Siesta Key Vacation Rentals

(209 rentals)
MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

8

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$167

per night

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Key Amenities

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

About this property

THE FIRST FLOOR UNIT AT 317 CANAL RD IS STILL AVAILABLE FEB 29- MARCH 14 WITH A 25% DISCOUNT! PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTS RATES! DUPLEX: 1 FIRST FLOOR 2 BED/ 2 BATH UNIT AND 1 SECOND FLOOR 2 BED/ 2 BATH UNIT. SHORT WALK TO VILLAGE OR BEACH. PRIVATE HEATED POOL, TIKI ...

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Property Type

Siesta Key Apartment

"Perfect location"
Reviewed March 13, 2020

Walking distance to anything found in The Village of Siesta Key. Our unit had everything that we needed and more. Very, very clean. Loved the privacy of the pool and the fact it was heated. Would definitely ...

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

$225

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"safe, secure, phenomenal ocean viewing from your lanai,"
Reviewed January 13, 2020

wonderful set up for a friendly get away. the lanai with the full open front to the ocean was wonderful. having your own bathroom attached to your bedroom, full kitchen with a good sized living room was ...

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"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2

$151

per night

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Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!320 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (upstairs) - 2 bed/ 2 bath-dishwasher, heated pool, great back yard for BBQ and gatherings. Combine all four units ...

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Property Type

Siesta Key Condo

"Banyon 2019"
Reviewed June 22, 2019

Loved the old Florida feel. Great location. Wonderful courtyard. Since we had 3 units rented, 1 unit was friends of ours, we had a great time in the courtyard. Only drawback was having to enter courtyard ...

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Fishermans Cove A302

2 BR | 2 BA | Sleeps 6 | Quick View

3

$164

per night

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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 Salt Life

6 BR | 4 BA | Sleeps 16 | Quick View

1

$404

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Salt Life! This private 6BR/4BA home is a unique combination of two units: “Sea Esta” & “Sea La Vie” (2328 sq. ft. total). Each unit features a 3BR/2BA configuration, each with their very own common space to include a kitchen, dining area, and private outdoor ...

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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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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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*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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West Shore

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

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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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The Water is Great! Siesta Key Inn #125

$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 House

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The Big Kahuna

8 BR | 6 BA | Sleeps 24 | Quick View

$577

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Big Kahuna! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 24!!!] can fathom. It also boasts the very BEST location, in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll ...

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Property Type

Siesta Key House

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Deja Blue – 5288R

2 BR | 1 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.3 miles to Siesta Key Beach (Access # 2)

$129

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

About this property

Welcome to Deja Blue, one of Siesta Key’s newest and coziest 2BR/1BA beach bungalows with heated pool and located in the heart of Siesta Key Village!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 ...

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Property Type

Siesta Key Bungalow

"Deja blue"
Reviewed January 22, 2020

It was wonderful. My husband and I thought the house was nice and clean and location was perfect. Would stay here again.Thanks, Cathy and Bill Tyler

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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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Ventana Rosa – 1905

3 BR | 2 BA | Sleeps 10 | Quick View

Distance to beach: 2 miles to Shell Beach

$139

per night

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Key Amenities

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

About this property

Ventana Rosa - One of The Cottages on the KeyWelcome to Ventana Rosa, one of Siesta Key's newest luxury homes with private heated pool! Minutes to world famous Siesta Key Beach and Village!This luxurious and recently renovated (as of 2019) 3-bedroom/2-bathroom home is located in close proximity ...

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Property Type

Siesta Key House

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Ocean’s Edge

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to Ocean's Edge! 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!Ocean's Edge is a luxuriously appointed penthouse in an extremely ...

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Property Type

Siesta Key Condo

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The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

1

$400

per night

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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

"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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Vinca – 5251D

1 BR | 1 BA | Sleeps 2 | Quick View

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

Welcome to Vinca, a charming 1BR/1BA home with heated pool located in the heart of Siesta Key Village and just steps from world famous Siesta Key Beach! This home is perfect for small families and groups.This adorable 1 bedroom/1 bathroom home is a unique combination of 4 units that can be rented ...

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Property Type

Siesta Key Cottage

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Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

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Key Amenities

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

About this property

Explore Casita Playa, a quaint 2BR/1BA bungalow located within walking distance from Crescent Beach/Village. This home is the perfect beach escape for small families and couples alike!This lovely 2BR/1BA beach bungalow is just a short walk to prestigious Crescent Beach and close to world famous Siesta ...

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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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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$330

per night

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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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Sol y Mar

4 BR | 2 BA | Sleeps 8 | Quick View

$284

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sol y Mar! A uniquely configured South Siesta Key private home with 4 bedrooms, 2 bathrooms that sleeps 8. May also be used as 2 separate units surrounded by lush gardens with a private beach access, a heated swimming pool and hot tub. Welcome to Sol y Mar. This COMPLETELY RENOVATED, single ...

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Property Type

Siesta Key House

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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

$80

per night

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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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Sandy Seahorse Cottage

6 BR | 6 BA | Sleeps 16 | Quick View

$284

per night

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Key Amenities

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

About this property

Welcome to the Sandy Seahorse Cottage!This uniquely configured private home [Sandy Cabana and Seahorse Cabana] is the perfect escape for you and your family and friends. This gorgeous beachy getaway comfortably sleeps 12 with a little room for more! The property has recently been updated with new ...

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Property Type

Siesta Key House

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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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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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Casita Lime – 303L

2 BR | 2 BA | Sleeps 6 | Quick View

$125

per night

View Details

Key Amenities

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

About this property

This adorable two bedroom/two bathroom home features a shared heated salt water pool (when booking Lime in a Coconut, pool is private). Casita Lime offers all of the amenities for the ultimate beach getaway at an unbeatable location in the heart of Siesta Key Village and just two blocks from world famous ...

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Property Type

Siesta Key House

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Isla Amor

4 BR | 3 BA | Sleeps 8 | Quick View

$578

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Isla Amor. An absolute one of kind, limited edition home located in the "heart of the Siesta Key" on the prestigous Palm Island (the island within the island). Featuring a private heated pool, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. ...

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Property Type

Siesta Key House

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The Hummingbird

6 BR | 6 BA | Sleeps 12 | Quick View

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

$286

per night

View Details

Key Amenities

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

About this property

Welcome to The Hummingbird, a delightful 6BR/6BA home with private heated pool! Located just steps from world famous Siesta Key Beach and Siesta Key Village This home is perfect for families and small groups.This private six bedroom/six bathroom home is a unique combination of four units: Lantana, ...

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Property Type

Siesta Key House

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Lantana – 5251A

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
  • Pet Friendly
  • Pool
  • Private Pool

About this property

Welcome to Lantana, a charming 2BR/2BA home with heated pool located in the heart of Siesta Key Village and just steps from world famous Siesta Key Beach! This home is perfect for small families and groups.This adorable 2 bedroom/2 bathroom home is a unique combination of 4 units that can be rented ...

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Property Type

Siesta Key Cottage

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Peacock Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$200

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Peacock Villa, a beautiful 3 bedroom, 3 bathroom townhome just steps from the beach. Along with its sister property Monarch Villa, reserve Casa de Mariposa for the ultimate corporate retreat, family reunion or destination wedding setting!The luxurious three (3) bedroom, three (3) bathroom ...

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Property Type

Siesta Key House

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Renovated 4 bedroom directly on No 1 rated beach. Unobstructed views of gulf.

$508

per night

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Key Amenities

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

About this property

December 2017 renovation expands fantastic views of beach, gulf and sunsets New windows, doors, bathrooms, floors, paint and landscaping A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms ...

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Property Type

Siesta Key House

"Doesn't get much better!"
Reviewed May 25, 2019

This amazing duplex is absolutely perfect for a family getaway! From the cute quiet brick street leading to the house, to the towels embroidered w/colorful fish, you won't be disappointed in the details ...

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Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

View Details

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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Sunset Fiesta

4 BR | 2 BA | Sleeps 12 | Quick View

$257

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sunset Fiesta, a unique combination of two units: “The Hidden Gem” and “Deja Blue.” This cozy beach villa features a private heated pool and is located in the heart of Siesta Key Village!This charming 4BR/2BA beach villa is centrally located in the heart of Siesta ...

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Property Type

Siesta Key House

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Sandpiper Cottage

5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.8 miles to Crescent Beach

$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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Coconut Grove

6 BR | 6 BA | Sleeps 16 | Quick View

$371

per night

View Details

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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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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Moonlight Cottage – 5034

4 BR | 2 BA | Sleeps 10 | Quick View

$330

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This alluring 4 bedroom/2.5 bathroom home offers a private heated pool and all of the amenities you need for your beach vacation. Moonlight Cottage is located just 1 mile from world famous Siesta Key Beach, continually ranked among the the top ten beaches in the USA! This home is perfect for families ...

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Property Type

Siesta Key House

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Sea Esta – 5319 (L)

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea Esta! This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? The Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea Esta offers a shared heated pool with ...

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Property Type

Siesta Key House

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Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$254

per night

View Details

Key Amenities

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

About this property

One of Siesta Key's most alluring homes, with private heated pool & spa! Siesta Dream House is perfect for family get togethers and romantic getaways alike.Welcome to Siesta Dream House! This enchanting 4-bedroom/3.5-bathroom home is located in Siesta’s North Key and is close to Siesta Key ...

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Property Type

Siesta Key House

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Heron House – 117R

3 BR | 5 BA | Sleeps 12 | Quick View

$314

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This luxurious and completely renovated (as of 2019) 3-bedroom/5-bathroom home has all the amenities for your beach vacation, including a game room and breathtaking ocean views from your very own roof-top deck! Heron House is centrally located in the heart of Siesta Key Village and just minutes from world ...

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Property Type

Siesta Key House

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

$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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Beautifully Renovated 2 Bedroom 2 Bath Waterview Condo, Pools, Tennis, Gym

2 BR | 2 BA | Sleeps 6 | Quick View

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

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The Hidden Gem – 5290L

2 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to Siesta Key Beach (Access # 2)

$129

per night

View Details

Key Amenities

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

About this property

Welcome to The Hidden Gem, one of Siesta Key’s newest and coziest 2BR/1BA beach bungalows with heated pool and located in the heart of Siesta Key Village!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 ...

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Property Type

Siesta Key Cottage

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"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

4

$143

per night

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Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!2 Bed/2 Bath unit with King Bed, Two queen beds, Open Deck, ground floor. Pool Access, WIFI, *W&D access.Local free shuttles so no need for a car.Located on the Voted number “#1 Beach in America” popular Siesta ...

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Property Type

Siesta Key House

"Perfection in Paradise"
Reviewed June 18, 2019

We stayed in this lovely condo for 10 nights, and enjoyed every minute.The condo was spotless when we arrived, and had all the amenities we needed with ample space.Right outside is the heated pool ...

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Sand Dollar Cottage

3 BR | 2 BA | Sleeps 8 | Quick View

$385

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sand Dollar Cottage! This lovely 3 bedroom, 2 bath north Siesta Key vacaiton home comfortably sleeps 6 in beds, with a soft ultra plush sofa sleeper in the living room for an extra 2. Enjoy heated pool and waterview of Intracoastal canal. Welcome to the completely remodeled, and newly furnished ...

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Property Type

Siesta Key House

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"Key West" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

1

$151

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!2 BEDROOM/2 bath, Large Deluxe unit, King bed, Queen bed and Queen sleeper sofa, 3 TVs, large deck with awning, small screened porch, an upstairs accommodation. Pool Access, WIFI, private W&D. Local free shuttles so no need for a ...

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Property Type

Siesta Key House

"Best and thoughtful rental company with beautiful beach"
Reviewed June 12, 2019

We have been visiting Siesta Key for the past 10 and renting from the same company. There accommodating attention to their guests has us coming back year after year. We never consider renting with any ...

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The Sun Dial

4 BR | 4 BA | Sleeps 12 | Quick View

$550

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Sun Dial! An absolute one of kind, limited edition home located in a beautifully secluded private neighborhood only minutes from Siesta Key's main beach access. Featuring a private heated pool, near America's #1 Beach, on the canal with intracoastal bay access and a boat dock. You have ...

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Property Type

Siesta Key Apartment

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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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Coral Breeze – 4576

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 quaint 3-bedroom/2.5-bathroom home is located near Siesta Key Village and just five minutes from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for small families and couples alike.Coral Breeze can accommodate up to 6 guests with a bedding configuration as follows:• ...

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Property Type

Siesta Key House

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

1 BR | 1 BA | Sleeps 4 | Quick View

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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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!