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The Lookout by Beach Boutique Rentals

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Your waterfront pool retreat awaits
Where the view becomes your backdrop
Welcome to The Lookout
Your beach escape begins inside
Light-filled living with coastal charm
3 bedrooms2 bathroomsSleeps 6130.1 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Anna Maria, FL
  • Place, Anna Maria Beach
    ‪1 min walk‬
  • Place, Bean Point Beach
    ‪4 min walk‬
  • Place, Bradenton Beach
    ‪4 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪35 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Master bedroom

1 King Bed

Queen bed 1

1 Queen Bed

Queen bed 2

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Garden
Dining area

About this property

The Lookout by Beach Boutique Rentals

Perfectly positioned directly on the water, The Lookout offers a private waterfront pool, an incredible covered gazebo lounge, and sweeping bay views that make every moment feel like a postcard.

*Features include*

* Direct beachfront location
* 3 bedrooms, 2 bathrooms
* Private waterfront swimming pool
* Huge covered gazebo outdoor living area
* Outdoor dining and lounge spaces overlooking the bay
* Cornhole, giant games and stand up paddleboards
* Bayfront loungers with umbrellas
* Outdoor firepit gathering area
* New top-to-bottom designer renovation
* Washer and dryer
* Beach chairs, umbrella and cart
* Minutes to Bean Point and Pine Avenue

Welcome to The Lookout, a stunning bayfront retreat on coveted North Shore Drive in Anna Maria. Fresh from a top-to-bottom designer renovation, this beautifully reimagined three-bedroom, two-bath home pairs relaxed coastal style with breathtaking views of Tampa Bay and unforgettable outdoor living.

Start your mornings with coffee as boats drift by, spend your afternoons lounging poolside in the sunshine, and end the day watching the sky turn shades of pink and gold over the water.

The outdoor living space is truly the star of the show. A spacious covered gazebo creates a breezy waterfront lounge where you can relax in the shade, dine alfresco, or gather with friends and family while enjoying uninterrupted views across the bay. Just steps away, the sparkling waterfront pool offers the perfect place to cool off while taking in the peaceful beauty of Tampa Bay. Lounge by the water under shaded umbrellas, or gather around the firepit in the evening as the sky turns shades of pink and gold over the bay.

Inside, the home has been completely transformed with a thoughtful designer remodel that blends bright coastal style with warm natural textures and elegant finishes. The open living and dining areas feel light and inviting, creating a perfect space for gathering after a day of exploring the island.

Each bedroom reflects the calm coastal palette found throughout the home, creating a relaxed atmosphere that perfectly matches the waterfront setting.The main living level features a spacious king bedroom and full bathroom, offering a comfortable retreat just steps from the heart of the home. On the ground floor, two private queen bedrooms share a Jack-and-Jill bathroom. These rooms can be accessed either through the ground-level entrance or via a spiral staircase inside the home.

Located on the quiet and highly sought-after North End of Anna Maria Island, The Lookout places you just moments from Bean Point, Pine Avenue’s shops and restaurants, and some of the island’s most beautiful beaches. Whether you spend your days biking the island, exploring nearby beaches, or simply relaxing by the water, this home offers an unforgettable Anna Maria Island experience.

With its incredible bayfront setting, stunning outdoor living spaces, and beautiful designer interiors, The Lookout is the kind of island retreat guests remember long after the vacation ends.

Please read: It's important to note that due to recent hurricanes, the sandy beach in front of the seawall has changed and may continue to change with the tides. At high tide the water will come all the way up to the breakwall.

ADDITIONAL INFORMATION

We generally require a minimum stay during the high season. We are more flexible in the off season so please send us a message if your dates appear unavailable. We may be able to accommodate you!

Housekeeping will provide a starter supply of toilet paper, soap, and garbage bags but guests will likely need to replenish the supply during their stay.

Our cleaning fee includes a professional linen service. When you stay with us you can rest assured that you will have high quality linens such as those at a fine hotel. We also provide plenty of luxury bath and beach towels.

Anna Maria Island is a family community and the city imposes a strict noise ordinance. Please adhere to our good neighbor policy and observe the local quiet hours between 10 pm and 8 am. No loud music or use of the pool is allowed during these hours along with any other noise which may disturb the neighbors.

This home provides off-street parking for up to 3 vehicles.

Booking Platform Note:
For VRBO bookings, the reservation payment is processed by Beach Boutique Rentals and will appear as Beach Boutique Rentals on your credit card statement. VRBO also charges a separate service fee directly to the guest as a separate transaction.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Minimum age to rent: 25
Upon booking, a rental agreement will be emailed to you for your electronic signature confirming that you acknowledge and accept the house rules.
Valid ID must be submitted to rental agent for property access.

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Anna Maria

Located in Anna Maria, this holiday home is near theme parks and on the beach. The area's natural beauty can be seen at Anna Maria Beach and Bradenton Beach. Travelling with kids? Consider Fish Hole Adventure Golf and H2O Watersportz. Discover the area's water adventures with kayaking and snorkelling nearby, or enjoy the great outdoors with cycling and hiking/biking trails.
Map
Anna Maria, FL

What's nearby

  • Anna Maria Beach - 1 min walk - 0.2 km
  • Bean Point Beach - 4 min walk - 0.4 km
  • Bradenton Beach - 4 min walk - 0.4 km
  • Bayfront Park - 8 min walk - 0.7 km
  • Anna Maria City Pier - 17 min walk - 1.4 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 53 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬11 min drive
  • ‪The Ugly Grouper - ‬8 min drive
  • ‪The Sandbar Restaurant - ‬4 min drive
  • ‪The Waterfront Restaurant - ‬13 min walk
  • ‪Ginny's & Jane E's - ‬3 min drive

Frequently asked questions

Does The Lookout by Beach Boutique Rentals have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at The Lookout by Beach Boutique Rentals?

As of 23 April 2026, prices found for a 1-night stay for 2 adults at The Lookout by Beach Boutique Rentals on 10 August 2026 start from NZ$1,717, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is The Lookout by Beach Boutique Rentals pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Lookout by Beach Boutique Rentals?

On-site parking is available at the property.

What time is check-in at The Lookout by Beach Boutique Rentals?

Check-in begins at 4:00 PM.

What time is check-out at The Lookout by Beach Boutique Rentals?

Checkout is at 10:00 AM.

Where is The Lookout by Beach Boutique Rentals located?

Nestled on the beach, this Anna Maria holiday home is within a 5-minute walk of Anna Maria Beach and Bradenton Beach. Bean Point Beach and Palmetto Avenue Beach are also within 10 minutes.

About the host

Hosted by Beach Boutique Rentals

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Languages:

English
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