Discover the perfect coastal escape with Siesta Key Luxury Rental Properties, offering a curated collection of luxury Siesta Key vacation rentals just moments from the powder white sands of Siesta Key Beach and Crescent Beach. Whether you are planning a romantic getaway, a family beach vacation, or a group retreat, our homes provide the ideal blend of comfort, style, and location on Florida’s Gulf Coast. From beachfront condos to spacious multibedroom homes with private pools and rooftop views, each property places you near the dining, shopping, and vibrant atmosphere of Siesta Key Village, making it easy to experience the best of Siesta Key during your stay.
Private Retreats to Grand Villas
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Our 1–2 bedroom Siesta Key vacation rentals are perfect for couples, friends, or small families seeking a relaxing Gulf Coast escape. These cozy Siesta Key beach rentals place you close to the powder white sands of Siesta Key Beach and Crescent Beach, with easy access to the dining, shopping, and nightlife of Siesta Key Village.
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Our 3–4 bedroom Siesta Key vacation rentals are ideal for families and small groups looking for spacious Siesta Key beach house rentals near the shore. Enjoy comfortable living spaces and convenient access to Siesta Key Beach, Crescent Beach, and the restaurants and boutiques of Siesta Key Village during your Gulf Coast getaway.
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Our 5–6 bedroom Siesta Key vacation rentals are perfect for large families and group trips seeking spacious luxury beach house rentals on Siesta Key. With private pools, outdoor living areas, and locations near Siesta Key Beach, Crescent Beach, and Siesta Key Village, these homes offer the ideal setting for memorable Gulf Coast vacations.
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Our 7+ bedroom Siesta Key vacation rentals offer expansive luxury beach homes on Siesta Key perfect for large groups, reunions, and multi-family vacations. Located near the world famous sands of Siesta Key Beach and the vibrant atmosphere of Siesta Key Village, these exceptional homes deliver the ultimate luxury Gulf Coast vacation rental experience.
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Specials
America’s 250th Birthday
Celebrating long weekends, coastal traditions, and time well spent, honoring America’s 250th with Prime Vacations. We’re inviting guests to share their favorite vacation memories and traditions for a chance to win our America 250 Grand Prize.
*Terms and Conditions Apply. Please see contest page for full details and how to enter.
Last Minute Savings
Summer vacation just got easier to plan. A fresh selection of Florida Gulf Coast Vacation Rentals are now available with newly opened dates for summer travel. Book within 28 days of arrival and save 12% with promo code LASTMINUTE12. Limited availability. Prime locations. Reserve your Anna Maria Island or Siesta Key summer stay today!
*Terms and Conditions apply.
Extended Stay Discount
Extended Beach Bliss: 30+ Nights, 15% Off Your beach house, your home base—for a month or more. Looking for a long-term coastal escape? Book 30+ nights and get 15% off select homes with utilities included. From island cottages to spacious villas, enjoy the comfort of home and the beauty of the beach—on your schedule. Book online using promo code EXTEND15 at checkout or call us at 941-779-0733 to book directly with our Reservations team!
*Terms and Conditions apply
Military, First Responder and Teacher Discount
Sunshine, Service, and Savings on Florida’s Gulf Coast. Active duty and retired military members, first responders, and educators can enjoy 10% off select vacation rentals across Anna Maria Island, Siesta Key, and Lido Key. To receive the Hero’s Discount, reservations must be booked directly with our local Reservations team by phone at the time of booking so eligibility can be confirmed before your reservation is finalized. Discounts cannot be added, adjusted, or applied after a reservation has already been booked online or confirmed. Eligible Guests Include:
- Active Duty & Retired U.S. Military
- First Responders (Police, Firefighters, EMTs, Paramedics)
- Certified Teachers & Education Professionals (K–12 or Higher Education)
*Terms and conditions apply. Valid on select homes only. Verification required at time of booking.
Florida Resident Vacation Rental Discount
Florida residents are only a short drive away from paradise! Enjoy 10% off select vacation rentals on Anna Maria Island, Siesta Key, and Lido Key when you book directly with our Reservations team.
To qualify for the Florida Resident Special, reservations must be booked by phone and the discount must be applied at the time of booking. Because residency verification is required before confirmation, discounts cannot be added to existing reservations or applied after an online booking has already been completed.
Skip the third-party fees and book direct with our local team for the best value on your next Florida Gulf Coast getaway.
Call 941-222-2101 to book direct and save 10%.
*Terms and conditions apply. Valid Florida ID required at time of booking. Offer valid on select properties only.