Pet Friendly Rentals
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
Cozy Cabana East
Holmes Beach
$240.00 - $750.00 / per night
2
bedrooms
2
baths
6
guests
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!
She's Always Right
Holmes Beach
$359.00 - $1,500.00 / per night
4
bedrooms
4
baths
8
guests
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
Beachy Villa Vista
Holmes Beach
$450.00 - $1,400.00 / per night
5
bedrooms
4
baths
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
Point's Hideaway
Anna Maria
$320.00 - $940.00 / per night
3
bedrooms
3
baths
8
guests
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
The Cottage on Pine
Anna Maria
$290.00 - $800.00 / per night
2
bedrooms
1
baths
4
guests
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
A Wave From It All
Anna Maria
$320.00 - $890.00 / per night
3
bedrooms
3
baths
8
guests
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
Sunset Margarita
Off Island
$210.00 - $480.00 / per night
2
bedrooms
2
baths
5
guests
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
Anna Maria Aloha
Anna Maria
$240.00 - $700.00 / per night
3
bedrooms
2
baths
6
guests
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
Casa Posada
Anna Maria
$210.00 - $520.00 / per night
2
bedrooms
1
baths
6
guests
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
Sea Mist
Anna Maria
$360.00 - $940.00 / per night
3
bedrooms
2
baths
6
guests
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
La Buena Vida
Anna Maria
$380.00 - $1,000.00 / per night
3
bedrooms
3
baths
8
guests
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
Blue Haven Beach House
Holmes Beach
$320.00 - $850.00 / per night
3
bedrooms
3
baths
6
guests
5
(8)
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