Pet-friendly holiday rentals in Siesta Key

Siesta Key, FL - Casa Berano

Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs

The Sand Castle - Backyard Oasis Mins from Siesta!

*UPDATED!* Your family will feel at home in this spacious home that has it all! With a gorgeous backyard, alluring HEATED pool, tropical tiki bar, ping pong and other lawn games, cozy and comfortable rooms, and a kitchen stocked with everything you need to prepare meals for many... you will be more than comfortable here! The location is super convenient- minutes from Siesta Key, downtown Sarasota, and every grocery store and restaurant you could ever want! Please message me if bringing 2+ pets

Blue Conch– Family Friendly-Read About 4th Bedroom

3D Virtual Tour QR Code on 2nd Slide! Welcome to The Blue Conch, a charming 3BR/2BA home just minutes from shops, restaurants, and Siesta Key Beach. Enjoy the screened-in pool and a large fenced yard perfect for pets. Need extra space? Add The Surf Shack—the detached 4th bedroom/guest suite with a private bath and kitchenette—for $39/night total (no tax or fees) Whether you're here to relax or explore, The Blue Conch offers comfort, convenience, and the charm of a perfect beach retreat.

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.

Summer House longboat key

Luxurious waterfront home with bay and and canal view, new custom kitchen with a view to the pool and your own private tiki bar, dock that can accommodate up to 21 ft boat , whole house just received a complete inside and out make over. Tropical coconut palms, outside patio and grill. Fish on the dock and watch dolphins and manatee. Truly a tropical paradise just 7 minute Walk to your own private beach. minutes from St Armand’s circle. feel free to reach out with any questions or requests

Serenity Springs | Private Heated Pool + Waterfall

BNB Breeze presents Serenity Springs! Experience this stunning, peaceful oasis in the heart of Sarasota, located moments from the picturesque beaches! This home is Fully Loaded with awesome amenities. - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Whole home Water filtration system - Rooftop Perch (the Best sunsets) - Outdoor Dining and Sitting Areas - Outdoor Ping Pong Table - Breville Espresso Machine + Syrups - 2 Stunning floors of stylish design

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

Siesta Key Village, Pool, Beach Access 4-min Walk

Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.

Private Home 2bed 2bath King Bed Spa

Canal-front single-family home in the heart of Siesta Key—an easy walk to the Village and the #1 beach in the USA. Enjoy a heated pool, hot tub, Tesla EV Charger, Weber grill, fast Wi-Fi, and streaming on 3 large TVs. Launch a canoe from the canal, bike to shops and cafés, or hop the free trolley/tip-only rides for a car-free stay. Thoughtful touches and a stocked kitchen make relaxing effortless - whether you spend the day on the sand, on the water, or out on the town.

Modern Studio · 5 min from Siesta Beach

Stylish ground-floor studio designed for couples or solo travelers, just a 5-minute drive from world-famous Siesta Key Beach. A great choice if you’re looking for a calm, well-located space with thoughtful comfort. Pet-friendly stay – $10 one-time pet fee per booking, unlimited pets. An ideal base for beach days, local dining, or a relaxed Florida getaway. About 1 mile from the property, guests may also enjoy access to a beautiful community pool that is heated.

Paradise Palms by Duncan Real Estate

Welcome to Paradise Palms! Casual and beachy this three-bedroom duplex with a private, heated pool and close proximity to the beach is the perfect choice for vacationers to relax and unwind when visiting Anna Maria Island. Your favorite dog is also invited for a small pet fee (50 lbs. max, please!). Paradise Palms is located two blocks from the powdery sand on Holmes Beach - so close you'll never miss a sunset.

Beachfront Villa | Pool + Lanai | Hosts 6

Welcome to your private slice of paradise on the coveted Longboat Key. Nestled beachfront, this two-bedroom villa offers barefoot luxury, breezy interiors, and a peaceful atmosphere that instantly slows the pace. Whether you’re here for a family getaway, a quiet reset, or just to listen to the waves with coffee in hand, this sun-drenched retreat delivers serenity in every square inch.