Siesta Key Vacation Rentals

(349 rentals)
Crescent Beach - 2 Bedroom - Beachfront Condo Complex - Heated Pool 305S

$185

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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Breathtaking Beachfront "House of the Sun" Rental

2 BR | 2 BA | Sleeps 6 | Quick View

5

Distance to beach: 200 feet to Crescent Beach

$193

avg/night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

"Paradise"
Reviewed February 9, 2020

I stayed in a dream come true condo. It was right on the ocean with a view to know your socks off. Be able to leave the sliding doors open( because the lanai was screened in) was heavenly , being able to ...

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Home away from home

2 BR | 2 BA | Sleeps 6 | Quick View

$248

avg/night

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Key Amenities

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

About this property

This two bedroom(master King bed), second bedroom double bed/ single bed (with pull out trundle) full kitchen, dining, living room and lanai open into living space. Out back you sit on the bay and across the street is number 1 beach in the U.S. Pool heated year round 80 degrees, grill areas and laundry ...

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Property Type

Siesta Key Condo

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The Palms Cottage - Ask About $99 down!

$397

avg/night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • 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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Beach, Beach, Beach! 1 BR Siesta Key Inn Pineapple Palm #2D

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Got Sunshine? Soak up the Florida Sunshine on Siesta Key! Email for availability.

Distance to beach: 150 yards to Siesta Key Crescent Beach

$227

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 invite you to relax, unwind and enjoy our casual Siesta Key way of life. The Siesta Key Inn Siesta Palms 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 ...

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Property Type

Siesta Key Condo

"Paradise by the beach!"
Reviewed November 20, 2020

We loved staying at this beautiful condo! Communication from the beginning was great- from the detailed initial response to the check-in and check-out process. We can't say enough about how this family ...

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

$267

avg/night

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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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Crescent Cottage - Ask About $99 Down!

$346

avg/night

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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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Sweet Tranquility! Siesta Key Inn Royal Palm #1B

2 BR | 2 BA | Sleeps 5 | Quick View

Owner special: Book your tropical escape now to the White Sand Beaches on Siesta Key! Leave the worries behind....

$289

avg/night

View Details

Key Amenities

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

About this property

Welcome to the Siesta Key Inn! Owned and operated on site by the Koch Family since 1979 (we are not an investor owned property). This Tropical Beach Get-away offers condos just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach. With no busy streets to cross, ...

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Property Type

Siesta Key Condo

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Location! Location! location! Bayside Siesta Key

$203

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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"
Reviewed February 23, 2021

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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206 Gulf Front Apartment

2 BR | 2 BA | Sleeps 6 | Quick View

$305

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen

About this property

Come stay in our recently updated Oceanfront condo on Siesta Key - best beach in Florida! Our spacious beachfront home 1080 Square Feet sleeps up to 6 guests and is directly ON the #1 Beach in America"! Unit #206 is part of The Casablanca Vacation Beach Resort and Crescent Beach is right outside ...

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Property Type

Siesta Key Apartment

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Serenity Cottage - Ask About $99 Down!

$282

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • 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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Vinca - Ask About $99 Down!

1 BR | 1 BA | Sleeps 4 | Quick View

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

$98

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 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

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Casa Ohana - Ask About $99 Down!

4 BR | 3 BA | Sleeps 12 | Quick View

3

$398

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

"Casa Coquina"
Reviewed December 10, 2020

These few houses have the same owner/same builder and are PERFECT for a couple families. The bed was the most comfortable bed I have ever slept on and the place was a perfect layout for privacy. There were ...

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Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach 404N

$243

avg/night

View Details

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 North ...

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Property Type

Siesta Key Condo

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Villa Vista Mare - Ask About $99 Down!

$375

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • 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 Townhome

"Vacation 2020"
Reviewed August 10, 2020

I visited siesta key and loved my stay. Stayed in the village Evey thing was In walking distance.beach was walking distance

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Mermaids Lookout - Ask About $99 Down!

4 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$470

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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Fishermans Cove A102 - On Turtle Beach on Siesta Key

$211

avg/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

"Heaven on Earth!"
Reviewed June 16, 2020

We stayed here to celebrate ten years together and it completely exceeded our expectations! The proximity to the beach (which is basically private) is unmatched and Carrie was so sweet and easy to work ...

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Villa Margarita-Ask About $99 Down!

$160

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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Gran Vista - Ask About $99 Down

6 BR | 4 BA | Sleeps 14 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$637

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet 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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105 Gulf Front Apartment

2 BR | 2 BA | Sleeps 6 | Quick View

$305

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Enjoy unobstructed views of the Gulf of Mexico and the white sand of Siesta Key Beach located on the 1st floor and end of the building. This apartment is a well appointed 2 bedroom, 2 bathroom with fully equipped kitchen. This unit features Private wireless internet, 1 King, and 2 Twin beds, and a sleeper ...

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Property Type

Siesta Key Apartment

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Seahorse Cabana - Ask About $99 Down!

$175

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

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Admirals Watch - Ask About $99 Down!

$483

avg/night

View Details

Key Amenities

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

"Wonderful Stay"
Reviewed July 1, 2019

Admirals Watch, Siesta Key was a great place to stay with an amazing view! Everything is just like the picture. The rental company "The Cottages on the Key" checked in with us a couple of times to make ...

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Gorgeous Views in this Siesta Key Condo

2 BR | 2 BA | Sleeps 6 | Quick View

6

Distance to beach: 0.3 miles to Crescent Beach on Siesta Key

$149

avg/night

View Details

Key Amenities

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

About this property

Siesta Key Condo - Siesta Key ParadiseLooking for a vacation rental in Siesta Key? Look no further... we have a two bedroom first floor condo located on the spacious, gorgeous landscaped grounds of Midnight Cove ii.Enjoy great views from our lanai watching boats, yachts, and wildlife on the Intracoastal ...

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Property Type

Siesta Key Condo

"Convenient, clean and inviting!"
Reviewed August 9, 2020

The condo is ground level and super convenient for coming and going. The view out the back is very pretty and you have plenty of privacy while watching the big boats comes by. The condo was spacious and ...

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Villa Castile - Ask About $99 Down!

3 BR | 3 BA | Sleeps 10 | Quick View

Distance to beach: 0.4 miles to Siesta Key Beach - Access # 8

$305

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

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 Villa

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Siesta Key Beachfront Condo with Gulf View!

$156

avg/night

View Details

Key Amenities

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

About this property

You will fall in love with this condo! Everything you would possibly need is provided. Enjoy relaxing on the lanai in the morning with your coffee or a glass of wine in the evening. Nice beach chairs, beach umbrellas, straw mats, small cooler, swim noodles and a beach bag are all in the condo for your ...

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Property Type

Siesta Key Condo

"Great Location"
Reviewed February 12, 2021

We rented this condo for two weeks to get away from the cold. The location is perfect -- loved listening to the gulf surf from the balcony and taking walks on the beach. Kevin and Missy were very responsive ...

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

$252

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 - Beachfront Condo - 2 BR – Free Boat Docks - Upscale -Renovated 205B

$221

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

"A Beachfront Dream"
Reviewed December 21, 2020

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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Sandpiper Cottage - Ask About $99 down!

5 BR | 5 BA | Sleeps 14 | Quick View

Distance to beach: 0.8 miles to Crescent Beach

$283

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 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 Cottage

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Casa Blanca D18 Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$224

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

$267

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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Coral Breeze - Ask About $99 Down

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$387

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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Newly Renovated Condo with Private Beach

$207

avg/night

View Details

Key Amenities

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

About this property

Newly renovated, 4th floor condo with gulf views, a private beach, and a private fishing pier. This space was completely renovated in 2020 with all new features (including central AC) and furniture throughout. The fully-stocked kitchen is equipped with everything you need for a home-cooked meal. With ...

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Property Type

Siesta Key Condo

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"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Summer Special 10% discount from 4/24-4/30

$177

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!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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Tropical beach getaway at Sandy's Siesta Key Condo

2 BR | 1.5 BA | Sleeps 4 | Quick View

15
Owner special: Fall 2021 dates available!!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$155

avg/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

"Beautiful and relaxing!"
Reviewed January 10, 2021

This is a great condo that is close to everything. It is very clean and spacious. There was a beach buggy, coolers, and beach toys available to use. The kitchen is well equipped with everything you need ...

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Casa De Siesta-Ask About $99 Down!

$320

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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New Listing! Villa Fiesta - Ask About $99 Down!

$160

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 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 Townhome

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Beach Walk Cottage – 451

3 BR | 3 BA | Sleeps 8 | Quick View

$390

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly

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 House

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Casa Blanca C05 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$218

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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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Tropical Escape 2 Br/2 B Siesta Palms Sea Escape #226

2 BR | 2 BA | Sleeps 5 | Quick View

Owner special: Rarely Available! Paradise awaits in this spacious 2Br/2B Condo. Steps to pool and beach.

$289

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 Palms 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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Villa Cascada - Ask About $99 Down!

$367

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 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 ...

View all property information

Property Type

Siesta Key House

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Siesta Dream House - Ask About $99 Down!

$284

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid 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 House

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Beautiful Siesta Key Beach Condo-GREAT LOCATION! 3 Min WALK to Beach!

$230

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

This 2-bedroom, 2 bath Siesta Key condo can sleep 6 comfortably with a pull-out queen sofa bed and total square feet of 1,773! The beautifully decorated condo, with two updated, tiled bathrooms offers a comfortable, home-away-from-home feel. Sit on your private 20 ft deck and enjoy the view of a lake ...

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Property Type

Siesta Key Condo

"wow, couldn't have asked for better."
Reviewed September 12, 2020

This was the first time I have ever rented a condo and this place was amazing. The place was huge! The main bedroom had a queen bed (kinda hard) and tons of closet place. Bathroom was very nice and couldn't ...

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

$256

avg/night

View Details

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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Sandy Cabana - Ask About $99 Down!

3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$150

avg/night

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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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Casa De Mariposa - Ask About $99 Down!

$591

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • 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

"Complete"
Reviewed April 13, 2020

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

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Located Directly on the Beach in Siesta Key-Beautiful First Floor-Walk Out

$170

avg/night

View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front).When we travel over 1,000 miles to enjoy a beach vacation we're not interested in being steps from the beach, across from the beach, or having what is often euphemistically advertised as, “a view of the beach.” ...

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Property Type

Siesta Key Condo

"So Close to the Beach!"
Reviewed February 23, 2021

We have stayed in A107 at Fisherman’s Cove for the last five years. We return each year because Russ and Dina have provided everything we need in this condo that allows us to step onto sand right outside ...

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Peacock Villa - Ask About $99 Down!

$287

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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Casa Blanca C18 Villa

2 BR | 2 BA | Sleeps 4 | Quick View

$224

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

"Welcome to one of the largest 2 Bedroom/2 Bath Villas in Casa Blanca -- and the only one with a glimpse of the gulf! Enjoy beach views from the family room as well as the large screened-in lanai. Just steps from the beautiful Crescent Beach, recently rated the #1 beach in the USA. The master ...

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Property Type

Siesta Key Villa

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Casa Blanca D12 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$218

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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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The Pearl by the Sea - Ask About $99 down!

$568

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 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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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!