Vacation rentals with outdoor seating in Anna Maria

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Top-rated accommodations with outdoor seating in Anna Maria

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Guest favourite

Home in Anna Maria

4.93 out of 5 average rating, 152 reviews

Private 30' Pool and Boat Dock - Rated best on AMI

* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles than staying at Sunshine Cottage, located in the City of Anna Maria!

Nov. 6 – 13

$820 CAD per night

Guest favourite

Home in Holmes Beach

4.95 out of 5 average rating, 158 reviews

Set 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.

Oct. 18 – 25

$440 CAD per night

Guest favourite

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

$824 CAD per night

Guest favourite

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

$209 CAD per night

Guest favourite

Apartment in Anna Maria

4.98 out of 5 average rating, 104 reviews

Beach Don't Kill My Vibe by Beach Boutique Rentals

*Features include* * Brand new vacation rental directly on Pine Ave! * King bedroom with TV * Queen bedroom with TV * Modern bathroom with walk in shower * Kitchenette with Full size refrigerator * Private deck with table and umbrella * Private back yard with putting green and outdoor seating * Trolley stop across the street * Steps to the beach! * Walkable to all shops and restaurants on Pine Avenue * Beach chairs, umbrella and cart * Off-street parking for one vehicle

Nov. 24 – Dec. 1

$909 CAD per night

Guest favourite

Guesthouse in Sarasota

5.0 out of 5 average rating, 100 reviews

Magical Guesthouse 1 mi from SRQ airport

Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum

Sep. 22 – 29

$211 CAD per night

Guest favourite

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

$418 CAD per night

Guest favourite

Guest suite in Bradenton

4.97 out of 5 average rating, 121 reviews

Florida West Coast Get-Away

Enjoy Florida's beautiful West Coast in your own cozy, private apartment . One bedroom, living room, kitchenette with breakfast bar, attached bath with shower. Central air and heat. Free wi-fi. Private drive and gated entrance. Everything you will need is here just waiting for your arrival. You'll find this a beautiful place near everything you will need to enjoy your Florida vacation. Not available for guests with infants.

Jun. 16 – 23

$118 CAD per night

Guest favourite

Home in Bradenton

4.98 out of 5 average rating, 196 reviews

My Sunny home on the Bay.

My Sunny Mobile Home is located within a 2 min. walk from the Palma Sola Bay right across from Anna Maria Island. Sit and enjoy the views on the little beach right on the bay. 5 min. drive to the most beautiful Gulf beaches. Watch the dolphins swim and relax on the beach. Snorkeling, fishing and great restaurants near by. Very quiet neighborhood with houses and mobile homes and close to everything for a relaxing vacation.

May 18 – 25

$212 CAD per night

Guest favourite

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. 16 – 23

$171 CAD per night

Guest favourite

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

$894 CAD per night

Guest favourite

Guesthouse in Bradenton

4.94 out of 5 average rating, 126 reviews

The Enchantment, Cozy guesthouse,7mi to the beach!

Enjoy the beach in style! We welcome you to the private studio on the West side of Bradenton. Beautiful beaches like Cortez Beach, Coquina Beach, Holmes Beach, and Anna Maria Island may be reached in about 20 minutes. Sarasota Airport, IMG, art galleries, Lido Key, Longboat Key, museums, theaters, 2 hours from Disney World Orlando, Marie Selby Botanical Garden, and Marina Jacks are all within 20-30 minutes!

Nov. 27 – Dec. 4

$165 CAD per night