Siesta Key Vacation Rentals

(201 rentals)
Casa De Mariposa

6 BR | 6 BA | Sleeps 16 | Quick View

$404

per night

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Key Amenities

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

About this property

Welcome to Casa de Mariposa! This gorgeous property is comprised of two units, Monarch and Peacock Villa which are both mirror images of one another. Each unite features a 3 bedroom, 3 bathroom configuration with their very own common space to include a kitchen, dining area, private balconies, and private ...

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Property Type

Siesta Key House

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Blue Lagoon Tropical Bungalow (2B/2B) - MONTHLY RENTAL

2 BR | 2 BA | Sleeps 6 | Quick View

2

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

Our Blue Lagoon Bungalow - 2bed/2bath -Short walk to Beach & Vllage. Pecky cypress home with gorgeous refinished hardwood floors that shine like a piece of furniture. It has two bedrooms and two bathrooms. The large family room has a wall of sliding glass windows onto a deck with park benches that ...

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Property Type

Siesta Key Bungalow

"Perfect Pet-Friendly Winter Haven"
Reviewed February 26, 2019

We greatly enjoyed our 2 months in the Blue Lagoon cottage. Anyone considering Siesta Key will enjoy staying in any of the cottages offered by Rich and Ali Light. They are well-maintained. Rich and Ali ...

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

$243

per night

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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

"Great beachfront"
Reviewed February 4, 2019

Terrific location on Crescent Beach - just as beautiful as Siesta Beach but less busy. Comfortable and clean condo in secure building and complex. Even when evenings were cool or too windy, we enjoyed gorgeous ...

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The Lily Patch Bungalow - MONTHLY RENTAL

2 BR | 2 BA | Sleeps 4 | Quick View

2

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

"The Lily Pad...a piece of paradise to cherish"
Reviewed February 26, 2019

The location offers you incredible privacy and easy access to the Siesta Key village and Sarasota proper.This is a great family-friendly bungalow that allows you to bring the family dog with added room ...

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Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

2

$143

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

"Beachside single storey"
Reviewed February 10, 2019

Had a great stay at this beautifully decorated and well equipped single storey pad. The beach is so close by as are grocery and other shops offering all you need. It really is quite special and so... ...

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Beautifully renovated condo, walk to Siesta Key Beach! See Special Summer Rate!

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.5 miles to Siesta Key Beach

$100

per 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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Casita Coco

1 BR | 1 BA | Sleeps 4 | Quick View

1

$85

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to Casita Coco, a 1 bedroom/1 bathroom Siesta Key vacation home with a shared heated pool. When reserved with Casita Bayou to become CocoBayou Cottage, you can sleep up to 10! Near beach, Crescent Village & the Intercoastal.Welcome to Casita Coco!Casita Coco is one part of the uniquely ...

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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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The Seascape

8 BR | 9 BA | Sleeps 16 | Quick View

$1100

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to The Seascape! The Seascape is the combination of two massive gulf front penthouses located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 16, it is the only way to experience Siesta Key.The Seascape is the unique ...

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Property Type

Siesta Key Condo

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Siesta Sunset Royale beach house $$$ DISCOUNTED RATES $$$

9 BR | 9 BA | Sleeps 26 | Quick View

Distance to beach: 100 yards to Crescent Beach Access #7

$967

per night

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Key Amenities

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

About this property

This is the ideal location for your next large get together on Siesta Key. Whether you are planning a small wedding, family reunion, get together with friends, company meeting or just a reason to have a beach party at a beach house, Siesta Sunset Royale beach house on Siesta Key is just waiting for all ...

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Property Type

Siesta Key House

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Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

1

$288

per night

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Key Amenities

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

About this property

Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy ...

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Property Type

Siesta Key House

"Great Family Vacation"
Reviewed March 1, 2018

The condo was great for our three generation family including a 3 year old and an infant. Private pool + easy walk to beach and restaurants met our needs. No parking issues to worry about. The Cottages ...

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Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$143

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Casita Bayou!Casita Bayou is the larger half of this uniquely configured private home called the Coconut Bayou Cottage and it is the perfect escape for you and your guests. This side of the gorgeous home has recently been updated with new furnishings and completely renovated on the interior. ...

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Property Type

Siesta Key House

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Admirals Watch

3 BR | 3 BA | Sleeps 8 | Quick View

$354

per night

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Key Amenities

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

About this property

Welcome to Admirals Watch! This beautiful, luxurious and modern 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous ...

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Property Type

Siesta Key Condo

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Sea the View - One of The Cottages On The Key

$440

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea the View - one of Siesta Key's most tranquil canal-front homes, with private heated pool and spa! This home is ideal for large families.This picturesque 4 bedroom/3 bathroom home features a brand new outdoor tiki bar and is located within walking distance to Siesta Key Village and ...

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Property Type

Siesta Key House

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Pura Vida Oasis

5 BR | 3 BA | Sleeps 13 | Quick View

$621

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Pura Vida Oasis, a canal front cottage with heated pool & spa features 5 bedrooms/3 baths and can sleep up to 13. Enjoy eclectic wine storage rack, private dock and amazing views. Close to beaches, Siesta Village & trolley stop. This spectacular bright cheerful, canal front cottage ...

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Property Type

Siesta Key House

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

1 BR | 1 BA | Sleeps 4 | Quick View

1

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

"Awesome Rental"
Reviewed May 27, 2019

We stayed at Sea Spray rentals for a week April 2019. This is the nicest, cleanest rental we have ever stayed at and management was very accommodating.

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MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

6
Owner special: Hurry -Last minute special!!! ***25% off any one week booking from 6/15 - 6/30. Ask about nightly!

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$167

per night

View Details

Key Amenities

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

About this property

PRICE PER INDIVIDUAL UNIT. DUPLEX: 1 UPSTAIRS UNIT AND 1 DOWNSTAIRS UNIT. SHORT WALK TO VILLAGE, OR BEACH. PRIVATE HEATED POOL, TIKI HUT, GRILL, EACH UNIT HAS OWN WASHER AND DRYER IN UNIT, FULL KITCHENS, WALK TO GROCERY STORE, GIFT SHOPS, RESTURANT'S, ICE CREAM STORE AND BARS.

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Property Type

Siesta Key Apartment

"PERFECT"
Reviewed June 11, 2019

We stayed for two weeks! We had the up & downstairs so our entire family was able to enjoy the privacy of just our family being at the pool! This is absolutely our favorite place to stay, it’s close to ...

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Breathtaking Beachfront "House of the Sun" Rental

2 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 200 feet to Crescent Beach

$171

per night

View Details

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

"The Total Package"
Reviewed April 24, 2019

This beautiful condo is well-appointed and well situated on the quiet end of the key. Everything you need is within walking distance or just a free trolley ride away; restaurants, shopping, groceries and ...

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The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$400

per night

View Details

Key Amenities

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

About this property

The Solaster is a combination of two units (Casita Morning Star and Casita Sun Star) within walking distance of Point of Rocks Beach. Each unit has 3 bedrooms, 3 bathrooms, their own heated pool & a private screened in lanai. Ideal for large groups! Welcome to The Solaster! Our newly renovated luxury ...

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Property Type

Siesta Key House

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The Hidden Gem – 5290L

2 BR | 1 BA | Sleeps 6 | Quick View

$143

per night

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Key Amenities

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

About this property

This charming 2BR/1BA cottage is located in the heart of Siesta Key Village and is just minutes from world famous Siesta Key Beach, continually ranked as one of the top 10 beaches in the USA! Combined with its sister property Deja Blue, both units make up Sunset Fiesta. This cozy beach bungalow is the ...

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Property Type

Siesta Key Cottage

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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
Owner special: Summer special for 6/15 to 6/22, $700 off the weekly rate! Come enjoy a true Siesta Beach Vacation

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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Sophie’s Quartier

6 BR | 5 BA | Sleeps 16 | Quick View

$594

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sophie’s Quartier, a waterfront compound consisting of two homes right near Siesta Key Beach! This is a perfect retreat for huge family and friends’ get togethers! Enjoy a heated pool, one hot tub, two docks overlooking The Grand Canal of Siesta Key. Minutes walk from the world ...

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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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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$143

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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Sandpiper Cottage

5 BR | 5 BA | Sleeps 14 | Quick View

$275

per night

View Details

Key Amenities

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

About this property

This captivating and completely upgraded (as of 2019) luxury villa is centrally located just 10 minutes from Siesta Key Beach, continually ranked as one of the top 10 beaches in the USA! With brand new furniture and beach décor throughout, you will truly be living the beach life! Sandpiper Cottage ...

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Property Type

Siesta Key Cottage

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Canal Place Bungalow - WEEKLY/MONTHLY RENTAL

3 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 0.5 miles to Siesta Beach access 7

$79

per night

View Details

Key Amenities

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

About this property

Enjoy this ‘Old Florida Charm’ beach cottage. It has three bedrooms and two bathrooms (stall shower in one and tub and shower in the other.) The large living room has French doors leading onto a screened in porch, which overlooks the gardens and a brick walkway to a large shared hot tub. It ...

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Property Type

Siesta Key Bungalow

"Fabulous location in a comfy pet friendly cottage"
Reviewed August 8, 2018

We (2 couples) have stayed at Canal Place in Siesta Key for 5 years. Our hosts, Rich and Ali Light, are gracious hosts and very responsive. Canal Place is in an excellent location, about 10min to the village ...

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"Menorca" 378 Canal Rd.

Studio | 1 BA | Sleeps 2 | Quick View

3
Owner special: Hurry -Last minute special!!! ***25% off any one week booking from 6/15 - 6/30. Ask about nightly!

$81

per night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool

About this property

Studio/Efficiency, Queen Bed, Next to pool. Pool Access, WIFI *W&D access, ground floor. Local free shuttles so no need for a car.Located on the Voted number “#1 Beach in America” popular Siesta Key in Sarasota, Florida, the perfect vacation getaway.The unit maintains that great ...

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Property Type

Siesta Key Studio

"Nice visit"
Reviewed June 13, 2019

We love the location of the rental and the friendly staff. During the last two times we stayed with the Banyan Tree on Canal ,the pool temperature could have been warmer and consistently warmer morning ...

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Casa Mahalo

4 BR | 3 BA | Sleeps 12 | Quick View

$288

per night

View Details

Key Amenities

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

About this property

Welcome to Casa Mahalo! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy ...

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Property Type

Siesta Key House

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SIESTA KEY HEAVEN

2 BR | 2 BA | Sleeps 4 | Quick View

$171

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

WE WE HAVE THE ABSOLUTE BEST SPOT ON THE ABSOLUTE BEST BEACH! (Reuters, May 27, 2011) 7 day Sat to Sat minimum stay.You will not find a more-convenient location or a better view anywhere else on the key! To take a couple short tours, see more photos, and to make your reservation without any service fees ...

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Property Type

Siesta Key Condo

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

2 BR | 2 BA | Sleeps 6 | Quick View

13

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

"Can’t Wait to Return!"
Reviewed June 13, 2019

I can’t say enough about how much we liked this condo and the wonderful beach access and views. I am from Ohio and have been booking Spring trips to Florida with my two daughters for many years. Now I ...

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"Village Resort" 316 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

3
Owner special: Hurry -Last minute special!!! ***25% off any one week booking from 6/15 - 6/30. Ask about nightly!

$151

per night

View Details

Key Amenities

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

About this property

(downstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Property Type

Siesta Key Condo

"Location and quiet environment with clean conditions"
Reviewed June 10, 2019

We have stayed at the Banyan Tree Resort Properties for about 20 years. The management and properties have all been very efficient and comfortable. We enjoy the Village and the location of the properties.

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Updated 3 Bed/2 Bath House 5min walk to Siesta Key Beach, Heated Pool

$83

per night

View Details

Key Amenities

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

About this property

Beautiful 3 bedroom 2 bathroom house situated in the quiet, secluded neighborhood of Palm Island within minutes of all that Siesta Key has to offer. This well appointed house is a short 5 minute walk to the famous beaches of Siesta Key Beach (private beach access 10) and a 15 minute walk to the exciting ...

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Property Type

Siesta Key House

"Would Return if We Could!"
Reviewed April 24, 2019

We were so sad to leave Jessica’s lovely house on Palm Island, Siesta Key, after a comfy and restful month in March 2019. The house is so well situated - a quick walk to the gorgeous beach and about ...

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Deja Blue – 5288R

2 BR | 1 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

This charming 2BR/1BA cottage is located in the heart of Siesta Key Village and is just minutes from world famous Siesta Key Beach, continually ranked as one of the top 10 beaches in the USA! Combined with its sister property The Hidden Gem, both units make up Sunset Fiesta. This cozy beach bungalow is ...

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Property Type

Siesta Key Cottage

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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

1
Owner special: Hurry -Last minute special!!! ***25% off any one week booking from 6/15 - 6/30. Ask about nightly!

$163

per night

View Details

Key Amenities

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

About this property

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 LIVING ROOM SET, AND MASTER BEDROOM SET, INCLUDING NEW MATTRESS AND BOX SPRINGS. WE ALSO HAVE NEW WINDOW SHUTTERS COMING JULY 2019.This ...

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Property Type

Siesta Key Condo

"Beautiful beach condo."
Reviewed June 12, 2019

Just steps from the water this condo is roomy and convenient for all attractions on Siesta Key. The beach could not be more beautiful. Looking forward to visiting again.

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"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

1
Owner special: Hurry -Last minute special!!! ***25% off any one week booking from 6/15 - 6/30. Ask about nightly!

$151

per night

View Details

Key Amenities

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

About this property

(downstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Property Type

Siesta Key Condo

"our 2 month stay"
Reviewed June 6, 2019

Everything went well with our visit. The place was clean and well stocked. I had to have help getting the tv to work as it was different from my tv at home. The year before i had the same tv set up in ...

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Stroll the Beach....Siesta Palms by the Beach #1D

1 BR | 1 BA | Sleeps 4 | Quick View

1
LAST MINUTE DEAL 6/15 - 7/27: Sweet Summer Deal 15% DISCOUNT FOR WEEKLY RENTALS! $1189 Per Week Plus $150 Cleaning Fee & 12% Tax

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

"Everything we needed!!"
Reviewed March 12, 2018

Great location! Very clean. Close to the beach. Was really perfect would stay again !

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DEAL
Pinacolada

3 BR | 3 BA | Sleeps 8 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Pinacolada! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 8, a shared heated pool, and quite literally in the heart of Siesta Village!Pinacolada is one-half of the exquisite "Coconut ...

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Property Type

Siesta Key Townhome

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Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

$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

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Sunset Fiesta

4 BR | 2 BA | Sleeps 12 | Quick View

$287

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This charming 4BR/2BA beach villa is centrally located in the heart of Siesta Key Village and just minutes from world famous Siesta Key Beach, continually ranked as one of the top 10 beaches in the USA! This home is the perfect beach retreat for small families and couples alike!

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Property Type

Siesta Key House

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Latitude Adjustment

4 BR | 4 BA | Sleeps 10 | Quick View

$294

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Latitude Adjustment! This breathtaking 4 bedroom, 4 bathroom home is perfectly situated between America's #1 beach in the world and Siesta Key's famous North Village! You will not be able to ask for more as you drive up to this tropical oasis, covered with vibrant hot pink bougainvillea flower ...

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Property Type

Siesta Key House

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CocoBayou Cottage

3 BR | 2 BA | Sleeps 10 | Quick View

$229

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to CocoBayou Cottage, a 3 bedroom/3bathroom home with a heated pool. Featuring two units (Casita Bayou & Casita Coco), CocoBayou Cottage sleeps up to 10 and is near the beach, Crescent Village & the Intercoastal. Great for a big group! Welcome to CocoBayou Cottage!This uniquely configured ...

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Property Type

Siesta Key Cottage

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"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Hurry -Last minute special!!! ***25% off any one week booking from 6/15 - 6/30. Ask about nightly!

$151

per night

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Key Amenities

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

About this property

(upstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Property Type

Siesta Key Condo

"Spotless property in great location"
Reviewed June 15, 2019

On a quiet street very near to the amenities.Lovely pool and bbq area.Just a short walk to the fab beach. Couldn't fault the property at all, everything was clean and of good standard. My only gripe would ...

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The Palms Cottage

4 BR | 2 BA | Sleeps 10 | Quick View

$385

per night

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Key Amenities

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

About this property

This charming recently updated four-bedroom, 2-bathroom home is just a short walk to Siesta Key Village and minutes from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for families and couples looking for their perfect tropical getaway.The Palms Cottage can accommodate up to ...

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Property Type

Siesta Key House

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Villa De Paradisio

4 BR | 2 BA | Sleeps 12 | Quick View

$385

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to the beautiful Villa De Paradisio! This gorgeous waterfront cottage is a very luxurious and large four [4] bedroom canal front heated pool home with two bathrooms in approximately 1,800SF of air conditioned living space with a heated pool overlooking the dock and canal. This home has been completely ...

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Property Type

Siesta Key House

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

$149

per night

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Key Amenities

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

About this property

Our villa is a tastefully furnished and fully equipped with state of the art kitchen on the widest part of Crescent (Siesta Key) Beach. The villa is located GULFSIDE just steps to the beach, no streets to cross, It is just two villas away and a short 20 second walk.The villa sleeps 4-6 people, ...

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Property Type

Siesta Key Villa

"Stay in Barbara's Unit was wonderful again ! Best Beach EVER !!!!"
Reviewed February 4, 2019

Barbara's unit is so close to the beautiful Siesta Key beach....only steps away. Unit is outfitted with everything you can think of and then some !! Love the convenience of being able to park right ...

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Serenity Cottage

3 BR | 3.5 BA | Sleeps 8 | Quick View

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Serenity Cottage!A pristine and elegant home so close to the most beautiful beach in the world most would say, Serenity Cottage offers a delightful and relaxing retreat with maximum comforts in mind, and a spacious abode designed around the needs and comforts of large families traveling ...

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Property Type

Siesta Key House

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Fishermans Cove A102 - On Turtle Beach on Siesta Key

$164

per night

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Key Amenities

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

About this property

My ground floor rental is directly on the beach on the Gulf of Mexico, with incredible views and sunsets!The lanai has a back door directly out to the Beach. The front of my unit faces the Lagoon where we have a FREE DOCK for your boat or other water craft. (So you have water views in both directions)! ...

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Property Type

Siesta Key Condo

"Barefoot living"
Reviewed April 27, 2019

The place was great, loved the layout. It is far from the action but we enjoyed the quiet beach. The biggest complaint I had was the sheets on the king bed, they were really pilled. Felt like sleeping ...

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West Shore

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to West Shore! A massive gulf front penthouse located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 8, it is the only way to experience Siesta Key!West Shore is a luxuriously appointed penthouse in an extremely private ...

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Property Type

Siesta Key Condo

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Coconut Grove

6 BR | 6 BA | Sleeps 16 | Quick View

$404

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Coconut Grove! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 16, a private heated pool, and quite literally in the heart of Siesta Village!Coconut Grove features a unique combination of two ...

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Property Type

Siesta Key House

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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!