Siesta Key Vacation Rentals

(361 rentals)
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2 BR | 2 BA | Sleeps 6 | Quick View

6
Owner special: 10% off for the weeks of August 20 to 27 or Aug 27 to Sept 3rd 2022

$244

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • 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

"Beautiful and tranquil getaway!"

Me and my husband had a wonderful vacation and plan on returning next year. The condo looks just like the pictures and was very clean and well equipped. The beach was so peaceful. It was away from the crowds, ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • 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

"Peaceful"

Really enjoyed staying at this quieter end of the island. It was a much needed break. Carrie is very sweet and easy to deal with. Will definitely be returning again.

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the ...

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Property Type

Siesta Key Condo

"A Beachfront Dream"

A slice of paradise. This unit was well equipped and designed for comfort at the beach. The flawless sunsets and the intoxicating motion music of the waves will make us return often. A very homey unit...lovely ...

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2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$241

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to beach: 100 feet to Crescent Beach

$250

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date and ...

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Property Type

Siesta Key Condo

"Siesta Key"

Owner is warm, professional and easy to talk to. Condo is large and open with a beautiful sunset view. Kid-friendly. Entrance to condo is first one on right after getting off bridge which is so convenient ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

A millionaire's retreat! This completely remodeled first floor unit with view of the Gulf of Mexico and amazing sunsets awaits you on Siesta Key. Walk out the lanai door directly to the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf within 100 ...

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Property Type

Siesta Key Condo

"Family-friendly beach front condo, perfect setting for a memorable beach vacation."

Our stay was nothing but excellent! Dina and Russ thought of everything to make our beach vacation memorable. From comfortable beach chairs and an umbrella to sand toys and beach towels, our hosts graciously ...

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2 BR | 2 BA | Sleeps 6 | Quick View

4.8 rating on other travel sites

$241

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...

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Property Type

Siesta Key Condo

"Cold escape"

We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!

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2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$253

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

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Property Type

Siesta Key Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This spacious, beautifully decorated and updated 2 BR/2.5 bath townhome overlooks the canal and boat basins and is located directly across the street from the gorgeous Siesta Beach. The kitchen and all baths have been renovated and the newly furnished living room features a sofa bed and 55” smart ...

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Property Type

Siesta Key Townhome

"Midnight Cove"

We stayed at Midnight Cove for spring break. Our condo was very nice! It overlooked the pool and the bay. The whole complex is beautiful and it was actually very quiet at night considering it was spring ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$192

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Enjoy a perfect vacation in this spacious 2 bedroom, 2 bath large villa. With 2 Queen and 2 Twin beds, this is the perfect villa even for a large family up to 6. From this villa, you are just steps to Crescent Beach - world renowned whitest sand. Enjoy Wi-Fi community internet access, a 32" flat ...

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Property Type

Siesta Key Villa

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This magnificent unit has been completely remodeled and is on the ground floor with beautiful water views and spectacular sunsets. Walk out the rear lanai door directly onto the beach where children can play within view or walk over the boardwalk to the blue-green waters of the Gulf of Mexico within 100 ...

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Property Type

Siesta Key Condo

"Excellent beach front condo"

We had an amazing stay but how could you not! The condo itself was decorated nicely and very clean. It has practically everything you will need besides groceries of course. Pack less as there is a washer/dryer ...

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2 BR | 2 BA | Sleeps 5 | Quick View

10
LAST MINUTE DEAL 7/30 - 8/6: Last minute cancellation. Save $700 for the week of July 30-Aug 6th

$377

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

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

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Property Type

Siesta Key Condo

"stunning view"

My family and I stayed here in JUNE. The views of the Gulf are absolutely amazing. Unit was very clean and every thing we needed for our stay was there.

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DEAL

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

VILLAGE WEST - Deluxe Ground Floor Vacation Condo in Siesta Key Village with Heated PoolLocated right in the Heart of Siesta Village, Sarasota FL - Short Walk to Crescent BeachVILLAGE WEST: This Siesta Key one bedroom ground floor condo vacation rental is located right in the heart of Siesta Village ...

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Property Type

Siesta Key Condo

"Great location!"

The location of this rental was perfect. We were able to walk into the village to shop and eat within a few minutes. Drive time to local attractions was minimal.

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2 BR | 2 BA | Sleeps 6 | Quick View

$192

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

2 Bedroom/ 2 Bath Large Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.Additional person fees may apply.

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 6 | Quick View

$192

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

C-17 Property Information Large 2 bedroom 2 bath Private Villa, is a few steps away from our Private Beach, Close to pool, Clubhouse and Laundry. C-17 is a large, newly-remodeled, open-concept villa. It has 2 Master bedrooms. One Master has a king bed and bath-shower combination. The second Master ...

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Property Type

Siesta Key Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The completely updated 6th floor unit in Casarina has a magnificent gulf view, exceptional pool, hot-tub and BBQ area, and a prime in-garage parking space, steps from the elevator.

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Property Type

Siesta Key Condo

"Wonderful apartement"

We really enjoyed our vacation in the great and large Apartement. Furnished great. Large kitchen with work island, dining bar with 2 high chairs and well equipped kitchen. The living room is practically ...

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2 BR | 1 BA | Sleeps 6 | Quick View

7
Owner special: SIESTA KEY! Mid Aug - Fall get $200 off 5 nts or more. Private villa in Resort. Beach/Pool.

$186

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

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 USA. The Beach has complimentary shade cabanas and beach chairsFeatures include 2 Bedrooms, 1Bath sleeping six with 1King and 2 queen beds. The kitchen is furnished ...

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Property Type

Siesta Key Villa

"Enjoying our first month of retirement."

The condo that we stayed at while we enjoyed our first month of retirement was very clean, comfortable and met all of our needs. We loved it so much, we have booked a return trip for 2023.

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2 BR | 2 BA | Sleeps 6 | Quick View

$188

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Casa Blanca is within walking distance of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. ...

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Property Type

Siesta Key Villa

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1 BR | 1 BA | Sleeps 4 | Quick View

5

Distance to beach: 20 yards to Siesta Key Beach

$179

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Getting away from Ohio cold and snow"

We liked staying at Sea Spray resort. Close to the beautiful Siesta beach nice short walk which we loved. Place was clean with necessary appliances needed. Liked using the grills outside they worked well ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

VERY SPACIOUS 4 BEDROOM 2 BATHEOOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS, SLEEPS 8, 1 KING, 1 QUEEN, 2 FULL, 2 TWIN BEDS. 1 MONTH MINIMUM ...

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Property Type

Siesta Key Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to La Siesta Unit 112! This quiet 2-bedroom 2- full bath end unit is located on the ground floor of the La Siesta Condominiums complex with a direct walk out access to all Siesta Key Beach amenities. ***We are COVID friendly, clean, and have ANTI-VIRAL UV LIGHT TREATMENT HVAC system***. We are ...

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Property Type

Siesta Key Apartment

"Awesome"

We were so happy with our stay ! The condo was perfect And the owner was so attentive if we had questions or concerns The location ! Can’t say enough Walking distance to the most beautiful beach ...

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2 BR | 1 BA | Sleeps 6 | Quick View

$186

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

2 Bedroom/ 1 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.Completely remodeled, spacious two bedroom villa with room for the whole family. Sleeps six with pullout couch. Brand new kitchen, flooring, paint and bedroom carpeting. Open floor plan is perfect ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 6 | Quick View

$192

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

This lovely unit has just been remodeled and is awaiting your arrival. There is free high speed internet and long distance telephone in the U.S. and Canada, heated pool and screened lanai. This unit can occupy up to 6 persons. Villa C6 features new living room furniture, a 50" Plasma HDTV with ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 6 | Quick View

1

$268

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large washer ...

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Property Type

Siesta Key Condo

"Beautiful Condo!"

This Condo is well appointed and is in the perfect spot right on the beach of the Gulf! We we're ableto walk out to the beach from our back door and see the canal out the front. We cooked in the kitchen ...

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2 BR | 2 BA | Sleeps 5 | Quick View

$192

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Casa Blanca is within walking distance of Crescent Beach Village restaurants and shops, with Siesta Key Village just a short drive north on the key. Our villas are located between the pool area and famous Crescent Beach. Each villa is individually decorated, fully equipped and professionally landscaped. ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: 15% OFF - Last minute opening July 6-22. Save hundreds!

$291

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

Welcome to Crystal Sands Unit 507! We would love to have you stay with us in our luxury 2-bedroom 2-bath fully furnished Gulf Front vacation rental on award winning Crescent Beach. Siesta Key is famous for beautiful turquoise water full of sea life and white powdery crystal sand beaches. Enjoy all our ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

4.5 rating on other travel sites

$241

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the Gulf on ...

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Property Type

Siesta Key Condo

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3 BR | 3.5 BA | Sleeps 5 | Quick View

3

Distance to beach: 0.3 miles to Crescent Beach

$338

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Convenient and Easy: 3-minute walk to the beach with private deeded access. 4-minute walk to the Crescent Beach Shopping Center with the Big Water Fish restaurant, Pizza and Brew, liquor store, and the Toasted Mango for breakfast. 5-Minute walk to Captain Curts, the Tiki, the Crescent Club and the ...

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Property Type

Siesta Key Townhome

"Incredible Space and Great Location"

We are beach people so we LOVE this location -- 2 minutes to the white sands of Crescent Beach. The condo itself is beautifully decorated and is super comfortable and clean. Tori, the owner, is great. ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Vacation rental with private beach on the # 1 beach in the USA - Siesta Key on the Gulf of Mexico (Sarasota)*** STAY SAFE *** In response to COVID-19, additional safety and sanitation measures are taken ***Siesta Key, awarded for its pristine, powdery white beaches and its azur blue waters is ...

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Property Type

Siesta Key Apartment

"Beautiful view"

Siesta Key is a favorite. The convenience of walking a short and healthy walk to the white sand is a plus. The property management was quick to take care of a few concerns we had upon arrival to make ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$188

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

This unit features a King bed in the master with a brand new bathroom, the guest bedroom offers a queen bed where there is a washer and Dryer in the unit for your convenience. The Second bathroom was added in late 2013. There is a new kitchen that will delight the chef in each of you. The living room ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 4 | Quick View

$192

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to D15 here you will truly find all the comforts of home, the owners have decorated this unit to give their guest the best with relaxation on everyone's mind you will find it here. The living room has all new furniture, including a 60" TV for your viewing pleasure. The Master bedroom features ...

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Property Type

Siesta Key Villa

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1 BR | 1 BA | Sleeps 4 | Quick View

1

$149

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Come and enjoy this wonderful 1Bedroom 1Bath Villa. Steps away from the pool and a short walk to private beach, where you can build an awesome sand castle or relax under a canopy or umbrella. Enjoy that first morning cup of coffee in the screened in lanai. Amenities: Personal secured wireless ...

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Property Type

Siesta Key Villa

"Best Resort Ever"

Wonderful time at Case Blanca. Our Villa was sweet, clean and handy to laundry and pool. The beach was perfect in every way and was impressed with how staff worked to keep everything clean. We would definitely ...

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool
  • Rentals by owner

About this property

This magnificent unit is on the third floor with spectacular unobstructed views of the Gulf! This unit has been completely renovated with beautiful natural stone tile throughout, updated kitchen and bathroom and brand new furniture, coastal pictures, decorative accessories, bedding, new paint throughout. ...

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Property Type

Siesta Key Condo

"Amazing!"

Perfect view and room, owners dropped off pillows for us. Very happy with the service at this unit as well.

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2 BR | 2 BA | Sleeps 4 | Quick View

$192

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

2 Bedroom/ 2 Bath Large Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.

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Property Type

Siesta Key Villa

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1 BR | 1 BA | Sleeps 4 | Quick View

$149

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to your home away from home! Casa Blanca unit D08 was entirely renovated at the end of 2015. Everything inside is brand new and beautifully updated. Features include a king size bed, walk-in shower, new furniture, new appliances, and brand new tile throughout. Casa Blanca is within walking distance ...

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Property Type

Siesta Key Villa

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Key Amenities

  • Air conditioning
  • Beachfront
  • 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

"Wonderful week at Crescent Arms 601S!"

Couldn’t have asked for a better location on the beach! Condo was absolutely spotless and everything about this rental was wonderful from the communications with the owner to everything inside the condo. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - Upscale Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the closest condos to the ...

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Property Type

Siesta Key Condo

"Pleasant stay!"

We rented B204 and the unit was fully equipped. The only ding would be the blinds that were broken in kitchen more of an eye sore than anything. I am awaiting the cleaning deposit return but other than ...

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$231

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

SIESTA BREAKERS - Siesta Key Beachfront Vacation Rental Condo on Crescent Beach (Two Bedroom Vacation Units for Rent)Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

4

Distance to beach: 100 yards to Crescent Beach

$180

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • 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 memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

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Property Type

Siesta Key Condo

"Just what you need for a getaway"

Love the convenience of the beautiful beach steps away, as well as, the warm well kept pool. The condo was perfect and well kept. The shops and restaurants were all across the street. We would love to ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$192

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Enjoy your stay at our remodeled private (no shared walls) detached large 2 bedroom 2 bath villa on Siesta Key (Villa "C15" at Casa Blanca Vacation Rentals (CBVR) - no common walls, 1100 sq. ft., sleeps 6 people). We remodeled C15 with a new air conditioner system, kitchen appliances, bedroom/living ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 4 | Quick View

8

Distance to beach: 0.2 miles to Siesta Key Beach

$172

avg/night

View Details

Key Amenities

  • Air conditioning
  • 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. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom ...

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Property Type

Siesta Key Condo

"Thank you for the hospitality."

We have stayed at this Unit 1344 in the first week of May, 2022. First of all, I would like to thank the owners of this Unit for their hospitality. Dave was always extremely nice and helpful. Also the ...

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2 BR | 2 BA | Sleeps 4 | Quick View

$192

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to one of the closest villas to the beach! Technology upgrades include dedicated WiFi. The living room features a home theater 55" HD flat screen TV with DVD player and HBO provided compliments of the owner. Each bedroom has its own flat screen TV while the master bedroom also has a ...

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Property Type

Siesta Key Villa

Show less

$274

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta Key Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The building is one of the ...

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Property Type

Siesta Key Condo

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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 house, great location"

great house, newly remodeled, comfortable and well appointed; great location, close to 2 pools and beach, easy walk to shops and restaurants nearby or short drive to Siesta Village. Will definately consider ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$206

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

2 Bedroom/ 2 Bath Large Private Villa, Close to Pool, Clubhouse, and in unit washer/dryer. A few Steps to our Private Beach. Additional person fees may apply.

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Property Type

Siesta Key Villa

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1 BR | 1 BA | Sleeps 3 | Quick View

7

Distance to beach: 150 yards to Crescent Beach

$216

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pool

About this property

1 Week Minimum Stay Required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with new top of the line appliances. New Top of the Line King Size Bed will give you a great night sleep after a wonderful day at the beach and a great night ...

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Property Type

Siesta Key Condo

"Fabulous Vacation!"

Our stay was amazing!! The condo was a perfect location. Beautiful view! We could hop the trolly or the other ride shares. Great food, Big Water Fish( the owner recommended) and it was the best we had ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach(Two Bedroom Beachview Unit for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

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Property Type

Siesta Key Condo

"Nice beach, bad red tide"

Unit was clean and close to the beach. Sufficient kitchen supplies, however, frying pans scratched up , wouldn’t use them. Linens and towels clean. Dishwasher and refrigerator clean and in working condition. ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$188

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to Villa A09. You will love this newly remodeled Villa. It is located on the beautiful white-sand shores of Siesta Key, rated the #1 beach in the USA. This is a non-smoking 2 bedroom, 2 bathroom private Villa, centerally located just steps from the beach and large heated pool. The master ...

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Property Type

Siesta Key Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

This vibrant and uniquely configured home is a combination of two units: Monarch Villa and Peacock Villa. Each 3 bedroom 3 bathroom unit is a mirror image of the other and features a total of 6 bedrooms / 6 bathrooms that offers their very own common spaces to include: a kitchen, dining area, balconies ...

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Property Type

Siesta Key House

"Complete"

Very beautiful place Excellent location Enough room for everyone We rented both sides Very beautiful top floor views

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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°

Find the Beach Vacation of a Lifetime with Siesta Key Vacation Rentals

Interested in a beach vacation for your next spring break or a long weekend away? Though the great state of Florida is known for its many scenic beach towns, there are some that cater more to those looking for a quiet, relaxing trip and some that are perfect for an exciting vacation full of non-stop fun in the sun. What if you could find a beach city that offers the best of both worlds for a truly well-rounded vacation? 

Nestled just south of Sarasota, Siesta Key, FL, is a spirited city along the Gulf Coast that offers just as many opportunities for R&R as it does for nightlife, watersports, and unforgettable adventures in the great outdoors. Though the island of Siesta Key itself is only about eight miles long, it’s jam-packed with enticing restaurants, unique shops, and glittering white sand beaches as far as the eye can see. 

As a major vacation destination along Florida’s Gulf Coast, there are many hotel options to choose from during your stay, with varying proximities to the beach. However, if you’re looking for a truly immersive experience during your trip to Siesta Key, you won’t get it at a crowded commercial hotel! 

Browse Siesta Key vacation rentals from FloridaRentals to find the perfect rental home for your beach vacation. Whether you’re looking for a sunny, romantic getaway for you and a loved one, or you’re bringing the whole family along, you’re sure to find an incredible property. Look for one that offers authentic local architecture, plenty of space to spread out during your downtime, and close proximity to all of the best features the city has to offer.

Siesta Key, Florida Travel Tips

There’s a reason why oceanside Florida cities like Siesta Key tend to be popular destinations during springtime. While temperatures may be warmest on average in the summer months, this time of year also has the highest levels of precipitation and humidity. Unfortunately, this makes it more difficult to enjoy outdoor activities. 

In mid to late spring, temperatures in the air and water are warm and comfortable without too much rain or humidity expected. This makes it easy to take part in all of your favorite pastimes, including surfing, boating, wakeboarding, or simply catching some rays on the sand. 

The closest airport to Siesta Key is the Sarasota/Bradenton International Airport, which lies around 11 miles north of the city center. Most visitors will fly into this airport for its easy access, though the area can also be reached relatively quickly by way of the Tampa International Airport.

How to Spend Your Vacation to Siesta Key House Rentals

It’s no surprise that most Siesta Key vacationers spend more time at the beach than anywhere else during their visits. The most popular beach destination is Siesta Key Beach, which was ranked the #1 Beach in the U.S. by TripAdvisor’s Traveler’s Choice Awards in 2020. The gentle waves, powdery white sand, ample parking, and plentiful concession stands are just some of the reasons why many visitors choose to lounge their day away at Siesta Key Beach. 
Those who are interested in an unforgettable outdoor experience shouldn’t miss out on a trip out on the water with Adventure Kayak Outfitters. You’ll have the choice of a guided kayak tour of the nearby Exotic Mangrove Tunnels or a kayak rental to make your own adventure. You’re sure to spot some incredible wildlife like dolphins, exotic birds, and manatees along the way.
Yearly Events in Siesta Key

Siesta Key is closely linked with the nearby city of Sarasota. The two cities share many of their annual events, creating even bigger and better celebrations for locals and tourists alike to enjoy. 

One annual event that’s already become a mainstay in the local culture is the Annual Downtown Sarasota Craft Festival. This unique arts and crafts show features a wide variety of media, including pottery, paintings, jewelry, photography, and much more, alongside the scenic white-sand beaches. Visitors can peruse and purchase unique wares from local artisans, including soaps, spices, plants, and even kettle corn. 
Runners visiting Siesta Key can get in a great workout while supporting a great cause at the Annual Andrew Monroe Memorial Scholarship 5K Run/Walk. All funds raised during this event are donated to the Sarasota Community Foundation Scholarship, which helps local athletes train to their full potential and achieve their goals.  

Best Eats Near Siesta Key Rentals

Whether you’re in need of some casual seaside grub for the family after a long day at the beach or looking forward to a romantic date night with your significant other, Siesta Key has a huge variety of delicious and eclectic eateries fit for every taste and occasion. 

For a hearty steak, you can’t do much better than Summer House Steak & Seafood. This stylish eatery offers sustainably sourced steaks alongside a variety of unique sides, salads, beverages, and desserts that are sure to satisfy. Additionally, Summer House offers a full menu of seafood dishes. It takes full advantage of the city’s close proximity to fresh seafood and offers plenty of surf and turf options for hungry visitors. 

Island House Tap and Grill is a local favorite for casual yet memorable eats in Siesta Key. With a varied menu that includes everything from tacos to burgers to ceviche, as well as plenty of refreshing cocktails, you’re sure to enjoy a delicious and satisfying dinner with your family.