Stay & Cruise
Your Summer Stay, Upgraded
When you book 7 nights at one of our select Holmes Beach homes, you’ll receive a complimentary 3-day golf cart rental through our sister company, Once Upon A Beach Carts 🛺
Because some of the best moments happen in between the plans, like riding to the beach at sunset, grabbing ice cream after dinner, or simply exploring the island at your own pace.
Why You’ll Love It
- Easy, breezy access to beaches, shops, and restaurants
- No need to worry about parking during busy summer days
- A fun, family-friendly way to experience the island
- Added value built right into your stay
✨ Valid on new 7-night reservations
✨ Blackout dates apply
If you’re ready to start planning your island escape, we’d love to help you find the perfect home.
📞 Call or text: (941) 584-5844
📧 [email protected]
Your summer story starts here 🌊
5 properties available
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere thoughtful design meets island energy, She’s Always Right blends modern artistry, resort-style comfort, and an unbeatable location just steps from t
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenie
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for BOTH units: Island Girl East & Island Girl West*The SpaceWith room for up to 10 guests, Island Girl East & West is thoughtfully designed for shared experiences and easy island living. Each side of t
Welcome to Kokomo!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
Welcome to Cozy Cabana East!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover Cozy Cabana East, where comfort, care, and connection come together in a thoughtfully designed, single-level home just a short walk from the beach. Blending
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