Waterfront vacation rentals in Holmes Beach

Bayfront Gem Pool, Spa & walk to Anna Maria Beach

Gorgeous home with direct bay views! Lounge in the private heated pool. Enjoy morning coffee while watching sunrises. Walk across the street to the beach to enjoy swimming in the most amazing water. Dock can accommodate large boats "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." VRC21-000105

Condo with a View 2: Beachfront!

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!

Luxury 2BD Oceanfront Condo + Private Parking

🏡 Modern Condo with Stunning Ocean Views: - Cozy turf patio - Smart TVs & high-speed WiFi - Fully equipped kitchen for easy meals - 2 private parking spots for hassle-free stays - 2-minute walk to the beach ✨ Unique Features: - Robot vacuum keeps things tidy - Insta-worthy grass wall adds charm - 2 comfy queen beds for a restful sleep - Queen-sized inflatable extra bed 📍 Prime Location: - Next to the AMI trolley stop for island exploring - Walking distance to dining, gym & more!

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.

Discount 33% June 3-Day and July 4-Day w/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.

Oceanfront living on Indian Shores Beach

Oceanfront condo right on the beach! Newly renovated with designer appointed accommodations. This beach front property makes you feel like you are staying in a 5 star hotel. PLEASE READ BEFORE BOOKING: This property will accomodate 4 adults. However, there is a blow up mattress for an additional two guests that can be used in the bedroom with the two twin beds. YOU MUST REQUEST 1 OR 2 MORE PEOPLE TO STAY BEFORE BOOKING!

Luxury 3BD Beachfront Retreat with Heated Pool!

Step directly onto the sand from this luxury Gulf-front retreat in the heart of Holmes Beach. With a private heated pool, three king bedrooms—each with en suite baths—and high-end design throughout, Sandy Bottoms Beach House offers a rare combination of beachfront serenity and modern comfort. Relax on the private patio, take the trail to the beach, and enjoy a front-row seat to Florida’s most stunning sunsets.

Now NEW AUG Openings! Sarasota #1 Lux BEACH Villa

BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

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

An unforgettable experience awaits you at this getaway apartment right on the white sand beaches of Anna Maria Island. Wake up every morning to the best views of the turquoise waves of the gulf and spend your days enjoying the warm waters, filling your social media with dolphin pictures and dramatic sunsets.