Places to stay near Anna Maria Island

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Top-rated holiday rentals near Anna Maria Island

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Top guest favourite
An aerial view captures a heated private pool surrounded by tropical landscaping. Deck chairs and a lounge chair provide seating options, and stone pathways lead to the pool. The pool curves gracefully, inviting relaxation in a serene outdoor setting.
Home in Bradenton Beach

Walk to it all! Restaurants + Heated Pool +Beach!

🌊🏖️Welcome to Making Waves on Anna Maria Island-where you are steps from the beach and centrally located to it all, footsteps to the trolley stop! Escape to paradise and experience the ultimate beach getaway at this stylish beach house with heated pool, nestled in the heart of Anna Maria. Walk outside the door to the pristine beaches, renowned local restaurants, and the vibrant Bridge Street with live music, restaurants, bars, and shopping. Our beach retreat promises an unforgettable vacation!

4.98 out of 5 average rating, 114 reviews
Top guest favourite
Apartment in Holmes Beach

Steps to the beach! Condo with pool at The Terrace

Just 200 steps from the white sands of Holmes Beach, this beautifully updated 2BR/2BA condo has everything to offer! Our unit features high-speed internet, Keurig , balconies off of each bedroom, 1-car garage, washer/dryer, heated shared pool, and access to all the beach necessities (toys, umbrellas, chairs, tent, bicycles, SUP, cart). This unit sleeps 6 (1-King, 1-Queen, & Full size sofa bed). LOCATION, LOCATION! You'll be just steps from restaurants, cafés, shops, and the free island trolley!

4.96 out of 5 average rating, 112 reviews
Top guest favourite
A sandy beach extends towards a calm ocean, where turquoise waters meet a clear blue sky. Colorful umbrellas provide shade for beachgoers, who are relaxing on vibrant towels. The shoreline features soft white sand, inviting visitors to enjoy the peaceful environment.
Townhouse in Holmes Beach

Getaway Family Beach Townhome w/Pool!

Wouldn't you like to get away?🌞 Just steps to the perfect family beach at this condo w/pool. Two bedrooms, two baths (+tub), sleeps six! King bed, queen w/twin bunk over, one convertible queen. Fresh updates: Washer-dryer, flooring, sofa, full kitchen, cable, wifi, beach toys, pack n play, baby gate. Did we mention the heated pool?🏊‍♀️ Next door to Walgreens, restaurants, bike rentals, shops, grocery. So many charming delights to discover on America's best beach, Anna Maria Island (AMI)!🏖

4.95 out of 5 average rating, 73 reviews
Guest favourite
Home in Holmes Beach

Carissa B | Beachside Retreat | Golf Cart | Pool

Carissa Loft B🏝️ A well-designed home offering comfortable spaces to relax, reconnect & experience all that AMI has to offer! Step inside to discover a private lower level retreat featuring a queen bed, sofa, TV and game table. Upstairs you'll find the fully stocked kitchen, inviting family room, 2-bedrooms & 2-full baths. The private outdoor oasis features a heated/cooled cocktail pool. 🚙Park the car & let the island adventures begin! The 6-person golf cart is complimentary with your stay!

5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Bradenton Beach

Studio - On the sand! Right on the beach. Sunsets

ONE SHELL COVE - Anna Maria Island, Bradenton Beach. Totally remodeled after Hurricane Helene. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves. The beach right outside your window. Grab your towel, take a few steps, and you're on the beach. The sand comes right up to your patio in this ground floor unit. Amazing Location Parking All Amenities Almost all 5 star reviews. Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

4.92 out of 5 average rating, 157 reviews
Top guest favourite
A private heated pool features a waterfall, surrounded by lush tropical landscaping and palm trees. Seating options include teal lounge chairs and white sunbeds, while the pool deck is complemented by a well-maintained lawn area. Colorful plants enhance the tranquil outdoor space.
Home in Holmes Beach

Salty Harbor AMI pool retreat near the Beach

Charming Salty Harbor sits in a quaint, exclusive corner of AMI and boasts a private heated pool and ample parking for 2 vehicles and even a boat: -Ask us if your dates don't fit our calendar! -If you don't have a single 50Lb pet, please discuss it with us -One of the twin boutique MyAnnaMariaStay homes, look us up! You'll love the luxury mid-century feel, lush yard, and a 6-min walk to the beach, Publix or the trolley stop. AMI was voted a top 50 vacation spot in the world in 2024

4.97 out of 5 average rating, 111 reviews
Top guest favourite
A private pool is surrounded by a tropical landscape, featuring palm trees and vibrant plants. The clear water reflects the blue sky, and a spacious deck with paver stones offers a welcoming area for relaxation. A canal can be seen in the background.
Home in Anna Maria

Private 30’ Pool &Boat Dock & Only Steps to Beach

o A beautifully renovated 3-bed 2-bath oasis designed for unforgettable family getaways, boating adventures, and pure relaxation. o While many rentals claim to be in Anna Maria, they are actually situated in the heavily congested Holmes Beach or Bradenton Beach areas. Nestled on the quiet, historic North End of Anna Maria City. Completely bypass the tourist traffic and long car lines, enjoying a peaceful, authentic neighborhood where everything you want is within a short stroll.

4.95 out of 5 average rating, 209 reviews
Guest favourite
An open living space is captured, featuring a dining area with a round table set for meals. Natural light fills the room, highlighting a stylish sideboard adorned with decorative items. A decorative mirror and green plants enhance the modern, welcoming atmosphere.
Flat in Anna Maria

Beach Don't Kill My Vibe by Beach Boutique Rentals

*Features include* * Modern vacation rental directly on Pine Ave! * King bedroom with TV * Queen bedroom with TV * Bathroom with walk in shower * Small kitchenette with full-size refrigerator * Private deck with table and umbrella * Private back yard with putting green and outdoor seating * Off-street parking for one vehicle * Trolley stop across the street * Walkable to all shops and restaurants on Pine Avenue * Beach chairs, umbrella, and cart * Steps to the beach!

4.96 out of 5 average rating, 209 reviews
Guest favourite
A charming cottage is set against a vibrant blue exterior, featuring a thatched umbrella over a small outdoor seating area with four chairs. Lush green shrubs and sandy pathways enhance the inviting entrance, while palm trees are visible in the background under clear blue skies.
Bungalow in Anna Maria

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

4.88 out of 5 average rating, 207 reviews
Top guest favourite
A private pool is surrounded by tropical landscaping, featuring a clear blue water surface that reflects soft lighting. Several lounge chairs are positioned nearby, providing relaxation space under the palm trees. The serene area is perfect for unwinding after a day at the beach.
Home in Anna Maria

Beach House w/Private Pool & Spa

Adorable beach cottage on the north end of Anna Maria Island! The beach access trail to the beautiful 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. Enjoy the private pool and spa, surrounded by tropical landscaping. Tons of beach gear included! It is located in a great area to explore by bike, ride to Pine Ave., Bayfront Park, the City Pier, etc....

4.96 out of 5 average rating, 109 reviews
Top guest favourite
A vibrant yellow cottage is surrounded by a sandy area with palm trees. Colorful adirondack chairs in pink, blue, and green are positioned on the white gravel. A covered outdoor seating area is visible to the side, enhancing the beachside environment.
Cottage in Bradenton Beach

Bradenton Beach Sunsets 2, Anna Maria Island, FL

NO BOOKING FEE! Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

4.98 out of 5 average rating, 262 reviews
Guest favourite
Flat in Holmes Beach

Beachfront Condo on Anna Maria Island

Beautifully decorated beachfront retreat, a 3-bedroom, 2-bathroom vacation rental just steps from the pristine white sands. The living area invites you to unwind after a day at the beach, with comfortable seating and coastal decor that soothes the senses. Sleeps up to six guests: the master suite features a king bed, the second bedroom offers a queen bed, and the third bedroom includes two full beds. Private balcony In-unit washer/dryer Beach gear provided

5.0 out of 5 average rating, 6 reviews

Popular amenities for holiday rentals near Anna Maria Island

Frequently Asked Questions

  • Where is Anna Maria Island located?

    Anna Maria Island is located on Florida’s Gulf Coast, near the entrance to Tampa Bay. This barrier island is known for its white sandy beaches, locally owned shops, and relaxed coastal atmosphere.

  • When is the best time to visit Anna Maria Island?

    Late spring and early fall are often recommended for lighter crowds and comfortable temperatures near 74–85°F (23–30°C). Many guests also explore during the winter months for mild weather and a more relaxed pace.

  • What are some things to do near Anna Maria Island?

    You can explore quiet beaches, nature preserves, and local art galleries around Anna Maria Island. The area also has fishing piers, family-friendly parks, and restaurants featuring seafood and locally inspired dishes.

  • How is the weather near Anna Maria Island?

    Anna Maria Island has mild winters around 51–74°F (10–24°C) and warm, humid summers reaching 91°F (33°C). Short rain showers are more frequent from June through September, while late fall and spring tend to feel drier and pleasantly warm.