Waterfront vacation rentals in Holmes Beach

~Shore Thing~ Coastal Exquisite Waterfront Condo

🏖️ Shore Thing Retreat 🏖️ 🌅 Sunset Serenity - Unwind with views as the sun melts into the horizon. 🚶 Beachside Bliss -Just steps away from powdery sands & shimmering waters of Treasure Island. 🐬 Marine Magic Awaits - Watch dolphins dance and manatees glide right by! ✨ Stylish Coastal Vibes - Immerse yourself modern interiors with a breezy beach flair. 🍽️ Chef’s Dream - Whip up delicious meals in a fully stocked, luxury kitchen. 👩‍💼 Service with Heart - Your comfort is my priority!

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

Conveniently located just 12 minutes drive from the beaches, close to IMG Academy and all amenities, this second floor corner condo has much to offer. Its picturesque lake view, modern upgrades, and spectacular open-concept design combine to enhance your vacation experience. Facilities at Shorewalk Palms include heated swimming pools, hot tubs, tennis court, basketball court, shuffle board court, pool table, ping pong table, BBQ area and a kid's playground. All are available for your enjoyment

Silver Sands By the Sea, Open Thanksgiving Week!

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!

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!

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.

Casa Bella-5BR/Waterfront/Pool/Spa-9 Min AMI

Beautifully renovated 5 bedroom home. Located 3 minutes from beach access and 9 minutes to Anna Maria Island. A massive waterfront patio with string lights and heated pool and spa encompass this house. Master bedroom with walk-out to spa. Custom double walk-in shower in master suite. Family room with 86" television, decorative fireplace, and 15' ceiling. Roku TV’s in every bedroom. Outdoor propane grill. Beach chairs, umbrella, and cart. We welcome you to Casa Bella.

Quiet Beachfront Bungalow on Florida’s Gulf Coast

Welcome to The Sunset Beach Bungalow! This top-floor luxury water-front home located in Indian Shores, FL has been completely remodeled. Our serene getaway is situated on the Gulfs Coast. The large deck looks out over the water, providing a calming sanctuary to which you can retreat any time of day or night. Our home is over 1000 sq. ft and is newly furnished with plenty of room to relax during your stay. Our beach is private so there aren’t large crowds!

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.

Relaxing 3BR Retreat+ Hot Tub + Pool +Beaches +IMG

🌴Welcome to Beachway Haven! This 5-Star ⭐️ hideaway is just mins from Anna Maria Island's Pristine Beaches & the Gulf of Mexico. Dive into relaxation with your own Heated Saltwater Pool & Spa Hot Tub, nestled in a tropical oasis. Only a skip away from Golf Courses, Nature Parks, IMG Academy, & Palma Sola Causeway's Beach Access – your gateway to Horseback Riding, Kayaking, & endless sandy adventures. Shopping & dining are only a few mins away too!

Discounted October Stays w/Private 30' Dock & Pool

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. *Less than a 3 minute walk to Bay Beach and a 15 minute walk to Bean Point.

Waterfront Retreat | Pool • Spa • Dock | Bridge St

🌴 Anna Maria Island Waterfront Oasis! Private dock + heated pool included. Relax by the pool, sip coffee on the dock, or walk just 5 minutes to the Gulf’s sugar-sand beach. Bright, updated home with stocked kitchen, fast Wi-Fi, smart TVs, and cozy beds—perfect for families or couples. Grill by the pool, dine outdoors, or fish from the dock. Boat/kayak friendly. Beach gear + parking included. Your peaceful island escape awaits.