Vacation Rentals
40 properties available
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2825 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower, Double Vanity, & Soaking Tub- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower- 1 Queen
Welcome to Island Time!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals & Property ManagementGround Level Spacious Home w/Lagoon Style Enclosed Heated Pool & Spa, Walk or Ride Bikes to Beach!2600 sq. feetHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and ensuite full bath- 1 Queen B
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The waterfront 3-bedroom home has a private heated pool, spa, and dock! This home's location is second to none, just steps to the bayside beaches and easy walking distance to B
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A spectacular vacation half-duplex that promises an unparalleled escape on Anna Maria Island.HIGHLIGHTS:- Short Walk to Beach- Kitchen, Dining, Indoor/Outdoor Living
Welcome to Mango Bay!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Gorgeously Renovated Spacious Home w/Pool, Spa, Game Room, Bikes, Walk to Beach! 2560 sq. feetHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Primary Suite w/ En-Suite F
Welcome to AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.1970 sq. ftHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and Ensuite Full Bath & Walk-In Closet- 1 Queen Bedroom w/ TV- 2 Bunk Beds w/Trundle
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Ground Level Fully Renovated Beach Cottage in Heart of Anna Maria2 Bed (sleeps 4), 1 Bath with Heated Pool directly on Pine Avenue. Short walk to Piers, Shops, and Gulf Side
Welcome to Coconut Lagoon!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Ground Level Completely Updated Luxury Historic Home3 Bed (sleeps 6), 2 1/2 Bath with Heated Pool easy walking distance to Pine Avenue and Gulf side beachesHIGHLIGHTS:- Kitchen, D
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBeautifully updated, fresh, and clean elevated 3 Bed, 2.5 Bath which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue1500 square feetHIGHLIGHTS:-
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.Renovated Pristine Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1 King Bedroom, En-Suit
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.Pristine Newly Built Spacious Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point Beaches & Downtown Anna Maria, Bikes Included!3650 sq. ft.HIGHLIGHTS:- Private Single Family H
Welcome to A Shore Thing!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A waterfront luxury home just a few blocks from the pristine sugary white sands of Anna Maria Island and quaint 'downtown' Anna Maria's Pine Avenue!HIGHLIGHTS:- Open la
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