Family-friendly holiday rentals in Holmes Beach

New Golf cart + 4bd/2b+ pool/shower/deck

Urban Oasis too is a privately owned home on Anna Maria Island. It has 3 bd 2 bth plus bonus room with a large pool, 10,000 sq foot yard, two large decks, outdoor bar and dining space AND a brand new 2024, 6 seater electric golf cart included! This private home features coastal hues, driftwood accents and comfortable furniture to enjoy your vacation. You will have premium linen service including all towels and linens changed with each stay. You can also check out our original Urban Oasis on AMI!

Kitchen · Family · Bathroom

Waterfront, Heated Pool, Elevator, Fire Pit, Dock

Escape to The Blue Ark, a 3-story home inspired by Noah’s Ark. Families will love this peaceful retreat, blending luxury and comfort. Discover the island's only natural lagoon, boasting stunning views, manatee and occasional dolphin sightings! Unwind by the heated pool, fish from the dock, or take an easy 4-5 minute walk to the beach. End the day with a drink by the fire pit on the top deck, watching the sunset. The Blue Ark has an elevator, 3 bedrooms + extra sleep space, 8 beds and 4.5 baths.

Family · Indoor spaces · Backyard

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!

Indoor spaces · Kitchen · Nearby

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)!🏖

Kitchen · Family · Comfort

#terraceLIFE | 2 Blocks to Beach | Heated Pool

Escape to our cozy beachside retreat, steps from the sand! Retire the car in the garage, fill the wagon w/beach supplies & head to the shoreline at sunset. Spend time sipping coffee on 1 of the 3 balconies or cooling off in the pool w/the lush landscape. There's no better way to relax & enjoy AMI! Bedrooms on 2nd floor giving the main level separation. Sleeps 4-5 comfortably but can accommodate 6 w/sofa bed. Forgot something? Walgreens is right next door along with restaurants, shops & more!

Kitchen · Indoor spaces · Nearby

Steps from Beach! Heated Pool & Spacious Lanai!

Your Dream Beach Getaway! One block from the sugar-white sands of Holmes Beach, this freshly renovated coastal retreat is ready for your perfect island vacation! Cruise around on our free bikes, paddle our boards, or hit the beach with all the gear you need for a day in the sun. When it’s time to relax, take a dip in the shared, HEATED pool! At night, enjoy the laid-back charm of the Island. Explore local shops, delicious eats, and island vibes—all just a short bike ride from our home. .

Indoor spaces · Family · Wi-Fi

Breezy Harbor AMI pool retreat near the Beach

Charming Breezy 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 open 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

Indoor spaces · Kitchen · Getting around

Beachfront Anna Maria Island, Walk to Shops!

Pool is open!! Book today! Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located beach front from the white sandy beaches. The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything you need to prepare delicious meals. The master bedroom has a king-size bed, the second bedroom has a queen-size bed and the third bedroom with two full beds.

Indoor spaces · Family · Accuracy

Gulf Front! Sunset Deck! + 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.

Indoor spaces · Family · Accuracy

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean & comfortable. Sandy Pointe II is in a secluded setting, an easy walk to a less crowded, quieter section of beautiful AMI beach. Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! *NOTE- This unit is a walk-up, no elevator. 33 steps, spaced with 3 landings VRC # 20-000-272 Minimum stay 7 nights, Adult occupancy/4 , parking 2 vehicles & Quiet hours, 10 PM untill 7 AM

Indoor spaces · Kitchen · Parks

NEW! w/ Pool - The Pearl Unit 2 on AMI

The Pearl (Unit 2) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*

Kitchen · Indoor spaces · Cleanliness

Private pool, only two blocks .3 miles from beach!

Just two blocks away from the beautiful white sands of Holmes Beach. Restaurants & night life even closer. Swimming pool and spa are inviting for both romantic getaways as well as families. You will have access to the entire beautiful two story townhouse. The property has a shared wall, but all space is private and quiet. The outdoors are separated and private as well. Plenty of parking, sun, & fun. New mattresses, new couch, and other furniture.

Indoor spaces · Family · Pool