Vacation rentals in Siesta Key
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Top-rated vacation rentals in Siesta Key
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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.
Private fenced yard, BEACH GEAR, and king bed!
This King studio sleeps two and Includes a private fenced outside area with EVERYTHING you need for the beach! It also features Netflix, HBO Plus, Disney+, Hulu, and Amazon. Within a mile you have everything you need! Grocery, CVS pharmacy, great dinning, Evie's mini golf & driving range, and more. Located off Bee Ridge within 10 miles from Siesta beaches, St. Armands Circle Shopping, Lido Beaches, Downtown, Moet Aquarium, Kayaking Mangroves, Big Cat Habitat, Sky Zone, Rental boats, and more!
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.
Tropical Oasis Heated Pool Hot Tub Near Siesta Key
Escape to The Funky Fish House! Your private 2BR/3BD/2BA tropical oasis boasts a heated saltwater pool, bubbling hot tub, outdoor shower, and BBQ grill for endless fun, relaxation, and sun-soaked adventures. Just 5 miles from world-famous Siesta Key Beach and steps from Trader Joe’s, this elegantly renovated, fully stocked, stylish retreat invites families or couples to lounge, entertain, soak up the Florida sunshine, and enjoy the ultimate Sarasota vacation in absolute comfort and style!
❤️ 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**
Studio Minutes to Siesta key, Lido Key, and SMH!
Enjoy sunny Sarasota, FL in our studio apartment. Located between Siesta Key and Lido Key. You can walk to Southside Village, Sarasota Memorial Hospital (SMH) and Arlington Park. Enjoy the beautiful neighborhood and easy access to Legacy Trail. Approximate driving times to popular local destinations: Siesta Key - 10 minutes Lido Key - 14 minutes SRQ airport - 15 minutes St Armands - 10 minutes Downtown - 7 minutes
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.
Lovebirds’ Retreat | Steps to Siesta Key Beach
Romantic Honeymoon Suite 💕 Steps from Siesta Key Beach, this 1BR/2BA townhouse is perfect for two. Enjoy 2 balconies with sunset views of the beach, pool & gardens, central AC, and a heated lagoon-style pool for dreamy evening swims. Max 4 guests. Complimentary Wi-Fi, beach chairs & parking for 1 car make this the ultimate couples’ escape.
Popular amenities for Siesta Key vacation rentals
Siesta Key beach vacation rentals
Bayside Sunrise Cottage on Siesta Key!
Siesta Key For Me @ The Palm Bay Club
On the Beach; Siesta Key SunBum Studio
JULY AVAIL! Sarasota #1 Luxury Villa w/PRIV BEACH!
Private Beach Siesta Key Resort Jamaica Royale
Siesta Key Gulf Front Condo
Sunset and beach view from your balcony Unit 403
★Right on the beach ★ Relax and Enjoy ♥ Sunsets!
Siesta Key home rentals
Quiet Retreat-5mi to Beach-Hot Tub, Outdoor Shower
Charming Villa 14 mins away from Siesta Key Beach
The Lovely Stay |6 miles to Siesta Key Paradise
New remodel- 150 Yds to Beach and Restaurants!
Pool Courtyard, patio w/ fire pit, 2 mls downtown
The Peachy Beach House, steps to the gulf
Backyard Oasis, Htd Pool/Hot Tub, Beaches, No Fees
Beach Retreat•Renovated Pool Patio•Near Siesta Key
Family friendly vacation rentals in Siesta Key
Sun and Sea Gem on Siesta Key
Coastal Retreat near Siesta Key Beach and Downtown
Cozy Cottage by the Bay
Amazing beach view! Entire unit renovated!
Entire Standalone Villa,1.2k sf,1 block Lido Beach
Breathtaking Beachfront Views in Siesta Key
Sarasota Surf & Racquet Club Siesta Key Condo
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 | G$55,146 GYD | G$70,604 GYD | G$76,244 GYD | G$65,590 GYD | G$53,057 GYD | G$52,848 GYD | G$52,639 GYD | G$47,626 GYD | G$42,822 GYD | G$44,493 GYD | G$48,462 GYD | G$56,190 GYD |
| 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
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 G$14,622 GYD 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, 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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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Caspersen Beach
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- Manasota Key Beach
- River Strand Golf and Country Club
- Englewood Beach
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- The Don CeSar
- Myakka River State Park
- Gulfport Beach Recreation Area
- Lakewood National Golf Club