Hotels & Lodging

5683 Midnight Pass Rd APT 105

1035 Seaside Dr

The Bay & Key Collection is a locally owned, family-run vacation rental and property management agency in Sarasota, Florida. Operated by Austin and Hayley Halliday — originally from Scotland — we offer beachfront condos, waterfront homes, and pet-friendly rentals across Longboat Key, Lido Key, Siesta Key, Anna Maria Island, and the Gulf Coast. Serving the community since 1995, we specialize in full-service property management, short-term and snowbird rentals, and concierge guest experiences. Whether planning a Florida beach getaway with heated pools and waterfront views, or seeking hands-off hosting with stronger performance, our hands-on approach delivers exceptional results.

Siesta Key Vacation Rentals...just steps to the beach and stunning Gulf of Mexico!

5235 Calle Menorca

1123 Crescent St

Welcome to The Cottages on the Key, an exclusive vacation rental management company with a boutique collection of luxury vacation homes located in Siesta Key, Lido Key, Anna Maria Island and the mainland of Sarasota, Florida. We offer complete vacation rental management and asset preservation services for owners/investors and our guest services are offered 24/7.

Welcome to Tivoli- A luxurious condominium located directly across from Siesta Key's beautiful white sand beach. Experience your dream vacation in one of the many gorgeous 2 Bedroom / 2 Bathroom condos featuring a spacious balcony to look out over the ocean! At Tivoli, guests have access several desired amenities, including a year round heated pool, Tennis/Pickleball Court, Putting Green, Grill Area, Rec Room, and more! Siesta Key is a lush, tropical island with an “Old Florida” essence. It provides year round outdoor activities such as boating, swimming, beach walking, tennis and fishing.

Mit unserem Konzept wollen wir all die Lücken schließen, die wir, in unseren Urlauben, als Individualurlauber, mit oder ohne Kinder, erleben durften. Angefangen bei Anfahrtsbeschreibungen, die keine sind, zu unzureichend ausgestatteten Ferienwohnungen, für die es keinen Ansprechpartner gibt und für die sich Vorort auch niemand zuständig fühlt, über den fehlenden Frühstückskaffee nach der ersten Nacht, bis hin zu nicht kalkulierbaren Zusatzkosten und Zuschlägen. Mit ihrer Buchungsbestätigung erhalten Sie eine Anfahrtsskizze, die Sie sicher und ohne Umwege zu uns führt. Unser Ziel ist Ihre Zufriedenheit, darum haben wir immer ein offenes Ohre für Ihre Wünsche und Anregungen.

Vaaraway is the go to destination for discerning travelers seeking amazing vacation rentals and unique experiences. We live by our mantra, “The generous and friendly treatment of visitors and guests,” and believe that every guest and homeowner deserves to experience the “WOW” factor. We hand select every vacation home and guarantee to provide personal service and hospitality that is generally considered a lost art in the world today.

1400 Cove II Pl #611

4795 Marlin Rd

1444 Roosevelt Dr

871 Jamaica Rd

916 Jamaica Rd

Venice Pool Retreat | Minutes to Beaches & Downtown Escape to this private, heated-pool home in beautiful Venice, Florida. Tucked away in a quiet neighborhood, this fully furnished 3-bedroom retreat offers the perfect blend of relaxation and convenience. Spend your days lounging by the screened-in pool, hunting for shark teeth on nearby Gulf Coast beaches, biking the Legacy Trail, or exploring the shops and restaurants of historic downtown Venice. Whether you’re planning a family vacation, a couples getaway, or an extended stay, you’ll enjoy comfortable accommodations, a fully equipped kitchen, high-speed Wi-Fi, and easy access to everything Florida’s Gulf Coast has to offer.

Venice Villas on the Beach is an independent, family owned Vacation Home Rental Company. Since 1998, we have been providing our guests with one and two-bedroom beachfront vacation rental condo accommodations that are situated within the community of Venice Villas and located directly on Golden Beach, on the beautiful Island of Venice, Florida. Our single story condos are positioned just steps away from our private beachfront and our huge Olympic swimming pool. All of our comfortable villas are tastefully furnished and decorated and include: fresh linens and towels, a full-equipped kitchen, central A/C, flat screen cable TVs, FREE WiFi, coin-operated laundry facilities, beachfront gazebos, and a quiet, uncrowded, relaxing atmosphere.

6154 Midnight Pass Rd # 5-A

Villa Grande is a spacious and fully stocked pet friendly vacation rental in Venice, Florida with a huge fenced back yard!

4696 Alligator Dr

Siesta Key. Our large and luxurious three-story holiday residence and boating home is the perfect place where you and your loved ones can get away and unwind together. We also have a fitness center, private tennis court, bicycles, boat dock, beach equipment, outdoor grilling along with a beautiful outdoor pool and spa you can enjoy! In minutes, you can boat, kayak, or paddleboard to Big Pass or Sarasota Bay to enjoy the open water or one of many nearby sandbars.

9000 Blind Pass Rd