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Holiday rentals in Siesta Key

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Quick stats about holiday rentals in Siesta Key

  • Total holiday rentals

    Explore 2,200 holiday rentals in Siesta Key

  • Nightly prices starting at

    Siesta Key holiday rentals start at €52 per night before taxes and fees

  • Verified guest reviews

    Over 40,870 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,820 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 390 rentals that welcome pets

  • Holiday rentals with a pool

    1,830 properties feature pools

  • Rentals with dedicated workspaces

    970 properties have a dedicated workspace

  • Wifi availability

    2,170 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!

Top-rated holiday rentals in Siesta Key

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A modern living room features a light-colored leather sofa and armchairs, complemented by a colorful area rug. A wall-mounted TV is positioned against a textured stone wall, with natural light filtering through sliding glass doors that lead to a screened-in patio.
Apartment in Siesta Key

❤️ Hidden Gem steps away from #1 beach 🏖 Siesta Key

Welcome to Mi Casa Siesta on 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

5.0 out of 5 average rating, 172 reviews
Top guest favourite
Bungalow in Sarasota

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Experience life 4 blocks from the Gulf, ½ mile to Siesta Key — America’s #1 Beach. Effortless access to Siesta’s white sand beaches, Sarasota’s dining/arts scene, St. Armand’s & Gulf Coast adventure! 2BR boutique bungalow • Sleeps 6 • 4 beds In Sarasota’s coveted ‘West of Trail’ Coastal District — marble chef kitchen, beach gear, Smart TVs, spa bath, laundry, fast Wi-Fi. Grill lobster under stars, unwind in your tropical garden & walk palm-lined lanes to cafés & glorious waterfront sunsets.

5.0 out of 5 average rating, 12 reviews
Superhost
A modern dining area is highlighted by a marble table with an elegant vase and tableware arranged for a meal. Stainless steel appliances and a large television are visible in the background, with natural light flowing in from sliding glass doors leading to an outdoor space.
Apartment in Siesta Key

Crystal House on Siesta Key Beach

This is an updated and renovated two bedroom suite on Siesta Key. Complete with marble dining table, stainless appliances and large televisions. There is a computer in the spare bedroom for your convenience along with an Xbox and DVD player. We tried to think of everything so please feel free to make suggestions after your stay. Your satisfaction is our number one concern. The sofa is a Laz-Y-Boy and is not a sleeper but is very comfortable!!! There is a set of twin-twin bunks in the main room!

4.88 out of 5 average rating, 146 reviews
Top guest favourite
A spacious living area features a comfortable sofa and two cozy armchairs. A wooden coffee table sits at the center, complemented by a geometric area rug. Large sliding glass doors provide natural light and lead to an outdoor seating area, showcasing a view of the beach.
Apartment in Siesta Key

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.

4.95 out of 5 average rating, 146 reviews
Top guest favourite
Home in Siesta Key

Steps to Siesta Key Beach! Sunset Balcony Views!

This beautifully appointed 2-bedroom, 1-bath condo (Sleeps 6) is centrally located directly across from the world-famous "sugar-white sands" of Siesta Key Beach. Unit 205 offers a perfect location with spectacular Gulf of Mexico sunsets from your private balcony. Enjoy a covered parking spot. The master suite has a King bed, a second bedroom with two twin beds, and a pull-out sofa in the living area. Nearby find rentals for bikes, scooters, water sports, parasailing, fishing, sunset cruise.

5.0 out of 5 average rating, 15 reviews
Guest favourite
The exterior of the condo displays a modern design with a light color palette. Palm trees are positioned around the landscaped area, and two garages are visible, along with a walkway leading to the entrance. The sunny sky enhances the welcoming appearance of the property.
Apartment in Siesta Key

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.

4.85 out of 5 average rating, 110 reviews
Top guest favourite
Home in Sarasota

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. *Brand new pool* VR24-00265

4.95 out of 5 average rating, 199 reviews
Top guest favourite
Flat in Siesta Key

Siesta Premier Location - The 'Calm of Siesta'

My place is right across the street from Siesta Key beach, family-friendly activities, and nightlife. You’ll love my place because of the location, the ambiance, the outdoors space, and the neighborhood. My place is good for couples, adventurers, business travelers, and families. Walking distance to the village and is at less crowded section of the public beach which equals perfect location!! Updated and beautifully decorated condo with breathtaking view of the beach, You will LOVE it!

4.94 out of 5 average rating, 143 reviews
Top guest favourite
A private patio with a round wooden table and two chairs overlooks a manicured lawn leading to the beach. Palm trees sway gently beside the outdoor seating area, offering a serene view of the Gulf waters in the background.
Apartment in Siesta Key

Beachfront Siesta Key | Gulf View + Private Beach

Sun Bum Studio is your Siesta Key Beachfront Escape Wake up steps from the white quartz sand of world-famous Siesta Key. Sun Bum Studio is located in the beachfront tower at Palm Bay Club, with a south-facing view of the beach and Gulf from the floor-to-ceiling glass doors and patio. Enjoy private Crescent Beach access with complimentary beach loungers, two heated pools, hot tub, fitness center, tennis and pickleball courts, fishing pier, boat docks, grills and free covered parking.

4.97 out of 5 average rating, 397 reviews
Top guest favourite
A single-story tropical home is presented with a light blue exterior and a metal roof. Lush palm trees and colorful plants border the pathway leading to the entrance. An outdoor umbrella sits near the entry, enhancing the welcoming appearance of the property.
Home in Siesta Key

Siesta Key Beach & Village 2BR/2BA Steps to Beach

This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located in the heart of Siesta Key Village. You will be within a 2 minute walk to Siesta Key Beach and Siesta Village. With a beach house décor and equipped with 3 smart TVs, WIFI, cable, refrigerator, microwave, W/D, grill, beach chairs, toys for the kids, beach wagon, 1 queen bed, 2 twin beds and sleeper queen sofa. This private beach home has everything you need for a beach vacation. Local ownership.

4.93 out of 5 average rating, 169 reviews
Top guest favourite
Apartment in Sarasota

Cottage on Siesta Key Beachside & Stunning sunsets

Come experience Siesta Key and relax in our beachside cottage. It is sure to refresh you , whether you prefer an incredible one of a kind sunset or a long leisurely walk on the beach with the cool sugar white sand beneath your toes! This is an escape you deserve. The pool is beautiful and conveniently located on your stroll to the beach. If you enjoy music , we are close to several places you can sit & enjoy under the Tiki Huts with refreshments!

4.92 out of 5 average rating, 172 reviews
Guest favourite
A modern living area showcases a comfortable sectional sofa and armchair, complemented by a wooden coffee table. A large flat-screen TV is positioned on a media console. Natural light floods the space through sliding glass doors that lead to a balcony, enhancing the open feel.
Apartment in Siesta Key

Spacious 2-Floor, 2BR, 2.5BA Condo Near Everything

A spacious and quiet 2-floor, 2 bedroom, 2.5 bathroom condo that lives like home and is close to everything Siesta Key offers. Spread out and enjoy YOUR vacation! Your condo features large rooms, comfy and modern surroundings, (2) Master Bedrooms upstairs, and you are steps away from a gorgeous heated pool that you can view from your lanai. This is the perfect condo for you and your family to relax in and simply enjoy your time in Siesta Key!

4.88 out of 5 average rating, 179 reviews

Popular amenities for Siesta Key holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Siesta Key's top sights

Siesta Beach

1,606 locals recommend

Sarasota Beach

80 locals recommend

Crescent Beach

70 locals recommend

Siesta Key Beach

169 locals recommend

Siesta Key

81 locals recommend

The Beach Club

70 locals recommend

Other great holiday rentals in Siesta Key

Top guest favourite
Apartment in Siesta Key

Oceanview Penthouse |1-Min Walk to Beach + Terrace

4.98 out of 5 average rating, 42 reviews
Top guest favourite
Guest suite in Siesta Key

Modern Siesta Key 2BR Gem | Near Village & Beach

5.0 out of 5 average rating, 13 reviews
Top guest favourite
Flat in Siesta Key

Beach Walk Bungalow

4.94 out of 5 average rating, 35 reviews
Guest favourite
A screened-in pool area features a clear blue pool surrounded by tropical greenery. Two lounge chairs with striped fabric are positioned nearby, alongside a shaded umbrella. The pool deck is spacious, inviting relaxation and leisure in a tranquil outdoor setting.
Home in Siesta Key

Siesta Key home 5 min from beach

4.95 out of 5 average rating, 58 reviews
Guest favourite
Home in Sarasota

Siesta Bliss ~ Luxury Waterfront Retreat

4.94 out of 5 average rating, 33 reviews
Top guest favourite
The image captures a vibrant sunset over the horizon, casting warm hues across the sky. Palm trees line the foreground, creating a tropical ambiance. The view also includes a peaceful road and glimpses of the beach beyond, emphasizing the proximity to coastal scenery.
Apartment in Siesta Key

Siesta Key Beach front 2 bedroom condo w/ parking

4.97 out of 5 average rating, 64 reviews
Top guest favourite
Home in Siesta Key

Siesta Key Village Home

5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Siesta Key

Walk To Siesta Key Beach & Village ; Renovated 2BR

4.99 out of 5 average rating, 70 reviews

When is the best time to visit Siesta Key?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price€242€312€348€276€233€241€220€199€179€186€202€234
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C18°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.

Destinations to explore