Vacation rentals with a pool in Anna Maria Island

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Top-rated rentals with a pool in Anna Maria Island

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Guest favorite

Home in Bradenton

4.87 out of 5 average rating, 205 reviews

Sunny Oasis Near Beaches With Pool

Shore's Oasis is minutes to Anna Maria Island and the gulf beaches. Our modern beach-style home features a lovely pool, barbecue area, porches, comfortable furnishings and fun decor. We are located close to the Cortez Fishing Village, restaurants, shopping, live music, rental shops, tours and Florida fun! As Bradenton, Florida natives we are happy to guide you towards a unique experience in our local community so that you don't miss a thing while you are visiting. Safe travels and see you soon!

May 6 – 13

G$28,004 GYD per night

Guest favorite

Home in Holmes Beach

4.95 out of 5 average rating, 158 reviews

Sea AMI

This stylish and light home offers single-level private accommodations. The recently updated interior and private backyard oasis with plunge pool offers the perfect space for a truly relaxing and enjoyable vacation. Inside, the stylish and comfy space has room for everyone to spread out and relax while enjoying the two flat screen TVs. No expense was spared in designing and furnishing this home. The sleeper sofa pulls out to a memory foam queen bed, meaning the cottage can comfortably sleep 4.

Nov 22 – 29

G$64,557 GYD per night

Guest favorite

Home in Bradenton Beach

4.97 out of 5 average rating, 153 reviews

Paradise! Steps2 Private Beach & Tropical Yard!

Less than a 2 minute WALK from the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. With large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with a bathroom on opposite ends of the house (a pocket door adds privacy). Private heated salt water pool sits amidst the lush tropical yard. Hop on the free A/C'ed trolley and explore Florida's gorgeous Anna Maria Island.

Dec 7 – 14

G$107,933 GYD per night

Guest favorite

Condo in Redington Beach

4.97 out of 5 average rating, 458 reviews

AmazingBeachCondo/NoCleaningFee/AwesomeAmenities

Welcome to our condo. We have provided you with just about everything you need to come and vacation at this amazing beach area. The condo is right by the heated pool and a 2-minute walk to the beach. The complex has high-speed internet throughout and a laundry facility. Shopping/Grocery/Pharmacy are all close by. Restaurants/bars very close by. This is an amazing area of Florida, with so many things to see and do. You will love it here. We have also provided bikes for your use to get around.

Sep 18 – 25

G$21,640 GYD per night

Guest favorite

Tiny home in Bradenton

4.95 out of 5 average rating, 307 reviews

Tiny Carriage House-Pool, Riverwalk, Downtown

In the historic district of Bradenton's riverside downtown the 2nd story 1898 Carriage House Retreat is an intimate 1room studio for a romantic weekend, a friends' getaway or business travelers. Fully renovated with every modern amenity, yet preserving its antiquity, it nestles behind our 1898 Queen Anne Victorian where we live. Where the horse and buggy would have been kept, the Carriage House sits with it's own private driveway & within steps of downtown's eateries, pubs, shopping & more!

Nov 2 – 9

G$35,125 GYD per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Dec 14 – 21

G$27,374 GYD per night

Guest favorite

Bungalow in Anna Maria

4.88 out of 5 average rating, 121 reviews

Bay Breeze Cottages #2

Bay Breeze Cottages is an Old Florida Charm Boutique Resort located on historic Anna Maria Island. Bask in the endless sun all year long, take a swim in our private heated pool with your favorite beverage, or head out anywhere on the island in our street legal gas powered golf carts to any of the local restaurants, piers, sand white sand beaches, and all other attractions the island has to offer. Come enjoy your own slice of paradise at Bay Breeze Cottages on Anna Maria Island.

Apr 14 – 21

G$83,960 GYD per night

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 143 reviews

1 BR direct beachfront! Now avail. 8/29-9/11.

Our condo is directly on the beach!! It is close to restaurants and dining, mini-golf, Clearwater and St. Pete's Beach. About 25 miles from Tampa, Florida for the Buccaneers NFL football and Lightning NHL hockey! We are about 37 miles from Busch Gardens. Only 95 miles to Disney World in Orlando! Mini-golf right across the street! You’ll love my place because of the neighborhood. My place is good for couples, small families, solo adventurers, and business travelers.

Dec 4 – 11

G$30,615 GYD per night

Guest favorite

Condo in Holmes Beach

4.96 out of 5 average rating, 116 reviews

Beautiful beachfront condo for perfect vacation

Beautiful, cozy, elegantly furnished, spacious (1350 sqf with a large terrace), beachfront, 2 bedroom - 2 bathroom condominium, in the best managed, boutique-style gulf front residential complex on Anna Maria Island in Florida for an ideal vacation. Heated pool and hot tub, 2 tennis courts, 2 elevators, top floor unit, high speed internet, washer/dryer in unit, beach chairs, close to supermarket (Publix) and restaurants, free island trolley, rich cultural life.

Jul 20 – 27

G$53,431 GYD per night

Guest favorite

Condo in St. Pete Beach

4.91 out of 5 average rating, 209 reviews

Sunset Beach Condo in Treasure Island

Enjoy a beach getaway in this newly renovated 1 bedroom/1 bath (one queen, twin pull out sofa and single bed foldout) condo with partial water views. This top floor condo (2nd floor) is equipped with new stainless steel appliances, new dishwasher and beach front pool. The perfect relaxation! Great view from the balcony. Across the street from the beach. Harbor House in Sunset Beach, is located on the southern tip of Treasure Island.

Nov 6 – 13

G$25,384 GYD per night

Guest favorite

Guest suite in Bradenton

5.0 out of 5 average rating, 187 reviews

Off Anna Maria Island ~10min to beach w/salt pool

Stay close to the beach and like a local at Off Anna Maria, a cozy, private guest suite attached to our home with separate entrance, saltwater pool, and shaded outdoor patio. Located ~10 mins from Anna Maria Island, 45 mins from Siesta Key, 1 hr from Tampa in a quiet suburban neighborhood. Your interior space is completely separate from ours. The pool and patio are shared with us. *Travel time estimates depend on traffic.

Jul 3 – 10

G$27,476 GYD per night

Guest favorite

Cottage in Anna Maria

4.98 out of 5 average rating, 207 reviews

Turtle Cottage - Anna Maria Island

Great 1 bedroom, 1 bathroom cottage on the quiet north end of the island. The house is conveniently located and within walking distance (two short blocks) to the beach and close to the intersection of Gladiolus Street/Alamanda Road. Spectacular sunrises are just a short walk away at the Rod and Reel Pier, and the sunsets at Bean Point Beach are second to none, just a few blocks away. This great getaway sleeps up to 4.

Dec 22 – 29

G$119,582 GYD per night