Vacation rentals in Siesta Key
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Top-rated vacation rentals in Siesta Key
Guests agree: these stays are highly rated for location, cleanliness, and more.
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.
Super Clean Cozy and Quaint steps from the beach
The best of all worlds, cleanliness and steps from the beach. Avoid the crowds at the public beach in this beautiful private beach with lounge chairs already at the beach for your convenience. Literally yards from the beach, exit the ground floor condo and walk 100 yards to the gate to the private beach. Only 2 miles from the village, with an easy close by trolley stop just outside the complex. Beach cart, umbrella, cooler, beach toys and towels provided for your convenience! Look no further.
Mid-Century Modern Beach Getaway
Heart of Southside Village 10 minutes from #1 beach in the USA, Siesta Key. Five-minute drive to downtown Sarasota, 10 minutes to St. Armand Circle, Lido & Longboat Key. Enjoy this peaceful space within walking distance to shopping, restaurants & groceries. Charming private guest house offers a queen bed, sitting chairs, table, dresser, large ensuite bathroom with a walk-in shower & private outdoor sunny space and patio. Use the grill to cook your next meal. It's the perfect couple's getaway!
The Mango House Beach Cottage
Our cozy boho beach cottage, The Mango House is the perfect place for a couple or small family to relax and enjoy all the best Sarasota amenities. It’s conveniently located right between both Siesta Key entrances, walking distance to restaurants, grocery stores, Trader Joe’s, gym and a block from the popular Walt’s Fish Market. This gorgeous bungalow is the front house of a duplex on a large lot with plenty of cozy private outdoor space to relax and take in all the wonderful Florida weather!
Sweet, pet friendly Siesta Suite
Sweet spot with the best of both Sarasota and Siesta Key - your private oasis for relaxing and rejuvenating. Whether you choose to chill or find adventure it is all within reach! Siesta Key beaches, Village with shops, restaurants, and bars; Sarasota culture, arts, and entertainment; quaint Gulf Gate shops and eateries ...the possibilities truly are endless. Regardless of how you choose to spend your time here, you will be sure to create lasting memories to share and leave wanting more.
❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key
Welcome to beautiful Siesta Key, the #1 beach in the country! Gorgeous newly renovated one bedroom condo within a 5 min walk to the powdery white sandy beach and stunning sunsets. Also next to restaurants, bars, kayak & jet ski rentals, and much more! Contact for monthly rentals available. Experience this modern oasis: • Chic Living Room • Quartz Kitchen Countertops • King Size Mattress • Beach gear • Wifi • Private Parking • Smart TVs • Screened-in Patio • Coin Laundry room on premises
Modern 1BR Near Siesta Key + Private Parking
Private coastal retreat minutes from Siesta Key Beach. This spacious 950 sq ft upstairs apartment features soaring ceilings, a bright open layout, and a private entrance. Enjoy a king-sized bed, full kitchen, in-unit washer and dryer, fast Wi-Fi, and dedicated parking. Perfect for couples or guests seeking a peaceful, comfortable stay near the beach. Consistently rated 5⭐ for cleanliness, comfort, and communication. Ideal for couples seeking a peaceful, comfortable beach stay.
Beachfront Resort, Ocean View, Pool, Tennis, Gym
Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.
Cozy Studio - quick walk to #1 Siesta Key Beach!
Recently renovated and updated! Adorable studio just steps from Siesta Key Village, and a quick walk to the beach. Spend your day exploring the key, swimming in the ocean, and experiencing the local restaurants and shops. Enjoy coffee in the mornings on the patio, and use the available bikes to catch a beautiful sunset each night. **Please note: - No excessive noise or Parties/Events will be allowed** - No Smoking inside the unit** - Quiet hours from 10 PM to 7 AM**
Sea Shell Ocean View On Beach Walk Everywhere Pool
Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 325+ reviews that ave FIVE STAR!
Siesta Key Beach Front Condo
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.
Beautiful White Sand Siesta Key Beach
This studio has lots of space and is across from the pool and just a few short steps from the beautiful Siesta beach. Known for it powder sand white beach and tropical breeze. Average Temperature is 70. The two large pools are heated all year. This unit has one king mattress . There are shuffleboard courts an tennis court and is close to everything.
Popular amenities for Siesta Key vacation rentals
Other great vacation rentals in Siesta Key
Luxury 3/3 with Heated Pool, Spa, & Putting Green!
Cozy Siesta Key Dream Inn Rental < 1/2 Mi to Beach
New! Siesta Beach Guest House with pool!
Beach Retreat - Jamaica Royale Unit #52
Surf Shack- Walk to Village/Boat Dock Included
Siesta key getaway!
Siesta Key condo with beach access - GBB 1204
Siesta Cool : Only Minutes Walk to Siesta 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 | $361 CAD | $463 CAD | $500 CAD | $430 CAD | $348 CAD | $346 CAD | $345 CAD | $312 CAD | $281 CAD | $292 CAD | $318 CAD | $368 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.
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 $96 CAD 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 and 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
Wifi availability
2,080 of Siesta Key vacation rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Beachfront, and Free parking on premises across Siesta Key rentals
4.8 Average rating
Siesta Key stays are highly rated by guests—averaging 4.8 out of 5!
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