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*Azure Guesthouse* Walkable! Patio! Beach 8 min!

Our charming and private guesthouse has the BEST location and all the comfort and tropical coastal charm you’re looking for in your next getaway! The Azure Guesthouse is completely private - outside there is a shaded and private outdoor space and inside an open loft that sleeps 2 adults, living area with sofa & smart TV, full bath, kitchenette with dining space, and laundry. Located in walkable Southside Village with restaurants and shops at your doorstep and 8 min drive to the best beaches!

Flamingo Royale — Beach Luxury Resort

Welcome to the Flamingo Royale — Your luxury sanctuary! This exquisite escape gives tropical elegance perfect for indulgent relaxation and unforgettable memories. Experience the charm of old Florida with a modern twist in a stylish setting. Step outside to your personal paradise—a shimmering pool surrounded by lush landscaping & palms galore. W/ beautiful Anna Maria Island just moments away, relish pristine beaches, boutique shopping, and fine dining. Experience paradise at the Flamingo Royale!

Urban Serenity among Mango Trees

A private tropical fruit garden view from a covered lanai. The house is located in the historic Indian Beach/Sapphire Shores Neighborhood in the Ringling Museum District, characterized by eclectic charm and Old Florida ambiance. Nestled within tree canopy streets, it is an eclectic mix of beautiful homes. Sapphire Shores Park is a wonderful place to see dolphins, manatees and enjoy breathtaking sunsets. Minutes from SRQ, downtown, Lido Key, St. Armands, Siesta Key. The ultimate Sarasota living!

Speakeasy Bungalow: 2/1 Spa home walkable downtown

Welcome to Speakeasy Cottage – a standalone 2BR guesthouse adjacent to our main Green Gatsby property, offering privacy, charm, and relaxation. Enjoy your own private hot tub under a curtained pergola, a string-lit patio amid lush tropical plants, and a chic interior with modern boho decor. Perfect for couples or small families (queen + bunk beds). Walk to downtown Bradenton and the Riverwalk (ferry to Anna Maria Island), with gulf beaches 8 miles away. EV charger on site for your convenience.

Near Anna Maria, LECOM & IMG—Renovated—Fenced Yard

This stylishly renovated bungalow blends classic charm with modern comfort. Features include a brand-new kitchen, 3 bedrooms, 2 bathrooms, deck, fenced yard (pet-friendly!), BBQ, fire pit & outdoor shower. Just 20 minutes from Sarasota Airport, it’s near Anna Maria Island’s award-winning beaches (Travel+Leisure Best Places to Travel 2024). Also enjoy proximity to downtown Bradenton, Sarasota, St Pete, Tampa, IMG Academy, LECOM Park & scenic kayaking, paddleboarding & hiking in local preserves.

HTD Pool/Walk 2 DWTN Farmer's Market & Riverfront

Escape the cold & settle into the sunshine at this Riverfront Retreat, where winter days are filled with coastal breezes and relaxed Florida charm. Mornings often begin with dolphins playing along the Riverfront, coffee on the porch, or breakfast at a local cafe. Just steps from the front porch enjoy easy walks along the riverfront, hop on the ferry for a day of island exploring, or spend Saturday mornings exploring the dwntn Farmer's market - local artists and produce. Winter done right.

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

Coolest Downtown Neighborhood - Ebikes, Beach Gear

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

Spacious 4BR Getaway – Perfect for Families!

This spacious home includes 4 bedrooms, 2 baths comfortably sleeps up to 10 guests.The house is equipped with all your basic essentials to make you feel like home, good for longer stays! A complete kitchen is available with all basic amenities. The screened-in patio has the perfect set for a year-round vacation with a heated pool, lounge chairs, outdoor dining table. At night the stringed lanai lights can be plugged in for a cozy ambiance and the pool can be light up for you to relax!

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

Twin Palms: Big House Steps to Beach w/Lush Pool

Twin Palms is home to NY Times best-selling food writer and chef and her tech husband. Infant/kid/pet-friendly just 5 min. walk to the beach. Private lagoon-style *heated* saltwater/low chlorine pool amid lush landscaping with gorgeous rock waterfall. New appliances, HVAC, 60-inch Sony HDTV, Italian leather reclining sofas, BBQ, beach gear, three king bedrooms, all linens provided. Classic Florida one-level home - no stairs. Managed directly by owners, so no crazy fees.

The Palms-Heated Private Pool Hot Tub-5mi to beach

THE PALMS is a single-family home with heated private pool in the heart of Sarasota. The home is 5 miles to the #1 beach in the USA: Siesta Key Beach. It offers 3 bedrooms, 2 bathrooms, a large living space & screened-in sunroom. The fully private, fully enclosed outdoor space is one-of-a-kind with a heated pool, hot tub, BBQ grill, fire pit, beach bar, outdoor TV & lounge chairs for families & snowbirds to enjoy Florida living in style!