Pet Friendly Rentals
16 properties available
Welcome to Island Girl East & 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.Introducing Island Girl East & West, an extraordinary duplex that guarantees an unforgettable escape to Anna Maria Island.HIGHLIGHTS:- Expansive tropical p
Island Girl - East & West
Holmes Beach
$340.00 - $980.00 / per night
4
bedrooms
4
baths
10
guests
5
(3)
Welcome to On Turtle Time!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Beautifully Recently Updated Ground Level Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1
On Turtle Time
Holmes Beach
$220.00 - $700.00 / per night
2
bedrooms
2
baths
6
guests
5
(3)
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
$324.00 - $880.00 / per night
3
bedrooms
3
baths
8
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
$440.00 - $1,550.00 / per night
4
bedrooms
4
baths
8
guests
5
(13)
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:-
Sol Mate
Anna Maria
$324.00 - $880.00 / per night
3
bedrooms
2
baths
8
guests
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
Casa Posada
Anna Maria
$240.00 - $500.00 / per night
2
bedrooms
1
baths
6
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
$54.00 - $880.00 / per night
3
bedrooms
3
baths
8
guests
5
(8)
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
$275.00 - $820.00 / per night
2
bedrooms
1
baths
4
guests
5
(4)
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
Serenity Now
Holmes Beach
$380.00 - $1,450.00 / per night
4
bedrooms
3
baths
8
guests
5
(4)
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 - $720.00 / per night
2
bedrooms
2
baths
6
guests
5
(5)
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
$202.50 - $432.00 / per night
2
bedrooms
2
baths
5
guests
5
(1)
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
Coconut Lagoon
Anna Maria
$315.90 - $900.00 / per night
3
bedrooms
2
baths
6
guests
5
(4)
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