Holiday rentals in Siesta Key
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Top-rated holiday rentals in Siesta Key
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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.
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!
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.
❤️ 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
Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach
The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a king-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional queen sofa-bed allows accommodations for three guests.
Toes In The Sand | Private Pool, Walk to Beach!
🦩Exclusive Amenities Include: • Private Heated Pool • 3 Minute Walk to Siesta Key Village • 1 Minute Walk to Siesta Key Beach • Outdoor Lounge Area • Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer • Starter Pack of Toiletry Essentials • Starter Pack of Home Essentials • Beach Towels, Chairs, Cooler, & Caddy • Gas Grill • Enhanced cleaning protocols by our CottageClean Team • Island Shuttle Transportation Available • Dog Friendly (1 dog up to 25 lbs with an additional fee)
Lux Pelican's Perch | Heated Pool + Hot Tub + Gym
BNB Breeze Presents: Pelican's Perch Welcome to Pelican's Perch, stunning Lux home. Located just a short drive from beautiful beaches and local attractions. Check out this fully loaded home. - Private Heated Pool - heated at NO extra cost from Nov 21 - April 1st - Built-in Hot Tub - Water filtration system - Beach Supplies - Luxe Modern New Construction - Garage Gym - Connected directly to the Legacy Trail with Bikes - Breville Espresso Machine w/ syrups
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. Enjoy 2 free bikes day rental with booking!
Unique tropical stay - 5 minutes to Siesta Key
Welcome to “The Stream” — a hidden tropical retreat tucked away in the heart of Sarasota. This one-of-a-kind space offers the perfect blend of seclusion and convenience. Just 5 miles from the world-famous Siesta Key Beach and 3 miles from downtown Sarasota. Stroll or bike to nearby cafés, acclaimed restaurants, boutique salons, Publix, Trader Joe’s, CineBistro, and more. Whether you’re here to unwind or explore, “The Stream” is your private paradise.
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
2/2 Beach House Apt on Siesta Key
Siesta Key Waterfront Apartment. Sleeps 6. Split plan 2 bedroom, 2 full bathroom “Beach House” w/ a full kitchen & recently updated! Bedroom 1: King. Bedroom 2: Queen. Living room: Sleeper sofa. 75” smart TV in the living room. A private screened lanai overlooking canal to Sarasota Bay. This is located in a super cute, quaint resort w/ other units. FREE KAYAKS & SUPs FOR GUESTS!
Popular amenities for Siesta Key holiday rentals
Other great holiday rentals in Siesta Key
Paradise on Prospect w/ Htd Saltwater Pool
Siesta Dunes 1st Floor Beach Front Retreat + Bikes
FL Mid-Century Hideaway (Full Bath+Outdoor Shower)
Ground Floor Ocean View: Open Wed & Thurs, $199/nt
Completely Remodeled "Beach House on Siesta"
Private/Peaceful Studio -Pet Friendly, Fenced Yard
Ben's Bungalow | 8 min to Siesta Key | Giga Wifi
Private apartment w/King bed+full kitchen
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $342 SGD | $438 SGD | $473 SGD | $407 SGD | $329 SGD | $328 SGD | $327 SGD | $295 SGD | $266 SGD | $259 SGD | $282 SGD | $308 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
How is the weather in Siesta Key?
Siesta Key enjoys a tropical climate with warm weather throughout the year. Summer temperatures can rise up to 90°F (32°C) while winter temperatures rarely drop below 50°F (10°C). The island gets a significant amount of rainfall, especially during the summer months.
What are some of the best things to do in Siesta Key?
Activities in Siesta Key often revolve around its beautiful beaches, where you can swim, sunbathe, or play beach volleyball. You can also explore the local shops and restaurants in Siesta Village, or take a boat tour to spot dolphins.
What is the best time of year to visit Siesta Key?
The most popular time to visit Siesta Key is during the winter and spring months when the weather is warm and comfortable. A notable local event is the Siesta Key Crystal Classic, an international sand sculpting festival that takes place every November.
What are the best places to stay in Siesta Key?
Popular areas to stay in Siesta Key include Siesta Village for its proximity to dining and shopping, Crescent Beach for its quiet atmosphere, and Turtle Beach for its family-friendly environment.
What are the best places to visit in Siesta Key?
Siesta Key is known for its stunning beaches such as Siesta Beach and Turtle Beach. You might also find exploring the Siesta Key Village and Point of Rocks interesting. The latter is a limestone formation on Crescent Beach attracting snorkeling enthusiasts.
What are some hiking trails in Siesta Key?
While Siesta Key is more known for its beautiful beaches, you can still explore walking trails such as the Palmer Point Beach trail or Turtle beach trail. These paths provide an opportunity to enjoy the island's natural beauty and spot local wildlife.
What are some family activities to do in Siesta Key?
Families can have fun exploring the Siesta Key beaches, perfect for swimming and building sandcastles. The Siesta Key Water Sports provide opportunities to engage in safe marine activities. For nature lovers, the Siesta Key Marina has dolphin watching tours.
What are some of the best day trip ideas in Siesta Key?
Popular day trips from Siesta Key include visiting the vibrant city of Sarasota, which has a lively arts scene, or exploring the Myakka River State Park, known for its diverse wildlife and hiking trails.
What types of vacation rentals are available in Siesta Key?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Siesta Key. From over 1,060 condo rentals to over 480 house rentals, we've got you covered.
Are there vacation rentals with a dedicated workspace in Siesta Key?
Yes! Work meets play with ease at over 940 vacation rentals in Siesta Key featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Siesta Key?
Four-legged friends are welcome in Siesta Key. Choose from more than 390 vacation rentals for guests traveling with pets.
Are there Siesta Key condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 890 condo rentals with pools in Siesta Key, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in condo rentals in Siesta Key?
Experience the best of Siesta Key with our condo rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do condo rentals in Siesta Key have a gym?
Absolutely! We offer over 320 condo rentals with a gym in Siesta Key. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Siesta Key have free parking?
Absolutely! We offer over 900 condo rentals with free parking in Siesta Key. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Siesta Key have self check-in?
Absolutely! We offer over 120 condo rentals with self check-in in Siesta Key. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly condo rentals in Siesta Key?
Siesta Key has more than 850 family-friendly condo rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Condo Rentals in Siesta Key?
Enhance your stay in our Condo Rentals with the most popular amenities: over 320 homes with a gym, over 120 homes with self check-in, over 900 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Siesta Key
Total holiday rentals
Explore 2,020 holiday rentals in Siesta Key
Nightly prices starting at
Siesta Key holiday rentals start at $13 SGD per night before taxes and fees
Verified guest reviews
Over 35,910 verified reviews to help you choose
Family-friendly holiday rentals
1,600 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 390 rentals that welcome pets
Holiday rentals with a pool
1,620 properties feature pools
Rentals with dedicated workspaces
940 properties have a dedicated workspace
Wifi availability
2,000 of Siesta Key holiday 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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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Caspersen Beach
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Vinoy Park
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Manasota Key Beach
- Splash Harbour Water Park
- Englewood Beach
- North Beach At Fort DeSoto Park
- Don CeSar Hotel
- Point Of Rocks