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SkyRun Vacation Rentals Anna Maria

SkyRun Vacation Rentals Anna Maria

Member since 2025
24 rentals
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Anna Maria Island Townhome
Sleeps 9, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Escape to our Gulf-to-Bay townhome on Anna Maria Island for a truly unforgettable vacation. With its ideal location, luxurious amenities, and proximity to the beach, this property is a haven for beach lovers and those seeking a taste of island paradise. Relax, explore, and create cherished memories in...

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$407
avg per night
Bradenton House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book this Coastal Escape: - Private Pool & Covered Lounge with Smart TV - Spacious 4BR – Perfect for Families & Groups - Pet-Friendly with Fully Fenced Yard & Beach Gear - Minutes to Anna Maria Island & Downtown BradentonWelcome to Coastal Escape,...

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$392
avg per night
Bradenton House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Experience the best getaway at Popeye's Poole Paradise, a beautifully designed 2-bedroom retreat in a peaceful Bradenton neighborhood, minutes away from AMI. The open layout, featuring a spacious living room, fully equipped kitchen, and a bonus living space, ensures quality family time. Step into...

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$252
avg per night
Cortez House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Top Reasons to Book: - Minutes to Anna Maria Island Beaches - Modern 3-Bedroom Smart Home in Quiet Hunters Point Neighborhood - Game Room with Pool & Foosball Tables - Private Patio Perfect for Grilling & Relaxing - In-House Elevator & Tesla EV Charger - High-Speed Wi-Fi...

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$329
avg per night
Anna Maria Island Townhome
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Island Time – Your Coastal Retreat in Bradenton Beach!Wake up to the gentle sway of palms and end your days with sunset views over the bay. Nestled within the sought-after Bradenton Beach Club community, this spacious coastal townhome offers a private, peaceful escape just moments...

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$408
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

As you walk into the property from the main entrance you will be welcomed with an open gathering room. To the left you will find two bedrooms one that has a queen bed and one bedroom has three beds (1 Single Twin and 1 Twin over Twin Trundle).  Between those two rooms you will also have a full guest...

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$400
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book: -Only 1.5 Blocks to the Beach -Private Pool with Swim-Up Tiki Table (Free Pool Heat in Cooler Months) -3 Bedrooms + Sleeper Sofa – Sleeps Up to 6 -All Bedrooms Have Ensuite Bathrooms -Fully Equipped Kitchen with Island Seating -Multiple Outdoor Spaces Including Front Deck...

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$432
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • WiFi

About this property

Welcome to "A Wave From It All" – your perfect retreat on Holmes Beach, Anna Maria Island, FL. Nestled within a charming triplex, our end unit offers front-row views of the Gulf of Mexico, ensuring a truly unforgettable stay. With its unbeatable location, spacious accommodations,...

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$394
avg per night
Bradenton House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Sunshine Rays, your home away from home nestled in the charming Palma Sola area of Bradenton. This spacious 3-bedroom, 2-bathroom single-family home offers the perfect blend of comfort and luxury, with an open floor plan, two living room spaces, a fully stocked kitchen, and a stunning backyard...

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$357
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book The Cranes Nest: - Prime Holmes Beach Location on Anna Maria Island - 3 Bedrooms · 3 Bathrooms · 3 Stories - Community Pool Access (Heated Nov–April) - Bikes, Beach Gear & Golf Cart Rental Available - Dog Friendly! (2 Max & Additional Fees Apply) -...

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$347
avg per night
Bradenton House
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Top Reasons to Book this Stunning Florida Home: -FREE POOL HEAT DURING STAY!!!! - Private Heated Pool & Hot Tub - Fully Equipped Outdoor Kitchen & Lounge with Smart TV - Mini Putting Green for Family Fun - Two Master Suites with Direct Pool Access - Short Drive to Anna Maria Island...

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$616
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

When you arrive at the property you will notice ample parking for your whole party.  When you enter the property, head up the stairs in the front of the home and enter your code.Once you enter you will see where the property gets its name, Crazy Mermaid! When you enter you will see off to the...

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$376
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Location: Welcome to Casa Palmera, a charming 3-bedroom, 2-bathroom single-family home ideally located in the Bradenton/Cortez area. Situated right next to the Cortez Bridge, this prime spot provides immediate access to the sunny and famous Anna Maria Island. Enjoy the serene, residential neighborhood...

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$440
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Kick off your shoes and settle into this bright, beachy condo just steps from the Gulf.Highlights: - Newly Remodeled 2-bedroom, 2-bathroom condo in Runaway Bay - Located on picturesque Bradenton Beach, FL - Open-concept living, dining, and kitchen layout - Private balcony with views of lush tropical...

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$215
avg per night
Bradenton House
Sleeps 12, 4 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book:Heated Pool Included for Free4 Bedrooms + Theatre Room – Sleeps Up to 12Direct Palma Sola Bay Access with Water Views85" OLED Movie Theatre with Surround SoundBeach Gear IncludedFree Beach Setup or Free Cleaning for 7+ Night StaysWelcome to 11...

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$586
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Just a 2 minute walk across the street to the beautiful beaches of Anna Maria Island. This updated coastal beach condo is all you need for a stay in paradise, so slow down and enjoy the Beach life at 3 on Avenue Sea. Bradenton beach is centrally located just south of Anna Maria and Holmes Beach, just...

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$209
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Pink Pearl, your dream coastal retreat! This stylishly renovated one-story home combines tropical charm with modern comfort—perfect for families or groups looking to relax, entertain, and explore beautiful Anna Maria Island.The Space: - Spacious, single-story home with 4 bedrooms...

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$668
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Charming 1-Bedroom Condo in Runaway Bay – Anna Maria IslandPrime Location – Steps to the Beach: - Located in the highly sought-after Runaway Bay community on Anna Maria Island - Just across the street from white sand beaches and crystal-clear waters - Walkable to shops, restaurants,...

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$234
avg per night
Bradenton House
Sleeps 10, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book: - Newly Renovated Pool & Hot Tub (new photos coming soon) - 4 Bedrooms + Sleeper Sofa – Sleeps Up to 10 - Game Room with Pool Table & Wall Games - Pet Friendly (2 Dogs Max, Fees Apply) - Beach & Baby Gear Included - Quiet NW Bradenton Neighborhood...

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$380
avg per night
Anna Maria Island House
Sleeps 5, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Castaway Cove, your relaxing home base on Anna Maria Island. Just steps from the beach and packed with everything you need for a stress-free stay, this cozy retreat is perfect for couples, families, or small groups looking to soak up the island vibe.The Space: - Just across the street...

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$203
avg per night
Bradenton House
Sleeps 7, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Escape to paradise in our charming 2-bedroom pool house, located just a short drive from the pristine beaches of Anna Maria Island. This beautifully appointed home offers the perfect blend of comfort and style, making it ideal for families or couples seeking a relaxing getaway.Step inside and be greeted...

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$278
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Why Guests Love It: -Just minutes to Anna Maria Island’s beaches, shops, and restaurants -Private heated pool with fully fenced yard and plenty of outdoor seating -Bright 3BR/2BA home with open floor plan, perfect for families and friends -Fully stocked kitchen, smart TVs, and beach gear ready...

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$251
avg per night
Bradenton Condo
Sleeps 5, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Top Reasons to Book this Island Getaway: - Prime Location in the Heart of Holmes Beach - Minutes to Anna Maria Island’s Pristine Beaches - Private Deck with Shaded Seating - Beach Gear Included – Chairs, Cooler, Umbrella & Toys - Spacious Master SuiteWelcome to Sunshine Siesta,...

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$194
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Dune Our Thing, your relaxing beachside getaway on Anna Maria Island. This thoughtfully designed unit is all about comfort, convenience, and making lasting memories—just steps from the sand and full of amenities that make your stay easy and enjoyable.The Space: - End unit in a quiet...

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$213
avg per night
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