Family-friendly vacation rentals in Holmes Beach

Breezy Harbor AMI pool retreat near the Beach

Stunning Fall 2024 renovation done! Charming Breezy Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately feel stress melting away. You'll love grilling in the lush yard and a 6-min walk to the beach or the AMI trolley stop. A supermarket is a couple of streets over. The home is perfect for families, couples, 1-50Lb pet, and working remotely. Ample Parking for 2 vehicles and toys. *Ask us for shorter stays and always discuss your pets with us*

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)!🏖

Beach Escape & Pool, steps to Beach & restaurants

One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

Pineapple Paradise~WATER SLIDE/ Heated Pool & Spa!

Enjoy the waterslide heated pool home! Perfect for adults & kids of all ages. Owner managed. This exceptional 4 bed, 6 & 1/2 bath vacation home is just a few steps away from the beach. To provide guests with an unforgettable experience, we have designed this house with a perfect backyard for entertaining & an incredible rooftop deck that offers stunning views of the Gulf! • Owner Managed • Rooftop deck • Private pool with waterslide & spa • Outdoor living space • Foosball/Ping Pong • Connect 4

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.

Crows Nest at Spinnakers Vacation Cottages

Close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love the location, the ambiance, and the high ceilings. Located in the lush tropical paradise of Spinnakers Vacation Cottages. Offers a spacious living area, with the bedroom and bathroom on the living floor with a spiral staircase leading to a loft with two twin beds. Great for couples, families and dogs (with small pet fee) Great private deck for star gazing! Spa maintains same temperature as pool

Brand New Remodeled Villa + Large Private Pool!

Remodeled cottage with a lush tropical backyard, which boasts a Private Heated pool with Waterfall and Swim-up Tiki Table, turf putting green ,Weber Grill, patio bar with 55” Outdoor Smart TV! Calypso is outfitted with a cozy Coastal decor, you feel that vacation vibe as soon as you walk in the door. The kitchen offers quartz countertops with Stainless Steel appliances. Both bedrooms have King size beds, living room has a queen sleep sofa. All furniture was brand new in December of 2024

Blanco and Sunset Villas on Anna Maria Island

Back Open Jan '25! Located just 200 steps from the beach you’ll have your feet in the sand in no time. A comfortable living area + fully equipped kitchen. Furnished with island décor and local art. Everything you need including a heated pool, large patio with a Tiki hut, tropical gardens, plus a private outdoor area with a shower for your comfort. Walk to everything – grocery, pharmacy, ice cream, breakfast, pizza, donuts, and the beach which is less than 2 minutes away.

Oceanview: Open Wed & Thurs, $225/nt + Fees!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located 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 onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Heated Pool & Spacious Lanai! Steps from Beach!

Welcome to Your Dream Beach Escape! Just one block from the sugar-white sands of Holmes Beach, this newly renovated home has everything you need for the perfect getaway. Bikes, paddle boards, and all the beach gear are included for endless fun! Unwind in the shared HEATED pool or soak up the charm of Anna Maria Island. Shopping, dining, and tropical attractions are just a stroll, bike, or trolley ride away. Perfect for families, reunions, and couples!

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Luxury 3/3 Margaritaville Resort

Our luxury 3 BR/ 3 Bath Margaritaville inspired condo features one of the best unobstructed water views of Anna Maria Sound and Tampa Bay in the community. The unit features a gourmet kitchen, high-end mattresses, furniture and electronics. The unit comes with bikes and plenty of beach gear. Come enjoy one of the best units in the only luxury development in the area. Skip the hassle of a trip to the off-site management office with keyless entry.