Beach house vacation rentals in Siesta Key

4.96 out of 5 average rating, 47 reviews

Home in Bradenton Beach

Walk 2 blocks to Beach + Private Pool + King Beds!

☀️Welcome to Bayberry Beach Cottage A on Anna Maria Island! Just +/- 400 feet (2 min walk) to the beach! With a heated private pool, fenced backyard, outdoor games, & grill, it’s the perfect spot for fun-filled days and relaxing nights! 🌴This recently renovated beach cottage has 2 king bedrooms, 1.5 baths. 📍You’re just a 2-minute walk to Salt, a trendy restaurant and craft cocktail bar with live music. More local favorites and beach bars are nearby, & lively Bridge Street is only 1 mile away

LocationFamilyCheck-in

5 out of 5 average rating, 12 reviews

Home in Holmes Beach

Carissa A | Beachside Retreat | Golf Cart | Pool

Carissa Loft A🏝️ A well-designed home offering comfortable spaces to relax, reconnect & experience all that AMI has to offer! Step inside to discover a private lower level retreat featuring a queen bed, sofa, TV and game table. Upstairs you'll find the fully stocked kitchen, inviting family room, 2-bedrooms & 2-full baths. The private outdoor oasis features a heated/cooled cocktail pool. 🚙Park the car & let the island adventures begin! The 6-person golf cart is complimentary with your stay!

FamilyLocationAccess

5 out of 5 average rating, 10 reviews

Steps to Siesta Key Beach! Sunset Balcony Views!

This beautifully appointed 2-bedroom, 1-bath condo (Sleeps 6) is centrally located directly across from the world-famous "sugar-white sands" of Siesta Key Beach. Unit 205 offers a perfect location with spectacular Gulf of Mexico sunsets from your private balcony. Enjoy a covered parking spot. The master suite has a King bed, a second bedroom with two twin beds, and a pull-out sofa in the living area. Nearby find rentals for bikes, scooters, water sports, parasailing, fishing, sunset cruise.

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An aerial view captures the beachfront property nestled among greenery, with sandy pathways leading to the beach. The top floor condo is highlighted, surrounded by other buildings, while the striking blue Gulf waters stretch in the background, meeting the clear sky.

5 out of 5 average rating, 48 reviews

Beachfront 180-Degree View, Walk to Village!

This secluded beachfront property offers panoramic 180-degree views of the beach and the gulf from this newly renovated top floor condo, ideally located an easy 5-minute walk from Siesta Key Village. This spacious 2 bedroom 2 bath is filled with light and stocked with everything you need for an amazing stay at America's best beach. Savor the sunrises and sunsets on the wrap-around porch while you watch dolphins, turtles, and diverse bird life on the quietest most natural part of Siesta Beach.

LocationFamilyGrill

4.94 out of 5 average rating, 104 reviews

The duplex features a light blue exterior with a welcoming porch adorned with yellow and blue chairs. Lush palm trees and vibrant landscaping enhance the outdoor space, while a clear blue sky adds brightness to the scene. Graveled parking is visible in front of the unit.

Home in Anna Maria

Do you love the beach?

Seaside Sanctuary is the ground floor unit of a beachfront duplex. It is the 2nd house from the beach with no roads to cross. The front yard is thirty steps from one of the most pristine beaches on the Gulf of Mexico. The house is located on a quiet residential street near the north end of the island. The front porch is a great place to watch the sunset. The house is clean, comfortable and well appointed. We welcome well behaved dogs and have a fully fenced yard for your pup to play.

LocationFamilyLayout

5 out of 5 average rating, 10 reviews

Home in Holmes Beach

NEW! w/ Pool - The Pearl Unit 1 on AMI

The Pearl (Unit 1) is a newly renovated oasis in the heart of Holmes Beach on Anna Maria Island. Just a 3–5 minute walk to the beach, this sunny AMI duplex home has everything — sparkling saltwater pool, fresh interiors, no stairs, beach gear, and parrots that may say hi on your morning walk! Centrally located and steps away from the AMI trolley to whisk you around the island! Relax, explore, and live your best island life. *pool is shared with one other unit in the duplex home*

FamilyLocationBeach

5 out of 5 average rating, 7 reviews

Home in Anna Maria

Beach Baby/4 Min Walk to Beach/ Pool/HotTub /Games

Welcome to Beach Baby – Your Laid-Back Island Escape Just a short stroll from the sugar-white sands, Beach Baby is your perfect Anna Maria Island getaway. Located only six houses from the Gulf and about a 4-minute walk to the stunning Bean Point Beach, this bright and breezy retreat is all about soaking up sunshine, salty air, and easy coastal living. Spend your days beach hopping, biking to local shops, or simply unwinding in your own private backyard oasis.

FamilyWalkabilityComfort

4.81 out of 5 average rating, 125 reviews

Newly Reno Cozy 1BR w/ Pool - Walk to Gated Beach

Newly renovated gated beach access apartment with a pool. This is a one bedroom and one bath apartment that makes up one unit in a quadplex. It is on a very quiet private road that leads to a gated beach access way that only residents on this street have access too. The house was completely redone and has all new furniture, sheets, pillows, towels, etc. The pool area was just upgraded with new pool/deck furniture.

ValueFamilyOutdoor spaces

A living area is depicted with a neutral color palette and light hardwood flooring. A blue sofa and a wooden coffee table sit in front of a television on a console. A dining area with a table and chairs is visible in the background, alongside large sliding doors leading to an outdoor space.

4.94 out of 5 average rating, 133 reviews

Siesta Beach home w/ private access, walk to town!

Welcome to your own private getaway directly on Siesta Beach! Meticulous, updated unit with amazing location to the village and access to tow You will literally, walk out your door, down the steps, and directly onto the beautiful, fine, powdery white sand of Siesta Key Beach. Private Paradise directly on the white powdery sand of Siesta Key! 2 bedroom 3 bathroom beachfront home with Gulf views that sleeps 8.

ValueLocationGrill

4.98 out of 5 average rating, 125 reviews

Home in Sarasota

Your DreamOasisAwaits: SiestaKeyEscape with Pool!

Welcome to your dream oasis near the world-famous Siesta Key! ✨ This immaculate 2BD/2BA home is a true coastal gem, offering a serene retreat with stylish design and luxurious amenities. Just 1 mile from the sugar-white sands of Siesta Key Beach, this home provides the perfect blend of comfort and convenience—an ideal spot to embrace relaxed Florida living at its finest. 🌴

LocationValueLong stay

Superhost

4.89 out of 5 average rating, 35 reviews

Located Directly on World Famous Siesta Key Beach!

Welcome to one of the few single family homes available directly on the white sands of Siesta Key! This 3 bedroom 2.5 bathroom house has a 2 car garage and is just steps to the beach and Gulf of Mexico. Walk to the Siesta Key Village where you can enjoy all the restaurants, shops, bars and entertainment that Siesta Key has to offer. Come stay in paradise. Book Today!

ValueFamilyView

A bright living room features a large sectional sofa adorned with various cushions. A flat-screen TV is mounted on the wall, presenting a serene beach scene. Natural light enters through sliding glass doors, which lead to a balcony, while decorative wall baskets add visual interest.