Vacation rentals in Siesta Key

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Top-rated vacation rentals in Siesta Key

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Guest favorite
A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.
Condo in Siesta Key
4.91 out of 5 average rating, 116 reviews

The Honeymoon Suite on Siesta Key Beach

This is a recently renovated honeymoon suite located directly across from the big end of Siesta Key. It is an elegant ground floor pool unit. This unit is equip with marble countertops, tigers eye, lapis lazuli tables, bladeless ceiling fan, alabaster lighting and giant TVs. All of the appliances are stainless/smart and the microwave can cook steaks. There is a gym. The geographic location on the key can not be beat! There is a floating television over the California King luxury memory foam bed.

Top guest favorite
A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.
Home in Siesta Key
4.91 out of 5 average rating, 123 reviews

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

Top guest favorite
The living area features a comfortable sofa and leather recliner, offering a relaxing space. A large window floods the room with natural light, and a table with two chairs complements the surroundings. A TV is mounted on the far wall, providing entertainment options.
Apartment in Bellevue Terrace
4.99 out of 5 average rating, 144 reviews

*Recently Updated* Cozy Oasis, centrally located

This cozy yet spacious apartment is very centrally located... Just 5 min from downtown, 10-15 min from Siesta and Lido bch and St Armands Crl, and within walking distance of the historic Amish district. The newly completed Legacy Trail (perfect for walking, biking...) is less than a 5-minute walk away. The space is very private and clean and Ive taken extra measures to ensure your absolute peace and comfort. It includes all the amenities you'll need to make your getaway a memorable one.

Guest favorite
The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.
Condo in Siesta Key
4.85 out of 5 average rating, 102 reviews

Comfy Siesta Key Condo

Ground floor 2 bedroom 2 bath condo in the heart of Siesta Key. Master suite with recently remodeled en suite bath. King bed in master. 2nd bedroom has a double bed and easy access to the full bath. Enjoy your morning coffee on the lanai before taking the easy walk Siesta Key private beach. Or just walk out the front door and spend the day at pool. Garage is stocked with beach and pool supplies like chairs, toys and a cooler. We have done some recent freshening up with new furniture.

Guest favorite
A two-story blue duplex is depicted, featuring large windows and a wooden balcony. A shared heated pool is surrounded by several lounge chairs, with umbrellas positioned nearby. Lush tropical landscaping provides a serene backdrop, and a fenced area creates a private outdoor space.
Cottage in Siesta Key
4.93 out of 5 average rating, 123 reviews

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.

Top guest favorite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Condo in Siesta Key
4.97 out of 5 average rating, 368 reviews

On the Beach; Siesta Key SunBum Studio

Welcome back to paradise ! STEPS to your private beach without the tricks or gimmicks found elsewhere on the Siesta Key. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. If we are booked check out our additional units under our profile.

Top guest favorite
A spacious living area is adorned with a light blue sofa and a comfortable armchair, complemented by a coffee table and decorative rug. A mounted TV is set against a striking blue accent wall, and natural light filters through sheer curtains, enhancing the coastal ambiance.
Apartment in Siesta Key
4.98 out of 5 average rating, 168 reviews

Cozy Coastal Getaway 2 min Walk to Beach & Village

Steps away (2+ min walk / Beach Access #3 & #4) from the #1 beach Siesta Key and to the many restaurants, bars, and shops in local village. Relax & recharge at this peaceful cozy coastal 1bd /1ba Siesta Key condo w/ queen Sofa sleeper. Fully stocked upstairs unit w/ private balcony & great natural lighting + a community deck w/ grill & fire pit. Beach gear provided: beach chairs, umbrella, cooler bags, sunscreen, toys. The warm sun, white sand & ocean waves await you!

Top guest favorite
Home in Siesta Key
5 out of 5 average rating, 157 reviews

Beach, Village, Dock & Private Pool! One-of-a-kind

Fully Restored Post-Hurricane and Ready to Welcome You!! RCC in Siesta Key is a one-of-a-kind coastal cottage perfectly located between the beach, canal, and village. Enjoy a private heated pool, private dock, and one of the best locations on the island. This 1,500 square foot standalone bungalow has been fully restored with fresh post-hurricane updates. If you want a charming, private beach home with no shared walls and no condo feel, you have found the right place!

Guest favorite
A cozy porch area features a hanging swing adorned with colorful cushions, complemented by a small dining table and chairs. The entrance is framed by green lattice work, creating a welcoming space. A sign with the text 'WELCOME' is mounted on the wall.
Cottage in Siesta Key
4.87 out of 5 average rating, 180 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

Top guest favorite
A cozy living area is highlighted by a comfortable sofa and two striped armchairs. Light-colored walls and tile flooring contribute to the bright ambiance, while natural light filters through wide vertical blinds. A wooden coffee table sits at the center, enhancing the inviting feel.
Home in Gulf Gate Estates
4.93 out of 5 average rating, 204 reviews

Cottage Getaway 2 miles from Beach

Cottage style decor. 2024 updated with paint inside & outside, new stainless appliances, new upholstered chairs & linens. Private fenced backyard with screened porch, outside eating, gas grill & hammock. Laundry room with washer & dryer. Shopping, grocery store, movie theater & lots of dinning choices 1-2 miles. Easy parking in driveway. Very Convenient location. The #1 Beach is 2 miles away. ***Please note this is a NON-SMOKING & NON-PET home***

Top guest favorite
A charming outdoor patio area features a wooden pergola overhead, providing shade. Potted plants and herbs are arranged thoughtfully around the space. Two sets of double doors lead inside, complemented by white garden furniture, inviting relaxation and connection with nature.
Guesthouse in Whitfield
4.98 out of 5 average rating, 288 reviews

Casita Lantana, a 1925 cottage in a Tropical Oasis

Welcome to my original 1925 Casita, built in the heyday of the John Ringling era. We are centrally located between Sarasota, Lakewood Ranch, and Bradenton, making it an ideal place to explore all the area has to offer. Getting around is easy since we are located very close to the Ringling Museum of Art. Plus, it is only a short 15-minute drive to downtown Lido Beach and St. Armands Circle.

Top guest favorite
Home in Sarasota
4.98 out of 5 average rating, 103 reviews

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. 🌴

Popular amenities for Siesta Key vacation rentals

When is the best time to visit Siesta Key?

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Avg. priceﺩ.ﺇ970ﺩ.ﺇ1,241ﺩ.ﺇ1,340ﺩ.ﺇ1,153ﺩ.ﺇ933ﺩ.ﺇ929ﺩ.ﺇ925ﺩ.ﺇ837ﺩ.ﺇ753ﺩ.ﺇ782ﺩ.ﺇ852ﺩ.ﺇ988
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Frequently Asked Questions

  • What are the best places to stay in Siesta Key?

    Many guests choose accommodations near Siesta Beach or around the lively Siesta Key Village for convenient access to shops, restaurants, and the shoreline. Quiet neighborhoods near Crescent Beach are also frequently suggested for a more relaxed atmosphere.

  • What are the best things to do in Siesta Key with kids?

    Explore sandy stretches at Siesta Beach, visit playgrounds, or try family-friendly kayaking in the gentle waters. Mini golf, ice cream spots, and shell collecting are often recommended for kids around the island.

  • What are some of the best things to do in Siesta Key?

    Siesta Key has powder-soft beaches, water sports like paddleboarding, and vibrant local shops in Siesta Key Village. Visitors often enjoy sunset walks, live music venues, and sampling fresh seafood at local eateries.

  • How is the weather in Siesta Key?

    Siesta Key has warm, humid summers around 90°F (32°C) and mild winters near 55–75°F (13–24°C). Rain is more common from late spring through early fall, while the winter and spring months are drier and sunnier.

  • What are the best places to visit in Siesta Key?

    Siesta Beach, Crescent Beach, and Turtle Beach are frequently suggested for their distinct shorelines. Siesta Key Village has lively shops, while Point of Rocks is favored for snorkeling.

  • What are some hiking trails in Siesta Key?

    Siesta Key has gentle beachside paths and coastal walking trails, especially near beaches and nature reserves. For more variety, nearby mainland parks around Sarasota add wooded trails and wildlife viewing.

  • What are some family activities we can do in Siesta Key?

    Families often explore Siesta Beach, bike along island paths, or take boat tours for dolphin spotting. Ice cream shops, playgrounds, and interactive nature programs round out popular activities for all ages.

  • What are some of the best day trip ideas from Siesta Key?

    Many guests explore nearby Sarasota for its museums, gardens, and cultural sites. Wildlife reserves, marine aquariums, and historic downtown areas around the Gulf Coast can add variety to your itinerary.

  • Are there any pet friendly accommodations available in Siesta Key?

    Siesta Key has pet-friendly accommodations in different neighborhoods, with many listings offering private outdoor spaces. While local beaches have restrictions for dogs, look for homes that include easy outdoor access for your pet to enjoy the island.

  • What are some local tips for visiting Siesta Key?

    Bring a reusable water bottle, and start beach days early for easier parking and quieter sands. Locals recommend checking out sunset drum circles and trying out watersports for a memorable experience.

  • What is Siesta Key known for?

    Siesta Key is often recognized for its powdery, quartz sand beaches, especially at Siesta Beach. The area has a laid-back atmosphere, locally owned shops, and a tradition of vibrant community events.

  • What are the best hidden gems to explore in Siesta Key?

    Point of Rocks is a favorite for snorkeling near natural limestone formations, while smaller stretches like Turtle Beach are known for quieter shorelines and shell collecting. Local artists’ galleries and tucked-away cafés are also worth discovering.

  • What are the best foods to try in Siesta Key?

    Fresh Gulf shrimp, locally caught grouper sandwiches, and key lime pie are frequently suggested around Siesta Key. Many eateries feature locally sourced seafood with tropical flavors, as well as casual beachside options.

  • What should I bring for a trip to Siesta Key?

    Pack lightweight clothing, sun protection, reusable water bottles, and swimwear. Water shoes and a sand-friendly tote can help when exploring beaches, while a light sweater is useful for cooler evenings or restaurants with air conditioning.

  • What is the nightlife in Siesta Key like?

    Siesta Key’s nightlife has casual beach bars, open-air music venues, and spots for evening bites in Siesta Key Village. Expect live acoustic sets, DJ nights, and a relaxed, welcoming vibe.

  • What are the most popular events or festivals in Siesta Key?

    The Siesta Key Crystal Classic draws many visitors each fall to celebrate intricate sand sculpting. The weekly Siesta Key Drum Circle gathers people on Siesta Beach for music and dancing, and community art shows are frequently suggested by locals.

  • Are there family friendly vacation rentals in Siesta Key?

    Family-friendly rentals are common across Siesta Key, particularly near the beaches and Siesta Key Village. Listings with extra space, outdoor areas, and amenities such as pools are often emphasized for group comfort.

  • When is the best time to visit Siesta Key?

    Spring and fall are often recommended for pleasant weather, fewer crowds, and vibrant local events. These seasons have comfortable temperatures and a mix of beach days and community happenings.

All about Siesta Key

Siesta Key is an eight-mile-long barrier island off the coast of Sarasota, known for its soft quartz beaches, turquoise waters, and abundance of marine life. Due to its location on the western Florida shoreline in the balmy waters of the Gulf of Mexico, the island experiences ideal conditions year-round for swimming, paddling, and watersports. This small coastal community offers a host of recreational opportunities outside of the beach as well. Wander the Siesta Key Village, where you can find the many live music venues, boutique art shops, and souvenir vendors scattered throughout the small but lively downtown area. Check out one of the weekly farmer’s markets, spend an afternoon picking through the gift shops, or just lounge one the one of the white-sand beaches waiting for the sun to set over the Gulf.

What are the top things to do in Siesta Key?

Point of Rocks

One of the best snorkeling sites on Siesta Key, this limestone rock outcropping is home to abundant marine life and migratory bird populations. Calm waters and clear conditions make this a perfect place for beginners and experienced snorkelers alike. Expect to see schools of tropical fish, crabs, ocean sponges, and manatees during the summer. You may even get lucky and spot some of the area’s resident dolphins.

Siesta Key Drum Circle

The Siesta Key drum circle is a weekly tradition held on Sundays at Englewood and Siesta beaches throughout the year. Beginning about an hour before sunset, local artists and dancers kick off an evening of music and dancing. Large crowds gather to watch the festivities as onlookers are encouraged to dance or grab a drum and beat along.

Deep-sea fishing

Sandwiched between the vast Gulf of Mexico and Roberts Bay, Siesta Key is a year-round fishing destination. The reefs attract cobia and grouper, and if you venture further out you’ll be rewarded with tuna and wahoo. July is peak season for red snapper, while the fall bait migration off the Florida coast is a big draw for anglers from October onward.

Quick stats about vacation rentals in Siesta Key

  • Total vacation rentals

    Explore 2,090 vacation rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 37,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    1,660 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 410 rentals that welcome pets

  • Vacation rentals with a pool

    1,700 properties feature pools

  • Rentals with dedicated workspaces

    970 properties have a dedicated workspace

  • Wi-Fi availability

    2,080 of Siesta Key vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Self check-in, Free parking on premises, and Beachfront across Siesta Key rentals

  • 4.8 Average rating

    Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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