Siesta Key Vacation Rentals

(300 rentals)
booking message booking message
Sea la Vie - Ask About $99 Down!

$258

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 ...

View all property information

Property Type

Siesta Key House

Show less

Coral Breeze - Ask About $99 Down

3 BR | 2.5 BA | Sleeps 8 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$412

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 ...

View all property information

Property Type

Siesta Key House

Show less

Admirals Watch - Ask About $99 Down!

$506

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 ...

View all property information

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 ...

See all reviews

Show less

Casa Tegula - Ask About $99 Down!

4 BR | 3 BA | Sleeps 12 | Quick View

1

$511

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 House

"Casa Tegula Review..."
Reviewed July 8, 2019

We LOVED Casa Tegula!!! The house was very clean and stocked with everything we needed. Location was wonderful, only a short walk to the ocean and shops. Sara at The Cottages on the Key was AMAZING and ...

See all reviews

Show less

105 Gulf Front Apartment

2 BR | 2 BA | Sleeps 6 | Quick View

$269

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 ...

View all property information

Property Type

Siesta Key Apartment

Show less

Top Floor, Penthouse View of the Gulf from your Lani...Private Beach Access

2 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to beach: 100 feet to Crescent Beach

$269

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full 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 ...

View all property information

Property Type

Siesta Key Condo

"Siesta Key"
Reviewed June 11, 2021

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 ...

See all reviews

Show less

Casa Blanca C05 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$195

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. ...

View all property information

Property Type

Siesta Key Villa

Show less

Siesta Dream House - Ask About $99 Down!

$322

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

Show less

Fishermans Cove FC Unit 311B. Siesta Key - Gulf - Front Retreat - 2 BR –

$279

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 ...

View all property information

Property Type

Siesta Key Condo

"Pleasant stay!"
Reviewed August 18, 2021

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 ...

See all reviews

Show less

Casa De Siesta-Ask About $99 Down!

$376

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

Show less

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

$295

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 ...

View all property information

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.

See all reviews

Show less

AVAIL MARCH/APRIL: Relaxing Renovated Townhouse With Access to Crescent Beach

4 BR | 3.5 BA | Sleeps 5 | Quick View

2

Distance to beach: 0.3 miles to Crescent Beach

$258

avg/night

View Details

Key Amenities

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

About this property

Convenient: 3-minute walk to the beach. 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 and the Crescent Club.6828 Midnight Pass Road is a townhouse ...

View all property information

Property Type

Siesta Key Townhome

"Amazing Island Townhouse close to the beach"
Reviewed August 15, 2021

WOW! This Siesta Key Townhouse was absolutely beautiful. Immaculately clean with all the amenities anyone could want/need. During the day (we were 2 couples/4 of us total), we took full advantage of the ...

See all reviews

Show less

Blu Sky Cottage 5037 – Ask About $99 down!

$447

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 ...

View all property information

Property Type

Siesta Key Cottage

Show less

Couples and Family Friendly. Some pet friendly units are available too.

1 BR | 1 BA | Sleeps 4 | Quick View

3

Distance to beach: 20 yards to Siesta Key Beach

$187

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 ...

View all property information

Property Type

Siesta Key Condo

"So close to beach access!"
Reviewed March 11, 2021

Very nice complex, some minor issues were handled nicely. We enjoyed our stay at Sea Spray. About a 10 min walk to the village was nice for restaurants and shopping.

See all reviews

Show less

Crescent Arms CA Unit 402S. Beachfront Condo - 2 - Bedroom - Luxury - Directly

$225

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 ...

View all property information

Property Type

Siesta Key Condo

Show less

Villa Margarita-Ask About $99 Down!

$188

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

Show less

Sandy Seahorse Cottage - Ask About $99 Down!

$441

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet 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 ...

View all property information

Property Type

Siesta Key House

"We had a excellent time!"
Reviewed August 20, 2020

Overall we had a very good time, everything was as we expected, except the BBQ that was very dirty and we had to clean it ourself.

See all reviews

Show less

Beach Walk Cottage – 451

3 BR | 3 BA | Sleeps 8 | Quick View

$412

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

Show less

Beachfront Siesta Key, FL.- 3 Bedroom Private Home W/Full Gulf Views!

3 BR | 3 BA | Sleeps 7 | Quick View

6

Distance to beach: 300 feet to Siesta Beach

$555

avg/night

View Details

Key Amenities

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

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with stacking glass sliding doors to catch the Gulf breezes ...

View all property information

Property Type

Siesta Key House

"Beautiful home"
Reviewed December 27, 2020

Just as pictured. Clean and comfortable. Beds were great. Nice patio and easy access to beach.owner easy to work with.

See all reviews

Show less

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

$259

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 ...

View all property information

Property Type

Siesta Key Condo

Show less

BeachWalk BW Unit A. Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated

$236

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

BeachWalk Siesta Key Townhouses Across from Crescent Beach Three Bedrooms - Heated Pool - Private Elevator Located across from Siesta Beach and five blocks from Siesta Key Village, Sarasota, FL BEACHWALK Townhomes; Three bedrooms, two and a half baths, garage, private pool (shared with BeachWalk townhome ...

View all property information

Property Type

Siesta Key Townhome

Show less

Fishermans Cove FC Unit 304B. Beachfront Condo - 3 BR - Heated Pool - Free

$282

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated 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 ...

View all property information

Property Type

Siesta Key Condo

Show less

Beachy Keen – 302L

3 BR | 3 BA | Sleeps 8 | Quick View

$272

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 House

Show less

Sweet Tranquility! Siesta Key Inn Royal Palm #1B

$418

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, ...

View all property information

Property Type

Siesta Key Condo

Show less

MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

9

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$189

avg/night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR AVAILIBILITY AND FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES! THIS PROPERTY BOOKS WEEKLY FROM SATURDAY TO SATURDAY. DUPLEX: 1 FIRST FLOOR 2 BED/ 2 BATH UNIT AND 1 SECOND FLOOR 2 BED/ 2 BATH UNIT. PLEASE NOTE THE RATE SHOWN IS FOR EACH INDIVIDUAL 2 BED/ 2 BATH UNIT. SHORT ...

View all property information

Property Type

Siesta Key Apartment

"Great vacation spot"
Reviewed January 3, 2021

We enjoyed our stay. We rented for one week and it is in an amazing location. You can walk to everything and it is extremely close to the store, which is awesome!

See all reviews

Show less

Spectacular Beachfront View and Location Directly On Siesta Key Beach Unit 404

2 BR | 2 BA | Sleeps 5 | Quick View

2

Distance to beach: 0.0 miles to Siesta Key beach also known as "Crescent Beach"

$254

avg/night

View Details

Key Amenities

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

About this property

Spectacular remodel with open concept design maximizing beach views and sounds. The million dollar view you always wanted and can now enjoy.Fully equipped modern, clean kitchen with beach view, stainless steel appliances, ice maker, dish washer, granite counters and back splashes and custom cabinets.Secure ...

View all property information

Property Type

Siesta Key Condo

"Fantastic Memories"
Reviewed June 8, 2021

Thank you and your wife for letting us use your home at the beach this past week. You didn’t lie when you said the beach was beautiful. We all head back to reality with sunburn and fantastic memories. ...

See all reviews

Show less

Fishermans Cove Fc Unit 310b. Beachfront Condo - Three Bedroom - Heated

$282

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLTop beachfront unit at Fisherman's Cove!! Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, ...

View all property information

Property Type

Siesta Key Condo

Show less

Casa Blanca C09 Villa

2 BR | 1 BA | Sleeps 4 | Quick View

$186

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to our little oasis on Siesta Key. We have just completed a full remodel, so be one of the first to enjoy this home. Tastefully decorated in a beach theme, the unit is fully tiled, has granite countertops and, a walk-in shower. We also added a new half bath in the master bedroom. And for your ...

View all property information

Property Type

Siesta Key Villa

Show less

Villa Vista Mare - Ask About $99 Down!

$458

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 ...

View all property information

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

See all reviews

Show less

Lantana 5251A - Ask About $99 Down!

$219

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 ...

View all property information

Property Type

Siesta Key Cottage

Show less

Sandy Cabana - Ask About $99 Down!

3 BR | 2.5 BA | Sleeps 8 | Quick View

1

$223

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 ...

View all property information

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.

See all reviews

Show less

La Casa Verde - Ask About $99 down!

$553

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 ...

View all property information

Property Type

Siesta Key House

Show less

* Fantastic Bay View Condo * Siesta Key * #1 Beach of the US

$143

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full 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 ...

View all property information

Property Type

Siesta Key Apartment

"Beautiful view"
Reviewed August 10, 2021

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 ...

See all reviews

Show less

Midnight Cove Bayside! Private beach, lounge chairs, umbrellas on beach!

$155

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Beautifully decorated ground floor and custom upgraded Bay side unit at popular Midnight Cove Beach to Bay on Siesta Key. Just a 5 minute walk across road to your own private piece of world famous Crescent Beach! The community private beach is equipped with lounges and umbrellas--Nothing to take but ...

View all property information

Property Type

Siesta Key Condo

"Sand, sun, and soccer!"
Reviewed July 14, 2021

We booked with Holly to have somewhere relaxing to stay while our daughter played in a national soccer tournament up the road. Siesta Key and Midnight Cove were the perfect place to rest and enjoy on her ...

See all reviews

Show less

Casa Blanca D06 Villa

2 BR | 2 BA | Sleeps 5 | Quick View

$204

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. ...

View all property information

Property Type

Siesta Key Villa

Show less

Isla Amor - Ask About $99 down!

$605

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 ...

View all property information

Property Type

Siesta Key House

Show less

Fishermans Cove FC Unit 304A. Beachfront Condo - 3 BR - Heated Pool - Free

$282

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 ...

View all property information

Property Type

Siesta Key Condo

Show less

A special SECRET retreat...#26

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 100 yards to Crescent Beach

$193

avg/night

View Details

Key Amenities

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

About this property

Simply relaxing one bedroom condo with a king bed facing the pool area and just a few steps to the private entrance to" Siesta Key #1 beach" white quartz sand beach . Additionally a Lazyboy queen Air Dream sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

View all property information

Property Type

Siesta Key Condo

"Great place to stay"
Reviewed July 23, 2021

We loved the unit and the closeness to the beach and area restaurants. We would definitely stay here again!

See all reviews

Show less

Fishermans Cove FC Unit 104B. Siesta Key - Gulf - Front Retreat - 2 BR –

$279

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • 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 ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$110

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 ...

View all property information

Property Type

Siesta Key Cottage

Show less

Villa De Paradisio - Ask About $99 Down!

$375

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 ...

View all property information

Property Type

Siesta Key House

Show less

Casa Blanca C15 Villa

2 BR | 2 BA | Sleeps 6 | Quick View

$204

avg/night

View Details

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 ...

View all property information

Property Type

Siesta Key Villa

Show less

206 Gulf Front Apartment

2 BR | 2 BA | Sleeps 6 | Quick View

$287

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 ...

View all property information

Property Type

Siesta Key Apartment

Show less

Steps to the Gulf! Beachfront Condo w/ Extras! 20% off for September!

2 BR | 2 BA | Sleeps 6 | Quick View

4
Owner special: 20% off for all rentals in September and October!

$287

avg/night

View Details

Key Amenities

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

About this property

There is no way you can get closer to the water than this! Sitting outside and having your morning coffee listening to the waves is so relaxing. Having a glass of wine and watching the sun set is the perfect way to end the day. This amazing unit has it all! The Primary bedroom has a king bed and its ...

View all property information

Property Type

Siesta Key Condo

"What a hidden gem!"
Reviewed February 8, 2021

This complex is truly a gem. The water is 30yds from the building, beautiful beach!! The canal is on the back where a boat can be parked. The condo is updated beautifully! Everything you need is there. ...

See all reviews

Show less

Charming! Siesta Key Inn Sabal Palm #1A

$310

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 ...

View all property information

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 ...

See all reviews

Show less

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

$240

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.” ...

View all property information

Property Type

Siesta Key Condo

"Terrific 1 BR condo, well stocked, just unpack your bags!"
Reviewed May 23, 2021

Great ground floor condo just steps to the beach! Just around the corner from the coin laundry, assigned parking spot right outside the door, it has everything including beach towels! Super comfy king sized ...

See all reviews

Show less

Casa Blanca B 03 Villa

1 BR | 1 BA | Sleeps 4 | Quick View

$153

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. ...

View all property information

Property Type

Siesta Key Villa

Show less

Florita's Key - Ask About $99 Down!

5 BR | 3 BA | Sleeps 12 | Quick View

1

Distance to beach: 0.4 miles to Shell Beach

$382

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

"Wonderful beach front property!"
Reviewed November 4, 2020

We stayed at Angler's Cover in Redington Beach for a week and it was a great place to get away and relax on the quiet beachfront property. When we arrived at the condo the place was spotless and everything ...

See all reviews

Show less

Seahorse Cabana - Ask About $99 Down!

$225

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 ...

View all property information

Property Type

Siesta Key House

Show less

The Solaster - Ask About $99 Down!

$650

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 House

"Great as advertised"
Reviewed October 31, 2019

A group of eight 80-ish college fraternity brothers got together for a reunion and rented Solaster. It was a great choice. The place is exactly as advertised: two attached units, six bedrooms with eight ...

See all reviews

Show less

Expand map | Close map
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!