Holiday rentals with a fire pit 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!

Private Island Old FL Waterfront Heaven on Earth

Discover the hidden secret of "Terra Ceia Island" (Heaven on Earth.) This 3 bed / 2 bath completely remodeled and charming A frame home offers breath taking sunrises from the bayfront private dock. Imagine enjoying your coffee in adirondack chairs while the sun rises over the Tilette Bayou. Enjoy bike rides through the old Florida country side (Bikes included). And rent a boat and cruise the pristine waterways around the keys. This home has everything you need for relaxation, peace, and fun.

A Sunny, Sandy Spring Escape @ The Solace Retreat

Welcome spring at The Solace Retreat, a beautifully remodeled duplex just steps from the sugar-sand shores of Anna Maria Island. Surrounded by blooming tropical beauty and gentle coastal breezes, this bright, inviting escape is designed for effortless relaxation. With access to both sides, it’s ideal for multifamily stays—offering the perfect blend of togetherness and privacy. Enjoy stylish, comfortable spaces, soak up the sunshine, and RECHARGE this season with our 5★ white-glove hospitality.

4BR Golf View-Heated Pool/IMG Academy/Near Beaches

Welcome to The Cortez Retreat! We are delighted to have you. This gorgeous home has been completely renovated in a peaceful neighborhood overlooking the IMG Golf Course. Pack your bags and get ready to escape to SW Bradenton, just 6 miles from SRQ Airport and 10 miles from downtown Sarasota. Siesta Key has been rated the #1 beach in the US, only 17 miles from the home. Additionally, Ana Maria Island is 11 miles, Lido Beach 12 miles, Coquina Beach 9 miles, and Longboat Key 12 miles from home!

BeachHouse:Sleeps 13:Ocean View:Spa:Rooftop Deck

☀️ This 4bdrm/4bath house is perfect for large groups or entertaining. Sleeps 14!!! 3 King beds and 2 bunkbeds (3 Twin, 1 Full), Trundle, & Pullout Sofa. Each room has its own private marble tile bathroom. Go upstairs to the Pool table room with built in bar. Then to the 3rd story Rooftop deck for sunbathing and sunsets. Backyard includes a firepit, 12 person swimspa, putting green, outdoor shower, grill, bikes, & beach amenity shed! Mere steps to the beach itself. Spacious & newly renovated!

100 yr Old Stone Home + Pool + 9 miles to beaches

Charming 100-Year-Old Restored Stone House with Italian Flair – Close to Beach & Downtown! Welcome to your dream getaway! This beautifully restored 100-year-old stone home blends old-world charm with modern luxury. Inspired by the elegance of Italy, this unique retreat is just minutes from the beach and vibrant downtown Bradenton. The home has abundant natural light and has 2 bedrooms, 2 half baths and a spacious yard! You will love the heated pool and outdoor firepit for year-round relaxing.

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Private Heated Pool Retreat for Two Families

🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

2nd House from the Beach with No Roads to Cross

Seaside Sanctuary is the upper level unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north tip of the island. The front deck is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

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.

3BR/3BA + Waterfront! Hot tub + Pool + Beaches!

🌊🌴Welcome to Kingston’s Hideaway, a beautiful waterfront oasis just 2 miles from the pristine Gulf beaches of Anna Maria Island! Whether you're seeking relaxation, adventure, or a bit of both, this home offers a tranquil and luxurious escape for your next vacation! Waterfront Canal: Direct access for boating and paddleboarding-(1 paddle board available for use) Private Dock: Conveniently dock your boat right at the house (27 ft max) Pool & Hot Tub: Relax and rejuvenate.