Family-friendly vacation rentals in Holmes Beach

A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.

4.95 out of 5 average rating, 111 reviews

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*

An outdoor lounge area is showcased under a wooden ceiling, featuring a heated pool and elegant patio furnishings. A television is mounted on the wall, and a dining set is positioned nearby, with a barbecue grill just outside the lounging space, surrounded by tropical landscaping.

5 out of 5 average rating, 48 reviews

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!

4.93 out of 5 average rating, 148 reviews

Adirondack chairs in soft blue are positioned on the sandy beach, offering scenic views of the ocean and coastline. The sun reflects off the water, enhancing the tranquil atmosphere, while a distant figure strolls along the shore. Lush greenery borders the sandy area.

Condo in Bradenton Beach

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.

A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.

4.96 out of 5 average rating, 195 reviews

Sea 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.

Apartment in Holmes Beach

A clear blue pool is surrounded by palm trees and a well-maintained patio area. Lounge chairs are arranged nearby, and a dining set is visible in the background, enhancing the outdoor space. The sun-filled setting creates a vibrant atmosphere.

4.97 out of 5 average rating, 194 reviews

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

4.98 out of 5 average rating, 127 reviews

A heated pool is surrounded by lush greenery and palm trees. Lounge chairs are positioned along the perimeter, and a gentle blue hue reflects off the water. The two-story buildings in the background create a tranquil resort-like setting.

Condo in Holmes Beach

NEW listing on AMI! Walk to fabulous beach front!

Updated, well appointed, clean and comfortable, my unit at Sandy Pointe II is in a secluded setting just a few minutes walk to a less crowded, quieter section of beautiful AMI beach. From here the Island is at your fingertips! Sink your toes into beautiful white sand, watch gorgeous sunrise and sunsets, enjoy the island vibe and music at our many restaurants! A FREE Island trolly stop is steps from our entrance with grocery, drug store, beach shops and so much more just across E Bay Dr.

4.99 out of 5 average rating, 158 reviews

A serene beach scene features soft white sand and gentle blue waters of the Gulf of Mexico. Beach loungers and umbrellas are arranged along the shoreline, with a few distant beachgoers relaxing. A clear blue sky complements the peaceful atmosphere.

Condo in Longboat Key

1-Bedroom Beach Condo Open Thursday $150/nt+Fees!

This charming seaside condo 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 one-bedroom condo is optimal for sunset viewing from a private, screened lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers and sun umbrellas. Enjoy a relaxing vacation at our peaceful condo at Silver Sands Gulf Beach Resort!

4.99 out of 5 average rating, 144 reviews

A spacious living area features a light-colored sofa against a vibrant tropical leaf mural. A sleek white entertainment unit holds a flat-screen TV, complemented by a decorative lamp and a colorful area rug underfoot. Natural light filters through window blinds.

Condo in Bradenton

KING Bed + AMI Beaches + Beach Gear!

🎙️🦩Welcome to the Retro Flamingo! Your tropical getaway that combines style, fun, and the serene beauty of the Gulf Coast. This cozy, vibrant themed condo is the perfect destination for your next Beach vacation. Walking distance to Palma Sola Beach Causeway, where you can enjoy sun-bathing, horseback riding, jet skiing, and fishing! 5 mins or less from the Gulf of Mexico and powdery white sand beaches of Anna Maria Island! Kick back and relax in this retro “Old Florida” themed condo!

A cozy outdoor seating area features two blue chairs positioned near a glass-top table with a glowing fire feature. The background showcases serene water views, surrounded by palm trees and residential homes, under a colorful sunset sky.

5 out of 5 average rating, 37 reviews

Waterfront, Elevator, Heated Pool, Close to Beach

Escape to The Blue Ark, a unique 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 private pool and spa, fish from the dock, or take a stroll on 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, 8 beds and 4.5 bathrooms.

4.93 out of 5 average rating, 150 reviews

The outdoor area features a heated pool with a rock waterfall, surrounded by lounge chairs. A thatched Tiki hut provides shaded seating, set within tropical landscaping. The villa's light blue exterior and white furnishings enhance the inviting atmosphere of the space.

Condo in Holmes Beach

Blanco at 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.

A private heated saltwater pool is surrounded by lush tropical landscaping. The pool features a waterfall wall and is complemented by two lounge chairs. A shaded area with nearby outdoor dining options can be seen in the background.

5 out of 5 average rating, 13 reviews

Grains of Sand by Beach Boutique Rentals

*Features include* * Amazing almost Gulf front location * Heated saltwater pool with waterfall feature * Pool Chiller for the hot summer months * Rooftop deck with sweeping water views * 4 king bedrooms each w/ ensuite bath * Bonus room w/ twin trundle beds * Indoor/outdoor living on all 3 levels * Patio dining for 6, plus lounge area * Outdoor TV, refrigerator, bar and ping pong * Beach chairs, umbrella, and cart * Home gym * Across the street from the beach!