# Anna Maria Island Weekend Vacation Rentals, Island Vacation Properties Updated: 2026-11-13 Take a spontaneous trip in one of our Anna Maria Island weekend vacation rentals, offering an idyllic escape, even if it's just for a couple days. Experience a world where every detail has been thoughtfully crafted to provide an experience of comfort and convenience. We have the perfect Anna Maria Island rentals for any traveler, whether you seek the charm of a cozy beachfront cottage or the sophistication of an elegant condo. Savor the personalized service and warm spirit that makes a weekend getaway on Anna Maria Island not just a vacation but an unforgettable retreat. Things To Do on Anna Maria Island Anna Maria Island is a haven of enchanting activities and breathtaking beauty. From its pristine beaches with powdery white sand to the crystal-clear waters that are great for snorkeling, surfing, or simply basking in the sun, the island is a paradise for both relaxation and adventure. Enjoy a bike ride along picturesque trails, indulge in gourmet dining at waterfront Anna Maria Island restaurants, or explore the unique boutiques and art galleries that add to the island’s charm. Every moment spent here celebrates the essence of island life, creating memories that linger long after your stay. Book Your Anna Maria Island Vacation Rental with Island Vacation Properties Choosing Island Vacation Properties for your next Anna Maria Island vacation rental ensures a customized experience that transcends ordinary travel. Our selection of Anna Maria Island short-term rentals includes luxurious condos, spacious homes, Anna Maria Island pet-friendly rentals to accommodate your entire family, and even monthly Anna Maria Island rentals for longer vacations. Our commitment to exceptional quality and personalized service guarantees a stay that is as comfortable as it is memorable. Escape to unparalleled elegance and warmth—book your dream getaway on Anna Maria Island with Island Vacation Properties, where every detail is tailored to exceed your expectations. Indulge in an extraordinary world of luxury, comfort, and heartfelt hospitality. ## Rentals in this collection (23) Live price for dates: add ?arr=YYYY-MM-DD&dep=YYYY-MM-DD&people=N to any property page. (arr = check-in date, dep = checkout date, people = number of guests) Rating = guest rating out of 5 (number of reviews). | Property | Location | Bedrooms | Sleeps | Pets | Rating | Page | Data | |---|---|---|---|---|---|---|---| | A Getaway Retreat A | Bradenton Beach, FL | 2 | 6 | Yes | 4.6 (18) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-207379/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-207379.md) | | A Getaway Retreat Both Units | Bradenton Beach, FL | 4 | 12 | Yes | 4.8 (5) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-207370/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-207370.md) | | Bayview Inn #101 | Bradenton Beach, FL | 1 | 4 | No | 4.9 (21) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-234316/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-234316.md) | | Beach House Resort 10 | Bradenton Beach, FL | 3 | 10 | No | 4.9 (43) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174526/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174526.md) | | Beach House Resort 3 | Bradenton Beach, FL | 1 | 4 | Yes | 4.7 (45) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174528/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174528.md) | | Beach House Resort 9 | Bradenton Beach, FL | 1 | 4 | No | 4.7 (54) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174533/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174533.md) | | Bliss & Tonic Both | Bradenton Beach, FL | 4 | 12 | No | 5 (19) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174460/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174460.md) | | Bliss & Tonic Down | Bradenton Beach, FL | 2 | 6 | No | 4.7 (26) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174461/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174461.md) | | Bliss & Tonic Up | Bradenton Beach, FL | 2 | 6 | No | 5 (16) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174462/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174462.md) | | Good Times Both Units | Bradenton Beach, FL | 4 | 12 | Yes | 4.3 (7) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174483/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174483.md) | | Good Times Downstairs | Bradenton Beach, FL | 2 | 6 | Yes | 4.3 (15) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174484/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174484.md) | | Good Times Upstairs A | Bradenton Beach, FL | 2 | 6 | Yes | 4.7 (26) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174485/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174485.md) | | Lazy Livin 6 | Bradenton Beach, FL | 2 | 6 | No | 4.7 (26) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216483/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216483.md) | | One Particular Harbour Sound View 379-401 | Bradenton, FL | 2 | 5 | Yes | 4.9 (35) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216784/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-216784.md) | | One Particular Harbour 379-101 | Bradenton, FL | 2 | 5 | Yes | 4.9 (24) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-230259/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-230259.md) | | One Particular Harbour 391-201 | Bradenton, FL | 2 | 5 | Yes | 4.8 (14) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-206004/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-206004.md) | | One Particular Harbour Lagoon View 395-103 | Bradenton, FL | 3 | 7 | Yes | 4.9 (52) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-198297/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-198297.md) | | Palma Sola | Bradenton, FL | 3 | 8 | Yes | 5 (8) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-231137/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-231137.md) | | Pelican Cove 15 | Bradenton Beach, FL | 2 | 4 | Yes | 4.8 (29) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174588/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174588.md) | | Shell Cove 9 | Bradenton Beach, FL | 2 | 6 | No | 4.8 (56) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174617/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174617.md) | | Sunset Villas | Holmes Beach, FL | 2 | 6 | No | 4.6 (10) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174448/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-174448.md) | | The Sunset Retreat at One Particular Harbour 384-202 | Bradenton, FL | 3 | 7 | No | 4.9 (34) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-204768/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-204768.md) | | Turquoise Turtle at One Particular Harbour 388-403 | Bradenton, FL | 3 | 6 | No | 5 (5) | [page](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-248571/) | [md](https://www.islandvacationproperties.com/vacation-rentals/rental/2531-248571.md) | ## Live availability for your dates For live availability and pricing across this collection on specific dates, open this filtered search and fill in the dates: https://www.islandvacationproperties.com/vacation-rentals/results/?searchform=1&cwrsearch=1&checkboxes=Long%20Weekend&arrive_date=M/D/YYYY&depart_date=M/D/YYYY (arrive_date = check-in, depart_date = checkout; dates as month/day/year, e.g. 12/15/2026) This runs the live search on the website; hand it to the guest for bookable, up-to-the-minute results across the whole collection.