Vacation Rentals

100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.


Properties Available 34 properties available
​We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolHur
Paradise Palms-Private Beach Access-Heated Pool-Water Views From Every Room
2 BR 2BA Condo
$152.00 - $570.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!​Cancel 14 days prior to arrival receive 100% refundCancel 7-13 days prior to arrival receive 50% refundExperience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolGulf of
Hot HOT 44
Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants
2 BR 2BA Condo
$169.00 - $665.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 (8)
Welcome to the Gulf to Bay Island Oasis—where the Gulf breeze, water views, and the island’s most convenient location come together for the perfect Anna Maria Island getaway.Just a one minute walk from the sugar-white sands, this beautifully updated condo offers the best of both worlds: the peaceful Intracoastal Waterway right outside your balcony
Gulf to Bay Island Oasis
2 BR 2BA Condo
$140.00 - $556.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Hot HOT 30
Anna Maria Island Beach Palms 8B
2 BR 2BA Condo
$134.00 - $469.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (21)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Hot HOT 29
Anna Maria Island Bay Watch Bungalow
2 BR 2BA Condo
$157.00 - $528.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 (25)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!​Cancel 14 days prior to arrival receive 100% refundCancel 7-13 days prior to arrival receive 50% refundExperience 24/7 Live Customer ServiceElevatorPrivate Beach AccessHeated Pool
Bradenton Beach Club Bliss-3 Bedroom-2 Bathroom Condo-Elevator-2 Pools-HotTub-Private Beach Access
3 BR - 2BR Condo
$191.00 - $661.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (9)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolWhat
Hot HOT 21
Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach
2 BR 2 1/2 BA Condo Pet Friendly
$135.00 - $476.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (9)
✨ Completely Remodeled Florida Vacation ​T​ropical Dream ✨Welcome to your perfect Florida getaway! This stunning vacation rental has been fully remodeled from top to bottom to offer the ultimate in comfort, style, and modern living.Step into a brand-new designer kitchen featuring elegant quartz countertops, sleek stainless steel appliances, and ple
Hot HOT 50
Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Pool
2 BR 2BA Condo
$125.00 - $531.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolThe
Hot HOT 33
Anna Maria Island Runaway Tropical Escape
2 BR 2BA Condo
$120.00 - $530.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (36)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated PoolHurr
Hot HOT 24
Anna Maria Island Beach Sands 101
2 BR 2BA Condo
$231.00 - $807.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (60)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Hot HOT 20
Island Time-Private Beach Access-Heated Pool-Water Views
2 BR 2BA Condo
$154.00 - $532.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
We understand that plans can change, and we want you to book your stay with peace of mind. That’s why we offer the most flexible cancellation policy in Anna Maria Island!100% refund if canceled at least 30 days before check-in; 50% refund if canceled 14-30 days before check-in.Experience 24/7 Live Customer ServicePrivate Beach AccessHeated Pool​Hur
Anna Maria Island Beach Palms 7A
2 BR 2BA Condo
$125.00 - $469.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (29)

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