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Holiday rentals in Siesta Key

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Top-rated holiday rentals in Siesta Key

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Top guest favourite
A charming yellow home is set against a backdrop of palm trees, with a brick paved driveway leading to a two-car garage. Lush greenery surrounds the property, providing a sense of privacy and tranquility.
Home in Siesta Key
4.91 out of 5 average rating, 122 reviews

Siesta Key, FL - Casa Berano

Quiet, private home on lovely Siesta Key. 1.6 miles from lovely #1 Beach in the country. 1.9 miles to Siesta Key Village. FREE shuttle to village & beach 7 days a week. Private saltwater pool/enclosed lanai. Spacious 3bd/3b. Pets, dogs only, welcome, pls add to your total guest reservation. Open floor plan, large living area. Kitchen opens into living area & 2 dining areas w/ large tables. 2 car gar. brick paved driveway, in home laundry. 6 Guests Max 2 pets Max (dogs only), under 50lbs

Guest favourite
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
4.9 out of 5 average rating, 134 reviews

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!

Top guest favourite
Home in Gulf Gate Estates
4.97 out of 5 average rating, 263 reviews

Your private retreat near Siesta Key Beach.

Completely Remodeled Private Retreat. COME RELAX, UNWIND, AND MAKE LASTING MEMORIES! From the moment you arrive, you’ll feel the calm, welcoming atmosphere that makes this property stand out. This spacious 3brm 2-bath features an amazing heated pool, a private backyard, and stylish finishes throughout. Whether you’re lounging by the heated pool, enjoying meals in the bright open-concept living space, or exploring the nearby beaches this home is perfect for an unforgettable vacation

Guest favourite
A view from above showcases the lush, landscaped grounds of the condo complex, featuring curving pathways and palm trees. In the foreground, a heated pool is visible, with beach access just beyond. The serene beach and expansive ocean create a welcoming atmosphere.
Apartment in Siesta Key
4.82 out of 5 average rating, 137 reviews

Sarasota Surf & Racquet Club Siesta Key Condo

Our newly renovated condo is located on Siesta Key's award winning Crescent Beach. Our unit is has all of the amenities of home for your convenience. The primary bedroom has a king sized bed and its own ensuite with walk-in shower. The second bedroom has 2 double beds and a large closet for all of your belongings. The complex has two heated pools, multiple charcoal grills and just steps away from the unit are 3 tennis courts and 2 pickle ball courts. Restaurants and shopping close by

Guest favourite
A cozy living room features a light-colored sofa paired with accent pillows. A flat-screen television is positioned across from a coffee table. Sunlight fills the space through large windows, enhancing the airy and open atmosphere. Neutral artwork complements the decor.
Chalet in Siesta Key
4.97 out of 5 average rating, 33 reviews

Beach Rd, 300ft to Beach Access & 500ft to Village

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.

Guest favourite
A tranquil backyard is framed by lush greenery, featuring a clear swimming pool with steps leading in. Outdoor seating is arranged around the pool, including lounge chairs and colorful Adirondack chairs. A hammock is suspended between trees in a relaxing corner.
Home in Siesta Key
5 out of 5 average rating, 38 reviews

Paradise In Siesta!

Come enjoy a little slice of paradise in this 3 bed 2.5 bath home located just a few minutes walk (.4 miles) to Siesta Key Beach & Siesta Key Village! Enjoy the white sand and crystal clear waters of Siesta Key Beach, hanging by the pool, or exploring everything Sarasota has to offer! This place will not disappoint! The home offers a fully equipped kitchen, deck, pool, grill, fire pit and rec room w/ ping pong table. Convenient location in the heart of Siesta!

Superhost
Home in Anna Maria
5 out of 5 average rating, 7 reviews

Mermaid's Treasure by Duncan Real Estate

Welcome to Mermaid's Treasure! A fabulous North-end beach vacation home with a private swimming pool, hot tub, and plenty of space for entertaining friends and family. This 2 bedroom and 2 bath getaway is just a quick walk away from pristine Gulf of Mexico beaches and is close to the famous Pine Ave, offering unique restaurants and shopping experiences. As you walk in, you'll notice the lovely beach vibe with a casual living area with comfy seating and a TV.

Guest favourite
A Tiki bar with a thatched roof provides a stylish overlook of a heated pool surrounded by lounge chairs. The design features natural wood accents and vibrant decorations, inviting relaxation and leisure. Sunlight reflects off the water, adding to the serene outdoor atmosphere.
Home in South Sarasota
4.95 out of 5 average rating, 73 reviews

Tiki Bar Paradise! Heated Pool & Gaming Oasis!

Welcome to one of our beautiful properties. 24/7 Host Support - no AI messaging or hidden fees. Gorgeous HEATED POOL & Tiki Bar. Corn hole, ring game, or water pong on dry land or play volleyball, basketball, or beer pong in the pool. Bring the competition inside to the Game Room to play billiards or any number of family card/board games. Relax in the cozy living room w/ fireplace & fully equipped kitchen. Minutes to Siesta Key, the Village & Downtown SRQ.

Top guest favourite
A wooden walkway leads from lush greenery to the beach, flanked by palm fronds. The clear blue sky meets the horizon, and the sandy beach stretches out with colorful umbrellas and sunbathers visible in the distance.
Villa in Siesta Key
5 out of 5 average rating, 20 reviews

Modern, Walkable, Updated, Private.

WALK/BIKE/TROLLEY to Siesta Beach and Village. Relax and unwind in our spacious, sun-filled villa that is situated in an idyllic private neighborhood. Enjoy quiet surroundings, perfectly situated within steps to all that Siesta Key has to offer. The community pool is heated and located in the center of the neighborhood just steps away from the villa. The entrance to the private pier is on our lane ready to show off the amazing Siesta Key skies at sunset.

Guest favourite
A mid-century modern home is framed by a large tree, with white walls reflecting the surrounding greenery. Potted plants add color to the entrance, while two decorative faces are positioned on a stone ledge. The area is bordered by white gravel, enhancing the peaceful ambiance.
Home in Siesta Key
5 out of 5 average rating, 8 reviews

Siesta Beach | Heated Pool | Pet Friendly |

☞ Sauna, Fire-pit, BBQ (gas) ☞ Giant Outdoor Chess♟️ ☞ King & 2 Queen Beds ☞ Ample Parking (RV, Boat, etc) ☞ Fast WiFi 🛜 ☞ 4 Smart TVs (largest 85 inches) ☞ Gourmet Kitchen Main side ☞ Kitchenette on Guest side ☞ 2 Onsite washer + dryers ☞ 2 Outdoor Showers 》30 mins to airport 》2 mins to Siesta Key Beach Bike to America’s #1 beach, morning coffee runs, sunset rides, live music, ice cream, shops or any of the amazing restaurants in Siesta Key village.

Guest favourite
The exterior of a single-story villa is showcased, surrounded by lush greenery and palm trees. A manicured lawn features various shrubs and plants. The building's neutral-colored walls are complemented by a terracotta roof, creating a harmonious blend with the tropical environment.
Home in Sarasota
5 out of 5 average rating, 20 reviews

Spacious Cozy Tropical Retreat!

You will be impressed with the new Kitchen. The spacious master bedroom has been designed with you in mind. King size bed, large walk in closet and private bath. Both bedrooms have brand new laminate flooring! Relax and unwind in the brand new leather reclining sofas and chair with a 65” smart TV in the main livingspace. The villa comes with high speed WIFI internet and premium tv channels to make you feel right at home. Private lanai with a great view.

Guest favourite
A bright living area features a white sectional sofa facing a modern fireplace set in a textured stone wall. A wooden coffee table sits atop a striped rug, with a beach-themed painting and a ceiling fan visible above, contributing to a relaxed ambiance.
Apartment in Siesta Key
4.88 out of 5 average rating, 115 reviews

Perfect Location in Siesta Key

Beautiful 1400 sq. ft townhome unit in the quiet, well-maintained and desirable Village West in Siesta Key. Relax and enjoy the finest crystal quartz sands just steps away. Only one minute walk to all shops, restaurants and main amenities in the famous Siesta Key Village.This 2 bedroom, 2 bathroom townhome offers split floor plan with cathedral ceiling. Everything included to have a seamless vacation.

Popular amenities for Siesta Key holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Siesta Key

Top guest favourite
An open-concept living and dining area is highlighted, featuring a white dining table with six chairs, a comfortable seating arrangement, and large glass doors leading to a balcony. A neutral color palette is complemented by a decorative mirror and modern lighting.
Apartment in Siesta Key
4.98 out of 5 average rating, 63 reviews

2 BR condo in Siesta Key w/ Private beach access

Top guest favourite
A serene outdoor space is highlighted by a heated saltwater pool and a six-person spa. Comfortable lounge chairs line the pool area, and an outdoor grill is situated nearby. The setting is complemented by a vibrant sunset, enhancing the tranquil atmosphere.
Home in Sarasota
5 out of 5 average rating, 84 reviews

Luxury 3/3 with Heated Pool, Spa, & Putting Green!

Superhost
Home in Gulf Gate Estates
5 out of 5 average rating, 4 reviews

Gulf Gate Dream 2bd 2ba Htd Pool Beaches Shopping

Guest favourite
Home in Holmes Beach
5 out of 5 average rating, 7 reviews

Pool, Bikes & BBQ Included! 2min to Beach!

Superhost
Bungalow in Sarasota
5 out of 5 average rating, 3 reviews

FlipFlopsOn III • ½ Mile Siesta Key • Walk to Bay

Guest favourite
A winding pathway is framed by lush green foliage and vibrant shrubs, leading toward a serene waterfront view. Large oak trees, adorned with Spanish moss, provide shade alongside the pathway, enhancing the tranquil outdoor environment.
Apartment in Siesta Key
4.92 out of 5 average rating, 223 reviews

Siesta key getaway!

Guest favourite
An outdoor area features a private pool surrounded by a stone deck, complemented by a hot tub and shaded by a large umbrella. Lush greenery lines the perimeter, with comfortable lounge chairs positioned near the pool for relaxation.
Home in Sarasota
4.95 out of 5 average rating, 120 reviews

Heated Pool & Jacuzzi walk to #1 beach in America

Top guest favourite
A vibrant sunset is captured over Siesta Key Beach, with palm trees silhouetted against the colorful sky. The horizon features a gradient of warm hues, creating a tranquil ambiance. Nearby structures are visible beneath the palms, offering a sense of proximity to the sandy shoreline.
Holiday home in Siesta Key
4.99 out of 5 average rating, 110 reviews

Siesta Beach View : Pineapple Bungalow Efficiency

When is the best time to visit Siesta Key?

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Avg. price€ 227€ 291€ 314€ 270€ 219€ 218€ 217€ 196€ 177€ 183€ 200€ 232
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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 € 60 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!

Destinations to explore

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