Beachfront holiday rentals in Anna Maria Island

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Top-rated beachfront rentals in Anna Maria Island

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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Guest favourite

Flat in Treasure Island

4.91 out of 5 average rating, 278 reviews

Attractive Beachfront Studio - Live Like a Local!

The true treasure of Treasure Island! Tucked right off of Gulf Blvd, on a secluded beach, this comfortable newly remodeled private studio is nestled on a lushly landscaped beachfront residential property with renters on-site. This cozy spot is all about barefoot luxury — you're just steps from the beach and biking or walking distance to laid back beach bars, live music & restaurants. Please note: There’s no guest parking available, but paid parking is nearby as well as a frequent public trolley.

24 Jun – 1 Jul

$201 SGD per night

Guest favourite

Flat in Indian Rocks Beach

4.93 out of 5 average rating, 119 reviews

Vintage Florida Beach Efficiency

Just a short walk to the beach, this a great beach getaway for couples or families with one child. On your way stop at the Cooky Coconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2022, this unit is updated, very clean & worry free. This cottage is located in a quiet residential neighborhood and a great place to relax. Laundry on shared screened porch. Dogs allowed ($35 extra) add them on # of guests page . Easy refund policy. Level 2 EV charger

25 Sep – 2 Oct

$118 SGD 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.

22–29 Nov

$421 SGD per night

Guest favourite

Guest suite in Bradenton

4.9 out of 5 average rating, 289 reviews

WOW-Walk 2 Restaurants-King Bed-Near Beaches & IMG

Affordable unit is an approx 450sq foot efficiency which includes a large King bed and bathroom, a full fridge, microwave and coffee pot. This unit does not have a kitchen but there is access to a grill with side burners on the shared back deck area. Off street parking. Bikes to use. There’s cable TV/Roku with fast WIFI. Unit is attached Downtown Bradenton location. It is around the corner from the Riverwalk, bars, and entertainment. Close to beaches. Great for couples or a single traveler.

18–25 Jun

$164 SGD per night

Guest favourite

Apartment in Madeira Beach

4.9 out of 5 average rating, 141 reviews

Experience the charm of Gulf Gardens. The Pelican.

Come visit the gem of Madeira Beach, and discover the charm that has visitors coming back for decades. Enjoy a quiet, clean tropical old Florida feel that's hard to find anywhere in this sought after beach community. This property features lush landscaping and one of the largest, cleanest pools you'll find. Our visitors appreciate the attention to detail the owners put into making Gulf Gardens a special place they want to visit year after year. The white sands of Madeira Beach are calling.

12–19 Aug

$176 SGD per night

Guest favourite

Flat in Treasure Island

4.92 out of 5 average rating, 162 reviews

Treasure Island Beach Apartment #1

Location! Situated on Gulf Blvd, directly across from the 123rd Street beach access in Treasure Island. Walk to John's Pass for restaurants, shopping, bars and music, boat trips and fishing. Two bedroom, one bath private apartment, with all the amenities you need for a great beach vacation - beach chairs, umbrella, cooler, barbecue, bicycles. Master bedroom has queen bed, and Roku tv. Smaller bedroom has twin trundle bed, perfect for the kids. Full kitchen. Off street parking for one car.

4–11 Jan

$173 SGD per night

Guest favourite

Flat in Treasure Island

4.84 out of 5 average rating, 357 reviews

Treasure Island Beach Unit

Privately owned Efficiency Unit on the 5th floor at the Island Inn Beach Resort right on Treasure Island Beach. Balcony of unit faces a view of part of the building, the street and Boca Ciego Bay. Beach directly to the left as step off of the elevators. NOTICE May 15, 2023 to Feb 26 GUESTS Building Renovations Scheduled on the exterior structure on these dates. There will be noise disturbances during the hours of 8am and 5pm weekdays, as well as the pool, pool deck, tiki bar closed

16–23 Apr

$186 SGD per night

Guest favourite

Cottage in Bradenton Beach

4.96 out of 5 average rating, 141 reviews

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.

28 Nov – 5 Dec

$372 SGD per night

Guest favourite

Apartment in Longboat Key

4.93 out of 5 average rating, 144 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf of Mexico and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

7–14 Sep

$419 SGD per night

Guest favourite

Apartment in Bradenton Beach

4.91 out of 5 average rating, 129 reviews

Beachfront condo in paradise

Relax, you made it, you’re at the beach now. No fighting traffic for 90 minutes to get over the drawbridge to Anna Maria Island and driving around looking for a spot to park. You only have to go down 14 stairs from this second floor condo to have your toes in the powder soft sand. Enjoy the sunset from your balcony as it sinks into the Gulf. Perfect for a romantic couple getaway whether it be an anniversary, birthday, or some overdue R&R. Or bring the kids for a fun stay at the beach.

8–15 Sep

$415 SGD per night

Guest favourite

Flat in Madeira Beach

4.89 out of 5 average rating, 108 reviews

Johns Pass Retreat #5 Flamingo Flair—walk to beach

Soak up the Florida Charm at this cool fishing village apartment! Peak a boo views of the canal and "mini marina" from the apartment and full enjoyment just outside in the back yard! 100 yard walk to Johns Pass, stroll the board walk full of restaurants, shops and water sports. Grab some ice cream and walk to the beach (5-7 mins)for the sunset! You can’t beat this location!*King bed*pull out couch*equipped kitchen*fast wifi*2 Smart TVs*Waterfront docks and a designated parking space.

6–13 Sep

$185 SGD per night

Guest favourite

Apartment 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.

4–11 Dec

$200 SGD per night