Pet Friendly Rentals


Properties Available 15 properties available
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
Hot HOT 14
Cozy Cabana East
Holmes Beach Pet Friendly
$240.00 - $750.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation RentalsThis spacious, bright, and luxurious island home is ready to bring some laughter and memories to you and your group! This home is located just a quick skip to the beach, local restaurants, shops and centrally located on the island!
Hot HOT 55
She's Always Right
Holmes Beach Pet Friendly
$359.00 - $1,500.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (12)
Welcome to Beachy Villa Vista!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2177 sq ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining seating 12, Living w/ TV- Plenty of outdoor deck and patio space including covered lanai- Deck with Gulf &am
Hot HOT 19
Beachy Villa Vista
Holmes Beach Pet Friendly
$450.00 - $1,400.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.HIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Walk in Shower- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Shower Tub Combo- 1
Hot HOT 21
Point's Hideaway
Anna Maria Pet Friendly
$320.00 - $940.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (5)
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
Hot HOT 19
The Cottage on Pine
Anna Maria Pet Friendly
$290.00 - $800.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (3)
Welcome to A Wave From It All!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/ Shower/Tub- 1 Queen Bedroom w/ TV, En-Suite Full Bathroom
Hot HOT 27
A Wave From It All
Anna Maria Pet Friendly
$320.00 - $890.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)
Welcome to Sunset Margarita!Bradenton, Florida (Just OFF Anna Maria Island, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.Less than 2 miles from the Anna Maria Public Beach in the highly desirable brand new Margaritaville’s One Particular Harbour complex, clean, beautiful and bright!Thir
Hot HOT 11
Sunset Margarita
Off Island Pet Friendly
$210.00 - $480.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 (1)
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Renovated, Designer Inspired, Ground Level Home on Beach Block Just Steps to Pristine Beaches of Anna Maria Island!HIGHLIGHTS:- Fully Equipped Kitchen, Dining, Living Room
Hot HOT 10
Anna Maria Aloha
Anna Maria Pet Friendly
$240.00 - $700.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (6)
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
Hot HOT 18
Casa Posada
Anna Maria Pet Friendly
$210.00 - $520.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (3)
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
Hot HOT 25
Sea Mist
Anna Maria Pet Friendly
$360.00 - $940.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
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
Hot HOT 38
La Buena Vida
Anna Maria Pet Friendly
$380.00 - $1,000.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (1)
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
Hot HOT 42
Blue Haven Beach House
Holmes Beach Pet Friendly
$320.00 - $850.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (8)

Tell us what you're looking for and someone will contact you with available options.

I agree