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Beachfront! 2 Masters!

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5 bedrooms, desk, iron/ironing board, travel cot
5 bedrooms, desk, iron/ironing board, travel cot
A heated pool
Fridge, microwave, oven, stovetop
Terrace/patio

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms6 bathroomsSleeps 8240 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Anna Maria Island, FL
  • Place, Bradenton Beach
    ‪1 min walk‬
  • Place, Bean Point Beach
    ‪9 min walk‬
  • Place, Anna Maria Island Museum and Historical Park
    ‪9 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪46 min drive‬

Room options

About the area

Anna Maria

A family-friendly stay in Anna Maria awaits you at this holiday home. Within steps you'll find Bradenton Beach and Bean Point Beach within a 10-minute stroll. Highlights at this beachfront holiday home include a kitchen, a private pool and a washing machine. .Home features free WiFi, 5.5 bathrooms and a balcony. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A living room, a fenced private garden and a Smart TV are also available. Change of bedsheets is available on request .Spend the day at the beach and enjoy the on-site gym and Hot tub. Additionally, you'll find free Wi-Fi in public areas and laundry facilities. .Attractions within a 20-minute drive of this Anna Maria holiday home include Anna Maria Beach and Coquina Beach.
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What's nearby

  • Bradenton Beach - 1 min walk - 0.1 km
  • Island Players - 8 min walk - 0.7 km
  • Bean Point Beach - 9 min walk - 0.8 km
  • Anna Maria Island Museum and Historical Park - 9 min walk - 0.8 km
  • Anna Maria Beach - 14 min walk - 1.2 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 48 min drive

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬9 min drive
  • ‪The Ugly Grouper - ‬6 min drive
  • ‪The Sandbar Restaurant - ‬10 min walk
  • ‪The Waterfront Restaurant - ‬14 min walk
  • ‪Ginny's & Jane E's - ‬9 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Beachfront! 2 Masters!

The Diamond Star Beach House

***Brand New 2025 Remodel***

Welcome to The Diamond Star! Experience beachfront living in the best location Anna Maria Island offers! We invite you to our family home, originally built by my grandfather, legendary left-handed pitcher Warren Spahn, affectionately known as “The Diamond Star.”

Marvel at uninterrupted beachfront views, white sandy shores, turquoise waters, and stunning sunsets — just a glimpse of what awaits at The Diamond Star! Our beachfront house combines all the comforts of home with the luxury of an unforgettable beach retreat.

While TVs are available throughout the house, who needs them when you can enjoy magnificent ocean views from both master suites, the living room, and the kitchen? Savor a sunset dinner on one of our private decks, or wander down our exclusive path to the beach for endless fun in the sun. Relish your morning coffee with a beach stroll, or dive into activities like snorkeling, kayaking, paddleboarding, flying kites, or building sandcastles! Keep an eye out for dolphins and manatees frolicking in the waves! We also provide most beach gear, including kayaks, paddleboards, boogie boards, beach chairs, coolers, towels, kites, sunshades, sand toys, and a handy push/pull cart for transporting everything to the beach.

After a sun-soaked day, unwind with a cocktail and watch the breathtaking sunset from the beach or one of our private decks. Cool off with a swim in the new pool or head to the sandbar for appetizers, dinner, and drinks as the sun dips below the horizon. And don’t forget your camera for family photos!

Our charming 5-bedroom home features 4 king beds and two sets of bunk beds, with each bedroom boasting its own full bathroom. Newly furnished in 2025, the house provides ample space for family fun — whether it's playing board games, starting a puzzle, or enjoying a movie night! Embrace outdoor cooking on our grill while engaging in yard games or taking a refreshing swim in the pool. We offer multiple board games, cornhole, ping pong, ring toss, bocce ball, and a giant Jenga set for your entertainment! Our kitchen is fully equipped with everything you need to prepare family meals, and we even have a highchair for the little ones! The Diamond Star offers super-fast (free) WiFi that extends throughout the inside and outside of our home! We also have an office with a printer and scanner for all your business needs!

Please note the following house rules:

- No animals of any kind are allowed in our home due to family allergies—no exceptions.
- No smoking or vaping of any kind is permitted in or on the premises.
- No parties or events** are allowed.
- The city of Anna Maria enforces a **strict noise ordinance**; quiet hours are from 10 PM to 8 AM.
- The minimum age of the primary renter** is 25 years old.

- OVERCROWDING CONSEQUENCES
Maximum occupancy of rental homes on Anna Maria Island are set by the Cities and are strictly enforced. An occupant is any person staying overnight, regardless of the number of nights. Due to recent issues of overcrowding in the area, if maximum occupancy is exceeded during your stay, a $1000 (one thousand dollar) overcrowding fee will be charged to the payment method on file and your party will be immediately evicted. We appreciate your understanding and cooperation to keep Anna Maria Island enjoyable for everyone.

For your safety, we have exterior-only video cameras on the premises. However, the cameras are turned off when tenants are present.

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The Retreat at Anna Maria Island Inn
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  • Pool
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  • Parking included
  • Free Wi-Fi
4.4 out of 5, Excellent, 127 reviews
The price is NZ$413
includes taxes & fees
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The Retreat at Anna Maria Island Inn

Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Car recommended
  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 5.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels
  • Stereo

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Garden
  • Walkway to water

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Computer monitor
  • Desk
  • Desk chair
  • Office
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Well-lit path to entrance
  • Smoke-free property

Services and conveniences

  • Change of bedsheets (on request)
  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near an outlet shopping centre
  • Near the bay
  • Near the marina
  • Near the ocean
  • On the waterfront

Things to do

  • Arcade/game room
  • Bicycle parking
  • Bicycles
  • Gym
  • Heated pool
  • Kayak
  • Table tennis
  • Tennis
  • Water sports equipment
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Scuba diving nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Water tubing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • At least 80% organic food
  • Bed sheets changed on request
  • Bicycle parking
  • Bicycles
  • Garden
  • Local artist showcase
  • Locally-owned and organised tours and activities
  • Unit size: 2,582 square feet
  • Water-efficient showers
  • Water-efficient toilets

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Guest is required to sign a Renter Agreement. Security Deposit Required of up to $500. Minimum age to rent is 25. 8 person capacity.
Renter Agreement must be signed within 24 hours after booking. Agreement must be signed before check-in info will be sent.
NO Smoking. NO pets. NO parties/events. Quiet Hours are from 10PM-8AM.

Pets

  • No pets allowed
  • Note from host: No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

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, a first aid kit and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.

Property is also known as

Beachfront Paradise at The Diamond Star Anna Maria
orp5b6e35bx
Beachfront Paradise at The Diamond Star Private vacation home

Frequently asked questions

Are there any beaches close to Beachfront! 2 Masters!?

Yep, Beachfront! 2 Masters! is a short 1-minute walk from Bradenton Beach. Fun beach activities include jet skiing, snorkelling and scuba diving. You can also find water sports equipment and motor boats.

Does Beachfront! 2 Masters! have a pool?

Beachfront! 2 Masters! has a heated pool and a pool.

What luxury perks are available at Beachfront! 2 Masters!?

This property features a heated pool, as well as a private pool and a private yard.

What makes Beachfront! 2 Masters! a romantic place to stay?

1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Beachfront! 2 Masters!.

Is Beachfront! 2 Masters! family-friendly?

You bet! With amenities such as a playground and an arcade, as well as baby monitors and highchairs, it's no surprise that Beachfront! 2 Masters! is a winner with our family travellers.

Is there a private hot tub at Beachfront! 2 Masters!?

Yep, there is a hot tub.

Is there a free airport shuttle available at Beachfront! 2 Masters!?

No, Beachfront! 2 Masters! does not offer an airport shuttle service.

What time are check-in & check-out at Beachfront! 2 Masters!?

Check-in begins at 4:00 PM. Check-out time is 11:00 AM.

Are pets allowed at Beachfront! 2 Masters!?

No, pets are not allowed.

Beachfront! 2 Masters! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 34 out of 36 reviews
Rating 8 - Good. 2 out of 36 reviews
Rating 6 - Okay. 0 out of 36 reviews
Rating 4 - Poor. 0 out of 36 reviews
Rating 2 - Terrible. 0 out of 36 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Jason C.

Liked: Cleanliness
Perfect house, perfect location, perfect host. By far our best experience on Anna Maria!!!
Stayed 7 nights in May 2026

10/10 Excellent

Terra D.

Stayed 25 nights in Mar 2026

10/10 Excellent

Steven E.

Liked: Cleanliness
Fantastic Villa. Incredible location right on the beach with incredible views. The villa itself was in amazing condition with great facilities and beautifully furnished. We (family of 6) had a great vacation there and Nicole (owner) was incredibly attentive and happy to help whenever. Will be returning very soon !!!
Stayed 10 nights in Apr 2026

10/10 Excellent

Marla K.

Liked: Cleanliness
What a fabulous house!! We loved every minute
Stayed 7 nights in Dec 2025

10/10 Excellent

Paul P.

Liked: Cleanliness
We stayed at the Diamond Star Beach House the week before Christmas for a family vacation and had a wonderful experience. The home is extremely well provisioned. Both the indoor and outdoor kitchens stood out with high-quality cookware, including a sous vide, making it easy to cook and enjoy meals together. We also really enjoyed the outdoor cooking and living areas, which were perfect for relaxing as a family.Just steps from the beach, the location is excellent, with beautiful sunsets that never get old. The home is also within easy walking distance of several restaurants, a coffee shop, and two bakeries, which was a great convenience. The house was clean, comfortable, and clearly well-maintained.Communication with the owner was outstanding. They were very responsive, both before and during our stay. We had a couple of minor issues, which were addressed immediately, something we really appreciated.Overall, this is a thoughtfully maintained home in a fantastic beachfront location with an attentive owner. We would absolutely consider staying here again and would recommend it to families or groups looking for a comfortable, well-equipped place right on the beach.
Stayed 8 nights in Dec 2025

10/10 Excellent

Brian S.

Liked: Cleanliness
Not only does the house have a great location the inside out outside of the home is beautiful. They also have everything you could possibly need in the kitchen and outside. The host is extremely responsive and gave us great recommendations before we arrived. We will be going back again in the near future.
Stayed 6 nights in Nov 2025

10/10 Excellent

J.R. K., Zionsville

Liked: Cleanliness
Stayed 7 nights in Oct 2025

10/10 Excellent

R. J. H.

Liked: Cleanliness
The house is beautiful, very close to the beach. Pool is nice. Putting green nice added bonus. Caretaker was very responsive and nice.
Stayed 8 nights in Oct 2025

10/10 Excellent

Steven A.

Liked: Cleanliness
This property is exceptional. We’ve stayed in several beach houses, but this one is by far our favorite. The layout of the house is perfect and they have anything you can possibly need at the house (spices, paper towels, tide pods, coffee, beach chairs, beach toys, etc). Nicole was extremely helpful and responsive. We will be going back!
Stayed 5 nights in Oct 2025

10/10 Excellent

Ryan K.

Liked: Cleanliness
Nicole could not have been a more hospitable host - we thoroughly enjoyed our stay and look forward to returning. Perfect for large families and children. Book it!
Stayed 5 nights in Sep 2025

10/10 Excellent

Rachel T.

Liked: Cleanliness
The PERFECT Anna Maria beach house! New, gorgeous, light-filled, immaculately clean: this house has been so thoughtfully designed and well-appointed, no detail is missed. Even better than the pictures. The vibe is luxurious but uncluttered, casual, comfortable elegance. Great views; best location on the island. The hosts are kind, attentive and easy-going. Can’t recommend it highly enough!
Stayed 5 nights in Jul 2025

10/10 Excellent

Linda D.

Liked: Cleanliness
AMAZING
Stayed 7 nights in Jul 2025

10/10 Excellent

Chad S.

Liked: Cleanliness

Perfect Beach Stay!

We can't say enough good things about this house and the owners! The location, amenities, cleanliness, and communication were all A.We will definitely stay here again!
Stayed 5 nights in Jun 2025

10/10 Excellent

Kara J.

Liked: Cleanliness

Most Beautiful VRBO I’ve Ever Been In

This house has everything for an extended stay! The kitchen was fully equipped to cook for our family, and the gas grill and burner worked wonderfully for dinners and breakfasts. The beds are new and very comfortable. Every bedroom has its own bathroom! The home's proximity to the beach and the supplied beach equipment made our trip perfect. Food, restaurants, and shopping are just two blocks away, plus there’s a fantastic beach bar about a third of a mile down the shore! Every night, the sunsets at the beach or on the deck were unforgettable. Nicole was amazing to work with and very responsive!
Stayed 2 nights in May 2025

10/10 Excellent

Chris M.

Liked: Cleanliness

AMI AT ITS’S BEST!!!

The Diamond Star has it all! The kitchen is fully stocked, and they provide everything you need for a day at the beach. There are tons of games for family! The house is immaculate, and the location is fantastic! We were able to walk to get ice cream, dinner, and breakfast effortlessly. Our family loved the pool and watching the sunsets from the decks! Nicole was a wonderful host, going above and beyond to ensure we had everything we needed!
Stayed 2 nights in May 2025

10/10 Excellent

Eric D.

Liked: Cleanliness

Best Beachfront House on Anna Maria Island

Our family recently had the pleasure of staying at a newly remodeled Diamond Star beachfront home in Anna Maria, and I can't say enough about how stunning it is! From the moment we arrived, we were welcomed by the serene beauty of the beachfront location, with breathtaking views of the ocean. The pool and decks game endless entertainment options for our family. The house itself is beautifully designed. The furniture is stylish and comfortable, high-quality furniture that makes the entire space feel very upscale. The living area has plush sofas, perfect for relaxing after a day at the beach, and the dining space is equipped with a wooden table that can accommodate 10.One of the highlights for me was the fully equipped kitchen. It’s a chef's dream with new appliances, ample counter space, and everything you need to whip up a delicious meal. I loved enjoying breakfast on the spacious patio, with the sound of waves providing the perfect backdrop.Another fantastic aspect of this home is its location. You can easily walk everywhere, whether it’s to the nearby beach, charming local shops, or delightful restaurants. It’s incredibly convenient to be able to stroll around without the need for a car.Overall, this beachfront home is an absolute gem. The blend of upscale comfort and a prime location makes it a perfect home for our family. We can't wait to return!
Stayed 5 nights in May 2025

8/10 Good

Scott M.

Liked: Cleanliness

Amazing location and great property.

Fantastic beachfront property, with the beach on the doorstep, cafes and shops within walking distance. Only negative would be the property is a little tired in places (exterior wood needs replacing, curtain rail on floor) But this doesn't detract from a lovely holiday and perfect location
Stayed 8 nights in Aug 2023

10/10 Excellent

DIXIE M.

Liked: Cleanliness

Anna Maria Vacation

Great property and location! Nicole was amazing to work with in planning our vacation and throughout our stay!
Stayed 10 nights in Feb 2023

10/10 Excellent

David B.

Liked: Cleanliness

Spectacular

I'm a little reluctant to write a review, as I wish I could could keep this place a secret. In additional to having a world-class beach view, every aspect of the property is just spectacular. An incredibly well-stocked and well thought out kitchen, towels - linens and pillows that you'd expect at a 5 star resort, every beach chair - umbrella - and beach toy you'd ever need, fantastic TV packages for rainy days, and on top of all that, the house is located on a quiet residential street in the desirable north AMI - yet still within walking or bike riding distance to all AM has to offer. Host Nicole has thought of everything, including being an wonderful Host to communicate with and rent from. Like the title says, all in all - just spectacular!
Stayed 14 nights in Feb 2023

10/10 Excellent

Chris J.

Liked: Cleanliness

A true Diamond!

This is an amazing property in an amazing location! The beach view is spectacular to wake up to every morning and enjoy all day. We felt like we were on the beach even when we weren't physically on the sand. The outdoor beach closet is well stocked with everything you may want for beach fun. Comfortable furnishings throughout and a well stocked kitchen too. The location was in walking distance to restaurants and shops. We didn't have to leave the north end of the island. Looking forward to a return visit!
Stayed 5 nights in Jan 2023

10/10 Excellent

Martha T.

Liked: Cleanliness

Christmas at the Beach

We had a fabulous trip. The area is wonderful and the house is in a perfect location….beachfront but walking distance to everything we needed. Beautiful view and a perfectly spotless house with everything we needed.
Stayed 5 nights in Dec 2022

10/10 Excellent

Sally D.

Liked: Cleanliness

Beautiful spot

Beautiful quiet location - but close to cute shops. Super responsive host. Great for family or couples get away.
Stayed 5 nights in Dec 2022

10/10 Excellent

Angela S.

Liked: Cleanliness

Perfect location

We loved our week on the island. There is not a better location or property. The beach was right there, not crowded in this area, quiet neighborhood - perfection!!
Stayed 7 nights in Jul 2022

10/10 Excellent

Alan F.

Liked: Cleanliness

Great Family getaway

Perfect location with quick access to the beach. A quick look out of the massive glass windows gives you immediate access to what's happening. Very private neighborhood. The outdoor shower on the deck provided easy sand clean-up every time we entered the home. This home was more than spacious for us.
Stayed 7 nights in Jun 2022

10/10 Excellent

Rhonda M., Athens, Georgia

Liked: Cleanliness

Wonderful visit

Our family thoroughly enjoyed our stay! The home was in the perfect spot for viewing the most beautiful sunsets each night. We have 5 children ages 15, 13, 7, 5 and 5 and they all loved AMI. The house was spotless and well equipped with everything we needed for our stay. The beds were super comfortable! We also didn't have to worry with bringing beach supplies with us because the home supplies beach chairs, an umbrella, boogie boards, a paddlebaord and kayak,, and the list goes on! This freed up valuable packing space in our vehicle for the drive. The owner was extremely responsive and genuinely concerned that we enjoyed our time on AMI. We would love to book this home again!
Stayed 7 nights in May 2022