Siesta Key Vacation Rentals

(246 rentals)
Siesta Salt Life - Ask About $99 Down!

$640

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

"Wow !!! Best place to stay."
Reviewed October 28, 2019

Your villa was just amazing. The villas were very clean and very spacious. I felt like it was home. Everything you need to go on vacation, it was there for you from linens to beach towels and chairs ,bikes. ...

See all reviews

Show less

The Pearl by the Sea - Ask About $99 down!

$679

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 ...

View all property information

Property Type

Siesta Key House

Show less

Home away from home

2 BR | 2 BA | Sleeps 6 | Quick View

$291

avg/night

View Details

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 ...

View all property information

Property Type

Siesta Key Condo

Show less

Sea Grape Cottage - Ask About $99 Down!

$531

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

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

"Family vacation"
Reviewed July 14, 2018

Sea grape cottage is stunningly beautiful and fit our family of 13 with room to spare. The pool was a hit with everyone. The home is furnished with everything you need for a wonderful group vacation,

See all reviews

Show less

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

$281

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

"Great get away!"
Reviewed January 16, 2021

Best vacation ever. Beautiful beachfront views including sunsets over the water each night. Lovely condo. Well equipped kitchen. Five stars!

See all reviews

Show less

Casa De Siesta

4 BR | 3 BA | Sleeps 12 | Quick View

$477

avg/night

View Details

Key Amenities

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

About this property

This uniquely configured vacation rental home is a combination of two units: “Villa Fiesta” and “Villa Margarita.” Each unit features their very own common spaces to include a living room, kitchen, dining area and a shared outdoor space. Casa De Fiesta is centrally located just ...

View all property information

Property Type

Siesta Key Villa

Show less

The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$426

avg/night

View Details

Key Amenities

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

About this property

This tranquil 4 bedroom/3 bathroom home features a private heated pool & spa, and is located within close proximity to Siesta Key Village and world famous Siesta Key Beach, voted the #1 beach in the USA! The Canopy Cottage is the ideal vacation home for couples and families alike.The Canopy Cottage ...

View all property information

Property Type

Siesta Key House

Show less

West Shore - Ask About $99 down!

$679

avg/night

View Details

Key Amenities

  • 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 Condo

Show less

Siesta Breeze beach house—- family friendly, pool, 5 minute walk to beach!

$334

avg/night

View Details

Key Amenities

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

About this property

Located on a quiet cul de sac street in a tropical setting, with only a half block to wonderful dining, and another block to beautiful Crescent beach. It is this proximity to the Beach and Village that enables us to be zoned a weekly rental. It doesn't get more ideal than this! Beautifully appointed ...

View all property information

Property Type

Siesta Key House

Show less

The Blue Serenity - Ask About $99 Down!

6 BR | 10 BA | Sleeps 22 | Quick View

Distance to beach: 0.2 miles to Siesta Key Public Beach - Access # 2

$1202

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

Enchanting and Carefree! Siesta Palms Sea Breeze #126

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Relax and Unwind - take a Beach Vacation to Siesta Key Inn our spacious fully equipped condo!

$277

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 Palms by the Beach 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 ...

View all property information

Property Type

Siesta Key Condo

"Paradise in Siesta Key"
Reviewed January 15, 2021

Linda and Mary Ann were so helpful and wonderful. The condo had everything we needed and more! Great location. Easy walk to the beach. They provide everything from beach chairs to pool towels!! They ...

See all reviews

Show less

Sand Dollar Cottage - Ask About $99 down!

$466

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

Isla Amor - Ask About $99 down!

$703

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

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

2 BR | 1 BA | Sleeps 4 | Quick View

Owner special: Soak up the Florida Sunshine on Siesta Key! Filling up fast - email for availability.

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

$336

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 ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$268

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 ...

View all property information

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 ...

See all reviews

Show less

Casita Lime - Ask About $99 Down!

$247

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 ...

View all property information

Property Type

Siesta Key House

Show less

Renovated 4 bedroom directly on No 1 rated beach. Unobstructed views of gulf.

$607

avg/night

View Details

Key Amenities

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

About this property

A front row seat for the famous sands and sunsets of Siesta Key Step barefoot directly on to the award-winning, powdery sand of Crescent Beach Two of four bedrooms have gulf views Ideal for families or small groups of up to 8 people Enjoy access to an Olympic-sized pool Fully equipped kitchen Screened ...

View all property information

Property Type

Siesta Key House

"Amazing!"
Reviewed December 2, 2020

Beautiful, gorgeous, breathtaking! If you are looking for a bungalow on the beach, look no further. Our family of five with 3 teenagers fit beautifully here. Wonderful accommodations with a stocked kitchen ...

See all reviews

Show less

Sol y Mar - Ask About $99 down!

$439

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

Siesta Dream House - Ask About $99 Down!

$419

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 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

"Village Resort" 322 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: March Special 20% off!

$225

avg/night

View Details

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 ...

View all property information

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 ...

See all reviews

Show less

B110

2 BR | 2 BA | Sleeps 4 | Quick View

1

$280

avg/night

View Details

Key Amenities

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

View all property information

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 ...

See all reviews

Show less

Turtles Watch – Ask About $99 down!

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta key Beach

$553

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

Crescent Cottage - Ask About $99 Down!

$449

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 ...

View all property information

Property Type

Siesta Key House

Show less

Vinca - Ask About $99 Down!

1 BR | 1 BA | Sleeps 2 | Quick View

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

$106

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 Cottage

Show less

Beautiful Renovated 2 Bedroom 2 Bath Waterview Condo, Pools, Tennis, Gym, Beach

2 BR | 2 BA | Sleeps 6 | Quick View

1

Distance to beach: 0.2 miles to Siesta Key

$262

avg/night

View Details

Key Amenities

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

About this property

NEWLY REMODELED - LUXURY WATERVIEW CONDO FOR COUPLES or Families GETAWAY - POOLS, GYM, TENNIS - Walk to beach, town, shopping, top restaurants, live music, and entertainment.Walk out of the front door of this fantastic condo, grab your beach gear and take a short walk and you'll hit the beach . ...

View all property information

Property Type

Siesta Key Condo

"The most beautiful and perfect get-a-way!"
Reviewed May 6, 2020

This condo was so beautiful! It was newly renovated and the decor was just stunning. The views were so incredible and the location was perfect. It is a very VERY short walk to the beach, which we loved. ...

See all reviews

Show less

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

$285

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 South ...

View all property information

Property Type

Siesta Key Condo

Show less

Coral Breeze - Ask About $99 Down

3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$471

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

Newly Renovated Condo with Private Beach

$239

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 ...

View all property information

Property Type

Siesta Key Condo

Show less

Renovated in 2017, Partial Gulf-VIew, Situated Directly on Turtle Lagoon

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.4 miles to Turtle Beach

$249

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

*NOW AVAILABLE FOR FEB 2021* This unit was recently renovated in 2017 and also features brand new, quality furnishings. Mariners Inlet is a 2BR, 2BA second floor condo nestled in a quiet 8-unit complex. Situated directly on Blind Pass lagoon... spot dolphins, manatees, native birds and kayakers go by ...

View all property information

Property Type

Siesta Key Condo

Show less

Siesta Key Gulf View Palm Bay Club in the Tower

$271

avg/night

View Details

Key Amenities

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

About this property

Beautiful 2 Bedroom, 2 Full bath condo. Close to everything, right on Crescent Beach, voted #1 beach twice in the last 5 years. King in the master, 2 full size beds in the second.

View all property information

Property Type

Siesta Key Condo

"perfect beach condo"
Reviewed December 2, 2020

sea shell condos room 104. condo was very clean and updated, perfect spot located on Cresent Beach with close shopping. we will be back to enjoy again

See all reviews

Show less

Tropical Resort-Like Oasis! 1 Br Siesta Palms Sea Spray #123

1 BR | 1 BA | Sleeps 4 | Quick View

1
Owner special: Got Sunshine? Soak up the Florida Sunshine on Siesta Key! Email for availability.

$277

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 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 ...

View all property information

Property Type

Siesta Key Condo

"Siesta Key Inn visit review"
Reviewed December 22, 2020

We went to Siesta Key for the first time Dec2-9. We had heard about Siesta Key Inn from a friend. We found our unit, #123 to be one of the cleanest places we have ever stayed in. It was so clean and private. ...

See all reviews

Show less

SEA SHELL - Siesta Key Beach View Vacation Condo - 2 BR - on Crescent Beach

$249

avg/night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront

About this property

Sea Shell Condominium Complex: Located directly on world famous Crescent Beach this Siesta Key beachfront condo is right across the street from South Village with fast access on/off the island. This vacation condo is located in the Sea Shell Condominium Complex. Sea Shell is a smaller, more intimate, ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$287

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 ...

View all property information

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 ...

See all reviews

Show less

Mimosa - Ask About $99 Down!

1 BR | 1 BA | Sleeps 2 | Quick View

1

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

$106

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

"Fantastic location, Clean and Comfortable"
Reviewed October 21, 2019

We thoroughly enjoyed our stay here... the location is awesome, less than 5 minutes to the beach. The condo was spacious, clean and very comfortable. The beds were good.. all amenities up to date. We ...

See all reviews

Show less

Sophie's Quartier - Ask About $99 Down!

$881

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

Sweet Tranquility! Siesta Key Inn Royal Palm #1B

2 BR | 2 BA | Sleeps 5 | Quick View

Owner special: Book a Winter Get-Away Now in this spacious Siesta Key fully equipped condo with a concierge touch.

$379

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

Fishermans Cove A102 - On Turtle Beach on Siesta Key

$291

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)! ...

View all property information

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 ...

See all reviews

Show less

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

$309

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, ...

View all property information

Property Type

Siesta Key Townhome

Show less

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

$213

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 ...

View all property information

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.

See all reviews

Show less

Casa De Mariposa - Ask About $99 Down!

$703

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 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

"Complete"
Reviewed April 13, 2020

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

See all reviews

Show less

Baybreeze - Ask About $99 Down!

$319

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 Townhome

Show less

Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale - elevator

$332

avg/night

View Details

Key Amenities

  • Air Conditioning

About this property

BEACHWALK Townhomes; Three bedrooms, two and a half baths, garage, heated pool (shared with BeachWalk townhome guests only), private elevator, en suite Jacuzzi tub, beach view, sleeps up to eight, steps to world famous Siesta Key - Crescent Beach... and so much more... We have two units (Unit A & ...

View all property information

Property Type

Siesta Key Townhome

Show less

Amazing Ocean View Beach Front Property Directly on the #1 Beach in the USA-#608

3 BR | 2 BA | Sleeps 6 | Quick View

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

$396

avg/night

View Details

Key Amenities

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

About this property

Unit 608 is a large 3 bedroom, 2 bath high-rise unit in Horizons West, Siesta Key, Florida. The unit has recently undergone a complete makeover 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 ...

View all property information

Property Type

Siesta Key Condo

Show less

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

$142

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, ...

View all property information

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, ...

See all reviews

Show less

Casita Coconut - Ask About $99 Down!

$247

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 ...

View all property information

Property Type

Siesta Key House

Show less

Casa Mahalo - Ask About $99 Down!

4 BR | 3 BA | Sleeps 12 | Quick View

2

$495

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 ...

View all property information

Property Type

Siesta Key House

"Birthday celebration"
Reviewed August 18, 2020

Loved staying at the Maharo home. Very spacious and very accommodating. Particularly loved the private pool given the pandemic crisis we are all experiencing.Enjoyed walking through Siesta Key village. ...

See all reviews

Show less

The Hummingbird - Ask About $99 Down!

6 BR | 6 BA | Sleeps 12 | Quick View

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

$575

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

Seaside Cottage - Ask About $99 Down!

$531

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 ...

View all property information

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.

See all reviews

Show less

The Big Kahuna - Ask About $99 Down!

$966

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

"Great experience."
Reviewed January 21, 2021

Everyone who was on the trip had a great experience at Atlantis! Plenty of room and lots to do in the house and on the island. The information you gave us about the island was very helpful. We had an issue ...

See all reviews

Show less

Honeysuckle - Ask About $99 Down!

$290

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

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 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!