Siesta Key Vacation Rentals

(279 rentals)
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2 BR | 1.5 BA | Sleeps 6 | Quick View

6

Distance to beach: 200 yards to Siesta Key/ Crescent Beach

$232

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is unit B07 in the Casa Blanca resort located on the GULFSIDE (or Beach side) of the island.It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and a ...

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Property Type

Siesta Key Villa

"Our Casa Blanca experience"

This was our second vacation in as many years at Casa Blanca. Both times we selected the same unit number and both times we were simply delighted with the experience. Everything exceeded our expectations. ...

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2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 30 feet to Turtle Beach

$256

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront

About this property

Within just a few feet of the beach, our condominium home features a well equipped kitchen with granite counter tops, luxury vinyl flooring, a leather sectional couch, recliner chairs, teak furnishings, ceiling fans in all rooms, a 55 inch smart TV in the living room and a flat screen TV in each bedroom ...

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Property Type

Siesta Key Condo

"Oldie but Goodie"

We’ve traveled many places in our lives ( especially all over Florida) and this is one of our favorites. From the moment we requested more info on Bill and JoAnn’s condo until today at check out the ...

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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 800 feet to Siesta Key Beach

$166

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Brand New Condo, completely renovated. 2 Bedroom, 2 Bath large condo with granite kitchen and baths. Tile deck flooring. Full water views from our 6th floor location. See all the way to end of Anna Marie on clear day. Ringling bridge, downtown Sarasota, Lido and Bird Key views. King bed in master ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 6 | Quick View

7

Distance to beach: 200 feet to Siesta Key Public Beach

$321

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Single family home with private heated caged pool. Large open floor plan in living area to kitchen and enclosed pool and deck. 3 bedrooms, 2 of which are master suites with ensuite full baths, flat screen TV's, king beds, and sliding glass doors to either caged pool deck or open air sundeck. 3rd ...

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Property Type

Siesta Key House

"Siesta Beach"

Absolutely the best location! House was clean and has everything you need. Especially liked pulling wagon with all the beach items the short distance to the beach. Owners very helpful and quickly replaced ...

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$189

avg/night

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Key Amenities

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

About this property

Located on siesta Key in Sarasota, FL. The Palm Bay Club has two heated pools both Bayside and Gulfside. A private marina, dock, spa, tennis courts, fitness rooms and is located on Crescent Beach voted number one beach USA 2014Sarasota is located approximately 40 minutes South of Tampa. 1 1/2 hour ...

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Property Type

Siesta Key Condo

"Beautiful condo, great value!"

Spacious, very clean, comfortable, and a very competitive price for what you are getting, would definitely stay here again

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

This cozy beach house awaits your visit! Magnificent view of the Gulf of Mexico and evening sunset from lanai.... Peaceful Intercoastal inlet views and sunrise from front door...This little nest has been newly "stem to stern" furnished and equipped for your comfort. Coastal Living as its ...

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Property Type

Siesta Key Condo

"Perfect sunsets, great lanai and best location"

Nice quiet location on Turtle Beach. Best sunset views, right on the beach and all the amenities one needs for a perfect beach holiday. Added bonus of docks for boats/kayaks, heated pool and gated entry. ...

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3 BR | 2.5 BA | Sleeps 8 | Quick View

$449

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront

About this property

Enjoy our updated beach front 3 bed 2.5 bath condo. Just steps to the best beach in the world and also steps to beautiful Siesta Key Village entertainment district! All the amenities that you need to have a relaxing vacation.

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 400 feet to Siesta Beach

$660

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Prime location, being only two minutes walk to Siesta Beach entrance from this attractive three bedroom, two bath florida ranch! You live around the ground level pool with large patio doors openings from the two living areas and kitchen/dinning area. The home has been freshened with a very nice decor ...

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Property Type

Siesta Key House

"Perfect Beach Getaway at Siesta Key"

Out stay at this beach vacation home was nothing short of spectacular! From the moment we arrived, we were captivated by the stunning views of the ocean. The home is just steps away from the pristine, powdery ...

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2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 30 yards to Turtle Beach

$256

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

Bright and inviting, this popular unit has floor to ceiling sliding glass doors from the lanai, offering breathtaking third floor views. Beautiful white porcelain tile leads to new bamboo laminate flooring, which is just one of the many recent upgrades. The open kitchen has comfortable counter seating ...

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Property Type

Siesta Key Condo

"Holmes Beach Rental"

We loved our visit and loved the condo. The views were amazing . The only compliant would be the living room furniture was not comfortable. And the kitchen could use more kitchen items. But we dealt with ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

The lifestyleLive the Siesta Key lifestyle: • Short walk to the beautiful white sand beaches • Linger in the vibrant cafes and shops of The Village • Kayak along the key’s Grand Canal • Spend afternoons relaxing in the pool • Enjoy Siesta’s famous sunsets ...

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Property Type

Siesta Key House

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1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$235

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pool

About this property

Sandcastles, sunrises, sunsets on Siesta Key! Experience the ultimate Siesta Key vacation with unit 509 - a stunning penthouse on Siesta Key Beach that offers the perfect blend of relaxation and luxury.Located on the top floor, this one-bedroom unit features 820 square feet of cozy comfort with breathtaking ...

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Property Type

Siesta Key House

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2 BR | 1.5 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.3 miles to Siesta Key Beach

$181

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*July- December (six-month lease) - $3900 per month plus utilities July- October (four-month lease) - $3500 per month plus utilities December - $6900 per month plus utilities January, February, and March- $8900 per month plus utilities April- $7900 per month plus utilities May ...

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Property Type

Siesta Key Bungalow

"Perfect location to enjoy Siesta Key – wonderful hosts – stay here!"

Choose this home for its fantastic location, hosts and amenities - easy walk to the beach or downtown Siesta Key, but feels miles away from the crowds in its tropical setting.The home was perfect for ...

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1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$210

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$208

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Experience an idyllic vacation on Siesta Key with this capacious one-bedroom suite, extending over 820 sq ft. Enjoy the breathtaking views of the Gulf Coast from the fourth-floor balcony, bask in the sunshine, and revel in the serene atmosphere. This suite boasts a comfortable king-sized bed, two flat-screen ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

1

$376

avg/night

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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

"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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3 BR | 2 BA | Sleeps 8 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$512

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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4 BR | 2.5 BA | Sleeps 10 | Quick View

$545

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

Welcome to paradise! Your oasis awaits you. 4 bedrooms, 2.5 bath luxury townhome with a private pool is just 1 block from Siesta Village and only 2 blocks from the beach! Five star amenities include; Fully stocked gourmet kitchen with granite counter tops, top of the line stainless steel appliances, laundry ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.5 miles to Siesta Beach access 7

$148

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

"My stay at the Canal Place in Siesta Bungalows"

I am thoroughly enjoying my stay at Siesta Bungalows!!! My place is clean, quiet, and in a fabulous location!! I am about a 5 minute walk to the village and only a 7 min walk from the breathtaking Siesta ...

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2 BR | 1 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.3 miles to Siesta Key

$161

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

2 Bed, One Bath Top Floor Condo overlooking Siesta Key Beach Relax and enjoy spectacular Florida sunsets overlooking world famous Siesta Key Beach. This upscale, coastal design condo comfortably accommodates 6 and features 2 bedrooms, 1 full bath, a full kitchen and a comfortable living room overlooking ...

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Property Type

Siesta Key Condo

"4B Crescent Royale, Siesta Key, FL"

We had a great time and worked throught the Ian Hurricane with the owners. Can't wait until next year!

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1 BR | 1 BA | Sleeps 3 | Quick View

10

Distance to beach: 0.5 miles to Siesta Key Main Beach

$227

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

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

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Stunning views of the Gulf of Mexico's Siesta Key Beach. Dr. Beach's #1 rated beach in the U.S." and its world renowned white quartz sand is only steps from vacationing at Crescent Royale's Unit 5A! This newly (2021) renovated and refurnished 2 bedroom/2 bath "Beachy" condo ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 0.7 miles to Siesta Key Beach

$499

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Hard to find home near #1 Siesta Key Beach and Village with all the amenities. The space Welcome to island life!Luxurious 3 bed/2 bath with spectacular water view and walking distance to the village restaurants, shopping, and #1 beach in America!Enjoy your heated pool, hot tub, fire pit, and ...

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Property Type

Siesta Key House

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2 BR | 2 BA | Sleeps 6 | Quick View

$328

avg/night

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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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3 BR | 3 BA | Sleeps 6 | Quick View

$718

avg/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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1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$227

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Condo 504, a beach-themed oasis nestled in the tranquil paradise of Siesta Key Beach. Allow yourself to be transported to a world of relaxation and tranquility upon entering this one-bedroom unit located on the top floor, spanning 820 square feet. The unit provides spectacular Gulf and Beach ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$234

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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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6 BR | 5 BA | Sleeps 20 | Quick View

Distance to beach: 4 miles to Siesta Key Beach

$697

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Create memories with friends and family at this unique, and spacious property only 10 minutes from Siesta Key Beach. It is perfect for large groups or reunions as this house includes separate living spaces and has a total of 13 beds. Right behind the main house, you will find a fun area to relax, play ...

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Property Type

Siesta Key Estate

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1 BR | 1 BA | Sleeps 4 | Quick View

$136

avg/night

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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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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$253

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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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1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$183

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Unit 108 at Crescent Royale Condominiums, your very own piece of paradise. Leave your worries behind and allow the sandy beaches to soothe your soul. This ground floor unit exudes the charm of a beach cottage, with a back entryway that leads you just 100 steps away from the globally renowned ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$136

avg/night

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Key Amenities

  • Air conditioning
  • Pool

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 4TH FLOOR AND IS A 1 BEDROOM / 1 BATH CORNER UNIT. WASHER/DRYER IN UNIT. COMPLEX OFFERS POOL, TENNIS, 1 ASSIGNED COVERED PARKING SPACE. UNIT HAS 2 TV'S, DVD. HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT ...

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Property Type

Siesta Key Condo

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3 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$378

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

The unforgettable views from this top floor unit will surely have you coming back and telling your friends about. Siesta Key and Crescent Royale's beach front rentals. Hope you are here to have that much needed vacation. Relax, enjoy the spectacular Sunsets and Beach life views from this newly renovated ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$245

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Condo 312, the epitome of luxury beachfront living. This gold-rated condo boasts an array of amenities to ensure you have a memorable vacation. With two bedrooms, two baths, and an expansive 1,220 square feet of living space, its beauty is simply breathtaking. Notably, it's situated right ...

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Property Type

Siesta Key Condo

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4 BR | 3 BA | Sleeps 8 | Quick View

$348

avg/night

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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

ENJOY THIS 4 BEDROOM, 3 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA ISLES. OPEN FLOOR PLAN WITH LOTS OF SPACE, HARD WOOD FLOORS, A CAGED PRIVATE POOL WITH STUNNING VIEWS FROM EVERY ANGLE. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND WIRELESS INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE ...

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Property Type

Siesta Key House

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2 BR | 2.5 BA | Sleeps 6 | Quick View

$444

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

Beautiful Crescent 2 Bedroom Penthouse Unit with partial Beach views, large balcony overlooking pool area in the center of the building and additional Beach Front pool offered. Appointed with Hardwood Floors, Large kitchen and laundry in unit, 3 TVs, Wifi internet( Siesta 4 Rent does not offer tech support). ...

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Property Type

Siesta Key Condo

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Studio | 1 BA | Sleeps 3 | Quick View

$165

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND POOLS. UNIT OFFERS A BRAND NEW QUEEN MURPHY BED, 32" LCD FLAT SCREEN TV, DVD / VCR AND CD PLAYER. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. COMPLEX ALSO ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

$253

avg/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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3 BR | 2 BA | Sleeps 7 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$315

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

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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1 BR | 1 BA | Sleeps 4 | Quick View

$205

avg/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

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$177

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to the fabulous Condo 209 at Crescent Royale! This condo features 1-bedroom, 1-bathroom pad is spacious, boasting over 825 sq. ft. of living space, leaving you plenty of room to spread out and relax.The Master bedroom is home to a king-sized bed that will make you feel like royalty. And there's ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

SIESTA KEY.GETAWAY Experience a luxury condo with a view. Located on the world renowned Crescent Beach at Siesta Key. Gulf and Bay Club is a 32 acre resort community with exceptional beach access, top notch amenities and amazing sunsets. 6 pickle ball courts. 5 hard court, 1 clay tennis courts. Gym. ...

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Property Type

Siesta Key Condo

"Perfect Stay for Relaxation and Fun!"

Our family had the pleasure of staying at this Gulf and Bay rental on more than one occasion. The condo is a hidden gem with a spectacular view, and just steps away from the beach. We could not have asked ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$169

avg/night

View Details

Key Amenities

  • Air conditioning
  • Pool

About this property

2ND FLOOR UNIT, COMPLEX OFFERS, POOL, WIFI AT THE POOL AREA ONLY. ( SIESTA 4 RENT DOES NOT OFFER TECH SUPPORT), NEAR SHOPPING, 2 BLOCKS TO THE PUBLIC BEACH ACCESS, END UNIT OFFERS A LITTLE MORE SPACE. 2 WEEK MIN. LAUNDRY FACILITY ON 1ST FLOOR. 1 King, 2Twin, 1SOFA BED. CLEANING FEE $185

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Property Type

Siesta Key Condo

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$304

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

Show less

4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 300 feet to Siesta Key Beach

$576

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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

"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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2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$231

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$121

avg/night

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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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2 BR | 2 BA | Sleeps 4 | Quick View

3

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$188

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

*Calendar month rentals only*May-October (six-month lease) - $3500 per month plus utilities November & December - $6900 per month plus utilities January, February, & March - $8900 per month plus utilities April - $7900 per month plus utilities50% deposit upon booking, balance 90 prior ...

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Property Type

Siesta Key Bungalow

"We Keep Coming Back"

It's all about The Lily Patch on Palm Island in the village of Siesta Key!!! We've love it so much that we've signed up again for 2021 (Winter #3) and sent in a donation to the neighborhood HOA this time. Bring ...

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$274

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 300 feet to Siesta Key Beach

$265

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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4 BR | 2 BA | Sleeps 8 | Quick View

$388

avg/night

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Key Amenities

  • Air conditioning
  • Private pool

About this property

A piece of Paradise..... Come relax in this beautiful 4 Bedroom, 2 full bath pool home offering large livingroom and family room, caged heated pool and spa, (spa is non-functional and is maintained at pool temperature.) 1 car garage ( owner keeps one car in garage), washer/dryer. Home located just 1 mile ...

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Property Type

Siesta Key House

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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 279 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 $86 per night with an average price per night of $255.

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 58 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 58 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!