
Family-friendly rentals near Anna Maria Island
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Top-rated family-friendly rentals near Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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.

Vitamin Sea Escape!
This charming seaside condo is 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and secluded beach. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort! To see all four of our listings, click on my Host photo and scroll down...!

Pineapple Suite: spacious, private, great location
Come stay in our "Pineapple Suite" where you'll enjoy our cozy, private suite within our family home. In your suite, you'll have your own bedroom, bathroom & family room with kitchenette. We're in a very safe neighborhood and perfectly located near many outdoor attractions! The beaches, kayaking, biking, & hiking are all within minutes of our home! You're a 12-min drive to Anna Maria Island, 5-min to Robinson Preserve, 15 min to IMG, & only 30 min to SRQ. Check out my 5-star reviews!

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

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

Beachfront Resort, Ocean View, Pool, Tennis, Gym
Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

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.

Beachfront Studio Retreat on Anna Maria Island
Escape to this charming, modern beachfront studio, perfectly designed for a relaxing and memorable vacation. Boasting a bright, fresh, beachy vibe with stunning porcelain wood-look tile flooring throughout, this cozy retreat offers breathtaking panoramic views of the Gulf of Mexico right from your private lanai. Please Note: The elevator and pool heater are currently out of service; pricing reflects this. Latest ETA of opening is 2026. This is a non-smoking, pet-free unit.

Newly Remodeled Beachfront Studio - On the sand!
ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and 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 door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

Ohana Hale North 1 Bedroom
Aloha and welcome to our Island Home - Your Ohana Hale Ohana is Hawaiian for family and that is who you are when you stay with us. This one bedroom suite is idea for a couples getaway or small family vacation. Our retreat is nestled on Anna Maria Island, Florida and is a short 7 minute walk to the white sand beaches and turquoise waters. This apartment has a 7 night minimum stay requirement but we have other great properties if you need a shorter stay, just contact us!

Darling Old Florida Beach Cottage Steps From Gulf!
Fully Renovated Coastal Gem! Welcome to Cottage By The Sea — a beautifully updated retreat just steps from the sugar-white sands and turquoise waters of the Gulf of Mexico on Anna Maria Island. Tucked away in the peaceful community of Bradenton Beach, this charming escape is one of the few remaining “Old Florida” cottages, lovingly restored with modern touches and cheerful, sun-filled décor. Leave your worries behind and unwind in your own slice of island paradise!
Popular amenities for family-friendly rentals near Anna Maria Island
Family-friendly home rentals with a hot tub

Turtle Cottage - Anna Maria Island

Luxury 3/3 Margaritaville Resort

Longboat Key-OCEAN FRONT- on the beach

A&A's Paradise near IMG & Anna Maria beaches

★Right on the beach ★ Relax and Enjoy ♥ Sunsets!

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

2 Hot Tubs+Pool+MiniGolf+Sleeps 16

Beachfront Anna Maria Island w hot tub & Gulf view
Family- and pet-friendly home rentals

New! Heated Pool~Steps to the Beach/Shops~Starfish

Dock of the Bay by Duncan Real Estate

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

Charming Beach house amongst huge Banyon Trees

Steps to the beach! Condo with pool at The Terrace

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

Walk 2 blocks to Beach + Private Pool + King Beds!

Short Stroll to the Surf! ~ Make Memories on AMI
Family-friendly home rentals with a pool

Sand & Sea Oasis: Condo with Private Beach Access

Getaway Family Beach Townhome w/Pool!

Poolside Oasis on Anna Maria Island!

Heated Pool, Elevator, Waterfront, Fire Pit, Dock

Sea Shack - 2bd/2ba POOL Home

Sunrise Villa - Tropical 3 bedroom home with pool

L'Oasis East w/Dip Pool

NEW listing on AMI! Walk to fabulous beach front!
Family-friendly home rentals with wifi

Romantic Quiet Luxury Tiny Home W/ Private Hot Tub

TOES IN THE SAND!

Rustic Coastal Cottage | 1BR W / Pool & Near Beach

Tranquility on the bay.

༄ Sunset Shore on Anna Maria Island ༄

Ground-Level AMI Gem: 3 Blocks to Beach & Shops!

New Modern Longboat Key*5 Steps to Sand*Heatd Pool

Bean Pt. Bungalow - Half duplex w/private pool
Quick stats about family-friendly rentals near Anna Maria Island

Total holiday rentals
Explore 2,410 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 36,360 verified reviews to help you choose

Pet-friendly holiday rentals
Find 790 rentals that welcome pets

Holiday rentals with a pool
2,050 properties feature pools

Rentals with dedicated workspaces
1,250 properties have a dedicated workspace

Wifi availability
2,400 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!
Destinations to explore
- Villa rentals Anna Maria Island
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