Siesta Key Vacation Rentals

(317 rentals)
Location! Location! location! Bayside Siesta Key

$206

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...

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Property Type

Siesta Key Condo

"Perfect"
Reviewed June 3, 2020

The unit was perfect for our family of four. It was very clean, spacious and in a great location. After a long day of being at the pool/beach, it was nice having a fully equipped kitchen to make meals ...

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Siesta Chillin Resort Condo Steps from #1 Rated Beach

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 200 yards to Siesta Key Crescent Beach

$167

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

We invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all the conveniences of home in an amazing vacation spot at The Anchorage Yacht and Tennis Club.When ...

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Property Type

Siesta Key Condo

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Couples and Family Friendly. Some pet friendly units are available too.

1 BR | 1 BA | Sleeps 4 | Quick View

2

Distance to beach: 20 yards to Siesta Key Beach

$198

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

We are full turnkey condos. Our laundry facilities, gas grills around the pool, in unit cleaning supplies and dishwasher detergent are complementary. We are easily within walking distance to the Main Siesta Key beach (100 ft & across beach road to access #10) and the "Village"(most of the ...

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Property Type

Siesta Key Condo

"Great Plae to Stay!"
Reviewed February 19, 2020

we wanted a central location and a nice place to stay and we got both! Clean, welcoming, staff was great. Free trolley right up the road and beach is a 3 minute walk. The pool was great, even a hot tub! ...

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Villa Champagne - Ask About $99 Down!

$425

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

"Indian Rock Beach Vacation"
Reviewed July 2, 2018

GREAT Views / Great house on beach / Quiet Our family of 9 had a ball

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BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS -RENOVATED 310B

$301

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront

About this property

op beachfront unit at Fisherman's Cove!! 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 to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront ...

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Property Type

Siesta Key Condo

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Amazing Ocean View Beach Front Property Directly on the #1 Beach in the USA-#113

1 BR | 1 BA | Sleeps 3 | Quick View

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

$257

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

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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Property Type

Siesta Key Condo

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Latitude Adjustment - Ask About $99 Down!

$454

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivalsThis includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

"Wonderful home-perfect location"
Reviewed January 7, 2020

We had a great stay at this home. It was very clean and comfortable and supplied everything we needed to enjoy the beach and pool. The kitchen was complete with everything needed to cook all meals- although ...

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Casa Tegula - Ask About $99 Down!

4 BR | 3 BA | Sleeps 12 | Quick View

1

$486

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

"Casa Tegula Review..."
Reviewed July 8, 2019

We LOVED Casa Tegula!!! The house was very clean and stocked with everything we needed. Location was wonderful, only a short walk to the ocean and shops. Sara at The Cottages on the Key was AMAZING and ...

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Tropical Resort-Like Oasis! 1 Br Siesta Palms Sea Spray #123

1 BR | 1 BA | Sleeps 4 | Quick View

1
Owner special: Filling up fast! Book your Tropical Escape to sunny Siesta Key! Complimentary bottle of wine.

$253

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Palms is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps to the Gulf ...

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Property Type

Siesta Key Condo

"Siesta Key Inn visit review"
Reviewed December 22, 2020

We went to Siesta Key for the first time Dec2-9. We had heard about Siesta Key Inn from a friend. We found our unit, #123 to be one of the cleanest places we have ever stayed in. It was so clean and private. ...

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Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Upscale -Renovated 205B

$246

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

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 to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

"A Beachfront Dream"
Reviewed December 21, 2020

A slice of paradise. This unit was well equipped and designed for comfort at the beach. The flawless sunsets and the intoxicating motion music of the waves will make us return often. A very homey unit...lovely ...

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Siesta Key Beach Front Ground Floor Condo104 Steps to the Beach WiFi

$284

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

About this property

Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6)If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience ...

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Property Type

Siesta Key Condo

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Crescent Cottage - Ask About $99 Down!

$413

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks –Upscale –Siesta Key 304B

$301

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

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 to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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Home away from home

2 BR | 2 BA | Sleeps 6 | Quick View

$274

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

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Property Type

Siesta Key Condo

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Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta key Unit 1BR 5239

$133

avg/night

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Key Amenities

  • Full Kitchen

About this property

SEASIDE VILLAS: This Siesta Key one bedroom garden apartment vacation rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, ...

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Property Type

Siesta Key Apartment

"Sunnyside properties"
Reviewed October 21, 2020

Beautiful week! Apartment was very clean!! We met Tina the cleaning machina! She was very helpful and gave us some beach towels

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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale 311B

$246

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

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 to the Gulf on all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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Sweet Tranquility! Siesta Key Inn Royal Palm #1B

2 BR | 2 BA | Sleeps 5 | Quick View

Owner special: Tired of Winter? Enjoy a week at beautiful Siesta Key Beach - Book Now!

$344

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to the Siesta Key Inn! Owned and operated on site by the Koch Family since 1979 (we are not an investor owned property). This Tropical Beach Get-away offers condos just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach. With no busy streets to cross, ...

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Property Type

Siesta Key Condo

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Isla Amor - Ask About $99 down!

$661

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Modernized Direct Waterfront Condo 2BR, 2B,HDTV, WIFI, Washer/Dryer, Gulf Lanai

$269

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool
  • Rentals by Owner

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

"Beautiful Condo"
Reviewed November 9, 2020

A-306 Beautiful clean condo with tile bath's & floors. Wonderful view from the sunroom. You can be almost on the beach without the sand & sunburn. Loved the big screen TV ! Kitchen had anything you might ...

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New Listing! Villa Fiesta - Ask About $99 Down!

$212

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Townhome

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Siesta Salt Life - Ask About $99 Down!

$616

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

"Wow !!! Best place to stay."
Reviewed October 28, 2019

Your villa was just amazing. The villas were very clean and very spacious. I felt like it was home. Everything you need to go on vacation, it was there for you from linens to beach towels and chairs ,bikes. ...

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Beach Time! - 2Br/2B Siesta Palms Sea Escape#225

2 BR | 2 BA | Sleeps 5 | Quick View

1
Owner special: Time to book your next Siesta Key Beach vacation! Comfy condo, Sunshine, blue skies, beach and pool.

$343

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Palms by the Beach is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps ...

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Property Type

Siesta Key Condo

"Wonderful"
Reviewed December 1, 2020

We absolutely loved it here. Everything was so nice. The room was so clean and decorated nice. All the furniture was so comfortable. We slept so good every night. The pool and hot tub was really nice and ...

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Seas the Day – 82

4 BR | 4 BA | Sleeps 13 | Quick View

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Casa Stolida - Ask About $99 Down!

$491

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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The Water is Great! Siesta Palms Sea Breeze #125

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Soak up the Florida Sunshine on Siesta Key! Email for last minute availability.

$253

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Palms by the Beach is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps ...

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Property Type

Siesta Key House

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Deluxe 6-Bedroom Siesta Key Townhouse Vacation Rental - With Heated Pool

$565

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

SEASIDE VILLAS: This Siesta Key combination of two deluxe 3-Bedroom townhouse rentals is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual ...

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Property Type

Siesta Key Townhome

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Villa Margarita-Ask About $99 Down!

$212

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Villa

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The Nautilus - Ask About $99 Down!

$983

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

"Beautiful Home"
Reviewed June 19, 2019

The Nautilus was a fantastic home on Siesta Key. Short walk to the beach and we had our own pool. House was well appointed and very comfortable and clean. We will be back and definitely recommend renting ...

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“SANDPIPER” Siesta Key Beach -Vote #1 beach in America with crystal quartz sand

$143

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTS RATES!VOTED #1 BEACH IN AMERICA! JUST MINUTES TO YOUR DOOR WAY. THREE POOLS, SHUFFLE BOARD, GRILLS, PRIVATE BEACH AREA, LAUNDRY FACILITIES, PATIO FOR COOKING AND EATING OUTDOORS. SHORT WALK TO SOUTH VILLAGE WITH RESTAURANTS, GROCERY STORE, NIGHT ...

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Property Type

Siesta Key Condo

"Sandpiper #23"
Reviewed January 8, 2020

The property was generally in good shape, clean and made for a pleasant stay. We also felt safe and the property was fairly priced.

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BOOK NOW April * Fantastic Bay View Condo* Siesta Key * #1 Beach of the US

$149

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Vacation rental with private beach on the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)*** STAY SAFE *** In response to COVID-19, additional safety and sanitation measures are taken ***Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is ...

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Property Type

Siesta Key Apartment

"Well equipped, artistic, and very comfortable"
Reviewed January 21, 2021

We especially appreciated the warm welcome of the host, Marion, and her wonderful artistic touches throughout the place. The condo is very well equipped with everything we needed to be comfortable, and ...

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*All New Villa* #1 Beach USA~ Gulfside Condo - Siesta Key

$200

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Our villa is located in Siesta Key, FL on Crescent (Siesta Key) Beach, FAMOUS for its powdery, sugar white sand and being VOTED #1 Beach in USA. The Beach has complimentary shade cabanas and beach chairsFeatures include 2 Bedrooms, 1Bath sleeping six with 1King and 2 queen beds. The kitchen is furnished ...

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Property Type

Siesta Key Villa

"Perfect relaxing getaway."
Reviewed December 16, 2019

Our stay at C-16 at Casa Blanca was fantastic. Literally a one minute walk to the beach. A huge heated pool and pretty close to everything you’d need while there. The Casa Blanca staff was super friendly ...

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Beautiful Renovated 2 Bedroom 2 Bath Waterview Condo, Pools, Tennis, Gym, Beach

2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.2 miles to Siesta Key

$236

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

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

"The most beautiful and perfect get-a-way!"
Reviewed May 6, 2020

This condo was so beautiful! It was newly renovated and the decor was just stunning. The views were so incredible and the location was perfect. It is a very VERY short walk to the beach, which we loved. ...

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Mermaids Lookout - Ask About $99 Down!

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$523

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Renovated 4 bedroom directly on No 1 rated beach. Unobstructed views of gulf.

$694

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

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Property Type

Siesta Key House

"Amazing!"
Reviewed December 2, 2020

Beautiful, gorgeous, breathtaking! If you are looking for a bungalow on the beach, look no further. Our family of five with 3 teenagers fit beautifully here. Wonderful accommodations with a stocked kitchen ...

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Tropical beach getaway at Sandy's Siesta Key Condo

2 BR | 1.5 BA | Sleeps 4 | Quick View

15

Distance to beach: 200 yards to Crescent Siesta Key Beach

$195

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

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Property Type

Siesta Key Condo

"Beautiful and relaxing!"
Reviewed January 10, 2021

This is a great condo that is close to everything. It is very clean and spacious. There was a beach buggy, coolers, and beach toys available to use. The kitchen is well equipped with everything you need ...

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"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2

$206

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!320 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (upstairs) - 2 bed/ 2 bath-dishwasher, heated pool, great back yard for BBQ and gatherings. Combine all four units ...

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Property Type

Siesta Key Condo

"Banyon 2019"
Reviewed June 22, 2019

Loved the old Florida feel. Great location. Wonderful courtyard. Since we had 3 units rented, 1 unit was friends of ours, we had a great time in the courtyard. Only drawback was having to enter courtyard ...

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Siesta Key Beachfront Condo with Gulf View!

$177

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

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

"Great Location"
Reviewed February 12, 2021

We rented this condo for two weeks to get away from the cold. The location is perfect -- loved listening to the gulf surf from the balcony and taking walks on the beach. Kevin and Missy were very responsive ...

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Spectacular Beachfront View and Location Directly On Siesta Key Beach Unit 404

$315

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Spectacular remodel with open concept design maximizing beach views and sounds. The million dollar view you always wanted and can now enjoy.Fully equipped modern, clean kitchen with beach view, stainless steel appliances, ice maker, dish washer, granite counters and back splashes and custom cabinets.Secure ...

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Property Type

Siesta Key Condo

"Great get away!"
Reviewed January 16, 2021

Best vacation ever. Beautiful beachfront views including sunsets over the water each night. Lovely condo. Well equipped kitchen. Five stars!

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Vinca - Ask About $99 Down!

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 5

$103

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key Cottage

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The Hummingbird - Ask About $99 Down!

6 BR | 6 BA | Sleeps 12 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 5

$536

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Coconut Grove - Ask About $99 Down!

$563

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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La Contento Casa - Ask About $99 down!

$449

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Beautifully updated 2BR condo with great gulf view

$219

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

The completely updated 6th floor unit in Casarina has a magnificent gulf view, exceptional pool, hot-tub and BBQ area, and a prime in-garage parking space, steps from the elevator.

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Property Type

Siesta Key Condo

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Villa Vista Mare - Ask About $99 Down!

$465

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Townhome

"Vacation 2020"
Reviewed August 10, 2020

I visited siesta key and loved my stay. Stayed in the village Evey thing was In walking distance.beach was walking distance

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"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

3
Owner special: Last minute 25% discount Feb 27- March 6!!

$206

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Private Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!318 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (upstairs) - 2 bed/ 2 bath-dishwasher, heated pool, great back yard for BBQ and gatherings. Combine all four units ...

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Property Type

Siesta Key Condo

"Great time!"
Reviewed March 2, 2020

We just needed to unwind from a 2 year ordeal with a 96&97 yo family issue and it worked. Recharging your batteries is a big part of life, so thank you for that. The place was nice, not fancy, which was ...

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Paradise Awaits! 2br Siesta Key Inn Royal Palm #2B

2 BR | 2 BA | Sleeps 5 | Quick View

Owner special: Rarely Available! Paradise awaits in this spacious 2Br/2B Condo. Steps to pool and beach.

$344

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

Welcome to our Beach Get-away...where we, The Koch Family, invite you to relax, unwind and enjoy our casual way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our Family owned and operated Tropical Siesta Key Inn. With no busy streets ...

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Property Type

Siesta Key Condo

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Sophie's Cottage - Ask About $99 Down!

$406

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Monarch Villa - Ask About $99 Down!

$346

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

View all property information

Property Type

Siesta Key House

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Beautiful Siesta Key Beach Condo-GREAT LOCATION! 3 Min WALK to Beach!

$265

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated condo, with two updated, tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...

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Property Type

Siesta Key Condo

"wow, couldn't have asked for better."
Reviewed September 12, 2020

This was the first time I have ever rented a condo and this place was amazing. The place was huge! The main bedroom had a queen bed (kinda hard) and tons of closet place. Bathroom was very nice and couldn't ...

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Florita's Key - Ask About $99 Down!

5 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 0.4 miles to Shell Beach

$421

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

View all property information

Property Type

Siesta Key House

"Wonderful beach front property!"
Reviewed November 4, 2020

We stayed at Angler's Cover in Redington Beach for a week and it was a great place to get away and relax on the quiet beachfront property. When we arrived at the condo the place was spotless and everything ...

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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°

Siesta Key condo rentals in gulf coast Florida's top barrier island

Siesta Key is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida. It’s known for its sandy beaches and friendly locals. Fine white sand and gentle gulf breezes keep visitors coming back year after year. An ideal escape for a couple looking for romance, or a family looking to escape the Disney or Panama City crowds.

Siesta Key has amazing beach front with available rentals for you. When staying in one of our Siesta Key vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you.

Climate

Prevalent sunshine and gentle coastal breezes should be expected daily. Sounds incredible, right? Well, it is. With well over 300 sunny days per year, you’d be hard pressed to visit Siesta Key at a “bad time”. Low humidity makes the area comfortable, as well as warm. Bring your sunblock to protect against UV rays and don’t forget a few pairs of swim trunks, as the warm gulf waters are perfect for boogie boarding and bodysurfing.

Getting around

From November to September the Siesta Key Trolley will take you from the southernmost part of the island to the north end. The 3 open air trolleys run 7 days a week from 8-Midnight between Turtle Beach to Siesta Village. They will pass by about every 20-30 minutes. So don’t worry too much about getting around this small barrier island. Plus, bike or scooter rentals are everywhere -- so you can exercise while you move from beach to beach.

For those who drive, two bridges link the island to the mainland. The north bridge, Siesta Drive, is within the City of Sarasota and provides convenient access to the city, its business and arts districts, and to the Sarasota/Bradenton International Airport via US Highway 41. The south bridge, Stickney Point Road, provides access to south Sarasota County and a direct route to Interstate 75.

Top activities and attractions

Let’s be serious: you’re visiting Siesta Key for the pristine beaches along the 35 miles of coastline. Here are the names to remember: Siesta Beach, Turtle Beach, and Crescent Beach. Each features soft quartz sand and warm gulf seas. The sand is cool on your feet, so you can take an extended walk by the ocean without fear.

Siesta Beach has relatively shallow waters and it is monitored by lifeguards year-round. Plus, there’s plenty of room to spread out and enjoy a long, relaxing day. Turtle Beach is the most active (think volleyball net and horseshoe pits) while Crescent Beach is known for its seclusion and relaxed atmosphere.

Just off the southern tip of Crescent Beach is Point of Rocks, one of the best places for snorkeling and underwater exploration along the Gulf Coast beaches. It is made up of large chunks of limestone covered with coral and sponges and a range of sea life inhabit these underwater formations.

Bring your clubs here, too. With over 100 golf courses in the area you’ll want to take advantage of the sunny days out on the links. There’s ample opportunity for water sports for those who shun dry land. Visitors can find companies offering kayaking, paddle boarding, deep sea fishing and much more.

Just north of Siesta Beach, Siesta Key Village has many stores ranging from hip and funky to high-end boutiques and, of course, we wouldn't be a beach town without the beach accessory and souvenir shops.

Events 

If you love carefully constructed creations, visit in May for the sand castle competition. Local sand artisans and amateurs try their hand at creating jaw-dropping scenery out of sand.

Every Sunday there’s the Drum Circle featuring a cacophony of sound from various instruments performed by locals and tourists. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants.

In April, the aptly named Siesta Fiesta takes place. Stroll along the beach while enjoying fine art and handmade crafts from 200 of the nation’s most talented artists and crafters. Showcasing an extensive collection of work ranging from life-size sculptures, spectacular paintings, one-of-a-kind jewels, photography, ceramics and more, this show truly has something for anyone. Complete with an additional green market, this spectacular show also features plants, body products, and tasty dips.

Siesta Key house rentals on FloridaRentals.com

Booking a condo for rent in Siesta Key on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!