Holiday houses 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.
Luxury Apartment in a House Near Siesta
Large modern construction 950 sq ft 1 bedroom apartment. Beautifully furnished apartment attached to the side of the main house. This upstairs unit has a private entrance with a modern interior & high ceilings. The apartment offers 1 King bed, full kitchen, a bathroom w shower, a washer and dryer, 2 tvs. Nestled on a quiet street with easy access to Siesta Key. Located 1 mile from the Stickney Point bridge with easy access to Siesta Key on . Guest must be able to climb one flight of stairs
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!
Magical Guesthouse 1 mi from SRQ airport
@Aloe_Stranger Dreamy + fresh! This 1-bedroom guesthouse has a king bed, full bath, kitchen, washer/dryer, daybed + sleeper sofa. NEW STOCK TANK POOL! Full of style - it feels like you're in your own art installation. 1 mile from SRQ Airport, it boasts a great location as well cushy comforts. 1/2 mile from Sarasota Bay, 15 min from Lido Beach, 15 min from Siesta Key and many beaches around the Sarasota/Bradenton area. 10 min from downtown Sarasota, 1 mile from the historic Ringling Museum
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.
Your Modern Beachside Getaway!
Search no more… we have it all! Enjoy this spectacular, newly remodeled beachside home in Siesta Key, equipped with a modern kitchen, hotel luxury pillow-top bed, and high-end finishes throughout! Amenities include private beach access (beachside 3 minute walk), pool access, patio, courtyard, BBQ, parking, and more. And the cherry on top, you’re right across the street for a plethora of restaurants, shops, and conveniences giving you everything you need to enjoy the best of Siesta Key!
❤️ 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
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**
Private Suite • 10-Min Walk to Siesta Beach, Shops
🌴 Welcome to Your Cozy Siesta Key Getaway Relax in this private, well-appointed pied-à-terre located in a quiet, walkable neighborhood, just a 10-minute (0.5 mile) walk to Siesta Beach Access #12. . Perfect for couples or solo travelers looking for a comfortable, convenient home base near it all. The kitchenette is ideal for light cooking/reheating, and includes: Microwave, Refrigerator, Keurig Coffee maker, Teapot Small stove/oven, Basic dishware and utensils
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!
Cozy 1BR Beach Condo on Siesta Key!
Experience the best of both worlds in this beautiful bayside 2nd floor unit! Sea Club II offers the charm of Old Florida with its shell driveway and old oak and palm trees throughout the property. Relax by the upgraded bayside pool or enjoy Happy Hour by the Tiki Hut or on the open lawn and watch the boats (BIG and small) pass by on the intercoastal. Grills are available for guests to use by the pool area. We also have a new fishing pier and boat dock.
Popular amenities for Siesta Key holiday rentals
Other great holiday rentals in Siesta Key
Stunning Views from Spacious Condo on Siesta Key!
Beach Haven on Siesta Key Beach
Cozy Top-Floor Stay on Siesta Key
Dreamview • 1BR - Siesta Key Beach Sunset View
Siesta Sunsets Suite
Siesta Key Village-Suite #2: A block to the Beach!
Siesta Beach View : Pineapple Bungalow Efficiency
Affordable- Siesta Key- Short walk to everything.
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $458 NZD | $586 NZD | $633 NZD | $545 NZD | $441 NZD | $439 NZD | $437 NZD | $396 NZD | $356 NZD | $347 NZD | $378 NZD | $413 NZD |
| 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 $121 NZD 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 and kid-friendly amenities
Pet-friendly accommodation
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
Wi-Fi availability
2,080 of Siesta Key holiday rentals include Wi-Fi 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
- Caspersen Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Cortez Beach
- Amalie Arena
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- Manasota Key Beach
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- St Pete Beach
- Englewood Beach
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- The Don CeSar
- Myakka River State Park