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Holiday houses in Siesta Key

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Top-rated holiday rentals in Siesta Key

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Guest favourite
A spacious bedroom features a modern white bed with plush pillows and a decorative brown pillow. A mirrored closet reflects the elegantly decorated space, which includes a stylish bedside table and soft lighting from a lamp. Natural light filters through the vertical blinds.
Condo in Siesta Key
4.93 out of 5 average rating, 113 reviews

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.

Top Guest favourite
A compact sleeping area is furnished with a wooden bed frame and a colorful assortment of throw pillows. A modern air conditioning unit is mounted above, while a bedside table holds a lamp. Light streams in through the window adorned with wooden blinds.
Apartment in Bayou Oaks
4.97 out of 5 average rating, 235 reviews

Modern Private Apartment 1 Block from Sarasota Bay

One block from Sarasota Bay - completely remodeled and fully furnished guest apartment with a Miami deco feel. The unit is a little over 300 sf with full kitchen, one bathroom w/ shower, comfy queen bed, several stools/ chairs, flat screen tv, wifi, off-street parking, six USB ports for easy charging and sitting area outdoors on front porch. Five minutes to downtown or SRQ airport, 15 minutes to Lido Beach, and 25 minutes to Siesta Beach with easy access to University Parkway or Fruitville Rd.

Superhost
Bungalow in Siesta Key
4.85 out of 5 average rating, 20 reviews

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

The Siesta Key Bungalows offer a heated pool, courtyard & a dock on Heron Lagoon. This is a resort that has something for everyone. The Coquina Bungalow features a bright & airy one bedroom space; with a living room & full-kitchen. With a king-size bed, private patio & private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating & cooking utensils. The living room has a sofa that turns into a queen size bed, allowing for a max occupancy of three.

Top Guest favourite
A charming outdoor patio features a wooden pergola draped with fabric, providing shade over a seating area with four chairs. Lush greenery, including a palm tree, surrounds the cottage, nestled on a gravel area, creating a serene and inviting atmosphere.
Home in Sarasota
4.99 out of 5 average rating, 120 reviews

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!

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.
Condo in Siesta Key
5 out of 5 average rating, 143 reviews

❤️ 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

Top Guest favourite
Apartment in Sarasota
5 out of 5 average rating, 239 reviews

Modern 1BR Near Siesta Key + Private Parking

Private coastal retreat minutes from Siesta Key Beach. This spacious 950 sq ft upstairs apartment features soaring ceilings, a bright open layout, and a private entrance. Enjoy a king-sized bed, full kitchen, in-unit washer and dryer, fast Wi-Fi, and dedicated parking. Perfect for couples or guests seeking a peaceful, comfortable stay near the beach. Consistently rated 5⭐ for cleanliness, comfort, and communication. Ideal for couples seeking a peaceful, comfortable beach stay.

Guest favourite
A screened lanai features a round table with two white chairs, providing a clear view of the Gulf of Mexico. Tropical greenery and a paved area with beach chairs are visible in the foreground, framed by large windows that allow for natural light.
Condo in Longboat Key
4.9 out of 5 average rating, 206 reviews

Beachfront Resort, Ocean View, Pool, Tennis, Gym

Beachfront on beautiful Longboat Key, this condominium offers all the amenities of a resort with the privacy and seclusion that has Silver Sands Beach Resort guests returning each year. Enjoy a coffee on your private patio looking at the Gulf and the beach. Relax on our private beach, walk on our soft white sand, take a dip in our heated beachside pool, or enjoy complimentary chaise lounges and beach umbrellas while breathing in the fresh air. You can't get closer to the beach.

Guest favourite
Guest suite in Siesta Key
4.9 out of 5 average rating, 194 reviews

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**

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 Sarasota
4.94 out of 5 average rating, 70 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.

Guest favourite
An aerial view of the Sea Shell condominium displays a four-story building with balconies facing the ocean. The bright blue sky and ocean can be seen beyond the structure, emphasizing the inviting coastal location.
Condo in Siesta Key
4.92 out of 5 average rating, 148 reviews

Sea Shell Ocean View On Beach Walk Everywhere Pool

Enjoy ocean views in this 2 bed 2 bath spacious beach side 4th floor condo at Sea Shell Updated coastal decor across from Capt Curts, restaurants, grocery, coffee, ice cream Easy to WALK everywhere No car needed Perfect location Great for families Sleeps 6- 1 king & 2 queens & walk in closets Balcony with GULF views Private beach steps away from bldg. Free beach loungers. POOL Siesta Beach #1 in US Quick Wifi Superhost- 325+ reviews that ave FIVE STAR!

Top Guest favourite
A bright living area features large glass sliding doors that open to a balcony with ocean views. The space includes a cozy sofa, a sleek dining area, and a kitchen with modern appliances. Natural light fills the room, enhancing its airy feel.
Condo in Siesta Key
4.97 out of 5 average rating, 33 reviews

Oceanview Penthouse |1-Min Walk to Beach + Terrace

Now available New Years (had cancellation)Penthouse Aqualina Ocean view luxury penthouse. Breathtaking views from private 400sqft terrace! 20 steps from grounds to Americas best beach. Impeccably and fully renovated in 2023. 4-minute golf cart or free trolley ride to shopping dining and entertainment in Siesta Key Village. Travelers agree, this is the top ocean-view rental on Siesta Key! Book an escape today!

Guest favourite
A dining table is set with elegant glassware and neutral tableware. A decorative figurine of a crane stands between two tall candlesticks, with a soft ocean view visible through the screened lanai in the background.
Condo in Siesta Key
4.92 out of 5 average rating, 89 reviews

Siesta Key Oasis with Gulf Views

Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 5th floor unit has an extra large lanai that provides some of the best Gulf views on Siesta Key! 2 bedroom/2 bath PRIVATELY OWNED vacation condo is steps away from world famous, breathtaking Siesta Beach - consistently VOTED #1 BEST BEACH IN THE USA year after year!

Popular amenities for Siesta Key holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Siesta Key

Superhost
The front view of the bungalow features a welcoming entrance framed by tall palm trees. The light blue exterior contrasts with the lush greenery surrounding the property. A driveway leads to the entrance, inviting visitors to explore the charming cottage just steps away from the beach.
Cottage in Sarasota
4.89 out of 5 average rating, 9 reviews

Charming 2BD Bungalow Close to Crescent Beach!

Top Guest favourite
Condo in Siesta Key
4.84 out of 5 average rating, 122 reviews

Beach Retreat - Jamaica Royale Unit #52

Guest favourite
A spacious living and dining area is illuminated by natural light. A modern dining set for six is positioned next to a comfortable seating area with a couch. Lush greenery is present in the corner, while large windows invite views of the outdoors.
Condo in Siesta Key
4.92 out of 5 average rating, 63 reviews

Siesta Oceanview Retreat-1 min walking to beach

Guest favourite
Two armchairs with soft cushions are positioned beside a small round table, facing a large window. The window offers a view of greenery outside, with a patio featuring outdoor furniture and an umbrella visible in the background.
Apartment in Sarasota
5 out of 5 average rating, 9 reviews

Lake View Condo

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.
Condo in Siesta Key
4.92 out of 5 average rating, 223 reviews

Siesta key getaway!

Guest favourite
A welcoming living area features a gray sofa adorned with a patterned throw pillow. A coffee table holds magazines and a candle. A flat-screen TV is mounted on the wall, and a large window allows natural light to brighten the space.
Apartment in Sarasota
4.88 out of 5 average rating, 119 reviews

Siesta Key Village-Suite #2: A block to the Beach!

Top Guest favourite
Apartment in Bradenton Beach
5 out of 5 average rating, 16 reviews

Beachfront Studio Retreat on Anna Maria Island

Top Guest favourite
Guest suite in Sarasota
5 out of 5 average rating, 38 reviews

siesta breeze suite

When is the best time to visit Siesta Key?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$442 NZD$566 NZD$612 NZD$526 NZD$426 NZD$424 NZD$422 NZD$382 NZD$344 NZD$357 NZD$389 NZD$451 NZD
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.

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 $117 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, 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!

Destinations to explore

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  5. Siesta Key