Siesta Key Vacation Rentals

(341 rentals)
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Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta key Unit 1BR 5239

$127

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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AVAIL APRIL & MAY: Relaxing Renovated Townhouse With Access to Crescent Beach

4 BR | 3.5 BA | Sleeps 5 | Quick View

2

Distance to beach: 0.3 miles to Crescent Beach

$259

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Managed by owner

About this property

Convenient: 3-minute walk to the beach. 4-minute walk to the Crescent Beach Shopping Center with the Big Water Fish restaurant, Pizza and Brew, liquor store, and the Toasted Mango for breakfast. 5-Minute walk to Captain Curts, the Tiki and the Crescent Club.6828 Midnight Pass Road is a townhouse ...

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Property Type

Siesta Key Townhome

"Amazing Island Townhouse close to the beach"
Reviewed August 15, 2021

WOW! This Siesta Key Townhouse was absolutely beautiful. Immaculately clean with all the amenities anyone could want/need. During the day (we were 2 couples/4 of us total), we took full advantage of the ...

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Seas the Day - Ask About $99 Down!

$692

avg/night

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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 ...

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Property Type

Siesta Key House

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Casa Blanca D18 Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$230

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Welcome to one of the closest villas to the beach! Technology upgrades include dedicated WiFi. The living room features a home theater 55" HD flat screen TV with DVD player and HBO provided compliments of the owner. Each bedroom has its own flat screen TV while the master bedroom also has a ...

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Property Type

Siesta Key Villa

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Luxury Condo, walk to Siesta Key Beach!

2 BR | 2 BA | Sleeps 4 | Quick View

4

Distance to beach: 0.5 miles to Siesta Key Beach

$153

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen
  • Managed by owner

About this property

Newly Renovated Vacation Rental on Siesta Key. Fully furnished, 2 bedroom/2 bathrooms in the prestigious Harbor Towers Yacht & Racket Club. Condo sleeps 4. King Bed in Master, 2 twin beds in second bedroom. New porcelain wood-look floors, new kitchen appliances, beautifully furnished, cable TV and ...

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Property Type

Siesta Key Condo

"Siesta Key paradise"
Reviewed September 21, 2021

The condo was in the perfect location, very clean. We were within walking distance to siesta key beach. Pool was nice and the bay was right there for fishing. Great place to rent:)

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Casa Blanca D03 Villa

2 BR | 1 BA | Sleeps 5 | Quick View

$188

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Quick notes: " 2 bedrooms, 1 bath " Sleeps 5 " Free-standing villa - no shared walls or floors/ceilings! " Private in-unit high-speed internet " Smart/HD TVs with Hulu in living room and bedrooms " Five-night minimum.Welcome to ...

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Property Type

Siesta Key Villa

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Siesta Sunset - Ask About $99 Down!

$514

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Full kitchen
  • Kid friendly

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 Condo

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Casa Blanca C15 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$217

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Enjoy your stay at our remodeled private (no shared walls) detached large 2 bedroom 2 bath villa on Siesta Key (Villa "C15" at Casa Blanca Vacation Rentals (CBVR) - no common walls, 1100 sq. ft., sleeps 6 people). We remodeled C15 with a new air conditioner system, kitchen appliances, bedroom/living ...

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Property Type

Siesta Key Villa

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Ocean front 2br/2ba Ocean View, only steps to #1 beach. Gulf Views

$228

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Oceanfront
  • Private pool

About this property

This 5th floor two bedroom, two bath condo is totally and completely renovated. Be one of the first guests to stay in this beautifully renovated condo. New tile throughout. There are two bedroom suites with private baths. Each bedroom has new slider doors that open to screened in lanai with beautiful ...

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Property Type

Siesta Key Condo

"Best Moms get away EVER!"
Reviewed September 8, 2020

Ruth was so amazing, Almost as amazing as her condo! She was so knowledgeable and so accommodating! Her remodeled condo is beautiful and love the extra touches. Owning rentals previously she did everything ...

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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

$300

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Managed 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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Vacation Paradise to Stroll the Beach....Siesta Key Inn Pineapple Palm#1D

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Relax and Unwind - take a Beach Vacation to Siesta Key Inn in our spacious fully equipped condo!

Distance to beach: 150 yards to Siesta Key Crescent Beach

$333

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Private pool

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

"House of sun"
Reviewed February 1, 2020

House of sun is everything you need for a perfect vacation . If your not in the mood for a beach day relax on the roof deck wich has an awesome view and Is very peaceful . Shops and restraints across the ...

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Casa Tegula - Ask About $99 Down!

4 BR | 3 BA | Sleeps 12 | Quick View

1

$654

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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

"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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Vinca - Ask About $99 Down!

1 BR | 1 BA | Sleeps 4 | Quick View

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

$138

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

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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Honeysuckle - Ask About $99 Down!

$411

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly

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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Casa Blanca B12 Villa

1 BR | 1 BA | Sleeps 4 | Quick View

$162

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Casa Blanca is within walking distance of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. ...

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Property Type

Siesta Key Villa

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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

$543

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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

"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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Casa Blanca C05 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$207

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Casa Blanca is within walking distance of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. ...

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Property Type

Siesta Key Villa

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La Casa Verde - Ask About $99 Down!

$523

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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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Crescent Beach, Siesta Key Old Florida Style 2 bed/1 bath budget-friendly!

$180

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Communal pool
  • Full kitchen
  • Kid friendly

About this property

Fun tropical colors! Relax in this Florida style first floor, 2 bedroom/1 bath, 800 s.f. located at Siesta Beach House condominiums. Quaint, comfortable and tastefully decorated beach apartment! Located gulf side of the road and only steps to the private piece of world famous Crescent Beach-beach chairs ...

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Property Type

Siesta Key Condo

"Wonderful private access to the beach!!!"
Reviewed June 16, 2021

We have stayed here multiple times. In fact, I booked late and stayed somewhere else one year and it was not the same, so now I make sure I book early enough to get this same place every year! Fob access ...

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Fishermans Cove FC Unit 311B. Siesta Key - Gulf - Front Retreat - 2 BR –

$302

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly

About this property

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

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Property Type

Siesta Key Condo

"Pleasant stay!"
Reviewed August 18, 2021

We rented B204 and the unit was fully equipped. The only ding would be the blinds that were broken in kitchen more of an eye sore than anything. I am awaiting the cleaning deposit return but other than ...

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Siesta Breakers SB Unit 515. Siesta Key - 2BR - Beachfront Condo on Crescent

$231

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...

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Property Type

Siesta Key Condo

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New Listing! Hidden Treasure - Ask About $99 Down!

$476

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 ...

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Property Type

Siesta Key House

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Seaside Cottage - Ask About $99 Down!

$475

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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

"Wonderful"
Reviewed May 3, 2018

Great place, very comfortable beds, all the items you need - kitchen equipped with great tools. Very clean.

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A special SECRET retreat...#26

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 100 yards to Crescent Beach

$202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Private pool

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen Air Dream sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

"Great place to stay"
Reviewed July 23, 2021

We loved the unit and the closeness to the beach and area restaurants. We would definitely stay here again!

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Seabatical - Ask About $99 Down!

$422

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Pet friendly

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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Blu Sky Cottage - Ask About $99 Down

$499

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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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The Hummingbird - Ask About $99 Down!

6 BR | 6 BA | Sleeps 20 | Quick View

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

$878

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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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Siesta Key Beach direct access from your front door

2 BR | 2 BA | Sleeps 6 | Quick View

3
LAST MINUTE DEAL 10/9 - 11/20: $1008/ week in November! 2 BR 2 BATH perfect location! 200 steps to beach easy walk to village!

$172

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly

About this property

Welcome to La Siesta Unit 112! This quiet 2-bedroom 2- full bath end unit is located on the ground floor of the La Siesta Condominiums complex with a direct walk out access to all Siesta Key Beach amenities. ***We are COVID friendly, clean, and have ANTI-VIRAL UV LIGHT TREATMENT HVAC system***. We are ...

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Property Type

Siesta Key Apartment

"Siesta key Beach Break"
Reviewed April 28, 2021

This was a lovely condo within steps a way from the beautiful beach! Perfect location from restaurants, shopping and grocery stores! The trolley made it easy to get around the island which was wonderful ...

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DEAL
Gorgeous Beachfront Condo directly on #1 Beach in USA - #111

1 BR | 1 BA | Sleeps 3 | Quick View

4

Distance to beach: 150 yards to Crescent Beach

$234

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Oceanfront

About this property

1 Week Minimum Stay Required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Kitchen fully remodeled in June 2017 with new top of the line appliances. New Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great ...

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Property Type

Siesta Key Condo

"Perfect in every way!"
Reviewed May 5, 2021

The condo had absolutely everything you would need, I was very happy with the amenities. The owner was very prompt with communication and I especially enjoyed the updates to the unit. The condo is situated ...

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Siesta Key Beach. November and December are Lovely!!

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 600 yards to Siesta Key Beach

$203

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen

About this property

There's plenty of room for everyone here at Our House. We have a split-level living area facing a large screen HDTV, so anytime you need a little down time from all the outdoor fun, settle in with your favorite movie, a bowl of popcorn, and frosty drinks. The kitchen's just a few steps away, and it's ...

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Property Type

Siesta Key Townhome

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Villa Cascada - Ask About $99 Down!

$498

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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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*All New Villa* #1 Beach USA~ Gulfside C-16- Siesta Key

$184

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Oceanfront

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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Casa Blanca B 03 Villa

1 BR | 1 BA | Sleeps 4 | Quick View

$162

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Casa Blanca is within walking distance of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. ...

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Property Type

Siesta Key Villa

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Casa Blanca D09 Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$217

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Oceanfront

About this property

Renovated and redesigned beach villa offering the very best in location and amenities. Upon arrival, just unpack your bags and enjoy. Everything is ready for your comfort and convenience with all the amenities of home. Even beach towels are provided. Sophisticated yet casual, this ranch villa is just ...

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Property Type

Siesta Key Villa

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Casa Blanca C06 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$217

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen

About this property

This lovely unit has just been remodeled and is awaiting your arrival. There is free high speed internet and long distance telephone in the U.S. and Canada, heated pool and screened lanai. This unit can occupy up to 6 persons. Villa C6 features new living room furniture, a 50" Plasma HDTV with ...

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Property Type

Siesta Key Villa

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Casa Blanca D11 Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$230

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen

About this property

2 Bedroom/ 2 Bath Large Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.

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Property Type

Siesta Key Villa

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2BR2BA 2nd Floor 800sqft Condo Siesta Key Crescent Beach + WiFi No Road to Cross

2 BR | 2 BA | Sleeps 7 | Quick View

8
Owner special: Last Minute Discount for 5 nights Oct 25-30...Ask

Distance to beach: 120 yards to Siesta Key Crescent Beach

$158

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Private pool

About this property

Open: Oct 25-30; Nov 28 - Dec 17; Jan 1-10; Feb 26 - Mar 5; Mar 19-26.... … ...YouTube Video-- ask!! ... Dr. Beach names Siesta Beach Best Beach in US - just Google 'dr beach names siesta beach best beach in us' and find out why. We have a new 360 degree picture layout of all rooms, similar ...

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Property Type

Siesta Key Condo

"Great"
Reviewed August 11, 2021

Perfect place to stay with kids or a group of friends. Right on the beach. The beach is amazing and so is the town

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The Palms Cottage - Ask About $99 Down!

$635

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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

"Peaceful family getaway"
Reviewed May 6, 2021

We loved the house. It was perfect for my husband and I and our two young kids. The pool was the perfect temp and having the back of the house covered in windows was great b/c we could keep and eye on ...

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Villa De Paradisio - Ask About $99 Down!

$581

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 ...

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Property Type

Siesta Key House

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Closest Condo to the Gulf of Mexico on Siesta Key - Direct Oceanfront

2 BR | 2 BA | Sleeps 6 | Quick View

23

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

$310

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Oceanfront

About this property

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

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Property Type

Siesta Key Condo

"The best of Siesta Key"
Reviewed July 30, 2021

We've literally driven every road between Anna Maria and Marco Island that goes to the Gulf of Mexico and can attest that this is the closest condo to the Gulf. At the busy northern end of Siesta Key ...

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Sophie's Quartier - Ask About $99 Down!

$1207

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly
  • 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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* Fantastic Bay View Condo * Siesta Key * #1 Beach of the US

$154

avg/night

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Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Managed 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

"Beautiful view"
Reviewed August 10, 2021

Siesta Key is a favorite. The convenience of walking a short and healthy walk to the white sand is a plus. The property management was quick to take care of a few concerns we had upon arrival to make ...

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

$137

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Communal pool
  • Full kitchen

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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Charming! Siesta Key Inn Sabal Palm #1A

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Got Sunshine? Relax in our tropical oasis, tranquil pool & spacious condo unit just steps to beach.

$342

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Managed by owner
  • Private pool

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

"Perfect"
Reviewed December 9, 2020

We had a fabulous stay recently at Sabal Palm #1A. The unit exceeded our expectations. Hosts could not have been nicer, nor better to work with. Unit was updated, well furnished, kitchen equipped with all ...

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Siesta Dream House - Ask About $99 Down!

$506

avg/night

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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 ...

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Property Type

Siesta Key House

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Plumbago - Ask About $99 Down!

$234

avg/night

View Details

Key Amenities

  • Air conditioning
  • Full kitchen
  • Kid friendly

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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105 Gulf Front Apartment

2 BR | 2 BA | Sleeps 6 | Quick View

$288

avg/night

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Key Amenities

  • Air conditioning
  • Full kitchen

About this property

Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach located on the 1st floor and end of the building. This apartment is a well appointed 2 bedroom, 2 bathroom with fully equipped kitchen. This unit features Private wireless internet, 1 King, and 2 Twin beds, and a sleeper ...

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Property Type

Siesta Key Apartment

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

2 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to beach: 0.0 miles to Siesta Key beach also known as "Crescent Beach"

$276

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Oceanfront

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

"Fantastic Memories"
Reviewed June 8, 2021

Thank you and your wife for letting us use your home at the beach this past week. You didn’t lie when you said the beach was beautiful. We all head back to reality with sunburn and fantastic memories. ...

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

$270

avg/night

View Details

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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Sun, Sand & *Save 15% to 30% per Week* at Midnight Cove #532 in Siesta Key, FL

2 BR | 1.5 BA | Sleeps 4 | Quick View

Distance to beach: 850 feet to Crescent Beach

$149

avg/night

View Details

Key Amenities

  • Air conditioning
  • Communal pool
  • Full kitchen
  • Kid friendly
  • Managed by owner

About this property

"Stop clicking around the web, and endless window shopping for your next Siesta Key Vacation Property Rental, and take advantage of the super accommodation cost savings offered in “Every-Day Deals” and “Sell-Off Deals”, with a Direct-with-Owner bayside Reservation at Midnight ...

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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°

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 15% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!