Anna Maria Island Vacation Rentals with Private Pool

Our collection of Anna Maria Island vacation rentals with private pools offers the perfect blend of relaxation and elevated coastal living. Whether you're spending the day at the beach or enjoying a quiet afternoon poolside, these homes provide a seamless indoor-outdoor experience designed for comfort and ease.

From sun-soaked lounging to evening swims under the stars, each home is thoughtfully curated to deliver a private, resort-style stay in one of Florida’s most sought-after island destinations.

For details on heating, operation, and what to expect during cooler weather, please review our Pool Information guide.

Properties Available 34 properties available
Welcome to Three Little Birds!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 SpaceStep into Three Little Birds — a bright, joyful island home designed for gathering, connecting, and letting the days unfold naturally. With Gulf views, a privat
Hot HOT 29
Three Little Birds
Three Little Birds
Anna Maria
$780.00 - $2,478.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (2)
Welcome to Hidden Palms!On Anna Maria Island in Holmes Beach, FloridaManaged by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency. Perfect for: Families, couples, and small groups looking for a comfortable island home with privacy, flexible gathering spaces, and convenient access to the beach.Highligh
Hot HOT 10
Hidden Palms
Hidden Palms
Holmes Beach Pet Friendly
$246.24 - $871.20 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Kokomo!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceDiscover Kokomo, where comfort meets calm in a thoughtfully updated beach cottage just a short walk from the Gulf of Mexico. Designed for rest and reconnection, this home
Hot HOT 8
Kokomo
Kokomo
Holmes Beach
$228.55 - $805.20 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (12)
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.The SpaceThoughtfully redesigned for simplicity and comfort, On Turtle Time blends the charm of an island cottage with the ease of modern living. Inside, natural light filt
Your Vacation Story: Your Vacation Story:
Your Vacation Story:
Relax by the private heated pool, lounge on the sunny patio, or fire up the grill for a fresh catch. Multiple covered porches offer shaded retreats. Just a 6–8 min walk to Anna Maria Island’s beaches, with easy access to the island via the free trolley!
On Turtle Time
On Turtle Time
Holmes Beach
$238.55 - $818.40 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (5)
Welcome to Casa Mariposa!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Casa Mariposa where the rhythm of island life slows, and beauty unfolds in every detail. Just one street north of Pine Avenue and four houses from the beach, this elegan
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Casa Mariposa
Casa Mariposa
Anna Maria
$453.60 - $1,911.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (16)
Welcome to Fins Up!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceYour serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenie
Hot HOT 14
Fins Up
Fins Up
Holmes Beach
$242.40 - $831.60 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (15)
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.The SpaceStep into Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike
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Coconut Lagoon
Coconut Lagoon
Anna Maria Pet Friendly
$329.67 - $1,029.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (18)
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.Experience Catching Waves — where laid-back island living meets everyday adventure. Just a short stroll to the white-sand beaches of Holmes Beach, this ground-level h
Hot HOT 9
Catching Waves
Catching Waves
Holmes Beach Pet Friendly
$214.70 - $778.80 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
Welcome to The Palm at Bean Point!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsWhere modern luxury meets laid-back island living, just moments from Bean Point.Tucked away in one of Anna Maria Island's most beloved neighborhoods, this beautifully renovated coastal retreat offers everything you need for a rela
Hot HOT 19
The Palm at Bean Point
The Palm at Bean Point
Anna Maria
$324.00 - $1,100.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
Welcome to She's Always Right!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceWhere thoughtful design meets island energy, She’s Always Right blends modern artistry, resort-style comfort, and an unbeatable location just steps from t
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She's Always Right
She's Always Right
Holmes Beach Pet Friendly
$338.58 - $1,214.40 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating 4.9 (21)
Welcome to Cozy Cabana 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.Where slow mornings and quiet evenings meet the rhythm of island life.Just a short stroll from Holmes Beach, this thoughtfully designed bungalow invites guests to rest, r
Hot HOT 15
Cozy Cabana West
Cozy Cabana West
Holmes Beach Pet Friendly
$235.47 - $831.60 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 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.The SpaceStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmos
Hot HOT 14
The Cottage on Pine
The Cottage on Pine
Anna Maria Pet Friendly
$234.00 - $903.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 (14)

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