
House rentals near Anna Maria Island
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Top-rated house rentals near Anna Maria Island
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Location! Beach Access/Trolley/ Restaurants!
📣‼️Location, Location! Welcome to “Island Pearl” 🐚 on Anna Maria Island, where you can leave the car behind! This stylish retreat features a heated pool and is nestled in the heart of the action! 🌴The Trolley Stop is at the end of our block and Bridge Street Pier, a block over. 🏖️Beach access is situated just across the street! Fish from the Bay or catch a sunset while dining at the infamous Beach House Restaurant on Gulf Drive. Many restaurants, bars, and shopping are just a short walk away! 🛍️💃

Walk 2 blocks to Beach + Private Pool + King Beds!
☀️Welcome to Bayberry Beach Cottage A on Anna Maria Island! Just +/- 400 feet (2 min walk) to the beach! With a heated private pool, fenced backyard, outdoor games, & grill, it’s the perfect spot for fun-filled days and relaxing nights! 🌴This recently renovated beach cottage has 2 king bedrooms, 1.5 baths. 📍You’re just a 2-minute walk to Salt, a trendy restaurant and craft cocktail bar with live music. More local favorites and beach bars are nearby, & lively Bridge Street is only 1 mile away

Luxury 3BD Beachfront Retreat with Heated Pool!
Sandy Bottoms Beach House is a luxury Gulf-front retreat where modern comfort meets Florida’s natural beauty. With three king bedrooms—each with its own en suite bath—this home is designed for families, couples, or groups seeking a premium beach getaway. Step through oversized sliding doors to a private patio with a heated pool, outdoor dining, and a direct trail to the sand. Spend mornings walking the shoreline, afternoons lounging by the pool, and evenings watching unforgettable Gulf sunsets f

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view
Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

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: -We typically have shorter stays available, just ask! -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

Birdsong-Steps to Bean Point Beach Heated Pool!
Welcome to Birdsong, a picture-perfect 2-bed, 2-bath home situated in Anna Maria, Florida. Recently refreshed with coastal décor, this inviting property is ideal for families or small groups seeking a relaxing getaway. With just a short 3-minute walk to the beach, Birdsong provides an excellent blend of comfort & convenience, allowing you to fully immerse yourself in the beauty of Anna Maria Island. The fenced backyard features a heated pool, outdoor dining, BBQ grill, beach chairs, & cart.

Bayfront Beach access with Heated Pool!
Our modern yet beachy retreat is the perfect oasis on the North end of Anna Maria Island w/breathtaking panoramic views of Tampa Bay & the iconic Skyway Bridge. The backyard oasis features a refreshing saltwater pool & fully fenced backyard, complete w/artificial turf & outdoor shower. Just steps away, you'll find full access to a stunning white sandy beach & the crystal-clear waters of Tampa Bay! Conveniences have been carefully considered, creating the most ideal vacation destination!

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

Casa Cay by Duncan Real Estate
Welcome to Casa Cay! This Bay front pool home on Anna Maria Island is an absolute paradise! With its prime location on the North end with stunning views of the bay and the Sunshine Skyway Bridge, and direct access to a private bay beach, it offers the quintessential Island experience. The layout of the house, featuring three bedrooms and three bathrooms, including two suites with Ensuite bathrooms, is perfect for families or groups of friends looking for comfort and privacy.

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!
Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Sea Shack - 2bd/2ba POOL Home
Welcome to Sea Shack, an inviting ground level vacation home with a pool just steps away from the beach! Visit Pine Ave’s locally-owned boutiques and restaurants just a five-minute walk away. This rental accommodates up to 6 guest. Fully equipped kitchen has plenty of storage space for all your cooking necessities. Friends and family can gather in the living area for movie night or a bored game. have a fun-filled day in your backyard oasis, swim in the gorgeous pool.

New Prof Decorated-Pool/Spa 5 minute walk 2 Ocean
This brand new rebuild on Anna Maria Island located within Anna Maria city has 3 Bedroom, 3 Bathroom home plus loft is professionally decorated throughout, with state-of-the art quartz counter tops, JennAir professional stainless-steel appliances, wide plank wood tile floors, bead board ceilings. All bathrooms have basket weave marble and quartz counters and there is a Whirlpool Washer & Dryer. The house has everything necessary for a perfect beach vacation.
Popular amenities for house rentals near Anna Maria Island
House rentals with a pool

Captain's Quarters at Spinnakers Vacation Cottages

༄ Sunset Shore on Anna Maria Island ༄

Turtle Nest! Private Heated Pool and Access to the

Batemans – AMI Canal-Front Luxury w/ Pool & Dock

Loggerhead - Private Pool + Golf Cart - AMI Oasis

Private Luxurious Ground Level Home

Unwind Sunshine: steps to locals' favorite beach

Sarasota Escape | Minutes to Beaches + Downtown
Weekly house rentals

Seconds to the Beach! Clean & Cozy NO flood damage

Beautiful Pool/Spa, Steps to sand, New Golf Cart

Shore Beats Work, Bean Point Beauty on Anna Maria

Private heated pool,2 minute walk to the beach! W

Waterfront Bungalow• Dock•Heated Swim Spa•Near AMI

Sandy Toes

Heated Pool•Mini Golf•Arcade•Spa•AMI 6mi•IMG

Beach House w/Private Pool & Spa
Private house rentals

Ocean72, 2bed 2bath with pool

Veselka - Canal front w private heated pool & dock

NEW saltwater pool/spa! Amazing outdoor space!

Feelin' Salty-Pool Modern Beach House w/Pool/Spa

Charming houseB 2 min walk to beach, 4+, baby pets

Manatee Retreat B

Perfect Hideaway- Heated Pool, 5 min Walk to Beach

Canal front, dock, heated Pool, near AMI+IMG
Pet-friendly house rentals

New! Luxurious Retreat w/ Resort Amenities by AMI!

Be an AMI

Twin Palms: Big House Steps to Beach w/Lush Pool

Pickleball, Axe Throwing, Mini-Golf, Bowling, IMG

Holiday-January Stays w/Private 30' Dock & Pool

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI

Modern, Bright Downtown SRQ A-Frame West of Trail

Stylish Pool Home • Near IMG & Beaches • Top Rated
Quick stats about house rentals near Anna Maria Island

Total vacation rentals
Explore 1,470 vacation rentals in Anna Maria Island

Verified guest reviews
Over 18,970 verified reviews to help you choose

Family-friendly vacation rentals
1,420 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 590 rentals that welcome pets

Vacation rentals with a pool
1,240 properties feature pools

Rentals with dedicated workspaces
660 properties have a dedicated workspace

Wi-Fi availability
1,470 of Anna Maria Island vacation rentals include wi-fi 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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