Siesta Key Vacation Rentals

(204 rentals)
The Nautilus - Only $99 down

8 BR | 6 BA | Sleeps 24 | Quick View

2

$529

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 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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Breathtaking Beachfront "House of the Sun" Rental

2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 200 feet to Crescent Beach

$179

per night

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Key Amenities

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

About this property

Unit 402 at the House of the Sun is an attractive condo offering resort living. The unit has just been painted throughout and redecorated. It has two bedrooms and two new full baths. The master has a king-size bed, large closets, full bath, a work/makeup station with makeup mirror, and large high-def ...

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Property Type

Siesta Key Condo

"Paradise"
Reviewed February 9, 2020

I stayed in a dream come true condo. It was right on the ocean with a view to know your socks off. Be able to leave the sliding doors open( because the lanai was screened in) was heavenly , being able to ...

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Beach, Village, Canal, Private Dock & Heated Pool... No Car Needed!

$400

per night

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Key Amenities

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

About this property

HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the first time.If you want a cute, private original bungalow ...

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Property Type

Siesta Key House

"Location, location, location!"
Reviewed March 19, 2019

Walkable to restaurants, groceries, shopping, nightlife AND the beach with its soft, white sand. Tennis courts on main beach. Basketball court a short drive away. Home is beautifully appointed and has ...

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The Grand Canal Cottage - Only $99 down

$495

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

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

$164

per night

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Key Amenities

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

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

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Property Type

Siesta Key Condo

"good"
Reviewed August 19, 2018

we have the time ok but the red tide not let us have good time

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Siesta Soul – 334

4 BR | 3 BA | Sleeps 8 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach - Access # 7

$243

per night

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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 ...

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Property Type

Siesta Key House

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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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Sea la Vie – 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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Tranquil 1 Bedroom Condominium Steps Away From Siesta Key Village & The Gulf!

$93

per night

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Key Amenities

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

About this property

Our little piece of paradise is a one bedroom condominium ideal for couples or young families. We are located at 73 Avenida Messina in unit #7 on the ground floor of the Gulf Holiday Apartments. We are 300 ft. from the Gulf of Mexico and about a five minute walk from the village - known for its shops, ...

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Property Type

Siesta Key Condo

"Unbelievable location of clean, cozy, quiet condo!"
Reviewed November 13, 2019

This will be our third time renting this condo from Mark and Victoria! When we first rented, couldn't believe how close we were to the water and in the other direction, to bars, restaurants and shops! Condo ...

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

1 BR | 1 BA | Sleeps 4 | Quick View

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

$214

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 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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Blu Sky Cottage – 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 Cottage

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Charming! Siesta Palms by the Beach #1A

$214

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

1 BR | 1 BA | Sleeps 4 | Quick View

2

Distance to beach: 20 yards to Siesta Key Beach

$171

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

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

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

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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

$171

per night

View Details

Key Amenities

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

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach . ...

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Property Type

Siesta Key Condo

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

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

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

$153

per night

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Key Amenities

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

About this property

Ask about last minute SPECIAL 2019!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 the USA. It is completely renovated and professionally decorated.Features include 2 Bedrooms, 1Bath sleeping six with ...

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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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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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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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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

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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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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

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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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Beach, Beach, Beach! 1 BR Siesta Palms #2D

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 150 yards to Siesta Key Crescent Beach

$199

per 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 Siesta Palms is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps ...

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Property Type

Siesta Key Condo

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Juicy Mango Cabana

2 BR | 2 BA | Sleeps 6 | Quick View

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Pool

About this property

Welcome to Juicy Mango Cabana, an adorable Siesta Key beach bungalow with heated pool. When combined with its sister property Honey Mango Cabana, both units make up Mango Manor.This tropical 2 bedroom/2 bathroom cottage is just a five minute walk to Crescent Beach and a short drive to The Village ...

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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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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 ...

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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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Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

3

$125

per 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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The Seascape - Only $99 down

8 BR | 9 BA | Sleeps 16 | Quick View

$1100

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 ...

View all property information

Property Type

Siesta Key Condo

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Plumbago – Only $99 down

2 BR | 2 BA | Sleeps 4 | Quick View

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

$96

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 Cottage

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Sandy Cabana - Only $99 Down

3 BR | 3 BA | Sleeps 8 | Quick View

1

$139

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

"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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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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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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SIESTA KEY DIRECT GULF FRONT CLEAN/NEAT WKLY RENTALS SECURE WEB

$243

per night

View Details

Key Amenities

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

About this property

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. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the Gulf views, breezes, ...

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Property Type

Siesta Key Condo

"Vacation"
Reviewed March 31, 2020

Sorry we never made it because of finances and availability. Will try again next year because we really liked the unit and it’s location!

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Villa Champagne - Only $99 down

4 BR | 3 BA | Sleeps 8 | Quick View

1

$286

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

"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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Sweet Tranquility! Siesta Palms By Beach #1B

$265

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 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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Heron House – 117R - Only $99 down

3 BR | 5 BA | Sleeps 12 | Quick View

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

$314

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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CocoBayou Cottage - Only $99 Down

$200

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 ...

View all property information

Property Type

Siesta Key Cottage

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Sophie’s Cottage - Only $99 down

$330

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 ...

View all property information

Property Type

Siesta Key House

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Siesta Key Inn 3Br/2B Sea Dream #223

$325

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 Condo

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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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Coral Breeze – Only $99 down

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$385

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

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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

Distance to beach: 150 yards to Siesta Key Crescent Beach

$199

per 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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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

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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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The Hummingbird - Only $99 down

6 BR | 6 BA | Sleeps 12 | Quick View

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

$286

per night

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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 ...

View all property information

Property Type

Siesta Key House

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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 ...

View all property information

Property Type

Siesta Key Townhome

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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 ...

View all property information

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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Siesta Key Beachfront Condo with Gulf View!

$135

per night

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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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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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Villa Vista Mare - Only $99 Down

3 BR | 3 BA | Sleeps 10 | Quick View

2

$286

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • 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 ...

View all property information

Property Type

Siesta Key Townhome

"Wonderful"
Reviewed October 30, 2019

Myself an family stayed in seista keys how was wonderful kids loved the pool house nice an clean had everything you needed came equipped with it can’t wait to go back beautiful weather very nice place ...

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Hanging at the Beach House! Siesta Key Inn #224

$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 ...

View all property information

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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SIESTA KEY #1 voted Beach in America- property right on Siesta Key Beach

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Summer special! 20% off.

$163

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES! This rental has a 2 week minimum stay during the prime winter season.This is a 2 Bedroom / 2 Bath unit on the Beach and within walking distance to the south Village. Just steps away from the beach! JUNE 2019- WE JUST INSTALLED A NEW ...

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Property Type

Siesta Key Condo

"Excellent choice"
Reviewed July 30, 2019

We stayed 1 week and everything was perfect. Great location, great accommodation and anything you need is within minutes away. It is definitely my home away from home. Looking forward to booking next year.

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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!