Siesta Key Vacation Rentals

(250 rentals)
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Siesta Key Apartment
9 BR | 9 BA | Sleeps 25 | Quick View
Sleeps 25, 9 bedrooms, 9 bathrooms
3 reviews

$315

avg/night

$315
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Our seven apartment beach house is located 100 yards from the beach at Access #7 and one-block from the tropical Village of Siesta Key. Heated pool and spa along with our poolside surfboard bar and barbecue give our guests many choices to very their daily routine. Our 1st and 2nd floor above ground level ...

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Property Type

Siesta Key Apartment

Featured review

"Best place in the keys"

This place is one of a kind. It has everything you need. Our family rents out the entire place every couple years. The location is amazing...right by the village and beach. The rooms are clean and bug free!!! ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$345

avg/night

$345
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

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Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$327

avg/night

$327
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the magnificent Condo 306 at Crescent Royale! This exquisite residence boasts a spacious 2-bedroom, 2-bathroom floor plan that spans over 1225 sq. ft. of living space, providing ample room for relaxation and entertainment.The Master bedroom features a king-sized bed that exudes a regal ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$329

avg/night

$329
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to your personal slice of paradise, where the Gulf's breath-taking vistas are yours to behold! Unit 115 is a 2-bedroom, 2-bathroom retreat spanning a spacious 1,250 sq. ft. With its screened-in lanai and rear exit, you'll feel right at home in this cozy cottage-like setting.Siesta ...

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Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$297

avg/night

$297
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Beautiful views of the Gulf of Mexico's Siesta Key Beach. Dr. Beach's #1 rated beach in the U.S. can be seen from Crescent Royale's Unit 2E! This newly renovated (2024) and refurnished 2 bedroom, 2 bath condo is an end unit that features a wrap-around screened lanai that offers panoramic ...

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Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$289

avg/night

$289
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Home away from home.... I enjoy my coffee and cocktails at waterfront lanai and when I travel, I would love someone to enjoy it as well. I live in this condo, therefore, this unit has everything you may need and more. Boating, fishing, paddle boarding, kayaking, biking to Siesta Key Beach or free trolley ...

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Property Type

Siesta Key Condo

Featured review

"Spectacular"

We’ve been vacationing in Sarasota/Turtle Beach for over 10 years. This condo is our ABSOLUTE FAVORITE! Very nicely decorated & accommodating. We love that it is located on the bay. It is GREAT for fishing ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$292

avg/night

$292
avg per night
View Details

About this property

Condo 205 is an exquisite 1 bedroom, 1 bathroom, second-floor unit that offers over 820 square feet of comfortable living space. The fully stocked kitchen featuring full-size appliances provides the perfect opportunity to showcase your culinary skills.With a king-sized bed, the bedroom is designed ...

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Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to the beach lover's paradise, Condo 409! This little treasure trove offers you front-row seats to the Gulf of Mexico's breathtaking views from the Siesta Key Beach. With over 820 sq. ft of living space, this 1-bedroom and 1-bath condo flaunt a king-sized bed, a queen-sized sleeper sofa, ...

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Siesta Key Condo

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Siesta Key Condo
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms
11 reviews

$806

avg/night

$806
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

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 ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$573

avg/night

$573
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Enjoy the only three bedroom unit, with a spectacular view of Siesta Beach. On a clear day you can see all the way to Venice. Our spacious living room and dining room are very easy to entertain while you are here. Come and share our fabulous sunsets and calming sounds of the Gulf of Mexico.

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Pool

About this property

Attention beach lovers! You're in for a treat with our Condo 407, where relaxation is the order of the day. With 1220 sq. ft. of space, 2 bedrooms, and 2 baths, this condo is a slice of heaven. And its location? Just a hop, skip, and jump away from Siesta Key beach!Sleep like royalty in either ...

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Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to your very own slice of paradise! This breezy 1-bed, 1-bath suite boasts over 820 sq ft of living space, all to yourself. Take a deep breath and soak up the sun on the fourth-floor balcony, peeking out over miles of stunning gulf coast. With a plush king-sized bed, a fully-loaded kitchen, 2 ...

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Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Unit 104 at Crescent Royale! Only a hop, skip and jump (well, technically 100 steps away) from the pristine Siesta Key Beach where you should be prepared to get swept off your feet by the jaw-dropping, sunset views from your very own screened lanai.This cozy 1 bedroom, 1 bath unit boast ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$338

avg/night

$338
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Prepare to be spellbound by the magnificent Condo 304! This four-person stay has undergone recent renovations, including state-of-the-art furniture, modern gadgets, and two 55-inch smart TVs. The accommodation offers a king bed, queen bed, and full sleeper sofas, plus a pack-n-play for families with young ...

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Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 100 feet to Crescent Beach

$430

avg/night

$430
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date ...

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Property Type

Siesta Key Condo

Featured review

"Perfect"

Siesta Breakers is the perfect place to get away. This condo was wonderful and had everything we needed! You couldn’t ask for more beauty, comfort, and relaxation! This is the perfect place.

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Siesta Key House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Distance to beach: 300 feet to Siesta Key Beach

$809

avg/night

$809
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is a newly remodeled developers double wide four bedroom three and half bath penthouse unit with over 2,000 square feet that offers spacious living and entertaining areas for gatherings of family and friends with stunning panoramic views of the beach from its seventh floor location. The two master ...

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Property Type

Siesta Key House

Featured review

"Excellent vacation stay"

The condo and property were fantastic. The location and view of Siesta Key were amazing. This condo was great for our family vacation and the swimming pool was very clean and spacious. Definitely want ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$307

avg/night

$307
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience the ultimate beach escape at Unit 110, just steps away from Siesta Key Beach's dazzling, white quartz sand.This 2-bedroom, 2-bathroom unit offers approximately 1,250 square feet of charming living space. Upon entry, you'll be welcomed by a cozy living and dining area that flows ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to have your socks knocked off while enjoying breathtaking ocean views from this newly renovated condo.This 2 Bedroom 2 Bathroom upgrade includes all new LVP floors throughout, fresh paint and trim, upgraded Whirlpool stainless steel appliances, a Reme Halo all in one Whole Home Air Purification ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 1 miles to Turtle Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

New Listing Siesta Key, Florida !!100% 5 Star reviews on AirBnB and VRBO, save fees by booking direct through owner on this site. Discounts for multiple monthly stays.Available June, August, September and October and December 15, 2024 - January 18, 2025 Not available January 18 - May 16, 2025Hibiscus ...

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Property Type

Siesta Key House

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Condo 303, the perfect home to experience and cherish your dream beach vacation at the number one rated beach in America - Siesta Key.This recently updated 2 bedroom and 2 bathroom condo boasts a traditional decor vibe and a fully equipped gourmet kitchen featuring Bosch appliances and ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Unit 5B at Crescent Royale, an idyllic vacation destination. This charming unit boasts 2 bedrooms, 2 bathrooms, and over 1200 square feet of living space, all offering stunning views of the Gulf. The fully stocked kitchen features full-sized appliances, and all you need to bring is your culinary ...

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Property Type

Siesta Key Condo

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Siesta Key House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
10 reviews

$686

avg/night

$686
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Hurricane Update: We lucked out! Hurricane Helene did not flood our beach house except for the carport. We need to replace the hot water heater, the washer and dryer, and some walls and doors made of wood. Hurricane Milton damaged some soffits but they have already been repaired.A front row seat ...

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Property Type

Siesta Key House

Featured review

"Perfect Getaway!"

We SO enjoyed our stay there! Our stay was to celebrate a milestone birthday of our sister and we couldn't have asked for a better spot! Our main goal was to relax, catch up and enjoy the beautiful beach ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to bask in the breathtaking Gulf of Mexico sunsets from your very own private beach retreat! Unit 201 is a dream come true, complete with two inviting bedrooms and two modern bathrooms spread across 1210 square feet of pure luxury on the second floor. This condo's exclusive corner positioning ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$715

avg/night

$715
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to be impressed by the breathtaking luxury of this 5th-floor penthouse. Boasting three bedrooms, three bathrooms, and 1,700 square feet of beachfront living, this unit is sure to delight.Recently renovated, this penthouse features an expansive lanai, complete with all of the amenities you ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$371

avg/night

$371
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos ...

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Property Type

Siesta Key Condo

Featured review

"GREAT!!"

These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.

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Siesta Key Condo
3 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$452

avg/night

$452
avg per night
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Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Georgeous Gulf Views from this top floor unit which has a double wide lanai. Large, spacious unit that provides a retro environment that provides hollywood style for all to enjoy. You'll be able to interact with the beach, view and Gulf of Mexico as you view it all from your 7th floor. Come and Enjoy!

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$349

avg/night

$349
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Pack your bags and prepare to be swept off your feet by the jaw-dropping magnificence of Siesta Key Beach - ranked numero uno for its powder-soft quartz sand and sunset spectacles! Nestled on the third-floor corner, Unit 301 is a luxurious haven, boasting two bedrooms, two full bathrooms, and over 1220 ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to visit Condo 415 at Crescent Royale. This condo has been stirring up a storm with guests and our team alike. This funky little gem has a cult following of returning visitors, so you better act fast!The kitchen is equipped with all the bells and whistles you'd expect from a five-star ...

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Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom
9 reviews

Distance to beach: 150 yards to Crescent Beach

$370

avg/night

$370
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

1 Week Minimum Stay Required except during Feb 1 to the first Saturday after Easter when 2 weeks are required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great ...

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Property Type

Siesta Key Condo

Featured review

"Cancelled"

Due to Helena, our condo was cancelled. Would have loved to be there but understand why we couldn't. Best to the owners as they recover. I am giving 5 stars because this was not the fault of the owner.

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$336

avg/night

$336
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Condo 402, your ticket to paradise! Get ready to be swept away by stunning views of the Gulf of Mexico from the Master Bedroom and screened-in lanai. With over 1220 square feet of living space, there's plenty of room to soak up the sunshine and catch some z's.The Master Bedroom ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$361

avg/night

$361
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to uncover Siesta Key's hidden gem - Condo 400! This fourth-floor beauty boasts a jaw-dropping panoramic view of the Gulf of Mexico from the Master Bedroom and a screened-in lanai. With over 1220 square feet of living space, you're in for a treat.This condo is a beach-lover's ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
44 reviews

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within ...

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Property Type

Siesta Key Condo

Featured review

"You WILL NOT be disappointed with this condo!!!"

I have nothing but rave reviews of this rental - the location, the condo itself and the owners. We had an amazing time and they had anything and everything that you could want in the condo. We will definitely ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$392

avg/night

$392
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to be awestruck by the sheer beauty of Siesta Key Beach - your perfect vacation destination. The breathtaking panoramic view of the beach from unit 502 at Crescent Royale Condominiums will transport you to a paradise-like setting.Recently renovated, this unit exudes a modern and relaxed beach ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$389

avg/night

$389
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large ...

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Property Type

Siesta Key Condo

Featured review

"Beautiful Condo!"

This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Siesta Key

$321

avg/night

$321
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach ...

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Property Type

Siesta Key Condo

Featured review

"Great place!"

This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$351

avg/night

$351
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Experience the ultimate Siesta Key vacation with the picturesque unit 515 at Crescent Royale. This spacious 2-bedroom and 2-bathroom condo offers a serene ambience with stunning views of sunrise and sunset from the screened lanai. The unit features traditional Florida decor and comes fully equipped with ...

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Property Type

Siesta Key Condo

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Siesta Key Villa
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 bedrooms, 2 bathrooms

Distance to beach: 0.0 miles to Siesta Key

$383

avg/night

$383
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Escape to your private oasis on Siesta Key! This spacious villa offers the best of both worlds: direct access to the #1-rated Siesta Key Beach through your own private beach area, and stunning views of the Intracoastal Waterway where you can watch boats go by or launch your own kayak.Unwind in comfort ...

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Property Type

Siesta Key Villa

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$362

avg/night

$362
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Step into paradise and say hello to the newly transformed Unit 103, a crown jewel of Crescent Royale!With fresh furniture, top-notch media gear, sleek stainless steel appliances, and a touch of style in every corner, it's the perfect spot for your dream vacation.Picture this: you're ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$367

avg/night

$367
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to be whisked away on a wild beach adventure at Siesta Key Beach - the crème de la crème of all beaches, with its shimmering quartz sand and sunset extravaganza! Tucked away on the third-floor corner is the ultimate luxurious hideaway, Unit 301. With two bedrooms, two full bathrooms, ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
78 reviews

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

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Property Type

Siesta Key Condo

Featured review

"PERFECT BEACH CONDO"

This condo was amazing! The hosts were very polite and responsive. The condo was clean and well-equipped with everything we needed, including a beach wagon, chairs, sand toys, umbrellas, a boogie board, ...

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Siesta Key Villa
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
5 reviews

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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 open-concept villa boasts an incredible recently renovated chef’s kitchen equipped with high-end ...

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Property Type

Siesta Key Villa

Featured review

"Fantastic"

We had a wonderful week staying at this place. Definitely as advertised. Spacious, well-equipped and very clean. You can certainly travel light when you stay here. The neighborhood is quiet with a secluded ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

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Property Type

Siesta Key Condo

Featured review

"Just what we wanted."

Just returned from a week in Karen’s condo. Her place is perfect. The balcony and view were wonderful. Sitting and looking at the beach was so relaxing. The condo was great. Gave you a beach feeling. ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$347

avg/night

$347
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Unit 1D is a luxurious ground floor unit offering two bedrooms, two bathrooms, and 1,210 square feet of living space. The décor is traditional yet sophisticated, and the open concept kitchen is fully-equipped, making it a gourmet's delight. The apartment is ideally situated just steps away ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
9 reviews

$254

avg/night

$254
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

You have access to a deeded walkway from your condo to the beach while living directly on the intercoastal waterway with a great view. The intercoastal waterway, with its parade of all types of boats and dolphins swimming by, is visible from practically every room. This 2nd floor, 1 Bedroom/1 Bath ...

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Property Type

Siesta Key Condo

Featured review

"Wonderful!"

This condo is perfect. Comfortable lanai with an excellent view of the intercoastal. Well appointed home (Best one we have ever stayed in). Everything in the condo was organzied and easy to find. Walk ...

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Siesta Key Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$379

avg/night

$379
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience the ultimate in tranquil living at Condo 4 E, the most idyllic location in Siesta Key. This two-bedroom, two-bathroom condo boasts over 1220 square feet of living space, complete with breathtaking full Gulf and beach views.This bright, airy, end unit is the perfect retreat for relaxation, ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

Distance to beach: 20 feet to Turtle Beach, Siesta Key

$372

avg/night

$372
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful beach inspired decor...Fresh, airy and calm...perfect relaxing unit with all the comforts of home and more to enjoy a fun filled time at the beach!!!!!

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Property Type

Siesta Key Condo

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$304

avg/night

$304
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to soak up the sun and sea with Unit 309, a gorgeous 1-bed, 1-bath condo with over 820 square feet of pure bliss! Breathe in the salty air, dip your toes in the white quartz sand, and watch the sunrise from your screened lanai while sipping your morning coffee. When the sun sets, get ready for ...

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Property Type

Siesta Key Condo

Show less

Siesta Key Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$213

avg/night

$213
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...

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Property Type

Siesta Key Condo

Featured review

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

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Siesta Key Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

$365

avg/night

$365
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

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Property Type

Siesta Key Condo

Featured review

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...

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Siesta Key Condo
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This first-floor 1 Bedroom/1 Bath unit is ideally located just a few steps away from the highly acclaimed #1 Siesta Key Beach. Experience a stress-free day in the sun with all the necessary amenities provided, including chairs, an umbrella, towels, a cooler, and even a beach wheelie. All you need to bring ...

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Siesta Key Condo

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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

Find the Beach Vacation of a Lifetime with Siesta Key Vacation Rentals


Interested in a beach vacation for your next spring break or a long weekend away? Though the great state of Florida is known for its many scenic beach towns, there are some that cater more to those looking for a quiet, relaxing trip and some that are perfect for an exciting vacation full of non-stop fun in the sun. What if you could find a beach city that offers the best of both worlds for a truly well-rounded vacation? Enter Siesta Key vacation rentals. 

Nestled just south of Sarasota, Siesta Key, FL, is a spirited city along the Gulf Coast that offers just as many opportunities for R&R as it does for nightlife, watersports, and unforgettable adventures in the great outdoors. Though the island of Siesta Key itself is only about eight miles long, it’s jam-packed with enticing restaurants, unique shops, and glittering white sand beaches as far as the eye can see. 

As a major vacation destination along Florida’s Gulf Coast, there are many hotel options to choose from during your stay, with varying proximities to the beach. However, if you’re looking for a truly immersive experience during your trip to Siesta Key, you won’t get it at a crowded commercial hotel! 

Browse Siesta Key vacation rentals from FloridaRentals to find the perfect rental home for your beach vacation. Whether you’re looking for a sunny, romantic getaway for you and a loved one, or you’re bringing the whole family along, you’re sure to find an incredible property. Look for one that offers authentic local architecture, plenty of space to spread out during your downtime, and close proximity to all of the best features the city has to offer.

Siesta Key, Florida Travel Tips


There’s a reason why oceanside Florida cities like Siesta Key tend to be popular destinations during springtime. While temperatures may be warmest on average in the summer months, this time of year also has the highest levels of precipitation and humidity. Unfortunately, this makes it more difficult to enjoy outdoor activities. 

In mid to late spring, temperatures in the air and water are warm and comfortable without too much rain or humidity expected. This makes it easy to take part in all of your favorite pastimes, including surfing, boating, wakeboarding, or simply catching some rays on the sand. 

The closest airport to Siesta Key is the Sarasota/Bradenton International Airport, which lies around 11 miles north of the city center. Most visitors will fly into this airport for its easy access, though the area can also be reached relatively quickly by way of the Tampa International Airport.

How to Spend Your Vacation to Siesta Key House Rentals


It’s no surprise that most Siesta Key vacationers spend more time at the beach than anywhere else during their visits. The most popular beach destination is Siesta Key Beach, which was ranked the #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards in 2020. The gentle waves, powdery white sand, ample parking, and plentiful concession stands are just some of the reasons why many visitors choose to lounge their day away at Siesta Key Beach. 
Those who are interested in an unforgettable outdoor experience shouldn’t miss out on a trip out on the water with Adventure Kayak Outfitters. You’ll have the choice of a guided kayak tour of the nearby Exotic Mangrove Tunnels or a kayak rental to make your own adventure. You’re sure to spot some incredible wildlife like dolphins, exotic birds, and manatees along the way.

Yearly Events in Siesta Key


Siesta Key is closely linked with the nearby city of Sarasota. The two cities share many of their annual events, creating even bigger and better celebrations for locals and tourists alike to enjoy. 

One annual event that’s already become a mainstay in the local culture is the Annual Downtown Sarasota Craft Festival. This unique arts and crafts show features a wide variety of media, including pottery, paintings, jewelry, photography, and much more, alongside the scenic white-sand beaches. Visitors can peruse and purchase unique wares from local artisans, including soaps, spices, plants, and even kettle corn. 
Runners visiting Siesta Key can get in a great workout while supporting a great cause at the Annual Andrew Monroe Memorial Scholarship 5K Run/Walk. All funds raised during this event are donated to the Sarasota Community Foundation Scholarship, which helps local athletes train to their full potential and achieve their goals.  

Best Eats Near Siesta Key Rentals


Whether you’re in need of some casual seaside grub for the family after a long day at the beach or looking forward to a romantic date night with your significant other, Siesta Key has a huge variety of delicious and eclectic eateries fit for every taste and occasion. 

For a hearty steak, you can’t do much better than Summer House Steak & Seafood. This stylish eatery offers sustainably sourced steaks alongside a variety of unique sides, salads, beverages, and desserts that are sure to satisfy. Additionally, Summer House offers a full menu of seafood dishes. It takes full advantage of the city’s close proximity to fresh seafood and offers plenty of surf and turf options for hungry visitors. 

Island House Tap and Grill is a local favorite for casual yet memorable eats in Siesta Key. With a varied menu that includes everything from tacos to burgers to ceviche, as well as plenty of refreshing cocktails, you’re sure to enjoy a delicious and satisfying dinner with your family.


FAQ

How many vacation rentals are there in/around Siesta Key?

There are 250 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $139 per night with an average price per night of $361.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 46 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 50 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!