Pet-friendly vacation rentals in Siesta Key

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties, only 9 minutes to Siesta Key Beach! 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

Quaint Cottage,150 steps away from Crescent Beach!

Nestled on the serene Crescent Street, this classic 1969 cottage, is just a short walk to the ground quartz sands of Siesta Key. The 500 sq foot private brick paver and stone backyard off the screened in lanai is fully fenced with custom built stainless outdoor kitchen, featuring a large grill, refrigerator, custom built stone bar with seating for 8 . Nearby is a blue glass gas fire pit with a seating area, over sized (9 ft. diameter) in ground "spool", loungers and a large circular daybed.

Gulf Front! Sunset Deck! + Walk to Bridge St Pier!

🌊🏄Welcome to The Surof House - where panoramic views of the Gulf of Mexico welcome you from almost every corner! 🏖️Experience the ultimate beachfront retreat at this unique & stunning property nestled across from one of the top beaches in the world. A perfect blend of luxury, comfort, & unparalleled views awaites. With an upstairs loft featuring 3 single beds & 2 downstairs rooms with king beds, it's an ideal getaway for families, friends, or anyone seeking a slice of paradise.

Modern, Bright Downtown SRQ A-Frame West of Trail

Enjoy this bright, newly renovated unique pool home on a street with mostly waterfront homes featuring 4 beds & 3 baths, office area options, loft reading nook, Bosch appliances, bedroom skylights, artful light fixtures and fully fenced with heated pool. Central to & minutes from Siesta Key, St. Armand's Circle/Lido Key, downtown. Walk to the Sarasota Arts Museum, grocery, Southside and downtown Restaurants & shops, Selby Botanical Gardens, Bayfront Park, & Marina Jack. VR24-00157

Siesta Key Condo: Beach, Pool & Village Fun!

Escape to paradise in our newly renovated 2-bedroom condo, perfectly situated a block from Siesta Key Village. Enjoy the convenience of walking to bars and restaurants, plus two parking spots if you prefer to drive. Relax by the community heated pool or take an 8-minute stroll to the award-winning beach. Explore the area using the free trolley, or venture to downtown Sarasota. This dog-friendly condo offers Wi-Fi, a smart TV, in-unit laundry, and essential home and beach gear.

Stylish Pool Home 4BR Near Siesta Key "Palm Noir"

Welcome to Palm Noir, a brand-new modern luxury retreat in Sarasota just 12 minutes from Siesta Key Beach and 9 minutes from Downtown. This stunning pool home features soaring ceilings, impact windows and doors, designer finishes, luxury furnishings, bright open living spaces, and a private heated pool with spa. Enjoy premium bedding, fresh towels, a fully equipped kitchen, outdoor dining, lounge seating, and everything needed for the perfect family vacation or group getaway.

Newly Remodeled Beachfront Studio - On the sand!

ONE SHELL COVE on Anna Maria Island has been totally remodeled after Hurricanes Helene and Milton. Wonderful studio floor plan with amazing kitchen. Beautiful view of the waves and the beach right outside your window. Grab your towel, take a few steps and you're on the beach. The sand comes right up to your door in this ground floor unit. Amazing Location Walk to some restaurants Free Trolley goes up and down the Island Rent Kayaks and Paddleboards and enjoy the Beach

The Siesta Key Retreat - An Island Garden Oasis!

Your family will be close to everything when you stay at this centrally-located place on Siesta Key while still enjoying the private garden oasis this home has to offer. Just steps from the quaint shell beach or a bike ride to the beautiful sand of Siesta Key beach to spend the day or venture to the cool vibes of Siesta Key Village for dinner and shopping!. Additionally, you're only a few miles from the vibrant downtown Sarasota and St. Armand's Circle (26-VR-000095)

Minutes to Siesta! 4BR 2BT Heated Pool Fenced Yard

Spacious 4-bedroom, 2-bath home with a heated private pool, just minutes from the #1 Siesta Key Beach! Located in the Gulf Gate area, you’re only a short drive to the beach, grocery stores, and dining. Enjoy a fully fenced backyard, plenty of parking, and outdoor grill. Inside, you’ll find beach supplies, a fully equipped kitchen, Keurig & drip coffee makers, and TVs in every bedroom—everything you need for a comfortable and convenient stay 🌴☀️

Zen Den: Bali Oasis near Siesta w/Pool & Hot Tub

Slip away to your own sanctuary just minutes from Siesta Key's legendary white-sand beaches. The Zen Den is a Balinese-inspired, 1-bedroom retreat wrapped in warm natural textures, soft lighting, and a seamless indoor-outdoor flow — designed for two people who want to completely unwind. Step through French doors to a the beautiful property grounds sparkling pool, bubbling hot tub, and a gazebo made for evening cocktails under the Florida sky.

Siesta Key Quaint Beach House

This home, built in the 1950’s, has old Florida highlights including cypress wood walls and terrazzo floors located in a peaceful neighborhood. It is all on one level and sleeps 4 adults with a private patio including a gas grill. It’s only a 5 minute walk to Siesta Key beach and includes a beach cart, chairs, umbrella, towels and a cooler. Only a 10 minute walk or 2 minute ride to the village with shops, restaurants, music and nightlife.

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Experience luxury at this newly remodeled home with a brand-new pool, spa, and putting green. Centrally-located near downtown Sarasota, Siesta Key, Lido Key beaches, and St. Armand’s Circle, it features a full kitchen, 3 king bedrooms, 3 full bathrooms, outdoor dining, high speed internet, a 75” outdoor TV, fire pit, and EV charger. Pet-friendly with a fenced yard, pet crate, bowls & treats. License # VR24-00208