
Cottage holiday rentals in Anna Maria
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Top-rated cottage rentals in Anna Maria
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Anna Maria Island Tree House
Escape to the AMI Tree House, your elevated island retreat in Bradenton Beach! This peaceful two bedroom, 1 and 1/2 bath, restored home offers a modern coastal feel, a full kitchen, and is perfect for families or small groups. You're just a short walk from private Gulf beaches and the serene Anna Maria Sound. Enjoy the best of island living with all the comforts of home, including free Wi-Fi and on-site parking. Pet Friendly! Automatic discounts applied for stays longer than 7 days and 30 days!

Pass-a-Grille Historic Cottage Unit 2
PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 2 - 2 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Ty's Canal Cottage
"Welcome to Ty's Cottage in Historic Cortez Fishing Village, which is one of Florida's last working fishing villages. Located within walking distance to well known Starfish, Swordfish, Tide Tables Restaurants and Tyler's Homemade ice cream. A short 1.3 mile walk to Anna Maria Island with gorgeous beaches. Short driving distance to beautiful golf courses such as IMG Academy Golf and Manatee County Golf Course. Local fishing charters for outstanding fishing. Outdoor sitting area on canal."

Bradenton Beach Sunsets 3, Anna Maria Island, FL
Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 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.

Bay Lake Cottage
You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

The Marlin: Heated Pool, 4 Houses to Beach
This apartment is a 2nd story unit with vaulted ceilings in the living room and an open floor plan that sleeps 2 with a maximum of 4 people. The bed makeup in this rental is a king bed in the master and a queen size sofa sleeper. This rental is great for longer stays or guests who like to cook since you have a full kitchen and all the items to cook any meal. There is also a washer/dryer in the apartment private for your use. Beach chairs and umbrellas are supplied to you at no charge.

Cozy Cottage for Lovers
Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Sea Breeze in Anna Maria With Private Dock
Welcome to Sea Breeze, our newly renovated home which is the Second Floor of a 2-story property at the North-end of Anna Maria Island. It includes 2 bedrooms / 2 bathrooms, a private dock, and an unobstructed, natural view of Bimini Bay. Smart TV, WiFi, washer/dryer, and a full kitchen are available. You can sailboat directly to Bimini Bay, walk to Pine Ave and City Pier, or eat in nearby restaurants. Our private home has everything you need for a perfect beach vacation in AMI!

Cortez ~ Grouper Cottage. BRING YOUR BOAT!
This waterfront home with a private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage—set in a private, tranquil setting, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

Ground-Floor Beachfront | Walk-Out to the Sand
Walk straight from your door onto the sand. This rare ground-floor, direct beachfront one-bedroom cottage sits right on the Gulf of Mexico with unobstructed water views and effortless beach access — no stairs, no elevators, no roads. Enjoy your private beachfront patio, a cozy and newly remodeled interior, and your own stretch of sand with lounge chairs just steps away. Perfect for couples or longer stays looking for a relaxed, front-row beach experience in Indian Shores.

Waterfront Retreat•Pool•PingPong•Near AMI Beaches
Relax at this cozy waterfront cottage with a private pool, & a short drive to Anna Maria Island’s white-sand beaches. 2BR/2BA with two living areas include a bright Florida room overlooking the canal. Enjoy ping pong and a putting green ⛳. Start your mornings with coffee on the dock, watching fish jump out of the water. Fast WiFi, workspace, beach gear, and a kitchen with cooking essentials. Perfect for beach days, family getaways, or a relaxing coastal escape.

Ohana Gulfside C Historic 1 Bed - 250 ft. to Beach
COMPLETELY REMODELED! Aloha and welcome to our bit of old Florida. Ohana Hale Gulfside is 250 feet to the white sand beaches and turquoise water. Come join us for your vacation in the sun. The ideal bungalow for a couple or small family. This one bedroom, one bath with kitchenette is made for your best vacation memories. This unit is only one block to the beach and one block to the Bridge Street shopping district and the pier! This unit is one-pet friendly.
Popular amenities for Anna Maria cottage rentals
Cottage rentals with a hot tub

Charming Home w/ Hot Tub, 20 min to Beach + Garden

Harbor Oasis | Hot Tub | Private | Lush Backyard

Beachy Keen Cottage A only steps to the Beach

Lemon Cottage Steps from Beach

Sarasota Cottage Near Beaches, Downtown & Airport

Family FUN~Pool, GameRoom+Bikes, Near Beach/Trail

Lake Ibis Retreat-Resort Perks Included

Cozy Cottage Near Beach | Hot Tub • Pet Friendly
Pet-friendly cottage rentals

Gasparilla Bayshore Good Vibes cottage

Artsy guest house; near downtown w/ private patio

Steps2Beach-Walk everywhere-Bikes & gear Included

Mermaid Cottage

Vintage Florida Beach Cottage B

Cozy up in a French Country nest NEAR EVERYTHING

Beachy Paradise

Cozy Cottage by the Bay
Private cottage rentals

Charming Newly Reno 1 min to Downtown Dunedin

2/2 Charming Riverfront Cottage w Deck & Kayaks

Safety Harbor Cottage

Aqua Breeze Cottage - Winter retreat 2 bd, 2 ba

Alafia River Cottage

Stylish Cottage Near IMG & Beach

Kamp Komfort Historic Family Beach House

Mattie’s Cottage by the Bay
Quick stats about cottage rentals in Anna Maria

Total holiday rentals
Explore 10 holiday rentals in Anna Maria

Nightly prices starting at
Anna Maria holiday rentals start at $325 NZD per night before taxes and fees

Verified guest reviews
Over 800 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Holiday rentals with a pool
10 properties feature pools

Wi-Fi availability
10 of Anna Maria holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Anna Maria rentals

4.8 Average rating
Anna Maria stays are highly rated by guests—averaging 4.8 out of 5!
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- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Caspersen Beach
- Amalie Arena
- Tiny House Siesta
- Dunedin Beach
- Bean Point Beach
- Cortez Beach
- Jannus Live
- Anna Maria Public Beach
- ZooTampa at Lowry Park
- Hard Rock Casino
- Tampa Palms Golf & Country Club
- Manasota Key Beach
- River Strand Golf and Country Club
- Tampa Convention Center




