Siesta Key Vacation Rentals

(210 rentals)
Casita Coconut - Ask About $99 Down!

$172

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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Casa De Mariposa - Ask About $99 Down!

$493

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • 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

"Complete"
Reviewed April 13, 2020

Very beautiful place Excellent location Enough room for everyone We rented both sides Very beautiful top floor views

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Isla Amor - Ask About $99 down!

$606

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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B110

2 BR | 2 BA | Sleeps 4 | Quick View

1

$196

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"Beautiful Condo!"
Reviewed November 25, 2019

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

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Pinacolada - Ask About $99 Down!

3 BR | 3 BA | Sleeps 8 | Quick View

1

$230

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 Townhome

"Paradise!"
Reviewed August 17, 2020

Absolutely loved this place. Very Roomy. Huge bedrooms, plenty of bathrooms. Right behind the VILLAGE. perfect location. Enjoyed the pool so much. Was equipped with everything like home. Even used the blender ...

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"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

3
Owner special: FALL SPECIAL! 20% OFF ONE WEEK BOOKINGS.

$163

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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Ocean’s Edge - Ask About $99 down!

$580

avg/night

View Details

Key Amenities

  • 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 Condo

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Sweet Tranquility! Siesta Palms By Beach #1B

$282

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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Luxury Siesta Key Beach House with private beach, pool and spa

$512

avg/night

View Details

Key Amenities

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

About this property

Welcome to Siesta Key Beach House, one of Siesta Key's most luxurious homes with private heated pool and spa. This luxurious and spacious 5 bedroom/4.5 bathroom home is located on Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for large families & groups.The space Luxurious, ...

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Property Type

Siesta Key House

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Blu Sky Cottage – Ask About $99 down!

$404

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 Cottage

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STAY HEALTHY *Fantastic Bay View Condo* Siesta Key #1 Beach of the US

2 BR | 1.5 BA | Sleeps 4 | Quick View

2
Owner special: Looking for a safe retreat on beautiful Siesta Key. 2 WEEKS SPECIAL October 2020. * Inquire NOW *

$141

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

"Fantastic"
Reviewed March 20, 2020

We loved the condo, clean, updated, beautiful view of the ICW, nice pool and great beach! We are coming back again next year!

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The Seascape - Ask About $99 down!

$1153

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 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 Condo

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Sol y Mar - Ask About $99 down!

$337

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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Latitude Adjustment - Ask About $99 Down!

$381

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

"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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Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

3

$152

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

The Sea Wave Casita of Villa Brisa Marina is one of two beautiful casitas, uniquely configured, featuring two bedrooms, 2 full bathrooms, a gourmet kitchen and a heated pool. One of 2 homes (along with Sea Shell Casita) that are Villa Brisa Marina.The Sea Wave and Sea Shell are two separate units ...

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Property Type

Siesta Key House

"Great locTION"
Reviewed March 11, 2020

The condo that I rented is adequate with everything one needs. It was not lacking and the owned was very helpful.

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Sea la Vie - Ask About $99 Down!

$247

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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Sandpiper Cottage - Ask About $99 down!

5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.8 miles to Crescent Beach

$301

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 Cottage

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Casa Mahalo - Ask About $99 Down!

4 BR | 3 BA | Sleeps 12 | Quick View

2

$366

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

"Birthday celebration"
Reviewed August 18, 2020

Loved staying at the Maharo home. Very spacious and very accommodating. Particularly loved the private pool given the pandemic crisis we are all experiencing.Enjoyed walking through Siesta Key village. ...

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The Big Kahuna - Ask About $99 Down!

$731

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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Mango Manor

4 BR | 3 BA | Sleeps 12 | Quick View

$337

avg/night

View Details

Key Amenities

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

About this property

Welcome to Mango Manor, a unique combination of two units: “Juicy Mango Cabana” and “Honey Mango Cabana.” When booked together, Mango Manor offers a private heated pool and is just a short walk to prestigious Crescent Beach!This tropical 4 bedroom/3 bathroom beach villa is ...

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Property Type

Siesta Key House

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Charming! Siesta Palms by the Beach #1A

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: It's all about the ambiance...comfortable, relaxed and carefree. Ask about or seasonal specials...

$224

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,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 Palms by the Beach. With no ...

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Property Type

Siesta Key Condo

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The Pearl by the Sea - Ask About $99 down!

$580

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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BEAUTY AT THE BEACH--Full front Gulf view!! Crescent Arms 601S

$242

avg/night

View Details

Key Amenities

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

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

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Property Type

Siesta Key Condo

"Perfect Location for our Family of 4"
Reviewed July 26, 2020

Elaine was great to work with and most accommodating with scheduling due to Coronavirus. Her unit was exactly as advertised! most clean and updated. I am originally from Sarasota and after staying at ...

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Home away from home

2 BR | 2 BA | Sleeps 6 | Quick View

$261

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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Vacation Paradise to Stroll the Beach....Siesta Palms by the Beach #1D

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Relax & Unwind! Book 5 nights at $235/night + tax and get 2 nights Free. Enjoy complimentary wine

Distance to beach: 150 yards to Siesta Key Crescent Beach

$211

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, 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 Palms by the Beach. With ...

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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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Casita Blanca

2 BR | 1 BA | Sleeps 4 | Quick View

$168

avg/night

View Details

Key Amenities

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

About this property

Explore Casita Blanca, a cozy 2BR/1BA bungalow located minutes from prestigious Crescent Beach. This home is the perfect beach retreat for small families and couples alike!This inviting beach bungalow is just a short walk to prestigious Crescent Beach and close to world famous Siesta Key Beach, continually ...

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Property Type

Siesta Key House

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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

$491

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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Carefree Sunny Fun! 1 Br Siesta Palms by the Beach #2A

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: It's not too late for that Vacation! Contact us for availability and current specials.

Distance to beach: 150 yards to Siesta Key, Crescent Beach

$224

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 Palms by the Beach! 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 ...

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Property Type

Siesta Key Condo

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Casa Stolida - Ask About $99 Down!

$339

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 Islander – Ask About $99 down!

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$491

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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CocoBayou Cottage - Ask About $99 Down!

$250

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 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 ...

View all property information

Property Type

Siesta Key Cottage

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Honeysuckle - Ask About $99 Down!

$183

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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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

$366

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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Monarch Villa - Ask About $99 Down!

$254

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 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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Lantana - Ask About $99 Down!

2 BR | 2 BA | Sleeps 4 | Quick View

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

$140

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet 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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Siesta Key Inn 3Br/2B Sea Dream #223

$338

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • 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 Key Inn 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

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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

5

Distance to beach: 120 yards to Siesta Key Crescent Beach

$111

avg/night

View Details

Key Amenities

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

About this property

Last Minute Openings Aug 21 - Sep 4 and Sep 17 - Nov 7 Siesta Key Condos are open again for short term rentals !! ... ...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 ...

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Property Type

Siesta Key Condo

"So close to the beach! Beautiful sand and water!!"
Reviewed June 7, 2020

The Siesta Beach House was in a good location such a quick walk to the beach through a private entrance (gated). Very friendly people all around. We loved having the beach chairs (on the beach provided ...

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Serenity Cottage - Ask About $99 Down!

$250

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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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$346

avg/night

View Details

Key Amenities

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

About this property

This tranquil 4 bedroom/3 bathroom home features a private heated pool & spa, and is located within close proximity to Siesta Key Village and world famous Siesta Key Beach, voted the #1 beach in the USA! The Canopy Cottage is the ideal vacation home for couples and families alike.The Canopy Cottage ...

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Property Type

Siesta Key House

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Siesta Key Beachfront Condo with Gulf View!

$147

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

"Beautiful view of a world-class beach!"
Reviewed November 16, 2018

The tidy condo was well located on the 4th floor allowing for a magnificent view of the beach from the lanai. Great place to take our coffee in the morning before our morning walk; or a glass of wine in ...

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Special $85/night, Aug - Nov 14, 20. Luxurious Condo walk to Siesta Key Beach!

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.5 miles to Siesta Key Beach

$121

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Rentals 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

"Nice Condo"
Reviewed June 7, 2019

Nice clean condo, nice location (2 minutes drive from the free beach parking), nice gated complex with harbor view, pool, tennis courts.

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Villa De Paradisio - Ask About $99 Down!

$404

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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Sandy Cabana - Ask About $99 Down!

$210

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

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

"Fabulous Place"
Reviewed February 19, 2020

Excellent Location close to the Crescent Beach and Restaurants. I would stay there again the next time I visit Siesta Key.

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Casita Coco - Ask About $99 Down!

$92

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 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

"Cute cottage."
Reviewed September 14, 2018

My daughter, my new grandson and I enjoyed the cottage immensely. The cupcake welcome was delicious. Everything was clean and we couldn't have asked for a better location. Loved the nearby restaurants. ...

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WALK to Siesta Beach from this vacation paradise!

$257

avg/night

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Key Amenities

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

About this property

Walk to Siesta Key Beach from this vacation paradise! Our 3 bed/2 bath home has a private screened-in pool and patio and enough space for your whole group!Our home has a living and dining area that will allow your whole group to be together and still have their own space. Hanging is a 58" Roku ...

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Property Type

Siesta Key House

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Enchanting and Carefree! Siesta Key Inn #126

$210

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 Key Inn 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

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Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

1

$337

avg/night

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Key Amenities

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

About this property

Explore Playa y Blanca, a charming 4BR/2BA beach bungalow located steps from Crescent Beach. This home is the perfect beach escape for small families and couples alike!Welcome to Playa y Blanca! This uniquely configured 4BR/2BA villa is a combination of two units: “Casita Blanca” and “Casita ...

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Property Type

Siesta Key House

"Great stay in Siesta Key!"
Reviewed February 9, 2020

Sarasota Surf and Racquet Club. We rented two condos at this property. They were clean and well appointed, with everything we needed. The location on the beach was perfect and the service was great! Would ...

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Sailors Lookout - Ask About $99 Down!

3 BR | 5 BA | Sleeps 10 | Quick View

Distance to beach: 0.2 miles to Siesta Key Public Beach - Access # 2

$450

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 ...

View all property information

Property Type

Siesta Key House

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Villa Champagne - Ask About $99 Down!

$349

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

"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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The Nautilus - Ask About $99 Down!

$678

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 ...

View all property information

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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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!