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SkyRun Vacation Rentals Anna Maria

SkyRun Vacation Rentals Anna Maria

Member since 2025
24 rentals
2 reviews
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Bradenton House
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Top Reasons to Book Sunshine Rays: • Private pool + spa (heated upon request for additional fee) • Fully fenced backyard — pet friendly (fee applies) • Spacious 3BR home with 2 living areas • Peaceful pond views from backyard • Minutes to Anna Maria Island beaches •...

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$221
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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$170
avg per night
Anna Maria Island House
Sleeps 10, 6 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Luxury Beach Home • Gulf Views • Heated Pool • Steps to Beach • Sleeps 10Welcome to Sunset Paradise, a stunning Anna Maria Island vacation home located just three houses from the Gulf and steps from the beach. With breathtaking Gulf views, a private heated pool, and multiple balconies...

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$925
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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$193
avg per night
Bradenton House
Sleeps 10, 5 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Luxury Beach Home • Steps to Sandbar Restaurant • Elevator • Sleeps 10 • Pets WelcomeWelcome to Villa Del Sol, a luxury Anna Maria Island vacation rental located just two houses from the beach and steps from the iconic Sandbar Restaurant.With Gulf views, heated swim spa, private...

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$820
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Top Reasons to Book 3 on Avenue Sea • 2-minute walk to Anna Maria Island beaches • 1st Floor Condo • Heated community pool just steps away • Prime Bradenton Beach location • Free trolley access nearby • Updated coastal interior • Free parking & WiFi •...

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$169
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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$174
avg per night
Bradenton House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book Popeye’s Pool Paradise: • Private heated pool (complimentary heat) • Brand new furnishings throughout • 2 spacious living areas with Smart TVs • Outdoor oasis with BBQ, TV & lounge space • Fully fenced backyard • Garage stocked with...

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$167
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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$399
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Top Reasons to Book: - Waterfront Canal Home Near Cortez Bridge - Private Pool/Spa (Additional Fee Applies) - Minutes to Anna Maria Island Beaches - Paddle boards Available for Guest Use - Boat Dock Access (Lift Not for Guest Use) - Pet Friendly (Additional Fee Applies) - Professionally ManagedWelcome...

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$325
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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$238
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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$240
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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$183
avg per night
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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$349
avg per night
Bradenton House
Sleeps 7, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Top Reasons to Book • Private heated pool + hot tub (complimentary heat) • Pet friendly (up to 2 dogs, fee applies) • Short drive to Anna Maria Island beaches • Fully equipped home with washer/dryer • Beach gear included (chairs + towels) • Quiet, relaxing neighborhood •...

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$198
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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$162
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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$342
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons to Book Crazy Mermaid • Waterfront canal views throughout the home • Private pool (heated upon request for additional fee) • Private dock for relaxing or fishing • Screened porch overlooking pool & water • Spacious 4BR layout for groups & families •...

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$328
avg per night
Bradenton House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Top Reasons to Book Sunset Oasis: • Waterfront canal home with private dock for manatee/dolphin viewing • Private pool + hot tub (heated upon request for additional fee) • Kayaks included for guest use • Outdoor fireplace + stunning sunset views • Spacious layout with multiple...

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Featured review

"Excellent House"

The house was very clean and well kept upon arrival. The pool area, outside space, and seawall deck were fantastic. The only slight blemishes were lack of basic kitchen needs like garbage bags, spices pot...

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$282
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 (Free Heat Included) - 4 Bedrooms + Theatre Room – Sleeps Up to 12 - Direct Palma Sola Bay Access with Water Views - 85" OLED Movie Theatre with Surround Sound - Beach Gear Included - Free Beach Setup for 7+ Night StaysWelcome to 11 Palms, a spacious...

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$486
avg per night
Bradenton House
Sleeps 14, 4 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Top Reasons Guests Love This Home: FREE Heated Resort-Style Pool – Swim Year-Round Expansive tropical backyard oasis with lawn games & firepit Private game room with ping pong + foosball Chef-inspired kitchen with gas cooktop & oversized island W/ Fully Stocked Kitchen ...

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$301
avg per night
Bradenton House
Sleeps 8, 4 bedrooms, 3.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Hey Sunshine! Your Private Florida Oasis Near Anna Maria Island.Why Guests Love This Home FREE Pool Heat for Your Entire Stay! Private Heated Pool + Hot Tub Resort-Style Outdoor Kitchen with Lounge with Smart TV Mini Putting Green for Endless Fun Two Luxurious Master Suites with Direct...

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Featured review

"Hey Sunshine"

We really enjoyed our stay at this property. The house was amazing. The back patio and pool area was our favorite. The house was clean and well furnished.

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$426
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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$322
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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$185
avg per night
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