
Holiday rentals with outdoor seating near Anna Maria Island
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Top-rated rentals with outdoor seating near Anna Maria Island
Guests agree: these stays are highly rated for location, cleanliness and more.

Breezy Harbor AMI pool retreat near the Beach
Stunning Fall 2024 renovation done! Charming Breezy Harbor boasts a private heated pool and sits on a quaint corner of AMI. Upon arriving you will immediately feel stress melting away. You'll love grilling in the lush yard and a 6-min walk to the beach or the AMI trolley stop. A supermarket is a couple of streets over. The home is perfect for families, couples, 1-50Lb pet, and working remotely. Ample Parking for 2 vehicles and toys. *Ask us for shorter stays and always discuss your pets with us*

New Renovated Condo + Walk to Bay + 5-Min to AMI
Experience the ultimate beachside retreat in this newly renovated 1/1 condo, located within walking distance to the serene beauty of Palma Sola Causeway Parks Bayfront beach, jet-ski rentals, and horseback riding and also a quick drive/bike from the beaches of Anna Maria Island. This well-positioned condo offers the perfect balance of convenience and tranquility, providing easy access to the natural wonders of the island and the vibrant attractions nearby, including canal fishing, jet skis, etc.

Book Family Tides 7 Nts get 3 FREE~Pool~Beach view
Let me know if you need a stay for a period not listed. Unbeatable location, HEATED POOL, ultimate makeover & NEW bedrm, bathrm, lounge, & covered patio additions for spacious beauty are a few things that set us apart! Hidden behind our private gate, the beach is just a few steps away & remains uncrowded-even during busiest season. Premium fixtures, appliances, & plush furnishings create elegance. Garage/parking for 6 cars! Near restaurants, Publix, activities! 30 steps to FREE TROLLEY pick up!

Beach Escape & Pool, steps to Beach & restaurants
One block from beautiful beach & waterfront dining. Newly renovated Villa in quaint quiet condo building close to everything on Anna Maria Island. Pickleball across the street. Pool literally out your back door. Perfect for a small family or a romantic getaway. *Min. renter age 25. Two minute walk to beach, trendy Bridge Street shops, marina, restaurants, bars, boat tours, mini golf and more. Brand new beds, furniture & appliances. Kitchen has everything you need. Beach supplies in hall closet.

Crows Nest at Spinnakers Vacation Cottages
Close to the beach, family-friendly activities, nightlife, and the free AMI trolley. You’ll love the location, the ambiance, and the high ceilings. Located in the lush tropical paradise of Spinnakers Vacation Cottages. Offers a spacious living area, with the bedroom and bathroom on the living floor with a spiral staircase leading to a loft with two twin beds. Great for couples, families and dogs (with small pet fee) Great private deck for star gazing! Spa maintains same temperature as pool

Bougie Bungalow at the Beach
This newly renovated, completely private, comfortable Anna Maria Island bungalow is super clean & very comfortable. It has an open, split floor plan, 2 king bedrooms, each with private baths, separate dining and Florida room & is only 3 houses from the amazing white sand beach, the bay & Pier. Only 1 block over is Historic Bridge Street with cool restaurants, mini golf, quaint shops & bars with live music. Once here, you never need to drive -everything is within a block walking distance!

Waterfront Gem/ Pool Spa+ Dock/ Near Bridge Street
Anna Maria Waterfront oasis! **5 min walk to beach, private dock, pool heat included!!** Relax in the private heated pool, sip coffee on the dock, or walk to the beach. This bright, updated home has spacious living areas, a stocked kitchen, smart TVs, fast Wi-Fi, and cozy beds. Great for families or couples! Grill by the pool, dine under the stars, or fish from the dock. Includes washer/dryer, beach gear, and parking. Your peaceful, sunny getaway awaits—book now!

Palm Retreat: #1 Top Rated Rental of Bradenton/AMI
Enjoy Florida sun in a stunning, newly renovated 4/2 pool home! We have provided almost everything we could think of including five 4k TVs w/ Netflix and cable, wifi, heated (optional) salt water pool w/ 7' privacy fencing, adult bikes, beach gear, Pack & Play, office, board games, relaxing lounge chairs, stocked kitchen, washer & dryer, garage parking, dog crate, all in a quiet and safe neighborhood. Oh, and of course it's just 5 miles to world renowned beaches.

Oceanview: Open Tonite & Tomm, $95/nt + Fees!
This sublime oceanfront studio is directly on the pristine white sands and serene blue waters of the Gulf of Mexico in exclusive Longboat Key, Florida! Located on the second floor, overlooking the heated pool and ocean, this dreamy studio condo is optimal for sunset viewing from a private lanai. Take a 30-second walk to the pool and onward to the secluded beach with loungers. Enjoy a relaxing vacation at our peaceful condo at The Beach on Longboat Key Resort!

Bradenton Beach Sunsets 2, Anna Maria Island, FL
Fully furnished water view beach cottage located on beautiful Anna Maria Island directly across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with the queen pull out couch. Beach chairs/umbrellas/Boogie boards/laundry room, etc. provided. Three blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

Beachfront Paradise! Ground level with Heated pool
Gulf-front getaway with unbeatable beach access—step out your back door and right onto the sand! Enjoy a king bed, queen sleeper, fully stocked kitchen, in-unit washer/dryer, and professional linen service. Beach towels, two chairs, and an umbrella are included. Relax or grill by the shared heated pool and soak in the stunning Gulf views. Everything you need for the perfect beach escape—just bring your sunscreen and unwind!

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.
Popular amenities for rentals with outdoor seating near Anna Maria Island
House rentals with outdoor seating

Seconds to the Beach! Clean & Cozy NO flood damage

SunSalt Cottage~5 min to Beach, Shops & Food~Pool

New! Boat Dock + Dolphins + Beaches + Hot tub!

Bayfront Beach access with Heated Pool!

Walk to Beach, Spa, Pool, Putt Putt, Games&More

The Cottage on Pine - Pine Ave Cottage w/ Pool

Perfect Hideaway- Heated Pool, 5 min Walk to Beach

Unwind Sunshine: steps to locals' favorite beach
Apartment rentals with outdoor seating

2 min walk to beach Paradise

Attractive Beachfront Studio - Live Like a Local!

NEW Luxury Apartment w/Bikes! Location Location!

Come Enjoy Our Peaceful Retreat

Ocean Front Condo!

Updated Old Florida Studio Getaway in Central SRQ

Ocean Blue adorable new studio !

St.Pete Modern Retro Oasis
Apartment rentals with outdoor seating

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Lux Condo w/ 2 balconies, Ocean & Marina views

New Luxury 3/3 Condo in Margaritaville Resort

Spectacular beach to bay views from this resort.

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

~Shore Thing~ Coastal Exquisite Waterfront Condo

Short Stroll to the Surf! ~ Make Memories on AMI

Private Ocean View Beach Retreat with Balcony
Other holiday rentals with outdoor seating

Romantic Luxe Tiny Home+ Hot Tub

AMI Ohana Beach Resort A with fabulous salt pool!

Hello Sunshine! BeachView Condo on Anna Maria Isl.

Location! Beach Access/Trolley/ Restaurants!

Brand New Remodeled Villa + Large Private Pool!

Beach a la Mode | Luxury Anna Maria Island Home!

Cozy Cottage - close to Manatee River

Flamingo Royale — Beach Luxury Resort
Quick stats about holiday rentals with outdoor seating near Anna Maria Island
Total rentals
1.4K properties
Nightly prices starting at
€ 52 before taxes and fees
Total number of reviews
31K reviews
Family-friendly rentals
1.3K properties are a good fit for families
Pet-friendly rentals
550 properties allow pets
Rentals with a pool
1.2K properties have a pool
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- Rentals with outdoor seating Manatee County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
- Siesta Beach
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Dunedin Beach
- Busch Gardens Tampa Bay
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Lido Key Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Gulfport Beach Recreation Area
- Jannus Live
- ZooTampa at Lowry Park
- Manasota Key Beach
- North Beach
- Adventure Island
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Splash Harbour Water Park