Siesta Key Vacation Rentals

(206 rentals)
Sandpiper Cottage - Only $99 down

5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.8 miles to Crescent Beach

$275

per night

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Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key Cottage

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Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

1

$287

per 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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Casita Coco - Only $99 Down

1 BR | 1 BA | Sleeps 4 | Quick View

1

$71

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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

$125

per night

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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)Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is the perfect escape from everyday life.Whether you are looking for a perfect destination for your vacation, ...

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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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Paradise Awaits! 2br Siesta Palms by the Beach #2B

2 BR | 2 BA | Sleeps 5 | Quick View

LAST MINUTE DEAL 7/7 - 8/18: Rarely Available! Paradise awaits in this spacious 2Br/2B Condo. Steps to pool and beach.

$265

per 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 Palms by the Beach. With ...

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Property Type

Siesta Key Condo

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DEAL
La Contento Casa - Only $99 down

$385

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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Tropical Resort-Like Oasis! 1 Br Siesta Key Inn #123

$199

per night

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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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Siesta Key - 2bdrm on the beach - amazing views!!

$236

per night

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Key Amenities

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

About this property

The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a smart couch to curl up and read ...

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Property Type

Siesta Key Condo

"Shh Turtle Beach"
Reviewed November 20, 2019

Lovely to stay on the quiet end of Siesta Key. Could hear the water lapping the shore all day. Took lovely long walks along the beach to Point of Rocks and snorkelled the days away. Kevin’s place is ...

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Sand Dollar Cottage - Only $99 down

$385

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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Mandevilla - Only $99 down

3 BR | 3 BA | Sleeps 6 | Quick View

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

$143

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key Villa

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Crescent Beach Resort, Heated Pool, Jacuzzi, Tennis, Barbeques

$185

per night

View Details

Key Amenities

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

About this property

Our condo is in a large, spacious, beautifully landscaped complex in the middle of Crescent Beach where couples as well as families are welcome. Our balcony is nestled in a quiet, lush tropical setting with birds serenading in the surrounding trees; yet close to all amenities. Short walk through our ...

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Property Type

Siesta Key Condo

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Sea Esta – Only $99 down

3 BR | 2 BA | Sleeps 8 | Quick View

$179

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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The Solaster - Only $99 down

6 BR | 6 BA | Sleeps 20 | Quick View

1

$400

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

"Great as advertised"
Reviewed October 31, 2019

A group of eight 80-ish college fraternity brothers got together for a reunion and rented Solaster. It was a great choice. The place is exactly as advertised: two attached units, six bedrooms with eight ...

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Siesta Key Beach Villa- #1 rated Beach in America - Casa Blanca Villa B07

2 BR | 1.5 BA | Sleeps 6 | Quick View

2

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

$159

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Villa

"Great stay"
Reviewed February 3, 2020

Loved everything about condo.. met some nice people there... definitely will want to return... very clean, comfortable, people are wonderful

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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: Too Good to Be True! Come stay at the Beach. Summer Specials available.

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

$214

per 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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Gran Vista – Only $99 down

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$633

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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Monarch Villa - Only $99 Down

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: Only $99 down 24 hour cancellation policy Deferred deposit payments until 14 days prior to your arrival 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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Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

3

$164

per night

View Details

Key Amenities

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

About this property

This colorful custom 3rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! This is an adults only unit, perfect for a mature couple who can take excellent care of things and appreciate the fine nature of this unit.From the modern ...

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Property Type

Siesta Key Condo

"Paradise at Christmas!"
Reviewed January 8, 2019

My family of four traveled to Siesta Key for Christmas week and enjoyed this precious condo on the beach! It was delightful! Fun colorful décor, comfortable, and all amenities included. The Sunset here ...

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Spectacular Gulf And Beach Views -Located Directly On The Beach!

1 BR | 1 BA | Sleeps 4 | Quick View

LAST MINUTE DEAL 7/25 - 8/1: IT'S TIME TO RELAX AND ENJOY THE BEACH IN OUR OCEANFRONT CONDO! 10% DISCOUNT AND MORE! SAT-SAT ONLY

$136

per night

View Details

Key Amenities

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

About this property

Our beautiful condo is completely RENOVATED and IT IS LOCATED DIRECTLY ON THE BEACH! This magnificent condo is one of the closest condos to the Gulf on Siesta Key. You could throw a tennis ball into the Gulf from this Siesta Key beachfront condo!Located on the island of Siesta Key , Florida, this ...

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Property Type

Siesta Key Condo

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DEAL
A special SECRET retreat...#26

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 100 yards to Crescent Beach

$140

per night

View Details

Key Amenities

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

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

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Siesta Key Condos - Gulf & Bay Club Bayside Condo

1 BR | 1 BA | Sleeps 2 | Quick View

1
Owner special: Contact owner for deals.

$111

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living. ...

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Property Type

Siesta Key Condo

"Fabulous"
Reviewed September 7, 2019

A beautiful complex with a beach house feel ! A very welcoming unit with a generous space. Making the best of the intercostal and gulf !

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Mimosa – Only $99 down

1 BR | 1 BA | Sleeps 2 | Quick View

1

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

$71

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

"Fantastic location, Clean and Comfortable"
Reviewed October 21, 2019

We thoroughly enjoyed our stay here... the location is awesome, less than 5 minutes to the beach. The condo was spacious, clean and very comfortable. The beds were good.. all amenities up to date. We ...

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Beach Haven 5858

2 BR | 2 BA | Sleeps 4 | Quick View

$116

per night

View Details

Key Amenities

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

About this property

Siesta Key Beach only 20 steps out the back sliding door. Come feel the powdery white sand that never gets hot from the sun!! This 2 bedroom 2 full bathroom villa is on the great Siesta Key Beach, come enjoy this 2 bedroom 2 bathroom with a walk-in shower and a carport for your vehicle. Sit out on ...

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Property Type

Siesta Key Villa

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The Pearl by the Sea - Only $99 down

$550

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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Siesta Dream House - Only $99 down

$243

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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Pura Vida Oasis - Only $99 down

$621

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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The Grand Canal Cottage - Only $99 down

$495

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

"Salt Life TWO THUMBS UP!"
Reviewed May 2, 2019

Location is literally right across a beach entrance a short 5min walk to the village. We rented both units and combined the common pool area for my whole extended family. It was fantastic!

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Siesta Salt Life - Only $99 down!

6 BR | 4 BA | Sleeps 16 | Quick View

1

$354

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

View all property information

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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Beachfront Siesta Key, FL.- 3 Bedroom Private Home W/Full Gulf Views!

3 BR | 3 BA | Sleeps 7 | Quick View

3

Distance to beach: 300 feet to Siesta Beach

$395

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

"Wonderful Location!"
Reviewed March 25, 2019

We had a great stay! We visited for spring break with our two school-age kids and their grandparents. The location was fantastic - right on the beach with your own private path to the beach, and near ...

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The Blue Serenity - Only $99 down

6 BR | 10 BA | Sleeps 22 | Quick View

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

$700

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key House

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The Nautilus - Only $99 down

8 BR | 6 BA | Sleeps 24 | Quick View

2

$529

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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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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Tropical beach getaway at Sandy's Siesta Key Condo

2 BR | 1.5 BA | Sleeps 4 | Quick View

3

Distance to beach: 200 yards to Crescent Siesta Key Beach

$127

per 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

"Sandy's siesta"
Reviewed October 21, 2018

This condo was perfect! It's absolutely beautiful, top end appliances, beautiful decor and all the comforts of home. The condo is close to the beach and pool. Totally worth it!

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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Honey Mango Cabana, one of Siesta Key’s most tropical beach bungalows with heated pool. When combined with its sister property Juicy Mango Cabana, both units make up Mango Manor.This tropical 2 bedroom/1 bathroom cottage is just a five minute walk to Crescent Beach and a short drive ...

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Property Type

Siesta Key House

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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$330

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

2 BR | 2 BA | Sleeps 6 | Quick View

18

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

$171

per night

View Details

Key Amenities

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

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

"Absolutely stunning, perfect vacation rental"
Reviewed September 14, 2019

First of all, I want to say that dealing with Paul, the owner, was the best experience I have ever had interacting with a vacation renter. He goes far above and beyond to answer questions, provide information ...

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Pinacolada - Only $99 down

3 BR | 3 BA | Sleeps 8 | Quick View

$186

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key Townhome

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Admirals Watch - Only $99 Down

3 BR | 3 BA | Sleeps 8 | Quick View

1

$314

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: Only $99 down 24 hour cancellation policy Deferred deposit payments until 14 days prior to your arrival 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

"Wonderful Stay"
Reviewed July 1, 2019

Admirals Watch, Siesta Key was a great place to stay with an amazing view! Everything is just like the picture. The rental company "The Cottages on the Key" checked in with us a couple of times to make ...

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

$115

per 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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Ocean’s Edge - Only $99 down

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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Property Type

Siesta Key Condo

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Hanging at the Beach House! Siesta Key Inn #224

1 BR | 1 BA | Sleeps 4 | Quick View

1
LAST MINUTE DEAL 7/4 - 8/15: Sweet Summer Deal 15% Discount for Weekly Rentals! $1189/week + $75 cleaning fee & tax.

$199

per 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 House

"Charming"
Reviewed February 15, 2019

Cheery and homey. Decor very pleasing. Lovely landscaping around the pool. Long walk to beach however

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DEAL
Latitude Adjustment - Only $99 down

$300

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

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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

$125

per night

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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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Siesta Key Beach direct access from your front door

2 BR | 2 BA | Sleeps 6 | Quick View

1
LAST MINUTE DEAL 7/11 - 8/22: $1010/ 7 nights no cleaning fees!! 200 steps to toes in the sand at Siesta Key Beach!! 2 BR 2 BATH.

$144

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

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 the closest home to the Sunset Pavilion, children's playground, and snack bar! Easily ...

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Property Type

Siesta Key Apartment

"Ultra convenient condo"
Reviewed January 27, 2020

Perfect location to walk across the street to the beach. Good communication from the owner and the on site management company is very attentive. Property is well maintained. Free trolley picks up and drops ...

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DEAL
Tropical Escape! Fabulous Amenities 1Br Siesta Palms by the Beach #1C

$199

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 Siesta Palms is less than a block from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach. We offer good "olde" fashioned Southern ...

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Property Type

Siesta Key House

"Nice place to relax in quiet surroundings"
Reviewed March 5, 2019

Perfect location to walk to beach ,bars , restaurants,a short drive over the bridge to Sarasota has all shopping you need. Very clean condo ,we met some very nice people that return every year.

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Lime in the Coconut - Only $99 down

$250

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

View all property information

Property Type

Siesta Key House

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Sandy Seahorse Cottage - Only $99 Down

$279

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

View all property information

Property Type

Siesta Key House

"Family Summer Beach Trip"
Reviewed June 15, 2020

Home was very accommodating and extremely clean. Layout of the home was a bit weird and that’s why I’m giving it a 4 star. You have to go through 2 of the bedrooms to get to the patio and pool. Lots ...

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Seahorse Cabana - Only $99 down

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

View all property information

Property Type

Siesta Key House

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Ventana Rosa – Only $99 down

3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Shell Beach

$139

per night

View Details

Key Amenities

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

About this property

Ventana Rosa - One of The Cottages on the KeyThis home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this ...

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Property Type

Siesta Key House

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Caribbean Sol – Only $99 down

5 BR | 5 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$523

per night

View Details

Key Amenities

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

About this property

This home qualifies for our Book Care Free option for 2020 arrivals which includes: • Only $99 down • 24 hour cancellation policy • Deferred deposit payments until 14 days prior to your arrival Ask us about how you can qualify for this special offer!We go above and beyond the industry ...

View all property information

Property Type

Siesta Key House

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The Lily Patch Bungalow - MONTHLY RENTAL

2 BR | 2 BA | Sleeps 4 | Quick View

3

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

$80

per night

View Details

Key Amenities

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

About this property

Situated in the quiet and secluded neighborhood of Palm Island, the Lily Patch is a cozy pecky cypress bungalow with two bedrooms and two bathrooms. Hardwood floors throughout add to its charm. Double sets of double French doors lead from the living and dining rooms onto the large private Mexican tiled ...

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Property Type

Siesta Key Bungalow

"We Keep Coming Back"
Reviewed March 2, 2020

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

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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!