Holiday rentals in Siesta Key
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Top-rated holiday 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.
Siesta Beach, 5 minutes from downtown.
My place is close to art and culture, restaurants and dining, great views, the Siesta Beach, Turtle Beach, and family-friendly activities. You’ll love my place because of the neighborhood, the comfy bed, the kitchen, and the coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids). Its located right next to the north bridge to Siesta Beach North Bridge Outlook Park, you can walk to the water. Certificate Number – The certificate number [VR24-00082]
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.
SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!
Your "Beach Home" w/ heated pool is a private home 1 and 1/4 mile drive to Beach Access 12 on Siesta Key. 3bedroom/2bathroom. It's ideal for families/couples. Everything you need for a great vacation!Fully equip kitchen,towels/linen, laundry room . Large pool w/ gas bbq & patio area. Use our chairs, cooler,umbrella,beach cart.STRICT OCCUPANCY OF MAX 6 PEOPLE INCLUDING INFANTS/KIDS AT HOUSE. NO OUTSIDE GUESTS DAY/NIGHT. DO NOT BOOK IF YOUR GROUP IS LARGER. No Pets. Min Age 26 to book
The Palm Bay Club on Siesta key Beach
Welcome to The Palm Bay Club on Siesta Key Beach Enjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips
Newly Remodeled Luxury Beach Villa on Siesta Key!
The newly remodeled 2 bed / 2 bath Villa sleeps up to 6 people. The Master bedroom features a king-size bed with an attached bathroom and HD TV and entertainment system. The Guest Bedroom features one twin size bed, a bunk bed with a full-size bottom bed, and a HD TV. The comfortable living room is furnished with plenty of seating, a HD flat screen with 5.1 Dolby surround sound system and bar area. The gourmet kitchen is loaded with anything you'll need for cooking and entertaining!
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.
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. VR24-00265
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.
Luxury Canal-Front Home + Heated Pool Near Beach
This is a thoughtfully renovated canal-front residence near Siesta Beach. A private pool and screened patio offer a refined and tranquil retreat with direct canal views. Bright interiors and carefully curated details create an atmosphere of timeless, understated luxury. Just an 8-minute walk from the world-famous beach, yet surrounded by complete peace and privacy. This home is designed for guests who appreciate discreet luxury and elevated comfort.
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.
Popular amenities for Siesta Key holiday rentals
Other great holiday rentals in Siesta Key
Sarasota Refuge & Pool Oasis
Gulf Gate Dream 2bd 2ba Htd Pool Beaches Shopping
Coastal Luxury*Pool*Hot Tub*Sunsets*Close to Beach
Family Getaway | 3BR Home Near Siesta Key Beach
FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay
AMI Bridgeport 202 -Beach View Retreat+Resort Pool
Walk to Siesta Village, Heated Saltwater Pool
Sunshine House- Sarasota Pool Retreat
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $339 SGD | $433 SGD | $468 SGD | $403 SGD | $326 SGD | $324 SGD | $323 SGD | $292 SGD | $263 SGD | $273 SGD | $298 SGD | $345 SGD |
| 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.
Quick stats about holiday rentals in Siesta Key
Total holiday rentals
Explore 2,090 holiday rentals in Siesta Key
Nightly prices starting at
Siesta Key holiday rentals start at $90 SGD per night before taxes and fees
Verified guest reviews
Over 37,170 verified reviews to help you choose
Family-friendly holiday rentals
1,660 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 410 rentals that welcome pets
Holiday 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 holiday 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!
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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
- Tampa Convention Center
- The Don CeSar
- Lakewood National Golf Club
- Myakka River State Park