Portfolio Vacations on Anna Maria Island

04/04/2026

Here's a list of some upcoming events on and around Anna Maria Island.

04/04/2026

Wake up on the beach, enjoy sunsets in the evening!

🏠 1 bdrm/ 1 bath/ sleeps 2
📺 High-speed WiFi + Smart TVs throughout with cable
🏊 Spa
🚋 Close to restaurants and trolley
🏝️ On the beach
🪑Lounge chairs on the beach
🏖️ Beach chairs provided

Welcome to The Beach House Resort #8, a slice of paradise right on the Gulf of Mexico! Immerse yourself in the beauty of Anna Maria Island with direct access to the white sandy beaches just steps away from your door. The beach stretches for miles in either direction! It features a large, private spa and spectacular beach views. Unit 8 even has a view of the bay from the bedroom!

Beach House Resort #8: Direct Gulf Front Beach Condo – Doesn’t get better 1 Bedroom 1 Bathroom Sleeps 1-2 DescriptionAmenitiesReviewsLocationAvailability Calendar Welcome to The Beach House Resort #8, a slice of paradise right on the Gulf of Mexico! Immerse yourself in the beauty of Anna Maria I...

03/27/2026

Looking for the perfect getaway?

Beach House Resort #8 offers a prime Anna Maria Island BEACHFRONT condo with stunning sunset views each evening. The trolley stop is right outside, making it easy to explore the island, and great restaurants are just a short walk away. Enjoy a laid-back coastal getaway in one of Florida’s most sought-after beach destinations. Book your stay today!

https://portfoliovacations.com/vacation-rentals/beach-house-resort-8/

03/26/2026

4-Bedroom Vacation Rental | Anna Maria Island | Holmes Beach l May Availability and Beyond

Stay on Anna Maria Island in this spacious 4-bedroom home, designed for families and groups who want comfort and location.

Available starting in May and continuing through the summer season.

What you get:

4 full bedrooms, ideal for larger groups (sleeps 8)
Heated private pool for year-round enjoyment
Short walk to the beach
Open living space with updated furnishings
Fully equipped kitchen
Outdoor area built for relaxing and entertaining
Beach chairs, umbrella and wagon + toys
Close to local shops and dining

Strong location. Solid amenities. Competitive rates for the area.

Prime dates move fast. Book early if you want the best weeks.

https://portfoliovacations.com/shore-to-please/

https://portfoliovacations.com/vacation-rentals/sail-away/

03/13/2026

Sail Away
Last minute SPRING BREAK DEAL with a new lower rate. Time to vacation on AMI

Available 3/21-3/28

Looking for the perfect getaway? Lounge by the pool, go to the beach,......

🏠4 bedroom/ 3.5 baths
🛏️ Sleeps 8
📺 High-speed WiFi + Smart TVs throughout
🧺 Washer & dryer in home for longer stays
💦 Sparkling private heated salt water pool with loungers + outdoor seating
🍔 Covered Lanai with kitchen/bar with tv, grill, & fridge
🚶 Walk or bike to the beach + island attractions
🏖️ Beach gear (chairs, umbrellas, wagon, toys, etc.)
🎴 Co****le boards
🍗 Close to restaurants and trolley
🚘 Driveway parking for convenience

Sail Away is a beautiful home with a private pool and plenty of room to relax and have a meal outside. Minutes to the beach. 4 bedrooms, 3 baths. The primary has a king bed, bedrooms 2 & 3 have kings also. The 4th bedroom has 2 twin beds.

Sail Away 4 bedroom home with private heated pool, perfect spot 4 Bedrooms 3 Bathrooms Sleeps 1-8 DescriptionAmenitiesReviewsMapAvailability Calendar Welcome home to your tranquil retreat! Whether you prefer curling up with a good book or catching up on your favorite TV shows, there’s ample space ...

02/14/2026

Happy Valentines Day💘

02/06/2026

Late spring and summer dates available!

🏠4 bedroom/ 3.5 baths
🛏️ Sleeps 8
📺 High-speed WiFi + Smart TVs throughout
🧺 Washer & dryer in home for longer stays
💦 Sparkling private heated salt water pool with loungers + outdoor seating
🍔 Covered Lanai with kitchen/bar with tv, grill, & fridge
🚶 Walk or bike to the beach + island attractions
🏖️ Beach gear (chairs, umbrellas, wagon, toys, etc.)
🎴 Co****le boards
🍗 Close to restaurants and trolley
🚘 Driveway parking for convenience

Sail Away is a beautiful home with a private pool and plenty of room to relax and have a meal outside. Minutes to the beach. 4 bedrooms, 3 baths. The primary has a king bed, bedrooms 2 & 3 have kings also. The 4th bedroom has 2 twin beds.

Sail Away 4 bedroom home with private heated pool, perfect spot 4 Bedrooms 3 Bathrooms Sleeps 1-8 DescriptionAmenitiesReviewsMapAvailability Calendar Welcome home to your tranquil retreat! Whether you prefer curling up with a good book or catching up on your favorite TV shows, there’s ample space ...

01/16/2026

01/07/2026

Superhost Again🏆
Another year as an Airbnb Superhost.
This recognition comes from consistent 5-star experiences, great communication, and a commitment to guest satisfaction.
Thank you to our amazing guests for trusting us with your stay.

01/06/2026

190 Runaway Bay 190: Runaway Bay Waterfront Condo

2 Bedrooms 2 Bathrooms Sleeps 1-6
DescriptionAmenitiesReviewsMapAvailability CalendarMap

Waterfront resort living on Anna Maria Island. Clean. Comfortable. Steps from the beach. Home to the largest swimming pool on the island.

Welcome to Runaway Bay 190, a ground floor two bedroom condo overlooking the intracoastal waterway. Start your mornings on the screened lanai with sunrise views. Walk across the street to the Gulf and white sand beaches. Spend afternoons at the island’s largest solar heated pool or fishing from the pier.

This home blends beach access with resort amenities in a well maintained, spotless setting.

Condo layout:
Two bedrooms
Two bathrooms
Sleeps six
King bed in primary bedroom
Two full beds in second bedroom
Sleeper sofa in living room
Ground floor unit
High cleanliness standards

Interior features:
Fully equipped kitchen
Full size refrigerator
Oven and stove
Dishwasher and microwave
Coffee maker and Keurig
Blender, toaster, cookware, dishes, and drinkware
Cable/smart TV and free WiFi
Electronic door lock for key free entry

Outdoor and beach ready:
Private screened lanai with water views
Deeded beach access across the street
Beach cart, chairs, cooler, and Cool Cabana tent
All linens and beach towels provided

Resort amenities at Runaway Bay:
Largest solar heated swimming pool on Anna Maria Island
Tennis and pickleball courts
Fitness center
Shuffleboard and bocce ball
Clubhouse with WiFi
Fishing pier
Kayak and canoe launch
Charcoal grills throughout the property

Location highlights:
Bradenton Beach location
Across from the Gulf
Free island trolley nearby
Walkable access to beaches and island attractions

Parking and rules:
Assigned parking for two vehicles
Gas golf carts only
Parking on the island is limited. Plan accordingly
Guest must be 25 years old
Separate rental agreement required after booking

Book Runaway Bay #190 today!

Our nearest Airport is Sarasota Bradenton International Airport (SRQ). It’s about 30 minutes away. Another popular choice is Tampa International Airport (TPA) which is about an hour away.

Our calendar is always updated in real time. If it shows available, it is. If we have a cancellation, it will show as available immediately.

License Number: TPL22-000059
Professionally Managed by Portfolio Vacations on Anna Maria Island

This condo offers waterfront views, direct beach access, unmatched pool amenities, and a clean, relaxing stay on Anna Maria Island.

Runaway Bay Waterfront Condo 2 Bedrooms 2 Bathrooms Sleeps 1-6 DescriptionAmenitiesReviewsMapAvailability CalendarMap Waterfront resort living on Anna Maria Island. Clean. Comfortable. Steps from the beach. Home to the largest swimming pool on the island. Welcome to Runaway Bay 190, a ground floor t...

01/06/2026

Perfect Island Interlude, pool and walk to beach

2 Bedrooms 2 Bathrooms Sleeps 1-6
DescriptionAmenitiesReviewsMapAvailability Calendar
Walk to the beach or laze by the backyard pool! Or jump on the free island trolley and see the sights.

Discover the charm of Anna Maria Island from our centrally located Holmes Beach home! This well-appointed 1/2 duplex accommodates up to 6 guests, making it ideal for family vacations, couples’ getaways, or trips with friends. The master bedroom boasts a king-sized bed and an en-suite bathroom with a shower, while the second bedroom features a comfortable queen bed. The hall bathroom offers a tub/shower combination. For additional guests, there’s a sleeper sofa in the living room.

What You’ll Love About This Home:
Location! 2.5 Blocks to the Beach!
2 Bedrooms / 2 Bathrooms
2 King Beds & Pull Out Sofa
Shared Heated Pool & Outdoor Shower
Outdoor Umbrella Patio Seating for 4
Pool Loungers & Adirondack Chairs
Gas BBQ Grill
Parking for 2 vehicles

The fully equipped kitchen includes a coffee maker, toaster oven, microwave, dishwasher, stove/oven, and refrigerator. Enjoy the convenience of a full-size washer and dryer. Stay connected with WiFi internet and unwind with cable TV in both living rooms. Take advantage of outdoor amenities, including a gas grill and beach chairs. We’ve made access hassle-free with a keyless entry system, allowing you to lock and unlock your door effortlessly as you explore the beach or the island’s attractions.

Welcome to your coastal paradise at Island Break and Island Interlude! Just a quick 2/10 of a mile stroll, and you’ll find yourself sinking your toes into the soft white sands of the nearby beaches. With an array of restaurants and bars within reach, the culinary delights of the island are at your fingertips.

Effortless exploration is facilitated by the free island trolley, providing easy access to the vibrant island life. Alternatively, indulge in a leisurely day by the backyard heated pool, shared between the two halves of the duplex. Picture this: Rent Island Break and Island Interlude together to accommodate groups of up to 12 (6 people per side) and create lasting memories as you share the pool with your favorite people. Your perfect island escape begins here!

Our nearest Airport is Sarasota Bradenton International Airport (SRQ). It’s about 30 minutes away. Another popular choice is Tampa International Airport (TPA) which is about an hour away.

Our calendar is always updated in real time. If it shows available, it is. If we have a cancellation, it will show as available immediately. In order to give our fantastic cleaners time with their families we are closed for arrivals and departures on Holidays, such as New Years Day, Mother’s Day, Memorial Day, Father’s Day, July 4th, Labor Day, Thanksgiving Day, Christmas Eve and Christmas Day.

Perfect Island Interlude, pool and walk to beach 2 Bedrooms 2 Bathrooms Sleeps 1-6 DescriptionAmenitiesReviewsMapAvailability Calendar Walk to the beach or laze by the backyard pool! Or jump on the free island trolley and see the sights. Discover the charm of Anna Maria Island from our centrally loc...