Vacation rentals in Siesta Key
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Quick stats about vacation rentals in Siesta Key
Total vacation rentals
Explore 2,200 vacation rentals in Siesta Key
Nightly prices starting at
Siesta Key vacation rentals start at $84 CAD per night before taxes and fees
Verified guest reviews
Over 40,870 verified reviews to help you choose
Family-friendly vacation rentals
1,820 properties offer extra space and kid-friendly amenities
Pet-friendly vacation rentals
Find 390 rentals that welcome pets
Vacation rentals with a pool
1,830 properties feature pools
Rentals with dedicated workspaces
970 properties have a dedicated workspace
Wifi availability
2,170 of Siesta Key vacation rentals include wifi 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!
Top-rated vacation rentals in Siesta Key
Guests agree: these stays are highly rated for location, cleanliness, and more.
Crystal House on Siesta Key Beach
This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!
NO Stairs, Siesta beachfront. Walk to the village!
Welcome to your own private getaway directly on Siesta Beach! This ground floor unit is just steps from the powdery sands of Siesta Key. NO STAIRS Enjoy the updated bathroom with quartz countertops, new fixtures, paint, new furnishings, and décor. You literally walk out your door 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 bedrooms 1.5 bathroom beachfront home with Gulf views that sleeps 6.
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.
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.
Modern 4BR Home *Heated Pool & Spa*
Discover elegance in this centrally located Sarasota gem, featuring four bedrooms and two bathrooms to accommodate up to eight guests. Enjoy a laid-back vibe while lounging at Sarasota's beaches or immersing yourself in local attractions. Siesta Beach and Lido Beach are within easy reach at 7.6 and 6.4 miles respectively. Rest easy knowing commitment to cleanliness aligns with your travel priorities. Your serene vacation awaits in this beautifully adorned home. *Brand new pool* VR24-00265
Private Heated Pool Retreat for Two Families
🌴 Welcome to your private Sarasota escape - designed for easy, extended stays, where two families can relax together around a private heated pool. With generous living spaces and thoughtful touches throughout, the home balances comfort and connection. Located minutes from Siesta Key, Lido Beach, and downtown Sarasota, and within walking distance of a park with playground, public pool, courts, fitness areas, and scenic trails. Relaxed, comfortable, and ideal for memorable family getaways.
Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
The Siesta Key Bungalows offer a heated pool, courtyard, sun loungers, gas-grills, laundry facilities, kayaks & a private dock on Heron Lagoon. The Dolphin Bungalow's one bedroom space; connects a welcoming living room, full-kitchen, and a private backyard patio. A king bed, two HDTVs and a full bathroom will further enhance your overall experience. Fully stocked with linens, care essentials, eating & cooking utensils. A queen sofa bed in the living room, allows for a capacity of three.
The Palms Away
This special place is close to everything, making it easy to plan your visit. 1 mile to Siesta Key. Built in the 50's but totally renovated to today standard's. Heated swimming pool, but if the water gets to hot the heater will also cool the pool. Very close to shopping. Large deck with view to tropical garden and waterfall. Gas fire pit with built in seating. Small putting green and Corn-hole game are available for your use. 5 TV's with wi-fi. A Gazebo with plenty of sitting area.
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)
Siesta Key Beach & Village 2BR/2BA Steps to Beach
This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.
Private Beach with Loungers · 2 Pools & Bay View
Beachside resort life for families, groups and remote workers seeking easy beach access and active days. This oversized & Fully Renovated 2‑bed, 2‑bath condo sits in a gulf-to-bay complex so you can walk to the famed Siesta Key sand and hop the island trolley outside your door. Enjoy bay views, unwind in heated pools and the hot tub, use the on-site gym and courts, and take advantage of provided beach chairs, umbrella and wagon for effortless beach days.
Modern Home Heated Pool near Siesta & Downtown
Escape to our brand-new, modern Sarasota home, perfect for families! Enjoy a private heated saltwater pool just steps from the master suite. Located minutes from the world-famous Siesta Key Beach and vibrant downtown Sarasota. This stylish oasis comfortably accommodates up to 10 guests, offering the ultimate Florida retreat with all-new furnishings and a fully equipped kitchen. Your private getaway awaits!
Popular amenities for Siesta Key vacation rentals
Other great vacation rentals in Siesta Key
New! Siesta Beach Guest House with pool!
Gulf and Beach Views-Steps from Beach and Village
Luxury Canal-Front Home + Heated Pool Near Beach
Heated pool & Infrared Sauna, 2 min to beach
Bike to Beach Double King Suites, Pool & Mini Golf
Oceanview Penthouse |1-Min Walk to Beach + Terrace
Siesta Key House, Pool & Hot Tub, 1 mile to beach
NEW! Renovated Pool Home Mins 2 Siesta Key Beach
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $391 CAD | $504 CAD | $563 CAD | $446 CAD | $376 CAD | $390 CAD | $354 CAD | $321 CAD | $288 CAD | $300 CAD | $326 CAD | $378 CAD |
| Avg. temp | 16 °C | 18 °C | 20 °C | 22 °C | 25 °C | 27 °C | 28 °C | 28 °C | 27 °C | 24 °C | 20 °C | 18 °C |
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
The beaches on this barrier island in Sarasota have a luxurious feel, thanks to the pure white sand along its 13 kilometers of pristine coastline. On each of the island’s three main beaches — Siesta Beach, Crescent Beach, and Turtle Beach — the sand is almost exclusively composed of tiny quartz crystals, believed to have originated in the Appalachian Mountains millions of years ago. Digging your toes into it, you’ll notice the soft sand stays cool, even under the hot Florida sun. The beaches here fade into aquamarine surf, and as you watch the sunset over the Gulf of Mexico, you’ll come to appreciate why Siesta Key Beach is such a popular destination.
This beach town has a lively vibe, especially around its main hub, Siesta Key Village. At the core of the village on Ocean Boulevard, you’ll find a variety of local shops and open-air bars and restaurants giving you plenty to do here both on and off the sand.
What are the top things to do in Siesta Key?
Siesta Beach
No trip to Siesta Key would be complete without visiting Siesta Beach, the most popular of the region’s three beaches. The white sand and warm water invite lounging and swimming, while volleyball courts offer a fun activity for groups. Concession stands with food and drink make it possible to spend the entire day at the water’s edge. There’s a longstanding tradition here on Sundays of winding down the week with a drum circle during sunset.
Siesta Village
A short walk from Siesta Beach will get you to Siesta Village, where you’ll find beach-style restaurants and tropical-themed bars. The bright-coloured shops, thatched-roof huts, and towering palm trees give the small district a vibrant atmosphere, while extra-wide sidewalks accommodate window shoppers and cyclists alike.
Point of Rocks
Point of Rocks is a beginner-friendly snorkelling area with shallow, calm water. This rocky sea wall located south of Crescent Beach hosts a myriad of sea life, including gentle manatees in the summertime. High tide is the best time to explore with a snorkel and fins, while low tide offers opportunities to examine tidal pools on land.
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- Anna Maria Island
- Siesta Beach
- Anna Maria Island Beach
- Raymond James Stadium
- Coquina Beach
- Lido Key Beach
- Bean Point Beach
- Turtle Beach
- Amalie Arena
- Caspersen Beach
- Tampa Convention Center
- Vinoy Park
- Manasota Key Beach
- Crescent Beach
- John's Pass
- Englewood Beach
- Tropicana Field
- Fort De Soto Park
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Cortez Beach
- Img Academy
- North Beach At Fort DeSoto Park
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