Featured Properties
85 properties available
Santorini by Anna Maria Island Accommodations TPL24-000118, DWE5105266Welcome to Santorini, a charming two bedroom, one and a half-bath cottage that blends Greek-inspired style with Florida’s coastal charm. Just a three-minute walk to the white sands of Bradenton Beach, this cottage is ideally located near local restaurants, shops, and a trolley st
Santorini
House
2
bedrooms
1
baths
1
Half baths
5
guests
4.7
(12)
Tiki Sunset by Anna Maria Vacations Duplex in Holmes Beach, Florida VRC16-000935Welcome to Tiki Sunset, an inviting three-bedroom, two-bath duplex, just a two-minute walk from Holmes Beach! This tropical-inspired home sits in a friendly neighborhood, featuring a shared lush backyard with a pool, outdoor seating, and a BBQ grill. Perfect for familie
Tiki Sunset
Duplex
3
bedrooms
2
baths
6
guests
4.5
(2)
Siesta Beach House #207 by Tropical Sands Accommodations Welcome to Siesta Beach House #207, a cozy and budget friendly 2-bedroom, 1.5 bath condo just a 2-minute walk from the white sands of Siesta Key Beach. Set in a relaxed community with private beach access, this comfortable retreat is ideal for families, small groups, and couples looking to en
Siesta Beach House #207
Condo
2
bedrooms
1
baths
1
Half baths
6
guests
5
(1)
Blissful Bungalow by AMI Locals VRC21-000131 Welcome to Blissful Bungalow by AMI Locals, a stylish three bedroom, two and a half bath vacation home that perfectly captures the charm of Anna Maria Island. Just an 8-minute walk to the pristine Gulf beaches, this beautifully updated ranch-style retreat offers a private pool, lush tropical landscaping,
Blissful Bungalow
House
3
bedrooms
2
baths
1
Half baths
6
guests
5
(13)
Please note: Due to Storm damage from Hurricane Helene, The pier will not be accessible until further notice. Important Notice: The Sand Dollar condominium building will be undergoing a roof replacement project from approximately November 30 through January 8. Guests may experience daytime construction noise during this time.Home Away from Home -
Sand Dollar 404
Condo
2
bedrooms
2
baths
6
guests
4.9
(107)
Seahorse Cottage by AMI Locals VRC16-000110 Welcome to Seahorse Cottage, a beautifully designed three-bedroom, three and a half bath vacation home just a six-minute walk from the white sands of Holmes Beach! Perfectly situated across the street from the free Anna Maria Island Trolley stop, this coastal retreat offers a private heated pool, relaxing
Seahorse Cottage
Duplex
3
bedrooms
3
baths
1
Half baths
6
guests
5
(14)
Ringling Cottage by Lido key VacationsMinimum stay duration of 7 days/nights Ringling Cottage by Lido Key Vacations is a charming two-bedroom, two-bath historic retreat designed for couples seeking a relaxed yet refined island escape. Originally built in the 1930s by John Ringling, this thoughtfully updated cottage blends classic character with mo
Ringling Cottage
Cottage
2
bedrooms
2
baths
4
guests
5
(12)
Private Beach House by Siesta Key Luxury Rental Properties Welcome to Private Beach House, a two-bedroom, two and a half bath coastal townhome designed for effortless island living. Located along Midnight Pass Road, this beautifully appointed retreat offers private beach access just a short walk from Siesta Key Beach and is moments from the dining
Private Beach House
Townhouse
2
bedrooms
2
baths
1
Half baths
8
guests
4.9
(58)
Casa Siesta 2 by Tropical Sands Accommodations Welcome to Casa Siesta 2, your ideal romantic beach getaway located just a 6-minute walk from Crescent Beach in beautiful Siesta Key. This cozy one-bedroom, one-bath ground level condo is perfect for couples seeking a relaxing coastal escape, offering comfort, convenience, and easy access to the islan
Casa Siesta 2
Condo
1
bedrooms
1
baths
4
guests
4.5
(2)
Heavenly Sunset by AMI LocalsVacation Rental License #TPL24-000103, DWE5105909Welcome to Heavenly Sunset, an upscale three-bedroom Bradenton Beach vacation rental located directly across the street from the sugar white sands of Anna Maria Island. Designed for family beach vacations and relaxed group getaways, this coastal retreat offers Gulf views,
Heavenly Sunset
House
3
bedrooms
3
baths
8
guests
4.9
(20)
Hamilton House 307 by JC Resorts Welcome to Hamilton House 307, a Gulf side vacation rental in Indian Rocks Beach. Located on the top floor, this spacious northeast corner condo features three bedrooms, two bathrooms, a private furnished balcony, and accommodations for up to eight guests. Gulf views, direct beach access, a heated beachfront pool, a
Hamilton House 307
Condo
3
bedrooms
2
baths
8
guests
4.8
(94)
Highlights • Canal front • 5-minute walk to the beach • Rooftop deck • Private pool with in-ground spa • Outdoor living space Aqua Bay by Anna Maria Vacations Home in Holmes Beach, Florida Welcome to Aqua Bay! This luxurious canal-front home has four bedrooms and three bathrooms, providing guests with a relaxing and top-notch getaway experience. Wi
Aqua Bay
House
4
bedrooms
3
baths
8
guests
5
(16)
Copyright © 2026 • Prime Vacations
All Rights Reserved.