Newly Listed


Properties Available 34 properties available
✨ 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 356
Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Pool
2 BR 2BA Condo
$125.00 - $534.00 / 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 Pool​Hur
Hot HOT 338
Anna Maria Island Beach Sands 201
2 BR 2BA Condo
$218.00 - $825.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (46)
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 348
Gulf Breeze Ami-2BD-2BA-Condo-Private Beach Access-Heater Pool-Water Views From Every Window
2 BR 2BA Condo
$130.00 - $496.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
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 339
Anna Maria Island Beach Palms 8B
2 BR 2BA Condo
$122.00 - $487.00 / 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 343
Anna Maria Island Beach Palms 5B
2 BR 2BA Condo
$154.00 - $609.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (24)
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 352
Anna Maria Island Beach Waves
2 BR 2BA Condo
$140.00 - $620.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (23)
This sun-drenched 2br/2ba beach cottage centrally located by Holmes Beach in the heart of Anna Maria has been described as one of the “prettiest vacation homes on the island.” This authentic 1947 beach bungalow has been completely (and splendidly!) renovated with raised ceilings, travertine floors, and showers, granite countertops in the kitchens a
Hot HOT 369
Anna Maria Island Edgewater Bungalow
2BR 2BR House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (8)
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 361
Anna Maria Island Beach Palms 2B
2 BR 2BA Condo
$136.00 - $542.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (57)
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 345
Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants
2 BR 2BA Condo
$189.00 - $650.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 (8)
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 343
Anna Maria Island Runaway Tropical Escape
2 BR 2BA Condo
$110.00 - $500.00 / 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 PoolHur
Hot HOT 336
Anna Maria Island Beach View 207
2 BR 2BA Condo
$120.00 - $470.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (18)
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 337
Anna Maria Island Beach Palms 7A
2 BR 2BA Condo
$125.00 - $473.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (29)

Tell us what you're looking for and someone will contact you with available options.

I agree