Anna Maria
Summary:
Welcome to Cloud 9, a stunning beachfront retreat where modern luxury meets relaxed coastal living. Perfectly positioned on the quiet north end of Anna Maria Island, this beautifully designed 5-bedroom home offers everything your group needs for an unforgettable island escape — from elegant interiors to effortless beach access just moments away.
The Space:
Experience luxury in our five-bedroom home, meticulously designed for comfort and enjoyment. Each of .......
ANNA MARIA Northshore & Pine Ave LOCATION! Northshore Beach Villa
Villa in Anna Maria
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 cup of coffee or enjoy a short stroll to eating wonderfully fresh baked pastries, breads, and roasted coffee at the local antique shop and bakery just off of Magnolia and Gulf Drive. In the afternoon just steps away are some of Florida's best sandy w.......
Oceans Blue Walk to the beach, stunning pool/spa private deck great location
Private Vacation Home in Anna Maria
Indulge in the ultimate beach escape to “Oceans Blue” located on the *premier corner* of Coconut & Los Cedros in Anna Maria. Oceans Blue is a very short walk (only 0.15 miles) to the gorgeous, white sandy beaches of Anna Maria Island, just north of Pine Ave. This *ultimate beach house* has been fully renovated in 2025. Updated photos forthcoming soon.
Enjoy *single-story beach house living* with *seamless flow* between the house and private pool/spa…no steps to climb!
Ameniti.......
Serendipity Deux: Luxury Beachfront Retreat + Elevator + Complimentary Golf Cart
Private Vacation Home in Anna Maria
Summary:
Escape to Serendipity Deux, a luxurious 4-bedroom house on Anna Maria Island, where refined interiors meet the laid-back island lifestyle. Enjoy premium beach access and a prime location near Bean Point and Rod & Reel Pier. This stunning retreat offers the perfect blend of comfort, privacy, and coastal charm for an unforgettable vacation.
The Space:
The primary suite on the main level features a king bed, spa-inspired bath with soaking tub and walk-in shower.......
Sol Mate – Pet Home w/ Heated Pool, Spa, Walk to Bean Point Beach & Pine Ave
Private Vacation Home in Anna Maria
Welcome to Sol Mate!
On Anna Maria Island (Anna Maria, FL)
The Space
Your island escape designed for families and friends to slow down, reconnect, and soak in the simple joys of island life. Nestled near Anna Maria's most scenic shoreline and moments from Pine Avenue, this modern, sun-filled home blends relaxed coastal style with thoughtful comfort.
Highlights
- Three Bedrooms + Sleeper Sofa — two king rooms, one twin-to-king convertible room, plus a queen sleeper sofa i.......
Beach à la Mode | Waterfront with Heated Pool, Canal Views, Steps to Anna Maria Beaches
Private Vacation Home in Anna Maria
🌴 Beach à la Mode | Waterfront Beach Escape with Heated Pool, Canal Views, Steps to Bayfront Park & Anna Maria Beaches
💖 Why You'll Love This Home
Wake up to shimmering canal views from your private luxury sanctuary on Anna Maria Island. Relax by the heated pool and spa, dine al fresco under the stars, or take in wide water vistas from the rooftop lookout — all just a short stroll to soft sandy beaches and local dining. This is effortless Florida living with a sophisticated co.......