Vacation Rentals
38 properties available
Welcome to Blue Haven Beach House!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Recently updated & AMAZING LOCATION!This LOVELY two story elevated island home has been recently updated with fresh coastal colors, new furniture, and decor. This ho
Welcome to Mariner's Crossing!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A newly constructed premier luxury home just across the street from the pristine sugary white sands of Anna Maria Island with views of the gulf from practically every
Welcome to Sandy Pants!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2150 sq. ft.HIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom - 1 Queen Bedroom - 1 Custom Bunk Room w/ 3 Twin Beds and 2 Double Beds- Sleeper SofaPool Area
Welcome to Salty Pirate!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Seaswept Mermaid (#1850215), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHT
Welcome to Seaswept Mermaid!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals2512 sq. ft.Need more room? Reserve the sister 4 bedroom home next door, Salty Pirate (#1678416), to stay at The Pirate and His Mermaid homes for a total of 8 bedrooms!HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Ple
Welcome to Sea Mist!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsElevated 3 Bed, 2 Bath in Anna Maria, Florida just STEPS to Pine Avenue & Anna Maria City PierSleeps 6, Max Occupancy 81742 Sq FtHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and ensuite full bath with walk in shower- 1
Welcome to Sea Glass on Park!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property Management2350 sq. feetHIGHLIGHTS:- Open Concept Kitchen, Dining Area, Living w/ TV- 1 King Bedroom- 1 King Bedroom- 1 Queen Bedroom- 3 Twin (Triple Bunk)- 3 1/2 Baths- Washer/DryerKitchen:Gas Stove, Oven, Microwave
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 Sunsets on Carissa!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.1950 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower and access to deck- 1 Queen Bedroom w/ TV- 2 T
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 Casa Posada!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Historic ground floor cottage but with all new interior paint and furnishings! Within easy walking distance to the gulf side beaches!DESCRIPTION:Casa Posada is a charming old Florida
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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