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Places to stay near Anna Maria Island

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Top-rated holiday rentals near Anna Maria Island

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Townhouse in Anna Maria
4.98 out of 5 average rating, 121 reviews

Green Jacaranda AMI Duplex B, 5 min walk to beach

Location!!! North end of Anna Maria . Steps to the Bean Point Beach and everything you need for your perfect AMI Vacation. The duplex property features fully remodeled units thoughtfully arranged around a free style heated pool, creating a private, resort-style atmosphere. Guests may reserve 1 unit or the entire property , total of 5 units avail for rent in multiple duplexes making it ideal for extended families or group gatherings seeking both togetherness and privacy. MAX Occupancy - 4 people

Guest favourite
A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.
Home in Holmes Beach
4.96 out of 5 average rating, 200 reviews

Be an AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Top guest favourite
Apartment in Longboat Key
4.98 out of 5 average rating, 228 reviews

Sun-Kissed Memories!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! On the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

Guest favourite
A lagoon-style pool is surrounded by a patio featuring lounge chairs and an umbrella, offering a shaded spot for relaxation. Lush palm trees line the space, and the elevated home is visible in the background, completing the serene outdoor setting.
Home in Anna Maria
4.89 out of 5 average rating, 63 reviews

Island in the Sun, luxury beach house,private pool

Welcome to Island in the Sun this newly renovated home on Ami offers charm, comfort, and luxury. No damage from hurricane Helene or Milton. This Anna Maria Island vacation rental is located just one block south of Pine Ave and just a few flip flop steps away from the City Pier Bay Beach and the popular restaurant - The Waterfront. The City Pier Bay Beach offers narrow white sand beaches, views of the of the City Pier, the Skyway Bridge and the boats traveling back and forth in Anna ...

Top guest favourite
The exterior of a modern two-story house is illuminated by soft evening light. A spacious deck is adorned with wooden chairs, and palm trees frame the entrance, enhancing the tropical ambiance. The house showcases a sleek design with large windows and a welcoming entrance.
Home in Bradenton Beach
4.98 out of 5 average rating, 102 reviews

Gulf Front! Beach Views!+ Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Guest favourite
Home in Holmes Beach
4.93 out of 5 average rating, 123 reviews

The Peachy Beach House, steps to the gulf

The perfect place for a combination family vacation and some romance-when the kids are in bed, turn on the spa and music. June, July and August, Saturday to Saturday only. If custom trip length is wanted- ask Two bedroom, 2 full bathroom, new heated private pool/spa Steps to semi-private gulf beach, on quiet street in N. HB Well-stocked kitchen, 2 TVs, large primary suite and amazing gulf views from bedrooms. Crib, high chair, beach chairs, wagon, umbrella, beach toys and towels

Top guest favourite
An inviting exterior view of Sunrise Villa showcases a well-maintained landscape featuring lush greenery and vibrant plants. A spacious driveway leads up to a garage, with decorative stone detailing accentuating the garden area. The home is framed by palm trees, contributing to the tropical ambiance.
Home in Bradenton
5 out of 5 average rating, 112 reviews

Sunrise Villa - Tropical 3 bedroom home with pool

Relax with the family at this tropical oasis. Sunrise Villa sits in the corner of a quiet cul-de-sac, just a quarter mile from Palma Sola Bay and 5 miles from the quaint island of Anna Maria and its sandy white beaches. Enjoy the tropical backyard paradise and the abundance of restaurants, beaches, and entertainment in close proximity. Lounge by the pool, take a bike ride along the bay, take a short bike/car ride over to the island, or take a short car ride to downtown Bradenton.

Top guest favourite
A bright living room features large windows allowing natural light to fill the space. A cozy sectional sofa is complemented by a decorative throw pillow. A circular wooden coffee table is situated in the center, with a small plant placed on top. A piece of wall art adds visual interest.
Home in Bradenton
5 out of 5 average rating, 10 reviews

The Riverview Nook in Downtown!

Stylish 2 bed, 2.5 bath cottage, walking distance to the beautiful Manatee river and historic downtown Bradenton. Only a 20 minute drive to Anna Maria Island and neighbors major cities, Tampa and Sarasota. A cozy house, with stunning professional interior design. Clean-ability was highly prioritized with this home, with virtually every surface, from the couch covers to the duvet inserts being washable, or bleach-able. Be advised the third bed is a pullout bed in the living room!

Guest favourite
Bungalow in Anna Maria
4.84 out of 5 average rating, 188 reviews

Bay Breeze Cottages #3

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.

Top guest favourite
A serene outdoor space is presented, featuring a private dip pool with tranquil blue tiles. Two white adirondack chairs frame a small table with a potted plant, surrounded by a landscaped area with gravel and grass. Lush greenery provides a natural backdrop.
Home in Holmes Beach
4.96 out of 5 average rating, 28 reviews

L'Oasis West w/Dip Pool

Completely remodeled, this beautifully 2-bedroom duplex, crafted to enhance your living experience. Every detail has been thoughtfully designed to create a serene and inviting atmosphere. New images showcase this stunning transformation, come visit us to see the beauty in person! Additionally, West and East are now available for rent together, featuring convenient adjoining doors through the utility room.

Guest favourite
Home in Anna Maria
4.93 out of 5 average rating, 57 reviews

Jungalow Bay by Beach Boutique Rentals

*Features include* * Private tropical heated pool * Plenty of outdoor furniture including Ledge Loungers in the pool * Outdoor living and dining spaces and tiki bar * Poolside bar, TV and gas grill * 3 bedrooms and 3 full bathrooms * Amazing master bathroom with indoor/outdoor shower * Spacious screened lanai * Body boards and pool floats * Beach chairs, umbrella and cart * Walk to Bean Point

Top guest favourite
Home in Anna Maria
5 out of 5 average rating, 88 reviews

Bean Pt. Bungalow - Half duplex w/private pool

Welcome to Bean Pt. Bungalow! A charming 3/2 villa with a private saltwater pool in the heart of Anna Maria. You're only 0.2 miles from the nearest beach access and 0.2 miles from the Rod and Reel Pier. The home comes equipped with 6 beach chairs and cart. This boutique rental is the perfect place for your next getaway! Primary - King Bed Front bedroom - King bed Bunk room - 4 twin beds

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.

Quick stats about holiday rentals in Anna Maria Island

  • Total holiday rentals

    Explore 2,810 holiday rentals in Anna Maria Island

  • Nightly prices starting at

    Anna Maria Island holiday rentals start at £7 per night before taxes and fees

  • Verified guest reviews

    Over 49,540 verified reviews to help you choose

  • Family-friendly holiday rentals

    2,410 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 910 rentals that welcome pets

  • Holiday rentals with a pool

    2,330 properties feature pools

  • Rentals with dedicated workspaces

    1,420 properties have a dedicated workspace

  • Wifi availability

    2,790 of Anna Maria Island holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Anna Maria Island rentals

  • 4.8 Average rating

    Anna Maria Island stays are highly rated by guests – averaging 4.8 out of 5!

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