Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!


Properties Available 43 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!​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 Pool​Hurrica
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Anna Maria Island Beach Palms 5B
2 BR 2BA Condo
$184.00 - $651.00 / 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
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Anna Maria Island Edgewater Bungalow
2BR 2BR House
$2,138.00 - $7,221.00 / per night
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!​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 PoolHurrica
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Anna Maria Island Beach View 207
2 BR 2BA Condo
$148.00 - $520.00 / 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!​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
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Absolute Paradise AMI-Private Beach Access-Water Views From Every Window-Heated Pool- Walk To 14 Restaurants
2 BR 2BA Condo
$201.00 - $712.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.8 (7)
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 PoolWhat's I
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach
2 BR 2 1/2 BA Condo Pet Friendly
$154.00 - $568.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (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!​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 Pool​Hurrica
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Island Time-Private Beach Access-Heated Pool-Water Views
2 BR 2BA Condo
$161.00 - $569.00 / 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!​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 Pool​Hurrica
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Anna Maria Island Beach Sands
2 BR 2BA Condo
$267.00 - $946.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 (60)
This sun-drenched 3br/3ba tropical 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 k
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Anna Maria Island Surfside Bungalow
3BR 3BR House
$4,000.00 - $9,745.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.7 (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!​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 Pool​Hurrica
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Anna Maria Island Bridge Port Beach Resort
2 BR 2BA Condo
$142.00 - $493.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (16)
Boasting a large, resort style heated outdoor pool with a hot tub, and a prime location on Anna Maria it's easy to fall in love with this island getaway. The private location on the north end of Anna Maria Island, near Bean Point is ideal to give you space and privacy and only a five minute walk to all local food and activities.Perfect for a romant
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Serenity Cottage
2BR 2 BR Cottage
$2,000.00 - $4,779.00 / per night
Bedrooms 1 bedrooms
Guests 4 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!​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 Pool​Hurrica
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Gulf Breeze Ami-2BD-2BA-Condo-Private Beach Access-Heater Pool-Water Views From Every Window
2 BR 2BA Condo
$147.00 - $520.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (1)
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 PoolThe prim
Specials Tag Special
Welcome Back Promo – Save $150!

Enjoy $150 off any stay when you book before June 28th.
Just use the code Welcome Back at checkout to claim your discount!

Anna Maria Island Runaway Tropical Escape
2 BR 2BA Condo
$143.00 - $584.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 (36)

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