We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Beach rentals and condos in Anna Maria, FL

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
All 185 Rentals in Anna Maria
loading...
Sort by
From
$500
Per Night
View Details
1 / 25
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Inquiry
From
$357
Per Night
View Details
1 / 23
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (5) Make Inquiry
From
$290
Per Night
View Details
1 / 38
Payment Protection
5 Bedrooms, 3 Bathrooms, Sleeps 12
Bookings
Details Reviews (6) Make Inquiry
From
$235
Per Night
View Details
1 / 107
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (12) Make Inquiry
Amenities & Details
  • Parking
  • Grill
  • Stove
  • DVD Player
  • TV
  • Patio
  • Washer
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long... View all property information
Make Inquiry
5 of 5 stars Reviewed August 12, 2014
We booked this home based upon other Trip Advisor reviews and were more than pleased! We have talked about booking it again for a stay next year! We had two different family...
5 of 5 stars Reviewed July 28, 2013
We stayed in the house at the end of June 2013. We had done a lot of research to find an affordable rental for our 6 person group and ended up with this house. Green Realty was...
See all reviews
From
$221
Per Night
View Details
1 / 24
Payment Protection
4 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Gym
  • Internet Access
  • Satellite TV
  • Parking
  • Ceiling Fans
  • Grill
  • Garage
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located on one of the prettiest streets in the village of Anna Maria, this lovely 4 bedroom, 2 and a half bath home is just 7 houses away from the beach. The quiet, tree-lined street evokes memories of Florida Gulf Coast islands in days gone by, with a shaded path providing access to the island's... View all property information
Make Inquiry
From
$100
Per Night
View Details
1 / 17
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Guest Count
  • Parking
  • Dishwasher
  • Number Of Bedrooms
  • # Of Bathrooms
  • Wi-Fi
  • Washer
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This elevated 2BR/2BA home is located directly across from the beach at the quiet North end of the Island. Enjoy the gulf breezes from the large screened lanai. Fully equipped kitchen including a dishwasher. Laundry room with Washer/Dryer. Bed sizes are a Queen bed, two twin beds and a sleeper... View all property information
Make Inquiry
From
$128
Per Night
View Details
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Patio
  • Air Conditioning
  • # Of Bathrooms
  • Number Of Bedrooms
  • Gym
  • Satellite TV
  • Internet Access
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they invite you to create some of your own treasured moments on your next visit to Anna Maria.... View all property information
Make Inquiry
From
$1,800
Per Week
View Details
1 / 25
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • Garage
  • Ceiling Fans
  • Grill
  • Parking
  • Air Conditioning
  • Patio
  • Gym
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Gaze out of your living room to the calming serenity of the canal as you sip on your favorite beverage at this comfortable and spacious home located in the prestigious north end of the island. This beautiful 3 bedroom 2 bath tastefully decorated home is invitingly awaiting your arrival for the... View all property information
Make Inquiry
From
$90
Per Night
View Details
1 / 20
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • # Of Bathrooms
  • Dishwasher
  • Guest Count
  • Washer
  • Dryer
  • Parking
  • Satellite TV
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Located in the heart of Anna Maria Village this recently updated one bedroom apartment is located just a few houses from the beautiful Gulf Beaches. Direct beach access with no streets to cross! 146 steps to the beach and less than a 2 minute walk. Bring your boats and wave runners as there is... View all property information
Make Inquiry
4 of 5 stars Reviewed January 6, 2015
I was a little hesitant to rent this property because I couldn't find any reviews, but it turned out to be a good choice. It's only 4 houses away from the beach, lots of great...
See all reviews
From
$99
Per Night
View Details
1 / 22
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Ceiling Fans
  • Terrace
  • # Of Bathrooms
  • Guest Count
  • Gym
  • Balcony
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Only a block to the pristine white sands of our Gulf of Mexico beaches, this lovely two bedroom/two bath duplex is nestled at the end of a long shell driveway, and overlooks picturesque Lake LaVista, a body of water that began its life as a natural lake frequented by the island's early settlers.... View all property information
Make Inquiry
Get the List
From
$3,750
Per Month
View Details
1 / 25
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Terrace
  • Garage
  • Guest Count
  • Patio
  • Ceiling Fans
  • Internet Access
  • Grill
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Spend your vacation just steps from our beautiful beaches and crystal-clear waters! Casa Blanca is in the heart of the village of Anna Maria, and west of Gulf Drive...there's no better place to be! Only 5 houses from the beach, you'll be steps from the sand AND just moments from shopping,... View all property information
Make Inquiry
From
$2,526
Per Week
View Details
1 / 23
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
From
$125
Per Night
View Details
1 / 8
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (10) Make Inquiry
Amenities & Details
  • Washer
  • Parking
  • Microwave
  • Stove
  • Refrigerator
  • TV
  • Dishwasher
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Charming, newly renovated, the Becker Beach Bungalow offers a comfortable stay less than 2 blocks from the beach. Accommodates 6 people comfortably; master bedroom with 1 queen bed, second bedroom with 2 twin beds, and an additional daybed with pop up in the sun room. The living room also has a... View all property information
Make Inquiry
5 of 5 stars Reviewed December 6, 2014
Wonderful location and exactly as advertised. We used the wired connection for the internet and it worked just fine. Excellent turn-key property which we recommend to others.
5 of 5 stars Reviewed September 5, 2014
I planned a surprise trip for my wife and found this place solely based on Trip Advisor reviews. I talked to the owner Sandy who was extremely helpful in giving me more details...
See all reviews
From
$170
Per Night
View Details
1 / 17
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Dishwasher
  • Air Conditioning
  • Microwave
  • Refrigerator
  • Dryer
  • Parking
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
As an artist this private three bedroom and two bath elevated vacation home has been a retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the best white... View all property information
Make Inquiry
From
$850
Per Week
View Details
1 / 14
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Refrigerator
  • Dryer
  • Stove
  • Grill
  • Dishwasher
  • Patio
  • TV
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This villa is quaint and adorable tucked in a quiet neighborhood just 9 houses from the Gulf of Mexico and white sandy north end Anna Maria Island beaches. Step outside your door and stroll down the street in 1 minute or less to the quaint shops and cafes along Pine Ave. Walk to everything the... View all property information
Make Inquiry
From
$150
Per Night
View Details
1 / 12
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (6) Make Inquiry
Amenities & Details
  • Refrigerator
  • Dryer
  • Patio
  • Grill
  • Stove
  • Microwave
  • Washer
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
1940’s Classic beach cottage located at 9901 Gulf Drive Anna Maria, recently renovated, two bedrooms, one bath, with an eclectic, artistic decorating style that will bring a smile to your face and make your stay here a memorable experience. Located only five houses from the white, sugar sand... View all property information
Make Inquiry
5 of 5 stars Reviewed July 10, 2014
MY husband and I go away every year for our anniversary,and this year I chose this location.WE loved it the place was the cutest,we had everything from food...
4 of 5 stars Reviewed June 27, 2014
If you've never been to Anna Maria before, and are reading this review, I want to make it clear that this house is exactly in the middle of everything there. It's sandwiched...
See all reviews
From
$400
Per Night
View Details
1 / 23
Payment Protection
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (3) Make Inquiry
Amenities & Details
  • Refrigerator
  • Deck
  • Dishwasher
  • Washer
  • Air Conditioning
  • Parking
  • Stove
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We call this home 'A Time Out' cottage and you will definitely say, 'We deserve a time out at this place!' This completely remodeled private home on Anna Maria Island's north end features four bedrooms, two baths and the most wonderful tropical and lush pool and patio area! On the main level of... View all property information
Make Inquiry
5 of 5 stars Reviewed February 20, 2014
When we walked into this adorable cottage, we couldn't believe our eyes. This place is too cute for words! It is the kind of rental you dream about with clean bathrooms...
See all reviews
From
$300
Per Night
View Details
1 / 14
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (10) Make Inquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Refrigerator
  • Patio
  • Safe
  • Washer
  • Microwave
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This is our personal Vacation Home. C-view is managed by a team we have selected, not a property management company. C-view Florida is one of the few canal homes (29 foot dock) close to the Gulf of Mexico. This newly renovated, 5 bedroom, 3 1/2 bathroom home has a large and beautifully... View all property information
Make Inquiry
5 of 5 stars Reviewed April 25, 2011
I'm torn; I want to keep this amazing house a secret, but I also want to give Ann props for building & maintaining such a gem. She thought of everything, right down to napkin...
See all reviews
From
$93
Per Night
View Details
1 / 28
2 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Dryer
  • Parking
  • Wi-Fi
  • Satellite TV
  • TV
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Canary Cottage has 2 bedrooms plus a bunkroom - and 2 full baths and will Sleep up to 8. Located in the heart of Anna Maria City- This Key West charmer is elevated and has been updated with new tile, fixtures, plus a new tub/shower! Updated furnishings, and appliances, which add to the charm... View all property information
Make Inquiry
From
$157
Per Night
View Details
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • TV
  • Patio
  • Washer
  • Microwave
  • DVD Player
  • Grill
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Grab your flip flops and your bathing suit for your fabulous vacation in this well-appointed Anna Maria home! Cook's Cove is located just steps away from the beautiful, white sand beaches of Anna Maria Island and the azure water of the Gulf of Mexico. Both elderly- and family-friendly, this... View all property information
Make Inquiry
From
$104
Per Night
View Details
1 / 18
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dryer
  • Satellite TV
  • Washer
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This cute 2BR/1BA beach bungalow is on the Gulf side very close to the beach and located at the quiet north end of the Island. Direct beach access just a few properties away. Enjoy the gulf breezes from the screened lanai or the open brick paver patio. This bungalow has plenty of room to relax with... View all property information
Make Inquiry
From
$136
Per Night
View Details
1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • Satellite TV
  • Washer
  • DVD Player
  • Dryer
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located at the quiet North end of Anna Maria this 3BR/2BA canal front home comes with exceptional views! There are two screened lanais, a boat dock and a garage. Brand new Kitchen with granite countertops and new appliances. Updated furnishings. There are two full size beds, one twin and a queen... View all property information
Make Inquiry
From
$165
Per Night
View Details
1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Washer
  • Wi-Fi
  • Number Of Bedrooms
  • Dryer
  • # Of Bathrooms
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Updated home with Pool!! Elevated 2BR/2BA home with open floor plan and large screened lanai. One short block with direct access to the beautiful white sand beach. This home has been updated with wood flooring, new carpet and granite countertops. Enjoy the outside pool area with beautiful brick... View all property information
Make Inquiry
From
$200
Per Night
View Details
1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Porch
  • Guest Count
  • Dishwasher
  • # Of Bathrooms
  • Microwave
  • Dryer
  • Number Of Bedrooms
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Nothing better than having the beach at your doorstep! Located in the heart of Anna Maria city this 2 bedroom, 2 bath Direct Gulf Front cottage has 100 feet of Gulf front beach. Enjoy the views from the enclosed sitting room or the observation deck. Amenities include washer/dryer, dishwasher,... View all property information
Make Inquiry
From
$1,600
Per Week
View Details
1 / 17
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
  • Single Beds:(2)
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Casa Allegria is just perfect! Beautiful cool beachy colors throughout and only a short walk from the beach. This spacious 3 bedroom, 2 bath ground level home is located in the most sought after area on Anna Maria Island! Close to Pine Avenue, trolley stops, and the SandBar Restaurant. Come and... View all property information
Make Inquiry
From
$158
Per Night
View Details
1 / 28
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • # Of Bathrooms
  • Deck
  • Washer
  • Internet Access
  • Number Of Bedrooms
  • Dryer
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Bring the family and come enjoy our beautiful beaches! This 4BR/4BA elevated home is only one short block to the beach with direct beach access. This spacious home has plenty of room for family with 2 king size beds, a queen bed and two twins. Large, fully equipped kitchen, laundry room with... View all property information
Make Inquiry
From
$125
Per Night
View Details
1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Wi-Fi
  • Dishwasher
  • Number Of Bedrooms
  • Dryer
  • # Of Bathrooms
  • Microwave
  • Washer
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Palm Court Villas are located in the heart of Anna Maria Village with a short stroll to great local restaurants, shops and the Community Center. Beautiful white sand beaches are just one short block away. You have direct beach access to one of the best beaches on the Island. This section of beach... View all property information
Make Inquiry
From
$97
Per Night
View Details
1 / 16
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Patio
  • # Of Bathrooms
  • Guest Count
  • Dryer
  • Washer
  • Number Of Bedrooms
  • Wi-Fi
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This Charming 2BR/1BA beach cottage is just a few properties to the beach and has direct beach access. No streets to cross to get to the beach! Updated kitchen with an apartment size electric range and full size refrigerator. The bedrooms have a Queen size bed and two twin beds. There is an open... View all property information
Make Inquiry
From
$229
Per Night
View Details
1 / 19
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Wi-Fi
  • Number Of Bedrooms
  • Washer
  • Satellite TV
  • Guest Count
  • Dryer
  • Dishwasher
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This vintage Island beachfront home has 4 sleeping rooms and 2 bathrooms. Enjoy the charm of yesterday in this great family beach house located between Palm and Magnolia Avenues. Excellent Gulf views, steps to beautiful, white sandy beaches. This home includes a washer/dryer, dishwasher, several... View all property information
Make Inquiry
From
$250
Per Night
View Details
1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Washer
  • Fireplace
  • Grill
  • Dishwasher
  • Hot Tub
  • DVD Player
  • Parking
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The Shady Mango was originally built in 1925. According to local history the heart pine used in constructing the original house came by steam boat to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the home's present site. In 2004 the home was given a major renovation... View all property information
Make Inquiry
5 of 5 stars Reviewed September 21, 2013
My husband, 2 kids & I stayed at the Shady Mango & LOVED it! It's the perfect place for a vacation for a small family. It's in a great location with walking access to the beach...
See all reviews
From
$172
Per Night
View Details
1 / 25
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Porch
  • Washer
  • Microwave
  • Dryer
  • # Of Bathrooms
  • Number Of Bedrooms
  • Dishwasher
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
If you’re looking for carefree living just blocks from the beach, look no further than the “Owl’s Hideout”. This 3 bedroom, 2 bathroom home is comfortably equipped with a king, queen and twin beds. There is a lovely screened-in porch that is perfect for relaxing and listening to the gentle waves of... View all property information
Make Inquiry
From
$128
Per Night
View Details
1 / 23
2 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • Dryer
  • Dishwasher
  • Satellite TV
  • Washer
  • Parking
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The best of both worlds on the Island is where the Gulf meets the Bay at the 'Tip' of Island in Anna Maria. Beautiful Sunsets, Fishing Piers, a Park and Bird Watching can be found at the Northern tip of the Island. This 2BR/2BA plus a Loft is located one property from the beach access at Bean... View all property information
Make Inquiry
From
$129
Per Night
View Details
1 / 20
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • Wi-Fi
  • Porch
  • Washer
  • Guest Count
  • Parking
  • Dishwasher
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
It doesn't get much better than this! Relaxing on the Screened lanai overlooking the blue waters of Tampa Bay and the Gulf of Mexico. This elevated 3 bedroom, 2 bath Direct Bay Front home has wonderful views from the master bedroom, living room and screened lanai. Private setting close to Anna... View all property information
Make Inquiry
From
$242
Per Night
View Details
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (4) Make Inquiry
Amenities & Details
  • Dryer
  • Stove
  • Washer
  • Microwave
  • Parking
  • Dishwasher
  • Refrigerator
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This gulf-front vacation rental cottage is located right on the beach on the secluded north end of Anna Maria Island. Step out Wave Crest's door and into the waiting lounge chairs and rub your toes in the beautiful white sand beaches of AMI or enjoy the views of the sparkling Gulf of Mexico waters... View all property information
Make Inquiry
5 of 5 stars Reviewed July 14, 2013
If you want the beach as your back yard, along with a quiet and empty beach, you just found it. This house was perfect for my wife and I and our two daughters. Having been to...
See all reviews
From
$500
Per Night
View Details
1 / 26
4 Bedrooms, 4 Bathrooms, Sleeps 12
Details Reviews (1) Make Inquiry
Amenities & Details
  • Guest Count
  • DVD Player
  • # Of Bathrooms
  • TV
  • Number Of Bedrooms
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Cayman Bay 505 Magnolia Ave. Anna Maria, Fl. 34216 Cayman Bay may well be one of the most exquisite private homes available for rent on all of Anna Maria Island. This 4 bedroom/4 bathroom 5300 sq. ft. custom home has all the fine touches and professional craftsmanship one would expect in a... View all property information
Make Inquiry
5 of 5 stars Reviewed August 19, 2014
We stayed here for two weeks this past August. This was our second trip to AMI - such a lovely place. This house was perfect for us. It is very spacious. All the bedrooms are...
See all reviews
From
$171
Per Night
View Details
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (4) Make Inquiry
Amenities & Details
  • Microwave
  • Stove
  • Patio
  • Stereo System
  • Dishwasher
  • Refrigerator
  • Washer
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
With its luscious landscaping, eclectic look and colorful Key-West style, Simpatico could be right out of Coastal Living Magazine. This bungalow is perfect for the ideal secluded island vacation! Located on the north end of Anna Maria Island, this canal home, with a boat dock and kayaks,... View all property information
Make Inquiry
5 of 5 stars Reviewed January 11, 2015
My husband and I and another couple stayed here for one week in December. This was our first stay on the island and we would definitely go back. We have rented homes all over...
4 of 5 stars Reviewed July 29, 2014
The entire grounds and unit are artfully decorated with many vignettes located throughout. Very quiet neighborhood but located within easy walking or biking distance of many shops...
See all reviews
From
$128
Per Night
View Details
1 / 23
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Stove
  • Grill
  • Parking
  • Washer
  • Refrigerator
  • Dryer
  • DVD Player
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Your time on Anna Maria Island should be perfectly charming in this classic beach-style cottage perfectly located on the west side of Gulf Drive in the city of Anna Maria. Only steps away from the azure blue waters of the Gulf of Mexico, this unique vacation rental boasts two very large bedrooms... View all property information
Make Inquiry
5 of 5 stars Reviewed November 12, 2014
On entering the cottage, the screened porch was a perfect cool place to relax in the evening with a drink or to take morning coffee and watch Anna Maria Island come to...
See all reviews
From
$214
Per Night
View Details
1 / 23
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Microwave
  • Patio
  • Refrigerator
  • Dryer
  • Stove
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Located in the city of Anna Maria on the north end of Anna Maria Island, this gorgeous three-bedroom dog-friendly vacation rental is the perfect place for a vacation retreat! With an estimated 2100 square feet, AMI Retreat has plenty of room to kick off your flip flops and enjoy your down time.... View all property information
Make Inquiry
5 of 5 stars Reviewed February 14, 2015
Our rental property was exactly how it was pictured on the web. Plenty of space with all the amenities you need to prepare food in our go out. The newly installed pool and spa...
See all reviews
From
$171
Per Night
View Details
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (6) Make Inquiry
Amenities & Details
  • Grill
  • Microwave
  • Dishwasher
  • Parking
  • Patio
  • Ceiling Fans
  • Refrigerator
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Location, location, location. Welcome to the quaint and quiet north end of Anna Maria Island! This classic AMI elevated, open floor plan vacation rental boasts three bedrooms and two baths with plenty of room for a large family or group to spread out and relax! Two queen-size beds, a full-size... View all property information
Make Inquiry
5 of 5 stars Reviewed September 2, 2014
Best vacation in a long time. Our house was great. The pool was so nice after a long day at the beach. The beach was perfect, warm, clear water, little waves. We rented from...
4 of 5 stars Reviewed August 18, 2014
This property is in a great location for the beach, local restaurants, cafés and local stores. The pool is super and ideal for spending time around. The property is spacious for a...
See all reviews
From
$175
Per Night
View Details
1 / 22
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (6) Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Grill
  • # Of Bathrooms
  • Shared Outdoor Pool...
  • Internet Access
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki... View all property information
Make Inquiry
From
$185
Per Night
View Details
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (7) Make Inquiry
Amenities & Details
  • Refrigerator
  • Fireplace
  • Grill
  • TV
  • Dishwasher
  • Patio
  • Dryer
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace,... View all property information
Make Inquiry
5 of 5 stars Reviewed November 3, 2014
We had the most wonderful stay at Whispering Pines, a beautiful cottage on Anna Maria Island. It couldn't have been more perfect. My parents, my two 12 year-olds and I thoroughly...
5 of 5 stars Reviewed August 28, 2014
Whispering Pines is an updated and classic Florida home. We traveled with one young child and we all had more than enough space to relax. The beautiful shores of the beach are...
See all reviews
From
$171
Per Night
View Details
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (5) Make Inquiry
Amenities & Details
  • Washer
  • Dryer
  • Parking
  • Refrigerator
  • Dishwasher
  • Microwave
  • Stove
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath... View all property information
Make Inquiry
5 of 5 stars Reviewed October 31, 2014
Great, private and quiet location. The house is equipped with all you and your family need. The short distance to the beach made us walk to the beach more than once a day. Any...
See all reviews
From
$157
Per Night
View Details
1 / 19
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (7) Make Inquiry
Amenities & Details
  • Dryer
  • Dishwasher
  • Refrigerator
  • Microwave
  • Washer
  • DVD Player
  • TV
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower and comfortable furnishings. The... View all property information
Make Inquiry
4 of 5 stars Reviewed November 13, 2014
The weather was nice several of the days and we really enjoyed less people than we encounter in July. Lots of beach walks and bike rides. My only issues were the dirty rug in...
5 of 5 stars Reviewed August 8, 2014
great home, the owners have thought of every mortal thing.. would def stay again and have also recommmended already to friends of mine
See all reviews
From
$188
Per Night
View Details
1 / 24
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (8) Make Inquiry
Amenities & Details
  • Washer
  • DVD Player
  • Dishwasher
  • Grill
  • Patio
  • Dryer
  • TV
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
BON AMI will be your 'good friend' after a vacation stay. Located on the north end of Anna Maria Island and a short distance to Bean Point, this heated pool stilt home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is spacious, airy, and... View all property information
Make Inquiry
4 of 5 stars Reviewed November 1, 2014
We're a family from Germany and booked Bon Ami via Homeaway/FeWo direkt. Our stay was all in all very nice: the location is nearly perfect, only a few steps to the beach. The...
4 of 5 stars Reviewed August 26, 2014
We spent a week here with our teenage boys and my parents. The house was large and clean with everything needed to cook full meals. Large balconies and patio to spend the...
See all reviews
From
$250
Per Night
View Details
1 / 25
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Number Of Bedrooms
  • TV
  • Patio
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Island Dream 157 Crescent Drive Anna Maria, FL 34216 An exceptional property with glorious views of the Sunshine Skyway Bridge from its entrance, this beautiful, newly built and elegantly furnished four bedroom and four bathroom home on the desirable north end of Anna Maria is situated in a... View all property information
Make Inquiry
From
$200
Per Night
View Details
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Inquiry
Amenities & Details
  • Microwave
  • Patio
  • Washer
  • Stove
  • Parking
  • Grill
  • DVD Player
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on a... View all property information
Make Inquiry
5 of 5 stars Reviewed November 4, 2014
My husband and I took our 15 year old son to Anna Maria for a weeks stay at Starfish Dreams. We had a really lovely relaxing holiday and the house is perfect. Excellent position...
5 of 5 stars Reviewed August 16, 2014
Having stayed on AMI before, we knew that we would love the island, but the location of this home made our trip even more successful. The property is on Pine Avenue, so walking...
See all reviews
From
$171
Per Night
View Details
1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Inquiry
Amenities & Details
  • Grill
  • DVD Player
  • Stove
  • Washer
  • Refrigerator
  • Patio
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Come and enjoy your own private Island Oasis! Located on the north end of Anna Maria Island in the city of Anna Maria, one block from the bay and a few blocks from the City Pier, this charming vacation rental will allow for some serious relaxation. This home-away-from-home offers two bedrooms and... View all property information
Make Inquiry
5 of 5 stars Reviewed October 5, 2014
This vacation rental is just perfect - the interior is so lovely, the kitchen well equiped,the surrounding amazing! We can totally recommend this home and would love to come back!
5 of 5 stars Reviewed July 17, 2013
My husband and I took a friend here for the weekend. It was very tropical around the pool. The house was clean and I loved the rain shower in my bedroom. Huge house with very...
See all reviews
From
$496
Per Night
View Details
1 / 24
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (7) Make Inquiry
Amenities & Details
  • Grill
  • Fireplace
  • Microwave
  • Garage
  • Washer
  • DVD Player
  • Patio
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located on the north end of Anna Maria Island in the city of Anna Maria, this family-friendly vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the putting green, kayak launch and boat dock, this house has... View all property information
Make Inquiry
5 of 5 stars Reviewed August 14, 2014
I searched for the perfect house for a family of 10 to celebrate our niece's vacation. All I can say is there was nothing on everyone's list that this house didn't have! We...
5 of 5 stars Reviewed August 2, 2014
This house was exactly as pictured and described. The attention to detail in how it was build was amazing. This place had everything you could imagine or want. Pool was...
See all reviews
From
$121
Per Night
View Details
1 / 19
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (4) Make Inquiry
Amenities & Details
  • Dishwasher
  • Washer
  • Stove
  • DVD Player
  • TV
  • Dryer
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint... View all property information
Make Inquiry
3 of 5 stars Reviewed August 18, 2014
The location is great, with the bayside on the property along with the pool and the beach just across the street. Our biggest problem was the cell phone signal (VERY LOW) and the...
See all reviews
From
$244
Per Night
View Details
1 / 30
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Patio
  • Grill
  • Washer
  • Stove
  • Ceiling Fans
  • Parking
  • Refrigerator
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Completely Remodeled 3 bedroom/2 bath home with private Heated pool. Beautiful new tile, Granite countertops, all new appliances, and living room overlooking the heated pool. Bright, open kitchen, dining and living area! Sleeps up to 8. 1500 Sq. ft. 204 Archer Way, Anna Maria 3 Bedroom/2Bath... View all property information
Make Inquiry
Go to map view
Book Online(15)
Use filters to find the best results!

Suitability

  • Wheelchair access (5)
  • Elder access (49)
  • Suitable for children (19)
  • Pet friendly (44)
  • Smoking allowed (0)

Amenities

  • Internet (142)
  • Parking (110)
  • All pools (85)
  • Other outdoor space (83)
  • Washer/Dryer (74)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List

More Beach destinations:

More Family destinations:

Filter search results by:
Book Online(15)

Suitability

  • Wheelchair access (5)
  • Elder access (49)
  • Suitable for children (19)
  • Pet friendly (44)
  • Smoking allowed (0)

Amenities

  • Internet (142)
  • Parking (110)
  • All pools (85)
  • Other outdoor space (83)
  • Washer/Dryer (74)
  • View all amenities