
Vacation rentals in Siesta Key
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Top-rated vacation 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!

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. Guest must be able to climb one flight of stairs

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!

❤️ 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

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!

Palm Bay Club! Resort Style Living on Siesta Key!
Meticulously Renovated Oversized, 2 Bedroom 2 Bath, Beach to Bay unit! Walk to the Famous Siesta Key beach, voted #1 beach in the US, with the worlds softest sand! This complex spans from the magnificent Bay with yachts and boats to the private beach with free access to Chairs and loungers, Cabanas are available to rent. Nearby Siesta Key Village has great shopping and restaurants. Access to free transportation around the island is right outside your door.

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.

Siesta Key Beach Front Condo
Located at CRESCENT ROYALE CONDOMINIUMS - one of the finest gated communities on Siesta Key. Large HEATED outdoor pool - this 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! This condo is nicely situated on the 2nd floor. The large screened lanai provides spectacular gulf coast views.

*NOV 50% LAST MIN! Sarasota #1 Luxery beach Villa
BOOK 2025 NOW, and stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

The Lovely Stay |6 miles to Siesta Key Paradise
Relax and recharge in this bright, cozy guest house just minutes from Sarasota’s top beaches, dining, and shops. Features: • Queen bed with soft linens • Kitchenette with essentials • Full private bathroom toiletries & fresh towels • Private entrance (100 ft from main house) • Quiet neighborhood • Shared pool access Perfect for a beach getaway or business trip!
Popular amenities for Siesta Key vacation rentals
Siesta Key beach vacation rentals

The Honeymoon Suite on Siesta Key Beach

Bayside Sunrise Cottage on Siesta Key!

Bradenton Beach Sunsets 1, Anna Maria Island, FL

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Sarasota Surf & Racquet Club Siesta Key Condo

Sunset and beach view from your balcony Unit 403

Oceanfront on LBK!

Shorewalk full condo AnnaMaria Beaches IMG
Siesta Key home rentals

Family Retreat w/Pool&HotTub 5 min to Siesta Key!

The Sand Castle - Backyard Oasis Mins from Siesta!

The Palms Away

Oasis by Siesta Key Beach and Downtown SRQ w/pool

Pool Courtyard, patio w/ fire pit, 2 mls downtown

Private Siesta Beach House Oasis with Heated Pool.

SIESTA BEACH HOUSE HEATED POOL☀️🌴3 MIN TO BEACH!!

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough
Siesta Key condo rentals

Beautiful White Sand Siesta Key Beach

Steps away from beach and village! #1 in Siesta!

Comfy Siesta Key Condo

Siesta Key Ground Floor Condo 2BR On Trolley Line

Sarasota Surf & Racquet Club Siesta Key Condo

Seaside on Siesta Key Beach

Oceanview Penthouse |1-Min Walk to Beach + Terrace

Siesta Key condo, beach access, heated pool
When is the best time to visit Siesta Key?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$55,210 GYD | G$70,686 GYD | G$76,332 GYD | G$65,666 GYD | G$53,119 GYD | G$52,910 GYD | G$52,700 GYD | G$47,681 GYD | G$42,871 GYD | G$41,826 GYD | G$45,590 GYD | G$49,773 GYD |
| 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 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 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 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.
All about Siesta Key
Siesta Key is an eight-mile-long barrier island off the coast of Sarasota, known for its soft quartz beaches, turquoise waters, and abundance of marine life. Due to its location on the western Florida shoreline in the balmy waters of the Gulf of Mexico, the island experiences ideal conditions year-round for swimming, paddling, and watersports. This small coastal community offers a host of recreational opportunities outside of the beach as well. Wander the Siesta Key Village, where you can find the many live music venues, boutique art shops, and souvenir vendors scattered throughout the small but lively downtown area. Check out one of the weekly farmer’s markets, spend an afternoon picking through the gift shops, or just lounge one the one of the white-sand beaches waiting for the sun to set over the Gulf.
What are the top things to do in Siesta Key?
Point of Rocks
One of the best snorkeling sites on Siesta Key, this limestone rock outcropping is home to abundant marine life and migratory bird populations. Calm waters and clear conditions make this a perfect place for beginners and experienced snorkelers alike. Expect to see schools of tropical fish, crabs, ocean sponges, and manatees during the summer. You may even get lucky and spot some of the area’s resident dolphins.
Siesta Key Drum Circle
The Siesta Key drum circle is a weekly tradition held on Sundays at Englewood and Siesta beaches throughout the year. Beginning about an hour before sunset, local artists and dancers kick off an evening of music and dancing. Large crowds gather to watch the festivities as onlookers are encouraged to dance or grab a drum and beat along.
Deep-sea fishing
Sandwiched between the vast Gulf of Mexico and Roberts Bay, Siesta Key is a year-round fishing destination. The reefs attract cobia and grouper, and if you venture further out you’ll be rewarded with tuna and wahoo. July is peak season for red snapper, while the fall bait migration off the Florida coast is a big draw for anglers from October onward.
Quick stats about vacation rentals in Siesta Key

Total vacation rentals
Explore 2,020 vacation rentals in Siesta Key

Nightly prices starting at
Siesta Key vacation rentals start at G$2,091 GYD per night before taxes and fees

Verified guest reviews
Over 35,910 verified reviews to help you choose

Family-friendly vacation rentals
1,600 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 390 rentals that welcome pets

Vacation rentals with a pool
1,620 properties feature pools

Rentals with dedicated workspaces
940 properties have a dedicated workspace

Wi-Fi availability
2,000 of Siesta Key vacation rentals include wi-fi access

Popular amenities for guests
Guests love Beachfront, Self check-in, 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
- Anna Maria Public Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- North Beach
- River Strand Golf and Country Club
- Splash Harbour Water Park
- Englewood Beach
- Manasota Key Beach
- North Beach At Fort DeSoto Park
- Point Of Rocks
- Don CeSar Hotel




