Holiday rentals with outdoor seating near Cortez Beach

AMI Dock of the Bay - "Over the Water" 2nd Floor

AMI Beach + Bay Home with Fishing Pier + Heated Pool on Sarasota Bay - "Dock of the Bay" - "Over the Water" / 2nd floor of duplex • Unbelievable views of water + birds + wildlife + night lights! • Relax with fish jumping and birds flying along 1 of only 34 coveted docks/piers south of Cortez Bridge! • Fish off our dock and rod holders! • Heated pool w/ spa jets/benches only 10 feet from Bay! • Walk 2 blocks to Bridge Street/Key West-style restaurants,bars • Live Music heard on dock + WiFi!

Bougie Bungalow at the Beach

This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

Island Time: Open Wednesday, $225/nt + Fees!

This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in Longboat Key, Florida! 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 secluded beach. Enjoy a relaxing vacation at our peaceful condo at The Beach at Longboat Key Resort! To see all four of our listings, click on my Host photo and scroll down...!

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.

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage—set in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

Beach Front Madeira Beach

PLEASE NOTE: SEVERAL UNITS UNDER CONSTRUCTION in the building. And our swimming pool is currently closed for renovations as well. Expected completion by May 31. Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away.

Modern 4BR Home *Heated Pool & Spa*

Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. VR24-00265

KING Bed + Anna Maria Island Beaches + Beach Gear!

⚓️🦩Welcome to the Coastal Flamingo! Your nautical 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 coastal escape!

Bradenton Beach Sunsets 2, 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.

Bayview Pointe! Luxury home! Near Anna Maria isle!

Welcome to Bayview Pointe, your home away from home, a brand new gorgeous three-level vacation home in an exciting new eco-friendly community that connects luxury with sustainable living. - Less than a Mile to World Class Beaches of Anna Maria Island - Gorgeous Bay View - Private Heated Pool - Elevator for easy access to different home levels - Tesla Charging Station - Close to Restaurants and Activities - Boat Launch Facility with Bay access

Seahorse Suite by Duncan Real Estate

Welcome to Seahorse Suite! This efficiency is located in a triplex in Bradenton Beach on a quiet dead end street within a short walk to Bridge Street. It is one of the 2 ground level rental units with the upstairs being used privately. The property sits only 5 houses from the Gulf Beaches and 2 houses from the Bay side. This little efficiency is the just the right size for one guest or a couple to enjoy a great island getaway.

Lovely 2 bedrooms, steps away from the beach.

This tropical beach style home will greet you upon arrival, with swaying palms creating instant serenity. The property is in Bradenton Beach on Anna Maria Island. With 2 Bedrooms, 1 Bath, and a beautiful backyard. Located Just few steps away from the beautiful waters of the Gulf. Within short distance from some of the best fresh local restaurants and bars in town you will feel the tropical vibes.