- Planning your perfect Anna Maria Island getaway but feeling overwhelmed by all the accommodation choices? I’ve been exploring this stunning Gulf Coast barrier island for years, and I know exactly how to help you find your ideal home base among the island’s 8 distinct neighborhoods.
In this comprehensive guide, you’ll discover the best areas to stay based on your travel style and budget, from luxurious beachfront resorts in Anna Maria City to family-friendly vacation rentals in Holmes Beach. What makes this 7-mile stretch of paradise so special is its laid-back island vibe, sugar-white beaches, and charming Old Florida atmosphere where golf carts outnumber cars and every sunset feels like a masterpiece painted just for you.
Best Hotels in Anna Maria Island, Florida🔥
- 💎 Luxury Hotel: Compass Hotel by Margaritaville Anna Maria Sound
- ✨ 5-Star: Waterline Villas & Marina, Autograph Collection
- 🏨 4-Star: Anna Maria Beach Resort
- 🛏️ 3-Star: Pelican Post at Anna Maria Island Inn
- 💸 Cheap: South Bay Inn
- 🏢 Apartment: Bay Breezes at Bayside Bungalow
- 👪 For Families: Palm Tree Villas
- 🏩 For Couples: Cedar Cove Resort & Cottages
Quick Guide to the Best Areas 📃
- 🏛️ Historic Island Heritage: Anna Maria City Pier Historic District Hotels
- 🎯 Central Island Convenience: Holmes Beach Central Location Hotels
- 💸 Budget-Friendly Beach Access: Bradenton Beach Affordable Stay Hotels
- 💎 Luxury Beachfront Experience: Anna Maria Island Beachfront Luxury Hotels
- 🛍️ Shopping & Dining Hub: Pine Avenue Shopping District Hotels
- 🌊 Direct Beach Access: Gulf Drive Beachside Hotels
- 🎵 Entertainment & Nightlife: Bridge Street Entertainment Area Hotels
- 🌿 Private Island Sanctuary: Bean Point Secluded Retreat Hotels
1. Anna Maria City – Where to Stay in Anna Maria Island for First-Time Visitors
Location. I found Anna Maria City at the island’s northern tip to be the perfect introduction to ami’s laid-back charm and a great place to stay when you visit island of Anna Maria. The historic city pier and nearby reel pier stretched into the Gulf of Mexico, offering panoramic views that made every sunset unforgettable.
Atmosphere. Walking along Pine Avenue felt like stepping back into Old Florida’s golden era. Golf carts replaced regular traffic, while local ice cream shops and boutique stores created an authentic island resort experience that larger resorts simply couldn’t match. Many island of Anna Maria rentals here keep the small-town feel alive while offering easy access to the seaside.
Beach Access. Bean Point Beach became my favorite morning spot for its pristine white sand and gentle waves. The seaside chairs were rarely crowded, and I could walk directly on the seaside from most rentals on island of Anna Maria to reach the shoreline within minutes. It’s one of the highlights of a beautiful island of Anna Maria vacation.
Dining Scene. The restaurant options impressed me with their fresh seafood and waterfront views. Bridge Street in the city of bradenton seaside offered everything from casual fish tacos to upscale dining, all within a short stroll from seafront residences and popular island of Anna Maria rentals.
| Activity | Price Range (USD) |
|---|---|
| City Pier Fishing | $5-15 |
| Golf Cart Rental | $45-65/day |
| Beach Chair Rental | $15-25/day |
Transportation. Getting around the island proved effortless with the free island trolley connecting all major areas. I discovered that most vacation homes included complimentary golf cart access, making exploration both fun and practical.
Accommodation Style. The mix of seaside houses, condos, and boutique inns suited every travel preference. Many properties featured private pools and were steps away from the sand, perfect for families seeking that ideal island of Anna Maria vacation rental experience.
Best Hotels in Anna Maria City
Expensive hotels
- Playa Esmeralda Boutique Inn – This boutique inn offers five luxurious suites in a stunning 3-story building just 200 feet from the white sandy seaside. The property features adults-only residences with premium amenities including a rooftop terrace, spa pool, hot tub, and game room, plus it’s within walking distance of Bradenton Beach’s restaurants and shops.
- Bridgeview Retreat – This spectacular bayfront vacation home accommodates up to 12 guests with 4 bedrooms plus a bunk room and 5 full bathrooms. Located on Anna Maria’s northern end, it boasts breathtaking bay views, a private heated pool with hot tub, rooftop deck, game room with ping-pong and foosball, and multiple entertainment areas with outdoor grilling space.
- Atlantis Beach House – This incredible nine-bedroom, six-and-a-half-bathroom vacation home sits just a 5-minute walk from the Gulf of Mexico. The property features a pool with waterslide and in-ground spa, elevator for convenience, rooftop deck with sunset views, game room, and bar area with two wine fridges.
Medium price range
- Palmetto Marriott Resort & Spa – This full-service resort offers 252 guest rooms with nautical-themed design and serves as the gateway to island of Anna Maria experiences. Guests enjoy The Revive Pool and Spa, fitness center, The Social restaurant, and access to The Beach Club at Riviera Dunes with seafront amenities including volleyball courts and waterfront cabanas.
- Bay Breezes at Bayside Bungalow – This coastal retreat features a shared heated resort-style pool and sits across from beautiful bay beaches with Gulf beaches just a 12-minute walk away. The duplex-style residence includes essential amenities like full kitchen, convertible sofa bed, and shared BBQ areas, plus it’s only a 2-minute walk to local restaurants and shops.
- Beach You To It – This vacation rental offers convenient seaside access with modern amenities in the heart of Anna Maria Island’s entertainment district. The property provides easy access to the island’s main attractions while maintaining a comfortable home-away-from-home atmosphere for families and couples.
Low price range
- Compass by Margaritaville – This boutique hotel features 123 rooms overlooking a marina on one side and Neal Preserve on the other, located at Anna Maria Island’s gateway. The pet-friendly property offers complimentary breakfast, on-site dining at Compass Bar & Chill, and signature Margaritaville amenities while being just 10 minutes from Sarasota Bradenton International Airport.
- Bo's Beach Bungalow – This charming mid-century style home offers two bedrooms and one bathroom in one of Anna Maria Island’s most desired areas. The bungalow provides an authentic island experience with vintage Florida charm while maintaining modern comfort standards for guests seeking a more intimate vacation rental experience.
- Quality Inn North Bradenton – This budget-friendly hotel offers reliable residences with standard amenities for travelers seeking affordable access to island of Anna Maria attractions. Located in North Bradenton, guests can easily reach the island’s beaches and attractions while enjoying consistent service and basic amenities that make it ideal for budget-conscious visitors.
2. Holmes Beach – Where to Stay in Anna Maria Island for Central Location
Getting Around. The city of holmes beach sits right in the middle of the island, which makes it super convenient for exploring everything. I loved how I could bike to Coquina Beach in 10 minutes or catch the free trolley that runs every 20 minutes from 6 AM to 10:30 PM daily, making it easy to reach any Island vacation rental or nearby spots in the city of bradenton beach.
Food Scene. Gulf Drive has some amazing local spots I discovered during my stay in the city of holmes beach. The Sandbar Restaurant serves killer grouper sandwiches for $16, while Eat Here offers breakfast burritos for $9 that kept me full until dinner. Many Anna Maria Island rentals nearby make it easy to enjoy these places on foot.
Beach Life. Manatee Public Beach became my go-to spot with its spacious parking and clean restrooms. The seaside stretches for miles, and I often spotted manatees swimming near the shore during early morning walks. Many stays here are directly on the beach, so it’s easy to step out of your Anna Maria Island vacation rental and enjoy the sand within minutes.
| Local Favorites | Price | Hours |
|---|---|---|
| Sandbar Restaurant | $12-28 | 11 AM-10 PM |
| Eat Here | $8-15 | 7 AM-3 PM |
| Anna Maria Island Ice Cream | $4-8 | 11 AM-9 PM |
Shopping Vibes. Bridge Street turned into my evening hangout with its cute boutiques and art galleries. Island Gallery sells local artwork starting at $25, while Ginny’s & Jane E’s has unique gifts and clothing that my friends back home couldn’t find anywhere else.
Family Fun. The area works perfectly for families since everything stays within walking distance. Kids love the playground at Bayfront Park, and parents appreciate how Gulf Drive connects easily to both Anna Maria City and Bradenton Beach without any hassle.
Best Hotels in Holmes Beach
Expensive hotels
- Ocean Star - 7 Bdrms, 7 Baths - Beaches Less Than 5min Walk to Beach – This stunning luxury vacation home features 7 bedrooms and 7.5 bathrooms, accommodating large groups with style. I discovered it’s positioned just 100 meters from the gorgeous Gulf Coast beaches and includes a private heated pool/spa complex with outdoor seating and BBQ area, plus seaside equipment for guest use.
- Beach Side Paradise Bradenton Beach – This gorgeous 6-bedroom, 4.5-bathroom home sits less than 100 steps from pristine white sandy beaches on island of Anna Maria. The property boasts a rooftop deck with unobstructed Gulf views, exclusive pool, and luxury amenities including 5 king-sized beds plus bunk rooms that can sleep up to 14 guests comfortably.
- Sea Forever Bradenton Beach – This brand new luxury 8-bedroom, 6.5-bathroom home offers spectacular 360-degree views of the Gulf waters, Bay, and Cortez Road Bridge from its spacious rooftop deck. Located just 200 steps from beautiful white sandy beaches, it features a private saltwater heated pool and spa, elevator access, plus unique amenities like pinball machines and arcade games for entertainment.
Medium price range
- Waterline Marina Resort & Beach Club, Autograph Collection – This sophisticated boutique hotel in Holmes Beach features two-bedroom condo-style suites with fully equipped gourmet kitchens and stunning marina views. I found it offers pet-friendly residences with health club, restaurant, pool facilities, and is perfectly positioned for access to Anna Maria Island’s white-sand beaches while maintaining luxury Autograph Collection standards.
- Bali Hai Beach Resort – This enchanting seafront resort spans two acres of lush tropical paradise with direct access to 300 feet of pristine, sugary ivory sand on the Gulf of Mexico. The property features newly renovated beachside and seafront suites with full kitchens, plus a full-service spa, pool with cabanas, and complimentary bicycles for island exploration.
- Anna Maria Beach Resort – This 4-star luxury resort offers 31 spacious rooms with stunning views of either the private seaside or lush resort grounds. I love how it provides complimentary seaside setups, an oversized resort pool with poolside cabanas, private balconies and patios, and spacious condo-like suites perfect for everything from romantic getaways to family seaside trips.
Low price range
- Haley's Motel – This charming historic property has been an island of Anna Maria icon since the 1950s, offering authentic Old Florida beach resort vibes with modern amenities. Located in Holmes Beach just 2 minutes walk to the beach, it features rooms with kitchenettes, private patios, a heated saltwater pool, and BBQ facilities for that perfect island experience.
- Pool Home on the Bay - Large Private Yard near AMI – This highly-rated vacation home boasts a 9.8 exceptional rating and features a personal pool with large yard space perfect for families. The property offers bayfront location near island of Anna Maria with easy access to both seaside and bay activities, making it ideal for travelers seeking a more secluded, home-like experience.
- Sunrise Garden Resort – This budget-friendly resort provides comfortable residences in a tropical garden setting on island of Anna Maria. I found it offers essential amenities for seaside vacations while maintaining affordable rates, making it perfect for travelers who want to experience the island’s beauty without breaking the bank.
3. Bradenton Beach – Where to Stay in Anna Maria Island for Budget-Friendly Options
Money-Saving Tips. Bradenton Beach gave me the most bang for my buck during my island adventure. Street parking costs only $1 per hour compared to $3 in other areas, and many restaurants offer happy hour deals from 3-6 PM daily. Staying in vacation rentals on anna maria or nearby rentals on Anna Maria Island made it easy to enjoy these savings while still being close to the action.
Local Eats. I discovered some hidden gems that locals frequent regularly. Bridge Tender Inn serves fresh fish tacos for $11, while Ugly Grouper has all-day breakfast specials starting at $7 that taste way better than expensive tourist traps. Many of these spots are popular with visitors who come to visit Anna Maria Island or are exploring the city of anna maria during a family vacation.
Beach Access. Coquina Beach offers free parking and becomes less crowded after 4 PM when day-trippers head home. The soft white sand stretches endlessly, and I found the best shell hunting spots near the jetty during low tide. Some rentals here are right on the beach, making it perfect for those looking for relaxing things to do on anna without driving far.
Nightlife Scene. The Seafood Shack transforms into a lively spot after sunset with live music every Friday and Saturday from 7-10 PM. Drinks run $6-12, which beats pricey resort bars, and the atmosphere feels authentically local rather than touristy. It’s an easy night out when staying in vacation rentals on anna maria, especially for those who want to mix local culture with fun evening activities.
| Budget Spots | Average Cost | Best Times |
|---|---|---|
| Bridge Tender Inn | $8-16 | 11 AM-9 PM |
| Ugly Grouper | $6-14 | 7 AM-2 PM |
| Seafood Shack | $7-18 | 11 AM-11 PM |
Adventure Activities. I rented a kayak from AMI Adventure Rentals for $35 per day and explored the Intracoastal Waterway. Their friendly staff provided maps and safety tips, plus they’re open from 8 AM to 6 PM seven days a week.
Best Hotels in Bradenton Beach
Expensive hotels
- The St. Regis Longboat Key Resort – This ultra-luxury oceanfront resort features 168 guest rooms and 26 suites across 18 acres of private seafront on prestigious Longboat Key. I discovered it offers world-class amenities including a 20,000-square-foot spa with 14 treatment rooms, multiple pools with a lazy river, and an exclusive saltwater lagoon with marine life, plus signature St. Regis Butler Service and eight on-site restaurants.
- Longboat Key Club – This prestigious 410-acre luxury resort sits on one of Sarasota’s most coveted barrier islands, offering an award-winning golf course and full-service spa. The property features legendary championship golf courses, tennis gardens, and five unique dining experiences with direct access, seaside making it perfect for golfers and luxury seekers who want a complete resort experience.
- AMI Lighthouse Cottage – This charming 750-square-foot cottage accommodates 2 guests and sits just one minute’s walk from pristine island of Anna Maria beaches. The property offers an intimate, boutique vacation rental experience with modern keyless entry systems and all the amenities needed for a romantic getaway or peaceful retreat.
Medium price range
- Anna Maria Island Inn – This exclusive collection features eight uniquely curated seafront properties ranging from sophisticated Gulf-front sanctuaries to tropical retreats. I found it offers multiple residence styles including oceanfront seafront units and bayside options, each thoughtfully designed to deliver a premium coastal escape with direct seaside access and modern amenities.
- Captain's Quarters by AMI Locals – This stylish 3-bedroom, 2-bathroom vacation home features three king beds and sits just 250 steps from the Gulf of Mexico in Holmes Beach. The property includes a shared heated pool, outdoor shower, gas grill, and complimentary seaside equipment, making it perfect for families or groups seeking a home-like experience with resort amenities.
- Playa Esmeralda Unit D – This boutique seafront unit offers direct Gulf access just 200 feet from sugar-white sandy beaches in a beautiful 3-story building. The property provides adults-only residences with premium amenities including access to rooftop terraces, spa pools, and game rooms, creating an upscale seaside experience.
Low price range
- Sea Gem One Bed One Bath Charmer – This cozy one-bedroom, one-bathroom holiday home in Bradenton Beach offers an intimate and affordable seaside experience just steps from the shore. The charming cottage provides essential amenities for couples or solo travelers seeking a simple yet comfortable base for exploring Anna Maria Island’s beaches and attractions.
- Bridgewalk A Landmark Resort – This 3.5-star aparthotel features 28 residences with full kitchens, washers/dryers, and private lanais just steps from Cortez Beach. Located at 100 Bridge Street, it offers two restaurants, outdoor pool, and spa services while being within walking distance of Historic Bridge Street Pier and multiple dining options, making it ideal for budget-conscious families.
4. Beachfront Properties – Where to Stay in Anna Maria Island for Luxury Experience
Premium Locations. The seafront area along Gulf Drive offers some of the most stunning direct beach front access I’ve experienced. I could literally step from my house rentals onto sugar-white sand within 30 seconds, making those early morning walks along the beaches on Anna Maria Island effortless and a highlight of any beautiful Anna Maria Island vacation.
Upscale Dining. The Waterfront Restaurant became my special occasion spot with incredible gulf views and fresh stone crab for $32 per plate. This popular restaurant on the island runs its sunset dinner menu from 5-9 PM, and reservations fill up fast during peak season for anyone enjoying a vacation to Anna Maria Island.
Exclusive Activities. I booked a private dolphin watching tour through Privateer Vessel for $75 per person that lasted 2 hours. The captain knew exactly where to find dolphin pods, and we saw over 20 dolphins playing in the wake—a memorable experience for guests staying in Anna Maria Island hotels or rental homes.
Spa Services. Island Spa Services offers in-room massages starting at $120 for 60 minutes, which felt amazing after long seaside days. They operate from 9 AM to 8 PM and book appointments through their website or phone, adding a relaxing touch to any beautiful Anna Maria Island vacation.
| Luxury Experiences | Price Range | Duration |
|---|---|---|
| Private Boat Charters | $400-800 | 4-8 hours |
| In-Room Spa Services | $120-250 | 1-2 hours |
| Fine Dining | $25-65/person | 2-3 hours |
Beach Amenities. Many seafront properties provide complimentary seaside chairs, umbrellas, and even paddleboards. I loved having a private pool and hot tub just steps from the ocean, creating the perfect luxury island holiday experience.
Best Hotels in Beachfront Areas
Expensive hotels
- Salty Sister - 302 – This luxury seafront vacation home sits directly on Anna Maria Island’s pristine white sand beaches with spectacular Gulf views. I found it features a heated private pool, rooftop deck, and premium amenities that make it perfect for special occasions or family reunions, with guests consistently praising its “amazing location” and proximity to restaurants.
- Benny's Bungalow - 2213 – This brand-new 7-bedroom construction offers a massive luxury vacation experience with private heated pool and easy seaside access. The property receives exceptional 9.5/10 ratings with guests highlighting the “sparkling clean” conditions and “excellent room comfort,” plus it’s managed by The Cottages Crew who provide outstanding communication throughout your stay.
- Island Oasis Anna Maria – This refreshed tropical oasis features 2 bedrooms, 2 bathrooms, and a stunning lagoon-style pool on Anna Maria’s quiet north end. The property includes a private dock for boat storage, elevated deck with beautiful views, and garage parking for 3 cars, making it perfect for couples seeking a peaceful retreat just 7-10 minutes walk from Pine Avenue shops.
Medium price range
- Sundance Cottage – This charming seaside cottage sits right across the street from the Gulf beaches and features a well-maintained private pool for relaxing after seaside days. Guests love the convenient location and peaceful setting, though I found they appreciate having easy seaside access without the crowds of larger resorts.
- Canalfront Anna Maria Cottage w/ Pool & Hot Tub – This waterfront gem sits on a 75-foot canal frontage and offers fantastic opportunities for boaters and water enthusiasts. The property features a 9.0/10 rating and guests consistently praise its “original Anna Maria charm,” plus it’s fully stocked with everything you need and maintains exceptional cleanliness standards.
- Holiday Inn Express & Suites Bradenton West – This newly renovated hotel sits less than one mile from IMG Academy and just 5 miles from beautiful Anna Maria Island beaches. I discovered it offers heated outdoor pool, 24-hour fitness center, and complimentary hot breakfast, plus each room includes modern amenities like 43″ adjustable TVs and Keurig coffee makers.
Low price range
- Sunrise Garden Resort – This budget-friendly resort offers comfortable residences in a tropical garden setting on Anna Maria Island with essential amenities for seaside vacations. I found it provides good value for money while maintaining decent standards, making it perfect for travelers who want to experience the island’s beauty without premium pricing.
- Getaway on Gladiolus – This affordable vacation rental provides a comfortable home base for exploring Anna Maria Island’s attractions and beaches. The property offers essential amenities and a convenient location that makes it easy to access the island’s main draws while keeping costs manageable for budget-conscious travelers.
5. Pine Avenue Area – Where to Stay in Anna Maria Island for Shopping and Dining
Shopping District. Pine Avenue runs through the heart of Anna Maria City and houses the island’s best boutique shopping. I spent hours browsing through Island Bazaar for unique souvenirs and discovered handmade jewelry starting at $15. It’s the perfect spot to soak up that relaxed island time vibe before heading back to one of the many rental properties nearby.
Restaurant Row. This area packs more dining options per block than anywhere else on the island. Duffy’s Tavern serves amazing fish and chips for $14, while Poppo’s Taqueria makes fresh fish tacos for just $8 each. Whether staying in anna maria and holmes beach or just visiting for the day, this strip is worth a stop when you book your Anna Maria Island holiday.
Art Scene. The Artists Guild Gallery showcases local talent with rotating exhibits that change monthly. I bought a beautiful sunset painting for $85, and the friendly artists often work on-site during afternoon hours from 1-5 PM. Many works capture the beauty of the beaches in anna maria and the charm of this barrier island off the coast.
Evening Entertainment. Pine Avenue comes alive after dark with street musicians and outdoor dining. The Roser Community Theatre presents local productions for $20 tickets, and shows run Thursday through Sunday at 8 PM. It’s a great way to end the day before you book your stay and enjoy another round of exploring anna maria and holmes beach.
| Pine Avenue Highlights | Cost | Operating Hours |
|---|---|---|
| Artists Guild Gallery | Free entry | 10 AM-4 PM |
| Roser Theatre | $15-25 | Thu-Sun 8 PM |
| Boutique Shopping | $10-100+ | 10 AM-6 PM |
Walking Distance. Everything on Pine Avenue stays within a 6-block stretch, making it perfect for leisurely strolls. I could grab morning coffee at Island Coffee Haus for $4, shop for gifts, and enjoy dinner without needing any transportation.
Best Hotels in Pine Avenue Area
Expensive hotels
- Legacy at IMG – This luxury resort sits on the prestigious IMG Academy campus in Bradenton, just 10 minutes from Anna Maria Island’s pristine beaches. I discovered it features world-class athletic facilities, multiple dining options, and upscale residences that attract professional athletes and discerning travelers who want resort amenities with easy seaside access.
- Don CeSar – Known as the “Pink Palace of St. Pete Beach,” this iconic luxury resort has been a Gulf Coast landmark since 1928. Located about 30 minutes from Anna Maria Island, it offers seafront suites, award-winning spa services, and multiple restaurants with stunning views of the Gulf coast, making it perfect for guests seeking historic elegance.
- Treasure Island Beach Resort – This upscale resort sits directly on Treasure Island’s white sand beaches, approximately 45 minutes from Anna Maria Island. The property features spacious suites with full kitchens, private balconies with Gulf views, and resort amenities including pools and seaside services for travelers wanting luxury residences within driving distance of Anna Maria Island.
Medium price range
- Barefoot by the Bay at Bayside Bungalow – This charming vacation rental sits right on Anna Maria Island with beautiful bay views and shared resort-style amenities. I found it offers easy access to both Gulf and bay beaches, plus guests can walk to local restaurants and shops while enjoying the peaceful bayside setting with pool access.
- Sandy's Getaway – This well-appointed vacation home provides comfortable residences on Anna Maria Island with modern amenities and a convenient location. The property offers multiple bedrooms and essential vacation features like full kitchen and outdoor space, making it ideal for families or groups seeking a home-like experience near the island’s attractions.
- Coconuts Gulf View 118 – This seafront condo offers spectacular Gulf coast views right on Anna Maria Island’s pristine shores. Located in the popular Coconuts complex, it provides direct seaside access, modern furnishings, and the convenience of being within walking distance of restaurants and shops while maintaining a peaceful beachfront atmosphere.
Low price range
- Paradise Palms - Chic Prime Spot Pool BBQ Alfresco – This budget-friendly vacation rental offers great value with pool access and outdoor BBQ facilities in a prime Anna Maria Island location. I discovered guests appreciate the clean residences and convenient amenities that make it perfect for travelers seeking affordable island access without sacrificing comfort.
- 2 Mi to Bradenton Beach Water-View Home with BBQ – This affordable waterfront rental provides excellent value with scenic water views and outdoor grilling facilities in nearby Bradenton. The property offers essential vacation amenities and easy access to Anna Maria Island beaches, making it ideal for budget-conscious travelers who don’t mind a short drive to reach the island.
- Cortez Gardens Cottage 11 – This economical three-bedroom vacation home provides comfortable family residences near Anna Maria Island at budget-friendly rates. The property includes basic amenities and sleeping arrangements for larger groups, making it perfect for families or friends traveling together who want to split costs while staying close to the island’s beautiful beaches and attractions.
6. Gulf Drive Corridor – Where to Stay in Anna Maria Island for Beach Access
Scenic Route. Gulf Drive stretches the entire length of the island and provides the easiest seaside access from any point. I loved how this main road connects all three cities while offering glimpses of the gulf between seaside houses and palm trees—perfect for peaceful beach walks during a getaway or a family vacation.
Beach Hopping. Staying along Gulf Drive meant I could explore different beaches daily without hassle. Bayfront Park offers playground equipment for kids, while Manatee Beach provides the widest stretch of sand and best facilities, with plenty of nearby rentals with private access to make each visit more comfortable.
Cycling Paradise. The island’s bike paths run parallel to Gulf Drive, making cycling safe and enjoyable. I rented bikes from Island Bike Rental for $20 per day, and their friendly staff provided maps showing the best routes and stops, ideal for exploring before or after long beach walks.
Fishing Spots. The Anna Maria City Pier extends 678 feet into the gulf and costs only $3 for fishing access. I caught redfish and snook during my early morning sessions, and the bait shop opens at 6 AM for serious anglers staying in rentals with private docks or beach access nearby.
| Gulf Drive Activities | Price | Best Times |
|---|---|---|
| City Pier Fishing | $3 entry | Dawn-10 AM |
| Bike Rentals | $20-30/day | All day |
| Beach Access | Free | Anytime |
Sunset Views. Every evening along Gulf Drive offers spectacular sunset viewing opportunities. I discovered that Bean Point Beach provides the most unobstructed views, especially during winter months when the sun sets directly over the water.
Best Hotels on Gulf Drive
Expensive hotels
- Gorgeous Top Floor Beach Condo at Breakers West – This spacious vacation condo in Sanibel offers 2 bedrooms and 2 bathrooms with beautiful sea views. It features a garden, patio, and is just 700 meters from Tarpon Bay, making it ideal for seaside lovers seeking tranquility.
- East Gulf Drive Sanibel Island – Located at 937 East Gulf Drive, this property offers excellent proximity to Sanibel’s restaurants and shops. It’s praised for its location and easy access to local attractions, perfect for exploring the island.
- Sanibel Island Beach Resort – A beachfront resort in Sanibel with free Wi-Fi and private parking, located 1.7 miles from the town center. Guests enjoy access to two restaurants, a pool, tennis courts, and direct seaside access just 800 feet away.
Medium price range
- Charming Suite with Balcony and Bikes at Historic Sandpiper Inn – This air-conditioned suite features a patio and is located in Sanibel. Guests enjoy complimentary bikes for island exploration and a charming historic setting close to local attractions.
- Creole Garden Cottage at Palmview Inn of Sanibel – A spacious cottage with garden views and free Wi-Fi, situated in a tranquil setting in Sanibel. It offers guests a relaxing atmosphere with a well-maintained garden area and easy access to the island’s amenities.
- Pirates Cove Cottage at Palm View Inn of Sanibel with Bikes – This cozy one-bedroom cottage is ideal for small groups or couples. Guests appreciate the proximity to Gulfside Beach just 1,300 feet away and the availability of bikes for convenient island travel.
Low price range
- Sunshine Island Inn – Located in Old Town Sanibel, this inn offers tropical surroundings with seaside access just across the street. Amenities include a pool, free parking, Wi-Fi, and BBQ facilities, making it suitable for families and couples seeking authentic island charm.
- Kona Kai Sanibel – This comfortable motel offers 19 well-appointed rooms with essential amenities, including refrigerators, microwaves, and free Wi-Fi. Guests enjoy an outdoor pool and easy access to local beaches and golf courses just 0.5 miles away.
- Ground Floor Condo Steps from the Beach Sanibel Island – This apartment condo offers easy access to the seaside with fully equipped kitchen and modern amenities. It provides excellent value for guests wanting a low-key stay near the island’s beautiful shores.
7. Bridge Street District – Where to Stay in Anna Maria Island for Entertainment
Entertainment Hub. Bridge Street serves as the island’s main party zone with live music venues and bustling bars. The Bridge Tender Inn hosts live bands every weekend from 8-11 PM, and the crowd stays friendly and laid-back rather than rowdy.
Fishing Central. Historic Bridge Street Pier attracts both tourists and locals for excellent fishing opportunities. I paid $2 for pier access and caught snapper and grouper using live shrimp from the on-site bait shop.
Nightlife Options. Several bars line Bridge Street offering different vibes for evening entertainment. Slim’s Place serves cold beers for $4 and has pool tables, while Mar Vista Restaurant provides upscale cocktails with waterfront views for $10-15.
Street Events. The area hosts regular festivals and events throughout the season. I stumbled upon a seafood festival with local vendors selling fresh catches for $8-15 per plate, and live entertainment kept the atmosphere lively all afternoon.
| Bridge Street Fun | Cost | Schedule |
|---|---|---|
| Pier Fishing | $2 entry | 24/7 access |
| Live Music Venues | $5-10 cover | Fri-Sat evenings |
| Bar Drinks | $4-15 | Daily 11 AM-2 AM |
Water Activities. Several charter companies operate from Bridge Street Marina offering fishing trips and dolphin tours. I booked a half-day fishing charter for $65 per person that included all equipment and bait, departing daily at 7 AM and 1 PM.
Best Hotels in Bridge Street Area
Expensive hotels
- Beach Serenity Anna Maria – This luxury 4-bedroom, 4-bathroom waterfront estate sits on Bean Point at Anna Maria’s northern tip, just steps from white sand beaches. I discovered it features a custom-built 3,781 sq ft main house plus a detached carriage house, complete with a heated pool, hot tub, outdoor kitchen, and private boat dock with 9,000 lb lift.
- Bay Dreamin! Walk to the Beach, Pier, & Pine Ave! Heated Pool! – This prime vacation home sits just 400 yards from Anna Maria City Pier and offers easy walking access to Pine Avenue shopping and dining. The property features a heated pool and strategic location that puts you within a 15-minute walk of Anna Maria Island’s main seaside areas.
Medium price range
- The Anna Maria Island Beach Palace – This stunning 4-bedroom, 3-bathroom luxury condo spans 2,678 sq ft and sits just 350 feet from Cortez Beach in Bradenton Beach. I found it features granite countertops throughout, three screened lanais with water views, a private heated pool, and a complete outdoor kitchen with wet bar.
- Bridgewalk A Landmark Resort – This beachfront resort offers 28 apartment-style accommodations directly on Anna Maria Island overlooking the Gulf coast. Located at 100 Bridge Street, it provides rates from $125-$187 and features a continental breakfast plan with meeting facilities for up to 72 people.
- Casa del Sol C Bradenton Beach – This trio of 2-bedroom suites features a private pool and sits steps from the seaside in the heart of Bradenton Beach. The property offers easy access to Bridge Street Pier plus modern amenities including free WiFi, full kitchens, and a shared washer/dryer for added convenience.
Low price range
- Hyatt Place Sarasota Bradenton Airport – This modern hotel sits directly adjacent to Sarasota-Bradenton International Airport and offers easy access to Anna Maria Island beaches. I discovered it features spacious rooms with 42″ flat-panel HDTVs, free hot breakfast for World of Hyatt members, and 24/7 dining options including Starbucks specialty coffees.
- Coastal Cheer – This 603 sq ft one-bedroom condo strategically sits within short walks to the seaside (900ft), marina (150ft), and Historic Bridge Street (800ft). The property features a heated pool, seaside toy closet, front screened lanai, and includes two Roku TVs plus all essential vacation amenities.
- 1 Mi to Anna Maria Island Pet-Friendly Retreat – This dog-friendly vacation home offers affordable accommodation just one mile from Bradenton Beach’s attractions. The property provides family-friendly amenities and serves as an excellent budget option for travelers wanting to explore Anna Maria Island while keeping costs manageable.
8. Bean Point Area – Where to Stay in Anna Maria Island for Seclusion
Peaceful Retreat. Bean Point sits at the island’s northern tip and offers the most secluded experience I found. The area stays quiet even during busy season, with only a few vacation rentals scattered among native vegetation and pristine beaches.
Nature Watching. This undeveloped area provides incredible wildlife viewing opportunities. I spotted dolphins feeding close to shore every morning around 8 AM, and various seabirds including pelicans and herons hunt in the shallow waters.
Pristine Beaches. Bean Point Beach offers the softest sand and clearest water on the entire island. The seaside stays uncrowded since it requires a short walk from parking areas, making it perfect for romantic walks or quiet relaxation.
Photography Paradise. The natural landscape creates stunning photo opportunities without tourist crowds. I captured amazing sunrise shots with the city pier in the background, and the unspoiled shoreline provides perfect Instagram-worthy moments.
| Bean Point Features | Access | Best Times |
|---|---|---|
| Secluded Beach | Short walk | Early morning |
| Wildlife Viewing | Free | Dawn/dusk |
| Photography | Unlimited | Sunrise |
Limited Services. Bean Point intentionally lacks commercial development, so I needed to bring my own food and drinks. The nearest restaurants and shops sit 10 minutes away in Anna Maria City, but the peaceful isolation made the extra planning worthwhile for a true escape.
Best Hotels Near Bean Point
Expensive hotels
- Palmetto Pointe Anna Maria – This luxury 5-bedroom, 5.5-bathroom three-story home sits just one block from Anna Maria Island’s sugar-white beaches. I discovered it features a private heated pool with spa, wrap-around balconies, rooftop deck with sunset views, plus built-in bunk beds on the third floor and elegant coastal design throughout, making it perfect for multiple families or large groups.
- High Tide AMI – This premium vacation rental offers sophisticated accommodations with modern amenities and prime positioning on Anna Maria Island. The property provides upscale features and convenient seaside access, making it ideal for travelers seeking a luxury island experience with all the comforts of home.
- Blue Crush Anna Maria – Located just a 1-minute walk from Anna Maria Island beaches, this unique island home offers distinctive styling and high-end accommodations. Guests consistently praise the cleanliness, high-end appliances, and overall accommodations, with reviews noting how the property makes visitors feel very at home.
Medium price range
- White Shell Anna Maria – This canal-front 3-bedroom, 2-bathroom vacation home features a private dock with two jet ski slips and a heated pool with spa. Located on 225 Gladiolus Street, it’s just a 5-minute walk to Bay beaches and 13 minutes to Gulf beaches, plus includes a game room with pool table, ping-pong, and foosball for endless entertainment.
- Magnolia Breeze Anna Maria – This highly-rated property receives a wonderful 9.2/10 rating and provides accommodation with private pool, free WiFi, and free private parking. Located at 527 Magnolia Avenue, it offers excellent value with modern amenities and convenient Anna Maria Island positioning.
- Shells And Sunshine Anna Maria – This 3-bedroom, 2-bathroom home receives excellent reviews with guests praising how “very clean” it is and highlighting the “well-stocked kitchen and beautiful ocean views”. The property maintains an 8.6/10 excellent rating and offers comfortable accommodations for up to 8 guests in a prime Anna Maria location.
Low price range
- Southern Breeze 2 Anna Maria – This budget-friendly property offers clean accommodations close to the seaside with pool access. Guests consistently mention it was clean and close to seaside with a “great pool”, and the Southern Breeze complex features modern beach-inspired interiors with spacious living rooms and fully equipped kitchens.
- Slo Mocean – This recently refreshed beach-styled cottage sits just one easy block from the Bay and maintains an excellent 9.0/10 rating. The property offers dog-friendly accommodations in a convenient Anna Maria location, making it perfect for budget-conscious travelers who want to bring their pets along for the island adventure.
FAQ About Staying in Anna Maria Island, Florida
How long does it take to get to Anna Maria Island from major airports?
Sarasota-Bradenton International Airport sits just 30 minutes away from Anna Maria Island, making it your quickest flight option. Tampa International Airport takes about 1.5 hours by car, while Orlando International Airport requires roughly 2 hours and 30 minutes of driving.
What’s the best way to get around Anna Maria Island without a car?
The free island trolley runs every 20 minutes from 6 AM to 10:30 PM daily and covers the entire 7-mile island. I love using this service because it stops at all major beaches and attractions, plus you never wait more than 20 minutes for a ride. Golf cart rentals cost around $45-65 per day and work perfectly for short trips since most island roads have 35 mph speed limits or lower.
Can you walk everywhere on Anna Maria Island?
Anna Maria Island is only 7 miles long, so walking between nearby attractions is definitely possible. I walked from my accommodation to restaurants and shops within each city area without any problems. Pine Avenue in Anna Maria City, Bridge Street, and the main seaside areas all have pedestrian-friendly layouts with sidewalks and crosswalks.
Is it safe to drive on Anna Maria Island?
Driving on Anna Maria Island feels very safe with low speed limits and light traffic compared to mainland Florida. The island has just two main bridges connecting to the mainland – the Cortez Bridge and Manatee Avenue Bridge – and both offer beautiful scenic views during your arrival. Most roads stay uncrowded except during peak season weekends when parking can become challenging at popular beaches.
How far is Anna Maria Island from other Florida attractions?
The island sits perfectly positioned for day trips to nearby attractions. Sarasota downtown is about 45 minutes away, while St. Petersburg takes roughly 1 hour by car. Tampa is approximately 1.5 hours north, and Orlando theme parks require about 2.5 hours of driving. I discovered that staying on Anna Maria Island gives you easy access to explore other Gulf Coast destinations while returning to a peaceful seaside atmosphere each evening.
What transportation works best for families with kids?
The free trolley system works wonderfully for families since kids love riding it and parents don’t worry about parking or directions. Golf cart rentals accommodate 4-8 passengers and feel like an adventure for children while being practical for seaside gear transport. Many families I met rented bikes with child seats or trailers for exploring the island together.
Do you need reservations for island transportation?
The free trolley requires no reservations and runs on a regular schedule throughout the day. Golf cart rentals should be booked in advance during peak season since they’re very popular and availability becomes limited. Bike rentals usually have same-day availability, but calling ahead ensures you get the style and size you want.
