Siesta Key Vacation Rentals

(252 rentals)
SIESTA KEY HEAVEN smack dab on the beach

$199

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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Gran Vista – 6906

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$633

per night

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Key Amenities

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

About this property

Welcome to 6906 Coronas Park, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 6-bedroom/4.5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key ...

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Property Type

Siesta Key House

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305 - El Presidente Condo on Siesta Key

$208

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Professionally decorated and renovated, 2 bedroom, 2 bathcondominium. Access the spacious balcony for views of the gulf from the livingroom or master bedroom. You will enjoy ceramic tile throughout the unit, fullyoutfitted kitchen with granite countertops and stainless steel appliances.Enjoy the Tommy ...

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Property Type

Siesta Key Condo

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Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

2

$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

"Fantastic Florida Rental"
Reviewed June 22, 2019

Casa Ohana was terrific. Family friendly, close to the beach and main attractions of Siesta Key. Will definitely be returning!

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MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

7

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

"Excellent location, great pool!"
Reviewed January 7, 2020

Magnolia House is superbly located yards from Siesta Key Village and only 200 yards from the beach. It is split into two apartments which is great for two families. The pool is warm and a good size and ...

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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

$133

per night

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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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Dreamy Property !!

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 500 feet to Crescent Beach

$112

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Midnight Cove II has 70 units available for rent. We may just have availability for you!!We only book Saturday to Saturday.Welcome to Midnight Cove II and thanks for checking us out! We think we are quite spectacular if we must say so ourselves! Siesta Key and our local community are brimming ...

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Property Type

Siesta Key Condo

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101 - El Presidente Condo on Siesta Key

$220

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Spacious 1836 Sq ft apartment. Large living/dining area is 15'x38'. The unit has a large sunroom with sliding patio doors/screens on two sides that open onto large wrap around balcony. Well equipped kitchen. King bed in master, 2 doubles in a guest room. Queen sleeper sofa. Unit sleeps 8. 1 Bath has a ...

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Property Type

Siesta Key Apartment

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Available mid March thru April. Quiet, private, yet walk to village and beach.

$199

per night

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Key Amenities

  • Air Conditioning
  • Private Pool
  • Rentals by Owner

About this property

Enjoy all the comforts in this cozy 2 Bedroom 1 bath Luxury Siesta Key Village location private retreat. Brand new fabulous furnishings and decor with king size select comfort bed and washer dryer in unit. Beautiful private heated pool and grill for use. Includes off street parking, 2 beach bikes, ...

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Property Type

Siesta Key House

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Dolphin" 378 Canal Rd. Just a short walk to the beach and Village

$103

per night

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Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!1 Bedroom, King Bed, Queen sleeper sofa, Ground level, Screen Porch. Pool Access, WIFI *W&D access, and ground floor. Across from Canal

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Property Type

Siesta Key Apartment

"Great "Old Village" Rental Experience"
Reviewed June 13, 2019

We are lucky to have found this rental property in Siesta Key Village! A well maintained unit, it is ideally located a short walk from the beach and a five minute walk to the village for dining, shopping, ...

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Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$286

per night

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Key Amenities

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

About this property

Welcome to Seaside Cottage, one of Siesta Key's most dazzling 4BR/3BA homes, with private heated pool. Steps from world famous Siesta Key beach and just minutes so Siesta Key Village!! This remarkable 4 bedroom/3 bathroom home features a private heated pool. With its location less than a mile from Siesta ...

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Property Type

Siesta Key Cottage

"Wonderful"
Reviewed May 3, 2018

Great place, very comfortable beds, all the items you need - kitchen equipped with great tools. Very clean.

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505 - El Presidente Condo on Siesta Key

$208

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Beautifully updated! All new granite kitchen countertops and stainless appliances. Top floor unit with amazing gulf view! Parking Space #38

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Property Type

Siesta Key House

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The Nautilus

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 luxurious 8 bedroom/six bathroom home is a unique combination of two units: “Casa Stolida” and “Casa Tegula” (4000 sq. ft. total). Each unit features a 4 bedroom/3 bathroom configuration, each with their own cabana room, separate living areas, private elevators and your very ...

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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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The Grand Canal Cottage

5 BR | 4 BA | Sleeps 12 | Quick View

2

$495

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Grand Canal Cottage, one of Siesta Key's most enchanting canal-front cottages, with private heated pool & spa. This idyllic 5 bedroom/4 bathroom home is just a short walk to Siesta Key Village and 2 blocks from Siesta Key Beach, voted the # 1 beach in the USA! The Grand Canal Cottage ...

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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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The Islander – 6931

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

per night

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Key Amenities

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

About this property

Welcome to The Islander, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 4-bedroom/4.5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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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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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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Hanging at the Beach House! Siesta Key Inn #224

1 BR | 1 BA | Sleeps 4 | Quick View

1
LAST MINUTE DEAL 2/17 - 3/30: It's not too late to Escape your Winter Blues. Sunshine, Blue Skies and Glorious Sunsets.

$199

per night

View Details

Key Amenities

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

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Key Inn is just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach at Point of Rocks. With no streets to cross, it's 75 steps to the Gulf ...

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Property Type

Siesta Key House

"Charming"
Reviewed February 15, 2019

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

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DEAL
504 - El Presidente Condo on Siesta Key

$208

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to our Siesta Key home located directly on the world famous white sand Crescent Beach! This unit was privately owned for almost 20 years and has been recently made available for rental. Our condo was totally remodeled in the last 12 months, meticulously maintained, 2 bedroom, 2 bath, with a breathtaking ...

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Property Type

Siesta Key House

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109 - El Presidente Condo on Siesta Key

$224

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Great 2BR/2BA with wonderful Gulf and beach Views from living room, master bedroom and large balcony! Completely remodeled in Fall of 2015 with everything new! Less than 50 steps away from the pool and beach!

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Property Type

Siesta Key House

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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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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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Siesta Key - Bay Oaks -Gulf Views

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.1 miles to Crescent Beach

$164

per night

View Details

Key Amenities

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

About this property

Submit for a quote. No Fees Enjoy the best that beautiful Bay Oaks has to offer. This 5th floor condo has beautiful views of the Gulf of Mexico. This updated 2BR/2BA condo has a living room, dining room, kitchen and screened lanai where you can enjoy morning coffee or evening refreshments. The spacious ...

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Property Type

Siesta Key Condo

"Review"
Reviewed August 20, 2019

I would definitely rent this unit again. It had problems, it should have been opened up and aired out before we got there. The linens for the pull out couch were on the bed, used before, I believe. Extra ...

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202 - El Presidente Condo on Siesta Key

$191

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Updated 2 Bedroom 2 Bath decorated with a relaxed beach theme with all the amenities... 3 flat screens TV's, HD cable, DVD, stereo, secured wireless internet, washer and dryer in separate utility room, king size bed in master with attached bath with walk in shower with grab bar, hair dryer, two full size ...

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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

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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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310 - El Presidente Condo on Siesta Key

$482

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Parking Space #17 Beautiful Gulf Front unit. 3BR 3Bath all remodeled. Gorgeous Gulf View

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Property Type

Siesta Key House

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Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

View Details

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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205 - El Presidente Condo on Siesta Key

$191

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Tastefully decorated tropical view 2BR/2BA unit with washer & dryer. King bed in master, 2 doubles in guest room. 2 walk-in showers. Beach towels included. Parking Space #41

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Property Type

Siesta Key House

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"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

4

$143

per night

View Details

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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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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206 - El Presidente Condo on Siesta Key

$191

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Recently remodeled, beautiful condo with open kitchen and new granite countertops, stainless steel appliances and furniture. Three Samsung flat screen TV's, with a DVD/VCR in living room and HDTV in living room and master bedroom. Cable TV in living room and both bedrooms, and free channel on demand in ...

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Property Type

Siesta Key Condo

"Great stay, friendly service!"
Reviewed June 5, 2019

Our family of 4 stayed 10 days in May at El Presidente. This unit is beautifully remodeled in this older condo and suited all our needs. Only steps to the beach and the pool was clean. The condo is conveniently ...

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Tropical beach getaway at Sandy's Siesta Key Condo

2 BR | 1.5 BA | Sleeps 4 | Quick View

3

Distance to beach: 200 yards to Crescent Siesta Key Beach

$127

per night

View Details

Key Amenities

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

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

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Property Type

Siesta Key Condo

"Sandy's siesta"
Reviewed October 21, 2018

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

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"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2

$151

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!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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Direct Gulf Beachfront Condo-Just walk out the back door on to the sand!

$171

per night

View Details

Key Amenities

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

About this property

The Gulf of Mexico is only 100 ft. from your private sand beach and lanai entrance. Listen to the surf from your master bedroom. Enjoy dining on the lanai while watching the sunset. During the day you can see dolphins, kite boarding and sea birds. This unit has all the comforts of home plus a full size ...

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Property Type

Siesta Key Condo

"The perfect place"
Reviewed February 7, 2020

We loved our stay! Look forward to next year. A103 will now be our second home. See you in the summer

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Siesta Salt Life

6 BR | 4 BA | Sleeps 16 | Quick View

1

$404

per night

View Details

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

2 BR | 2 BA | Sleeps 6 | Quick View

18

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

$171

per night

View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

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Property Type

Siesta Key Condo

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

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

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106 - El Presidente Condo on Siesta Key

$208

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Great 2BR/2BA with wonderful Gulf Views from living room, master bedroom and large balcony! Completely remodeled in Fall of 2016 with everything new! Stainless appliances, bright decor, ceiling fans and flat screen TV's in all rooms! King in master, 2 Queens in guest room and sofa sleeper in living room. ...

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Property Type

Siesta Key Condo

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Florita's Key – 156

4 BR | 3 BA | Sleeps 10 | Quick View

$229

per night

View Details

Key Amenities

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

About this property

This coastal 5-bedroom/3-bathroom home features all the amenities you can think of for your beach vacation and offers an unbeatable location. Viento Del Mar is located just minutes from Shell Beach and close to world famous Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for families ...

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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

View Details

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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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

View Details

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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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

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

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Property Type

Siesta Key House

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Ocean’s Edge

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 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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La Casa Verde

4 BR | 2 BA | Sleeps 10 | Quick View

$495

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

The waterfront cottage, ‘La Casa Verde’ is a very luxurious and large four [4] bedroom canal front heated pool home with two very large bathrooms in approximately 2,800 square feet of air conditioned living space. As you approach the home you are immediately drawn into it by volumes of lush, ...

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Property Type

Siesta Key House

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Casa Stolida

4 BR | 3 BA | Sleeps 8 | Quick View

$264

per night

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Key Amenities

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

About this property

Luxurious 4BR/3BA villa features a private heated pool and cabana room. Casa Stolida is just steps from prestigious Crescent Beach and is centrally located in close proximity to Siesta Key Beach, voted the #1 beach in the USA!Once inside the home, you will see that Casa Stolida is the definition ...

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Property Type

Siesta Key House

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108 - El Presidente Condo on Siesta Key

$224

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Great 2BR/2BA with wonderful Gulf Views from living room, master bedroom and large balcony! Completely remodeled in Fall of 2016 with everything new! Stainless appliances, bright decor, ceiling fans and flat screen TV's in all rooms! King in master, 2 Queens in guest room and sofa sleeper in living room. ...

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Property Type

Siesta Key House

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Tropical Escape 2 Br/2 B Siesta Key Inn #226

$265

per night

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Key Amenities

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

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Key Inn 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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408 - El Presidente Condo on Siesta Key

$374

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Over 2500 sq. ft. 3BR/3BA with stunning Beach Views! Sleeps up to 6. No washer/dryer in unit, but there are laundry facilities on the 1st floor. Grab bars in master bath. Parking Space #32

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Property Type

Siesta Key House

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Sophie’s Quartier

6 BR | 5 BA | Sleeps 16 | Quick View

$594

per night

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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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Adorable Condo -- On Beach and Bay, 2 Bdr. Ground Floor

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to Siesta Key Beach

$136

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. The complex is a gated resort community featuring unique “Old Key West style” condominiums only a ...

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Property Type

Siesta Key Condo

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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 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!