Siesta Key Vacation Rentals

(339 rentals)
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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

$189

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"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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Siesta Key Beach Front Ground Floor Condo104 Steps to the Beach WiFi

$250

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

About this property

Condo, 2 Bedrooms, 2 Baths, Sleep Sofa (Sleeps 4-6)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. This is the ‘Best Location’ on ‘Crescent Beach.’ Experience ...

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Property Type

Siesta Key Condo

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Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach 402S

$224

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront

About this property

Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront condos are walking distance to South Village. Crescent Arms has one-story villas as well as two seven-story towers that are directly on the beach. Our vacation condos are located in the South ...

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Property Type

Siesta Key Condo

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Honeysuckle - Ask About $99 Down!

$294

avg/night

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Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivalsThis includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Condo

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Casa Blanca B02 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$198

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Find your Happy Place here in this LARGE 2 bedroom/2 bathroom, private entrance villa. There is new granite in the kitchen which is fully equipped. The master bedroom is furnished with a king size bed. The master vanity for the ladies comes with a hairdryer. The master bath features a walk-in shower ...

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Property Type

Siesta Key Villa

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Casa Blanca C06 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$198

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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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Siesta Key -2BR -Beachfront Condo on Crescent Beach -Heated Pool -Tennis Cts 515

$196

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

BEAUTIFUL NEW LISTING: This beautiful, two bedroom, two bath, luxury Villa is located directly on the world famous Crescent Beach in the desirable Siesta Breakers Condo, notable for its resort-style amenities. Very stylish and contemporary in design with high end amenities inside and out. The exterior ...

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Property Type

Siesta Key Condo

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Casa Blanca C17 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$198

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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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The Islander – Ask About $99 down!

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$468

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Seaside Cottage - Ask About $99 Down!

$438

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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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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Casa Blanca B05 Villa

2 BR | 1 BA | Sleeps 4 | Quick View

$184

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

The owners have just replaced the carpet in this beautifully appointed 2 bedroom one and one half bathroom unit. There is private wireless for your enjoyment, while being just steps away from the refreshing pool and a short walk to the beach this unit is waiting for you.

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Property Type

Siesta Key Villa

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Crescent Cottage - Ask About $99 Down!

$326

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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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

avg/night

View Details

Key Amenities

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

About this property

If you are looking for a terrific vacation spot tastefully decorated, clean, and comfortable, you just found it. You can be as lazy as the sun and free as the Gulf breeze. We are not underselling ourselves when we say we have the 'Best Location' on 'Crescent Beach.' Experience the Gulf views, breezes, ...

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Property Type

Siesta Key Condo

"Vacation"
Reviewed March 31, 2020

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

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

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Summer Special! 20% discount for a 2 week stay.

$172

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"Excellent choice"
Reviewed July 30, 2019

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

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Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta key Unit 1BR 5239

$115

avg/night

View Details

Key Amenities

  • Full Kitchen

About this property

SEASIDE VILLAS: This Siesta Key one bedroom garden apartment vacation rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, ...

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Property Type

Siesta Key Apartment

"Sunnyside properties"
Reviewed October 21, 2020

Beautiful week! Apartment was very clean!! We met Tina the cleaning machina! She was very helpful and gave us some beach towels

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Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks - Upscale 311B

$186

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

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 all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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Upscale 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village 3BR 5241

$233

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

SEASIDE VILLAS: This Siesta Key deluxe 3-Bedroom townhouse rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, pubs and clubs, ...

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Property Type

Siesta Key Townhome

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Villa Margarita-Ask About $99 Down!

$145

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Villa

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B110

2 BR | 2 BA | Sleeps 6 | Quick View

1

$196

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • 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!"
Reviewed November 25, 2019

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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Casa Stolida - Ask About $99 Down!

$392

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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

$425

avg/night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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

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

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Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta Key Unit 1BR 5241

$115

avg/night

View Details

Key Amenities

  • Full Kitchen

About this property

SEASIDE VILLAS: This Siesta Key one bedroom garden apartment vacation rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, ...

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Property Type

Siesta Key Apartment

"Nice place & convenient location"
Reviewed January 25, 2021

This condo is a 4-plex and is steps away from the village with groceries, shopping, restaurants, and bars. It is a quick 1 1/2 block walk to the beach. We had access to beach chairs, beach towels, coolers, ...

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Casa Blanca D18 Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$198

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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

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Peacock Villa - Ask About $99 Down!

$273

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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Plumbago 5251C - Ask About $99 Down!

$197

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivalsThis includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Cottage

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Casa Blanca B06 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$198

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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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La Contento Casa - Ask About $99 down!

$385

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for ...

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Property Type

Siesta Key House

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Deluxe 2-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village 2BR 5239

$226

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

SEASIDE VILLAS: This Siesta Key deluxe 2-Bedroom townhouse rental is located in the heart of Siesta Village – just steps to all the shops and restaurants and only a three minute walk to world famous Siesta Key Crescent Beach! Siesta Village has dozens of shops, fine or casual dining, pubs and clubs, ...

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Property Type

Siesta Key Townhome

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Casa Blanca A 14 Villa

2 BR | 1 BA | Sleeps 5 | Quick View

$184

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Villa A14! You'll love this newly-remodeled (January 2019) villa! It is located on the beautiful white-sand shores of Crescent Beach, recently rated the #1 beach in the USA! This is a 2 bedroom, 1 and a 1/2 bath private villa just steps away from the beach and the heated pool. The master ...

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Property Type

Siesta Key Villa

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Seabatical – 304U

3 BR | 3 BA | Sleeps 8 | Quick View

$306

avg/night

View Details

Key Amenities

  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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Best location! Luxury Canal Home in Siesta Key Village! Pool/Spa Done July 2021

2 BR | 2 BA | Sleeps 8 | Quick View

2

Distance to beach: 0.4 miles to Siesta Key Beach

$249

avg/night

View Details

Key Amenities

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

About this property

Location, location, location!!Canal home in heart of the Siesta Key Village, no need for a car! Steps away from great restaurants, shops, and even the local supermarket! Plus, only an 6 minute walk to the #1 ranked Siesta Key beach.Your needs are complete for a day at the beach with a beach ...

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Property Type

Siesta Key House

"Home Away from Home/Great Location"
Reviewed May 2, 2021

We loved the location of this home. Not only because it’s located on a canal and very private, but it’s only a two-minute walk to Siesta Key Village. The beach is also a short walk of only 6-7 minutes. ...

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Turtle Beach - Gulf-Front Condo - 2BR - Free Boat Docks - Siesta Key 212B

$186

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

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 all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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Blu Sky Cottage 5037 – Ask About $99 down!

$385

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivalsThis includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key Cottage

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“SANDPIPER” Siesta Key Beach -Vote #1 beach in America with crystal quartz sand

$119

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTS RATES!VOTED #1 BEACH IN AMERICA! JUST MINUTES TO YOUR DOOR WAY. THREE POOLS, SHUFFLE BOARD, GRILLS, PRIVATE BEACH AREA, LAUNDRY FACILITIES, PATIO FOR COOKING AND EATING OUTDOORS. SHORT WALK TO SOUTH VILLAGE WITH RESTAURANTS, GROCERY STORE, NIGHT ...

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Property Type

Siesta Key Condo

"Sandpiper #23"
Reviewed January 8, 2020

The property was generally in good shape, clean and made for a pleasant stay. We also felt safe and the property was fairly priced.

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Sandy Cabana - Ask About $99 Down!

3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$174

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

"Fabulous Place"
Reviewed February 19, 2020

Excellent Location close to the Crescent Beach and Restaurants. I would stay there again the next time I visit Siesta Key.

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"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

3

$171

avg/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!318 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

"Great time!"
Reviewed March 2, 2020

We just needed to unwind from a 2 year ordeal with a 96&97 yo family issue and it worked. Recharging your batteries is a big part of life, so thank you for that. The place was nice, not fancy, which was ...

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Casa De Siesta-Ask About $99 Down!

$291

avg/night

View Details

Key Amenities

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

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

View all property information

Property Type

Siesta Key Villa

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Monarch Villa - Ask About $99 Down!

$291

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This home could qualify for our BookCareFree promotion for 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer!We go above and beyond the industry standard for cleanings ...

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Property Type

Siesta Key House

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Midnight Cove 2 Bed With Den & Water Views; Private Beach!

$185

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Water, water everywhere! Spacious, spectacular and nicely decorated third floor 2 bedroom/2 bath with den; corner unit, light and bright overlooking the intra-coastal waterway. Watch the boats glide by! Only a brief walk across road to a private piece of world famous Crescent Beach with beach chair ...

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Property Type

Siesta Key Condo

"Perfect Condo"
Reviewed May 18, 2021

We just returned after a week at this condo . The place was so clean and was perfect for us. The rooms were spacious and very comfortable. Sitting on the lanai and watching the boat traffic was so relaxing... We ...

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Tropical Escape! Fabulous Amenities 1Br Siesta Key Inn Coconut Palm #1C

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Longing for that feeling of powdery white Siesta Key sand between your toes? We have a deal for you.

$234

avg/night

View Details

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 Siesta Palms is less than a block from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach. We offer good "olde" fashioned Southern ...

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Property Type

Siesta Key House

"Nice place to relax in quiet surroundings"
Reviewed March 5, 2019

Perfect location to walk to beach ,bars , restaurants,a short drive over the bridge to Sarasota has all shopping you need. Very clean condo ,we met some very nice people that return every year.

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Casa Blanca D03 Villa

2 BR | 1 BA | Sleeps 5 | Quick View

$177

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Quick notes: " 2 bedrooms, 1 bath " Sleeps 5 " Free-standing villa - no shared walls or floors/ceilings! " Private in-unit high-speed internet " Smart/HD TVs with Hulu in living room and bedrooms " Five-night minimum.Welcome to ...

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Property Type

Siesta Key Villa

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BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS -RENOVATED 310B

$233

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

op beachfront unit at Fisherman's Cove!! 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 all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront ...

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Property Type

Siesta Key Condo

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Only on Siesta! Siesta Key Inn Majesty Palm #2C

2 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Time to book your next Siesta Key Beach vacation! Comfy condo, Sunshine, blue skies, beach and pool.

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

$391

avg/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 Key Inn, it's a leisurely ...

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Property Type

Siesta Key Condo

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Charming! Siesta Key Inn Sabal Palm #1A

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Filling up fast! Book your Tropical Escape to sunny Siesta Key! Complimentary bottle of wine.

$234

avg/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 Key Inn. With no busy streets ...

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Property Type

Siesta Key Condo

"Perfect"
Reviewed December 9, 2020

We had a fabulous stay recently at Sabal Palm #1A. The unit exceeded our expectations. Hosts could not have been nicer, nor better to work with. Unit was updated, well furnished, kitchen equipped with all ...

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Amazing Ocean View Beach Front Property Directly on the #1 Beach in the USA-#113

1 BR | 1 BA | Sleeps 3 | Quick View

Distance to beach: 20 yards to Crescent Beach, Siesta Key

$214

avg/night

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Key Amenities

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

About this property

Unit 113 is one of the largest, 1 bedroom hi-rise units in Horizons West, Siesta Key, Florida and has recently undergone a full renovation by a Chicago designer. The interior was fully demolished and rebuilt. No detail or expense was spared in completing the perfect beach condo: large panoramic ocean ...

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Property Type

Siesta Key Condo

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"Village Resort" 322 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2

$171

avg/night

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Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!322 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

"Great location for a relaxing stay!"
Reviewed June 6, 2019

Rental was very clean and well stocked with towels, kitchen items, and even beach towels and folding beach chairs. Location is great for a relaxing and walking to the beach and village. Enjoy seeing ...

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Casa Blanca B07 Villa

2 BR | 1.5 BA | Sleeps 6 | Quick View

4

$184

avg/night

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Key Amenities

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

About this property

Our vacation home is just steps away from the #1 rated beach in the USA - Siesta Key beach. It is unit B07 in the Casa Blanca resort located on the GULFSIDE (or Beach side) of the island.It is a comfortable villa with a master bedroom, guest bedroom, living room, kitchen with dining area, and a ...

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Property Type

Siesta Key Villa

"Wonderful!"
Reviewed December 6, 2020

Our villa was perfect! There was anything and everything that we needed for our week long trip. Loved being so close to the beautiful Siesta Key beach.

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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks –Upscale –Siesta Key 304B

$233

avg/night

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Key Amenities

  • Air Conditioning
  • Beachfront

About this property

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 all of Siesta Key. You could throw a tennis ball into the gulf from this Siesta Key beachfront condo! Located at Turtle Beach on ...

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Property Type

Siesta Key Condo

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Casa Blanca D01 Villa

1 BR | 1 BA | Sleeps 4 | Quick View

$153

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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

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Casa Blanca C15 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$198

avg/night

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Key Amenities

  • Air Conditioning
  • Full 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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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 15% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!