Situated in Manatee County, Florida Anna Maria boasts pristine beaches, turquoise waters and a laid-back ambience. Start your holiday with the region’s beautiful beaches such as Holmes Beach, Manatee Beach and Longboat Key Beach. Visit The Rod and Reel Pier to get a taste of old Florida and see some wildlife in the ocean. You can also take a stroll on Anna Maria City Pier, a landmark built in the early 1900s. Get an overview of Anna Maria by parasailing from great heights or explore the city by renting a bicycle. For your shopping needs, Pine Avenue has plenty of shops for clothing and jewellery. Pine Avenue also has eateries you can stop by such as Poppo’s Taqueria for Tex-Mex, and The Donut Experiment. After a long day of sightseeing, kick back and unwind in one of the top vacation rentals with pool in Anna Maria, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 14, 2024.
1. The Castaway Cottage (from USD 500)
Indulge in a captivating vacation at this poolside rental. Perfect for small groups, this retreat offers a private tropical pool, ideal for refreshing dips and sun-soaked relaxation. The pool is heated or chilled depending on the time of the year. Moreover, a hot tub is available if you want to unwind after a hectic day out. The fully equipped kitchen allows convenient meal preparation while the plush bedrooms ensure restful nights.
The rental also has a Wi-Fi connection and a flat-screen TV. You can also spend time listening to music on the DVD player, board games and books on days you want to stay in. The property welcomes pets and children and offers amenities such as beach toys, beach towels, beach chairs, umbrellas and life jackets for a fun day at the beach.
2. Beach Nest (from USD 633)
This property offers the perfect blend of relaxation and luxury and is an excellent choice for groups or families. The bedrooms include a children’s room with a trundle, pull-out twin bed and child-friendly decor. Dip your toes in the private pool which can be heated in the colder months, or unwind in the spa whirlpool.
If you want to stay productive the property has a desk, printer and a Wi-Fi connection. A fully equipped kitchen with cookbooks will help you prepare meals to be enjoyed in the dining area which seats eight and offers scenic views. On lazy days, you can watch TV, read books or play the piano and guitar.
Top guest reviews
Amenities & Room:
No one wanted to leaveand everything is of the highest qualityThe house was very comfortable and had all the amenities we neededWe all agreed it was the most relaxing holiday we had enjoyed for a long time The house is beautifully decorated and is a real home away from home with everything provided especially in the kitchenI think my favorite part was the lush beautifully maintained landscaping Going kayaking out on the canalCleanliness:
The owner had the place decorated for Christmas which was a lovely touchThe bedrooms are beautifully decorated and the house is in easy walking distance to the beaches (gulf and bay)Host:
Liza was awesome to work with and even let us check in earlyThey hung out almost all dayShe provides tons of information about the island with recommendations for all ages You can rent kayaks beach carts bikes that are at the house upon arrivalWe really appreciate all of the little touches she didpool hot tub bicyclesRead more reviewsLocation:
wonderful waterside restaurants quirky cafes and individual shopsbut I really enjoyed jumping on a bicycleThe house is in a very quiet residential neighbourhood at the North end of AMIWe have stayed at the Beach Nest for vacation 3 times nowIt is an easy walk or bike ride to amazing beaches for sunsets
3. Cosy and luxurious canal-front home (from USD 673)
This stunning vacation rental is an excellent choice for big groups as it can welcome up to eight people. It has a private pool surrounded by sea oats, mangroves and palms for a rejuvenating experience. The poolside includes two dining areas with a gas grill and chaise lounges. The fully equipped kitchen caters to your culinary desires.
The rental is air-conditioned and has a Wi-Fi connection. On lazy days you can watch one of the three flat-screen TVs, play board games or read books. You can also lounge in the backyard dock and enjoy views of the native wildlife.
4. Sapphire Surf (from USD 360)
This charming rental seamlessly combines convenience and comfort. It has two bedrooms with flat-screen TVs and ample closet space. Take a refreshing dip in the private pool - heated October-April - surrounded by palms for a tropical experience. The poolside offers chaise lounges along with two dining areas and a Weber gas grill.
Stay connected with Wi-Fi, beat the heat with air-conditioning and lounge in the open-plan living area. The living area is connected to the fully equipped kitchen and dishwasher. Options for leisure include a DVD player, board games and books.
5. Elegant custom home (from USD 700)
This rental is an excellent choice for large groups or families. Unwind in the private outdoor pool after a tiring day out or lounge by the poolside with deck chairs. A fully equipped kitchen allows for convenient meal preparation. The rooms are air-conditioned and equipped with a Wi-Fi connection.
On days you want to stay in you can pass the time with LED TVs with satellite, cable TV and DVD player, read books or play ping pong in the games room. The rental has child-friendly amenities such as a high chair, baby gate and travel cot.
6. Nest on the Beach (from USD 2231)
Nestled in a picturesque setting, this property offers a private oasis for relaxation. This exquisite vacation rental has a heated saltwater pool and a hot tub where you can kick back and relax. It also has elegant decor and fantastic sunset and beach views from the deck.
A fully equipped kitchen allows for convenient meal preparation and an open-plan dining area with a large glass dining table ensures a lively dinner with friends or family. Stay productive with a Wi-Fi connection and a desk. The rental allows free parking for up to two vehicles.
Top guest reviews
Host:
liza & kit were wonderful hostsliza hands down was the perfect host she greeted us and showed us around her lovely homethe owners had great communication and were very quick to answer questionsRead more reviewsLocation:
it was the perfect vacation great property location and island
7. Sassy Seahorse (from USD 417)
This exquisite rental is the ultimate vacation haven for small groups and families. It has a large private pool with a tiki hut on the poolside and a spa whirlpool for relaxation and rejuvenation. The outdoors also includes decks with a Weber grill and chaise loungers.
Indulge in modern luxury and convenience with well-furnished interiors and a fully equipped kitchen. On days you want to stay in, an entertainment centre in the house has games and books to help you pass the time. The property is air-conditioned and offers access to Wi-Fi.
8. Sunshine Cottage (from USD 322)
This poolside retreat is the perfect choice for a sunny holiday in Anna Maria. It has a large private pool nestled within a tropical landscape. During the colder months, the pool is heated from October to April for a fee of 20 USD per day. On lazy days, you can dip your toes and fish in the fishing deck or watch your favourite movies and TV series on the family room 50-inch HDTV with cable and streaming channels such as Netflix, Hulu and Disney+.
Stay productive with a dedicated workspace and Wi-Fi connection and prepare delicious meals in the fully equipped kitchen. Free parking on the premises and on the street is available.
Top guest reviews
Amenities & Room:
the sunshine cottage was tastefully appointed extremely comfortable with modern appliances amenities and a sparking poolthe outdoor furniture and pool were awesomethere are pool loungers and chairs and an absolutely gorgeous (warm ) swimming poolthe fish that jump and swim off the dock were amazingvery nice house with pool dock with kayak and bicycles for those that wish to rent themCleanliness:
fridge was very cleaneverything updated and cleanthe house was clean and comfortablethe house was very clean and well taken care ofthe house is as beautiful as shown in the photographs clean and "beachyHost:
our host michelle responded very quickly to any questions we had and was very helpfulmichelle was an amazing hostmichelle is a great hostmichelle as host is great and everything went more than perfectwe very much appreciated that our hosts arranged a pack and play crib for our daughterRead more reviewsLocation:
great location to downtownthe location was excellentvery nice location on anna maria islandawesome place and perfect locationnice and quiet location
Superhost
9. Luxurious and spacious townhouse (from USD 300)
This elegant townhouse offers a luxurious retreat for its guests. It has three bedrooms with plush bedding, flat-screen TVs and doors opening to one of the porches. A fully equipped kitchen is available to help you make delicious meals. On lazy days lounge by the pool oasis which includes a barbeque grill and wicker lounges all nestled within tropical plants and palms.
The open-plan living room includes a breakfast bar, flat-screen TV and a Sonos speaker to help you unwind after a hectic day of sightseeing. If you have to work to do a Wi-Fi connection and a dedicated workspace are available. Guests are allowed to park for free on the premises and on the streets.
Top guest reviews
Amenities & Room:
the furniture and beds were comfortable and cleanwe appreciated the beach chairs pool toys beach wagon and abundance of towelsfelt comfortable with gates at tops of both sets of stairsthe beautiful backyard pool and the two relaxing porches were icing on the cakeCleanliness:
clean and comfortable big enough for our family of 5)the place is so clean snd has everything you could needthe space (indoor and outdoor) was very spacious and cleanted’s place was beautifully decorated very clean and just a short walk to the beachRead more reviewsLocation:
convenient location and comfortable staylocation was superb— about 1/4 mile to the gorgeous beach and walking distance to shops and restaurantsreally an ideal home in a perfect locationted’s place couldn’t be more perfectly locatedwhat a great place to get away for a week
10. Turtle Cottage (from USD 314)
Turtle Cottage is a lovely rental for an enchanting beach retreat. Ideal for singles and couples, this cosy getaway offers a fully equipped kitchen and a charming bedroom that opens up to a private patio.
Savour your meals in the patio’s outdoor dining area which features an oversized umbrella, an electric grill and a high-top table. Lounge in the heated pool or the spa and enjoy modern amenities such as Wi-Fi and TV. The property allows free parking on the premises for its guests.
Top guest reviews
Amenities & Room:
the cottage is super cute and having a private pool is a nice extrakitchen has all the necessities you need to cook if you desire including a small outdoor grilla huge plus to the turtle cottage is the private pool and jacuzzigreat location awesome heated pool and jacuzzi and the house had everything we neededpool and hot tub are amazingCleanliness:
super clean and had everything you needeverything was super cleanwell kept very cleanvery clean what on this days is very importantpool and house were both very cleanHost:
amazing hosts as wellthe hosts were quick to answer or questions & help with any issuesamazing place and wonderful hostgustavo is a great host and responded quickly to any questions we hadgustavo is always an amazing hostRead more reviewsLocation:
perfect size & location for a couples get awaythe location of the house is perfectthere are many restaurants that are close by to enjoysuper close walk to the beachvery nice place and location
Have a memorable getaway in Anna Maria
Pristine beaches, turquoise waters and a laid-back ambience make Anna Maria a wonderful must-see destination. Head to Anna Maria and select your accommodation from one of these dreamy rentals.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
-
11 Best Beachfront Hotels In Sarasota, Florida - Updated 2024Natália Cagnani -
-
-
-
-
-
-
-
Create an account to