Pet Friendly Rentals


Properties Available 17 properties available
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 33
Point's Hideaway
Anna Maria Pet Friendly
$360.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (5)
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 48
Sea Mist
Anna Maria Pet Friendly
$360.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
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 31
The Cottage on Pine
Anna Maria Pet Friendly
$340.00 - $720.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (3)
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 107
She's Always Right
Holmes Beach Pet Friendly
$520.00 - $1,350.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 5 (12)
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Covered Porch/Balcony off living area- 1 King Bedroom w/ TV, En-Suite Full Bathroom (shower, tub, double sink), Walk-in
Hot HOT 43
Serenity Now
Holmes Beach Pet Friendly
$420.00 - $1,250.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (4)
Welcome to Catching Waves!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.HIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa TV- 1 King Bedroom, En-Suite Full Bathroom w/ walk in shower- 1 Queen Bedroom- Hall Full Bathroom w/ tub shower c
Hot HOT 262
Catching Waves
Holmes Beach Pet Friendly
$290.00 - $648.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
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:-
Hot HOT 20
Sol Mate
Anna Maria Pet Friendly
$360.00 - $920.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (9)
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 42
Casa Posada
Anna Maria Pet Friendly
$279.00 - $450.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 5 (3)
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 65
Cozy Cabana East
Holmes Beach Pet Friendly
$310.00 - $675.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
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
Hot HOT 60
Coconut Lagoon
Anna Maria Pet Friendly
$351.00 - $900.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
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 42
Anna Maria Aloha
Anna Maria Pet Friendly
$279.00 - $650.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (7)
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 19
A Wave From It All
Anna Maria Pet Friendly
$369.00 - $880.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (8)

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