Siesta Key Vacation Rentals

(260 rentals)
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Siesta Key Condo
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$786

avg/night

$786
avg per night
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Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

**Any advertised discounts on website do not apply to this unit*** also the spiral staircase from this units balcony to the pool deck is no longer available.** THIS 2ND FLOOR LUXURY CONDO HAS ONCE AGAIN BEEN UPDATED WITH DESIGNER FURNITURE AND FURNISHINGS. ALL BEDS NOW HAVE 800 COUNT VERA WANG COTTON ...

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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

$282

avg/night

$282
avg per night
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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 Apartment
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
6 reviews

$205

avg/night

$205
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Vacation rental close to the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.*** It seems like a miracle that Midnight Cove II again was extremely ...

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Property Type

Siesta Key Apartment

Featured review

"Perfect"

We spent 18 days at the unit. The Unit is beautiful and clean. We enjoyed the location and hope to return next year.

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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

$286

avg/night

$286
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

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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

$308

avg/night

$308
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Welcome to Condo102 at Crescent Royale - a ground floor 2-bedroom, 2-bathroom condo boasting 1,210 square feet of beachfront opulence. The master suite is furnished with a king-sized bed, while the guest room features two queen-sized beds, making it the ideal location for families or couples seeking a ...

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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

Distance to beach: 300 feet to Siesta Key Beach

$314

avg/night

$314
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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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

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to dive into a tropical paradise at Condo 512! This dreamy dwelling boasts drop-dead gorgeous views of The Gulf and Siesta Key Beach from its fourth-floor location, giving you a front-row seat to America's number one beach!With two bedrooms and two full bathrooms, this 1220 sq ft condo ...

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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

$399

avg/night

$399
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Welcome to Siesta Key living in this charming ground floor duplex in Siesta Village. This tropical oasis offers a perfect blend of comfort and convenience. Nestled in the heart of the village, this unit offers 2 bedrooms and 2 baths with a large shared pool with the unit upstairs. This clean and bright ...

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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

$343

avg/night

$343
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to soak up some serious rays in our beachy haven, Condo 3D, located in the paradise of Siesta Key Beach! With 1220 sq. ft. of space, 2 bedrooms, and 2 baths, you'll have plenty of room to stretch out and catch some Z's.This beach-themed unit will transport you to a world of tranquility, ...

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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
10 reviews

Distance to beach: 0.5 miles to Siesta Key Main Beach

$245

avg/night

$245
avg per night
View Details

Key Amenities

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

About this property

Sweet Siesta Key Condo, Spacious and Quiet One Bedroom with 2 Queen beds. Please note that RATES ALREADY INCLUDE 13% TAXES. Condo is walking distance to Siesta Key Main Beach, and a nice 0.9 mile sidewalk walk (or bike or free trolley) to Siesta Key Village. Six new Pickleball courts and 2 Tennis Courts ...

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Property Type

Siesta Key Condo

Featured review

"Great place to stay"

Perfect location, situated right in the middle of the village and the south bridge. Restaurants and entertainment either way. It's a 2 min walk to the beach. The condo had everything I needed to make my ...

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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

Escape to a serene paradise at Crescent Royale, Siesta Key Beach, and experience the luxurious accommodations of Unit 107. This elegant unit offers two bedrooms, two bathrooms, and a spacious 1,250 square feet of living space, meticulously prepared to cater to your every need and ensure your comfort.Located ...

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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

$290

avg/night

$290
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

1 BEDROOM, 1ST FLOOR CONDO W/ PRIVATE SCREENED LANAI, NEW PERGO FLOORS, NEW KITCHEN, WASHER/ DRYER IN UNIT. LOCATED ONLY 1 BLOCK FROM THE SHOPS AND RESTAURANTS IN THE VILLAGE, 1 BLOCK TO THE BEACH, SEPARATE DINING ROOM, HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). POOL ...

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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

$375

avg/night

$375
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This is located on the 3rd floor of the clubhouses located on the beachside of Palm Bay Resort, just steps from the beach. Custom cabinets, granite counters, stainless kitchen appliances, screened lanai, 3 LCD TV's, stackable washer/ dryer in unit, and Wi fi. (Siesta 4 Rent does not offer tech support). ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2.5 bathrooms

$273

avg/night

$273
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$343

avg/night

$343
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Get ready to soak up the sun and surrender to the ultimate beachside escape! This third-floor 2 BR 2 BR condo will have you feeling like royalty with its stunning view of the Gulf of Mexico's pristine beaches. It's a year-round oasis where every moment will take your breath away!The open ...

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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

$343

avg/night

$343
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
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
9 reviews

$249

avg/night

$249
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 House | On the beach
3 BR | 3 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 3 bathrooms
7 reviews

Distance to beach: 300 feet to Siesta Beach

$739

avg/night

$739
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

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Property Type

Siesta Key House

Featured review

"Great property on the sand."

We had a great week despite the heat of summer. This house although dated was clean, cool and comfortable. It was a two minute walk through the back yard to the sand. We had a few minor house keeping ...

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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

$343

avg/night

$343
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare to embark on an unforgettable beach escapade at Siesta Key Beach, the epitome of all beaches, with its sparkling quartz sand and stunning sunset views. Nestled away on the third-floor corner is the ultimate luxurious hideaway, Unit 3C. With two bedrooms, two full bathrooms, and 1220 sq. ft. of ...

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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

$343

avg/night

$343
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
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 300 feet to Siesta Key Beach

$675

avg/night

$675
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
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom

Distance to beach: 300 feet to Siesta Key Beach

$272

avg/night

$272
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to this spacious 1 Bedroom 1 Bath unit, covering over 820 square feet of open living space. Located on the fourth floor, this unit comprises a king-sized bed, a fully equipped kitchen, a full bathroom, 2 flat-screen TVs, and a beach kit that includes chairs, a beach umbrella and towels.The ...

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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

$245

avg/night

$245
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Beautiful 1 Bedroom w/ den in Bayside community of Bay Oaks. 3 TV's, 1st floor unit with new furnishings. Sleeps 4, King in the master bedoom. The den has a twin bed and the livingroom has a sleeper sofa. No cable, Streaming only. Highspeed internet. (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT).1 ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$310

avg/night

$310
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

This is a Gem, 2nd/3rd floor Bayfront townhome, Living area on second floor and interior stairs lead to bedrooms on 3rd floor. Top of the line unit, offering travertine floors, new kitchen and baths, leather furnishings, 1/2 bath on the 2nd floor and 2 baths on the 3rd floor. Unit offers highspeed internet ...

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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
1 review

$281

avg/night

$281
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$422

avg/night

$422
avg per night
View Details

Key Amenities

  • Pool

About this property

**Any advertised discounts on website do not apply to this unit***Beautiful 7th floor beachfront condo in Crescent Arms North building. Screen lanai with beach views, washer/dryer right outside your door, elevator, heated pool, community grills and beach chairs provided by association. Located just about ...

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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

$166

avg/night

$166
avg per night
View Details

Key Amenities

  • Pool

About this property

Beautiful ground floor unit with screened porch at White Sands located just a few blocks from Siesta Key public beach. Unit sleeps 4, 2 Cable TV's , wireless internet ( Siesta 4 Rent is not responsible for tech support), community coin laundry right outside the door, covered parking, community pool ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$421

avg/night

$421
avg per night
View Details

Key Amenities

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

About this property

Comfortable private 3bedroom 2 bath home, open concept floor plan. The hone has a salt water heated pool. You can bike ride or walk to the main siesta key beach pavilion. There you can play pickleball or enjoy the service at the snack bar or continue out to the white quartz sand and clear waters of the ...

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Property Type

Siesta Key House

Featured review

"Definitely more than 5 stars for this property"

I’ve rented several Siesta Key properties, but this is definitely my favorite. The home is located very close to the public beach down a quiet cul de sac. The neighbors were all friendly and the area ...

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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

$275

avg/night

$275
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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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 1.5 bathrooms

Distance to beach: 250 feet to Siesta Key

$209

avg/night

$209
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

On Siesta Key - Quick walk to Siesta Key's world famous beach. Beautiful and private, this updated condo with granite kitchen and tile floors overlooks the bay inlet and boat basin. Across street from world famous beach. Fully amenitied condo in amentied condo complex. Large community pool, tennis ...

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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

$306

avg/night

$306
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
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$236

avg/night

$236
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Spectacular, modern 1 bedroom , 2nd Floor unit in Siesta Key Village offers great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 1 flat screen TV. Complex offers heated community pool and laundry ...

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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

$338

avg/night

$338
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Get ready to feel like royalty in our jaw-dropping silver-rated condo, in the heart of Florida's tropical paradise! Imagine waking up to the sound of waves gently kissing the shore, and sipping coffee while gazing out your window at the endless blue ocean. Our condo is the perfect spot for your dream ...

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Property Type

Siesta Key Condo

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Siesta Key Studio
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
5 reviews

Distance to beach: 0.3 miles to Siesta Key Beach access 10

$161

avg/night

$161
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

*Calendar month rentals only*******SPECIAL - March and April 2024 - $200 per night plus utilities - 14 night minimum****May - November (seven-month lease) - $1750 per month plus utilities May - November (three-month lease) - $2500 per month plus utilities December - $3900 per month plus utilities January, ...

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Property Type

Siesta Key Studio

Featured review

"Perfect peaceful pet friendly bungalow"

I recently had the pleasure of staying for three months in this cozy bungalow on Palm Island in the heart of Siesta Key. Nestled amidst lush vegetation and just a short walk from the beach and Siesta Key ...

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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

$272

avg/night

$272
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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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

$168

avg/night

$168
avg per night
View Details

Key Amenities

  • Pet friendly

About this property

Quaint 1 bedroom bungalow with Murphy Bed that folds into the wall during the day providing additional living space. Living room w/leather furniture, french doors opening to a private brick patio. 2 TV's with DVD players. Kitchen offers a mini convection oven w/built in rottiserie for up to full ...

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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

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Indulge in a perfect beach vacation at Condo 511, offering stunning views of The Gulf and Siesta Key Beach from the fourth floor. This 1220 square foot condo features 2 bedrooms, 2 full bath rooms and has a relaxing and casual beachy vibe, inviting you to unwind and enjoy America's top-rated beach.The ...

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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

$307

avg/night

$307
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Prepare yourself for a luxurious experience in your very own slice of paradise! Envision yourself savoring a refreshing beverage while taking in stunning sunsets from your private screened lanai, situated just a short distance from Siesta Key's pristine sugar sand beach. After a day filled with fun ...

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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

$355

avg/night

$355
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

Get ready to be swept off your feet by the ultimate beach paradise - Siesta Key Beach! With its sparkling quartz sand and gorgeous sunset views, this beach is THE place to be. And the cherry on top? You'll be staying in the most luxurious beach vacation home on the fourth floor, Unit 403.This ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$356

avg/night

$356
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Condo 4A, an exquisite tropical paradise that will undoubtedly leave you in awe! Situated at the Crescent Royale Condominiums, this luxurious vacation home stands out as one of the properties’ crown jewels, boasting stunning beachfront views of America's #1 beach, Siesta Key Beach, ...

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Property Type

Siesta Key Condo

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Siesta Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$526

avg/night

$526
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this ranch style home delivers on location and lifestyle. Featuring three bedrooms and two baths and a one-car garage, laundry room with washer and dryer. Gorgeous heated pool looks out to the grand canal, boat dock available to launch ...

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Property Type

Siesta Key House

Featured review

"Beautiful!"

Siesta 4 rent was very accommodating and responsive. It was very clean and great location. Would definitely rent again! Thank you!

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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

Stop the vacation rental search, the ultimate getaway is here! Get ready to sink your toes into the sand at Crescent Royale's vibrant community, where unit 106 is waiting for you with 2 bedrooms and 2 bathrooms, beautifully decorated with over 1250 sq. ft. of living space.The screened-in lanai ...

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Property Type

Siesta Key Condo

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

Distance to beach: 300 feet to Siesta Key Beach

$326

avg/night

$326
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Paradise, where you can bask in the glory of Siesta Beach, the number one beach in the United States, just 100 steps away from your doorstep! Condo 311 offers 2 bedroom and 2 full Bathrooms featuring over 1220 sf of open living space, with panoramic views of the gulf. Imagine enjoying your ...

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Property Type

Siesta Key Condo

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Siesta Key Cottage
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
4 reviews

Distance to beach: 0.5 miles to Siesta Key Beach

$180

avg/night

$180
avg per night
View Details

Key Amenities

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

About this property

*Calendar month rentals only*May - November (seven-month lease) - $2000 per month plus utilities May - October (three-month lease) - $2900 per month plus utilities December - $4900 per month plus utilities January, February, and March - $5900 per month plus utilities April - $4900 per month plus ...

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Property Type

Siesta Key Cottage

Featured review

"Excellent pet-friendly bungalow"

This studio was perfect for our 4 week stay in Siesta Key! The neighborhood is beautiful and quiet-and everyone we met was so friendly-to us and to our dog! Every day we walked into the Village-where ...

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

$463

avg/night

$463
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

BREATHTAKING, DIRECT OCEANFRONT, 2 BEDROOM / 2 BATH UNIT WITH PANORAMIC VIEWS OF THE BEACH AND SARASOTA SKYLINE. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S ( 65 LIV ROOM) I-POD DOCKING STATION, WASHER / ...

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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

$463

avg/night

$463
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool

About this property

BREATHTAKING GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE BEAUTFUL CRYSTAL SANDS COMPLEX. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH ...

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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

$517

avg/night

$517
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool

About this property

Completely Remodeled Beachfront 11th Floor unit at Crystal Sands. Gulf views from each bedroom and living room south on Crescent beach. (The view in picture #3) is the view from your screened lanai. Elevator down to Pool located on the white sands of Crescent Beach, beach chairs provided by Crystal Sands. ...

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Property Type

Siesta Key Condo

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Siesta Key Condo
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
1 review

$256

avg/night

$256
avg per night
View Details

Key Amenities

  • Pool

About this property

*** 20% OFF FOR WEEKLY RATES IN APRIL 2025*** ENJOY THIS SOUGHT AFTER GROUND FLOOR BAY VIEW UNIT WITH LARGE SCREENED LANAI OVERLOOKING THE CANAL. 2 TV'S W/DVD AND GORGEOUS POOL, TENNIS, WASHER DRYER IN UNIT. BEACH ACCESS RIGHT ACROSS THE STREET (NO BEACH CHAIRS OR EQUIPMENT PROVIDED) AND COVERED ...

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Property Type

Siesta Key Condo

Featured review

"Very Good Except"

We were given no access code for the tennis courts or pickleball courts. Unable to use because it was a SundaySome stole own personal noodles (2) that were on the Lanui. No lock on the Lanui.Washer ...

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

Distance to beach: 300 feet to Siesta Key Beach

$350

avg/night

$350
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Welcome to Condo 505, an opulent vacation home located in the Crescent Royale Condominiums at the stunning Siesta Key! This unit is highly sought after and promises breathtaking beachfront views over America's top-rated beach, offering 1220 sq ft of luxury living space.With two cozy bedrooms, ...

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Property Type

Siesta Key Condo

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

$641

avg/night

$641
avg per night
View Details

Key Amenities

  • Air conditioning

About this property

3 Bedroom/ 3 Bath Beachfront Townhome in Siesta Village, offering beautiful sunsets from your 2 balconies. Note that the beach directly in front of the property is private and may not allow access. Public beach access is always available just a few steps away. Go a block behind the unit to all the restaurants ...

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Property Type

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 260 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 $160 per night with an average price per night of $336.

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 50 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 54 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!