Siesta Key Vacation Rentals

(312 rentals)
booking message booking message

2 BR | 2 BA | Sleeps 6 | Quick View

45

Distance to beach: 0.0 feet to We are directly on the beach and direct oceanfront

$363

avg/night

View Details

Key Amenities

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

About this property

Our condo is directly on the beach and is direct oceanfront (Gulf-front). Unfortunately, there are properties on this site that falsely claim to be beachfront / oceanfront. We encourage travelers to ask property owners to verify those claims.When we travel over 1,000 miles to enjoy a beach vacation ...

View all property information

Property Type

Siesta Key Condo

"Wonderful condo"

The condo was fabulous! It was everything we could imagine and more! Everything we could have needed was there. Beautiful, relaxing, peaceful atmosphere. Not only were we impressed, but we will be booking ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

$399

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

View all property information

Property Type

Siesta Key Condo

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.2 miles to Siesta Key

$421

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

"Awesome condo!"

Loved everything about the condo and the grounds! Great pool area and views everywhere! Condo has all you need and owner was great to work with! Can't wait to be back!

See all reviews

Show less

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Condo

"Thanksgiving at the beach"

My mother, daughter and I enjoyed our staycation in unit B106. Thanksgiving at the beach. What could be better? We enjoyed meals at SKOB,Turtles,Pizza and Brew, and a little nightlife at SKOB and Crescent ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

15
LAST MINUTE DEAL 12/1 - 12/24: DEC 10-17 or Dec 17-24 REDUCED BY $200! Located Directly on the Beach in SIESTA KEY! Renovated

$301

avg/night

View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Condo

"Happy"

We loved hearing the ocean. The condo was fully equipped and we overpacked. I was able to set up computer and work. Super enjoyed our stay. Can't get any closer to the beach and the view was amazing. ...

See all reviews

Show less

DEAL

2 BR | 1 BA | Sleeps 5 | Quick View

$215

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

2 BR | 1 BA | Sleeps 6 | Quick View

7
LAST MINUTE DEAL 11/29 - 12/10: Dec 10 for five nights last-minute discount. Stay five pay for four nights.

$222

avg/night

View Details

Key Amenities

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

About this property

Our villa is located in Siesta Key, FL on Crescent (Siesta Key) Beach, FAMOUS for its powdery, sugar white sand and being VOTED #1 Beach in USA. The Beach has complimentary shade cabanas and beach chairsFeatures include 2 Bedrooms, 1Bath sleeping six with 1King and 2 queen beds. The kitchen is furnished ...

View all property information

Property Type

Siesta Key Villa

"Enjoying our first month of retirement."

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

See all reviews

Show less

DEAL

5 BR | 4 BA | Sleeps 13 | Quick View

10

Distance to beach: 400 feet to Siesta Beach

$842

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage on a Navigable Canal to the Bay And Then The Gulf of Mexico , Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. ...

View all property information

Property Type

Siesta Key House

"Best vacation"

Perfect house! The beach is right there! The house is gorgeous and had everything we needed for the beach! 18 years of vacationing with friends and family and this was just perfect! David is fantastic ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$241

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

$399

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$362

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

View all property information

Property Type

Siesta Key Condo

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$399

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

2 BR | 1 BA | Sleeps 5 | Quick View

$225

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 20 feet to Turtle Beach, Siesta Key

$341

avg/night

View Details

Key Amenities

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

About this property

Beautiful beach inspired decor...Fresh, airy and calm...perfect relaxing unit with all the comforts of home and more to enjoy a fun filled time at the beach!!!!!

View all property information

Property Type

Siesta Key Condo

Show less

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Condo

Show less

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Condo

"Amazing, Relaxing and Perfect Beach Condo"

The location of the condo is a perfect place between the hustle and bustle of the town and somewhere private and relaxing. The space itself has everything you would need from a girls trip (which we had), ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Condo

"Great location!"

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

See all reviews

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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 ...

View all property information

Property Type

Siesta Key Condo

"What a Fantastic Little Gem!"

Siesta Key have become our favorite vacation spot and #409 at Crescent Royale was where my wife and I got to experience the very best thanks to Karen who accepted us in her beautiful and awesomely appointed ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 25 feet to Whispering Sands (private); Crescent (public)

$230

avg/night

View Details

Key Amenities

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

About this property

Enjoy living steps away from the cool, pure-white sands of the award-winning beach of Siesta Key! Drink in the sunsets over the Gulf from the private balcony, from the living room, or from the master suite -- where you can also watch the moon setting from your king-sized bed! The private beach with ...

View all property information

Property Type

Siesta Key Condo

"BEST place on the key! Closest to the sand and to the village."

We couldn't have been happier with this home. There is no better location on all of Siesta Key. You can easily walk to the village (not this case with most condos south on the key) but it's also very quiet, ...

See all reviews

Show less

6 BR | 5.5 BA | Sleeps 14 | Quick View

5.0 rating on other travel sites

$1464

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

This tranquil canal-front home is a unique configuration of two units: Sophie's Cottage and Villa Champagne. Each home offers their own common spaces that include a kitchen, dining area and outdoor living spaces with a private heated pool. Sophie's Quartier is centrally located near Siesta Key Village ...

View all property information

Property Type

Siesta Key House

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront

About this property

Renovated and redesigned beach villa offering the very best in location and amenities. Upon arrival, just unpack your bags and enjoy. Everything is ready for your comfort and convenience with all the amenities of home. Even beach towels are provided. Sophisticated yet casual, this ranch villa is just ...

View all property information

Property Type

Siesta Key Villa

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$185

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

View all property information

Property Type

Siesta Key Condo

"quaint and quiet"

This was our 1st visit to Siesta Key, and won't be the last. We stayed in unit 311-B and it was a wonderful stay. The unit had everything a family needs to enjoy their vacation. We loved the Gulf in ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$241

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Condo

"great house, great location"

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

See all reviews

Show less

4 BR | 4 BA | Sleeps 12 | Quick View

9
Owner special: HOLIDAY SPECIAL!! 20% DISCOUNT ENDS DEC 24.

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$283

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

PLEASE CONTACT US FOR AVAILIBILITY FOR EACH UNIT 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. ...

View all property information

Property Type

Siesta Key Apartment

"Great vacation spot"

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

Key Amenities

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

About this property

This second-floor condo offers privacy, seclusion, a view of the bay, and a host of other great amenities.You will enjoy access to two shared pools, a fitness center, and two lovely tennis courts on the community grounds.It even grants access to a private beach nearby!Things to know: Free ...

View all property information

Property Type

Siesta Key Condo

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

$225

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

View all property information

Property Type

Siesta Key Condo

"A Beachfront Dream"

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

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

9
Owner special: HOLIDAY SPECIAL!! 10% DISCOUNT FOR ONE WEEK BOOKINGS ENDS DEC 24.

$192

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Pool

About this property

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

View all property information

Property Type

Siesta Key Condo

"Sandpiper #23"

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

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

3 BR | 3.5 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.3 miles to Crescent Beach

$330

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

6828 Midnight Pass Road is a townhouse style condo three level unit with 3 main bedrooms plus a bonus 4th guest bed/bath and laundry on the ground floor. Each bedroom has a queen bed, and all furniture and mattresses were purchased new in 2019.Convenient and Easy: 3-minute walk to the beach with ...

View all property information

Property Type

Siesta Key Townhome

"Incredible Space and Great Location"

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

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

1

$185

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

"too bad i can't stay all year!"

Casa Blanca is older, built in the sixties but very well kept and clean. I like the fact that you are only several yards from the beach and by the way you won't find any beachs anywhere better than this. ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.4 miles to Crescent Beach

$225

avg/night

View Details

Key Amenities

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

About this property

Perfectly located on Siesta Key, this beautiful 2-bedroom, 2-bath condo will surround you with everything Sarasota has to offer. Featuring space for 6 guests, a shared pool, hot tub and shared laundry this condo is perfect for longer stays. Walk to Crescent beach and enjoy dancing sunsets as you look ...

View all property information

Property Type

Siesta Key Apartment

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$264

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

This 1 bedroom Apartment is centered on the second floor it has a king bed in the master bedroom a sleeper sofa in the living room, enjoy lunch on the screened in Lanai over looking the Gulf of Mexico. The kitchen has recently been updated this unit features Flat screen TV's and private wireless for ...

View all property information

Property Type

Siesta Key Apartment

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

View all property information

Property Type

Siesta Key Villa

Show less

2 BR | 1 BA | Sleeps 4 | Quick View

$215

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

Enjoy the beach life in this recently upgraded villa just a few steps from beautiful Siesta Key Beach. The entire villa has been newly painted and contains all new windows, window treatments and flooring. The master bedroom features a queen bed with new coastal furniture, and the guest bedroom has 2 twin ...

View all property information

Property Type

Siesta Key Villa

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$249

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

2 Bedroom/ 2 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.Welcome! Villa C13 is a beautiful 2 bedroom, 2 bath beach accommodation located in the exclusive Casa Blanca beachside condos on the pristine shores of Siesta Key's coveted Crescent Beach rated ...

View all property information

Property Type

Siesta Key Villa

Show less

Key Amenities

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

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

"Terrible staff"

Was a alright place but the manager took my key fobs couple days for no reason and then kept the 500 dollars security money for no reason.

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

9

Distance to beach: 0.1 miles to Siesta Key Beach

$298

avg/night

View Details

Key Amenities

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

About this property

NEWLY UPGRADED - BEAUTIFUL LAKEFRONT CONDO FOR THE PERFECT GETAWAY FROM THE COLD Right across from Siesta Key Beach, minutes from Siesta Key Village - or the South VIllage - shopping, top restaurants, live music, and entertainment. Walk , bike or take the free trolley.Sit on the balcony for a ...

View all property information

Property Type

Siesta Key Condo

"Nice Condo in Great Location"

Within walking distance of beach. Very centrally located around numerous attractions. Stayed for a month without any problems at all.

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

17
LAST MINUTE DEAL 12/1 - 12/17: DEC 10-17,22 REDUCED BY $200 FOR THE WEEK! Located Directly on the Beach in SIESTA KEY. Renovated!

$364

avg/night

View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Condo

"LOVE LOVE LOVE this place!!"

My best friend and I stayed here in April and talked my hubby into going back in November (this is a person who didn't want to go florida) He actually had a great time and walked the beach with me EVERY ...

See all reviews

Show less

DEAL

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Private pool
  • Rentals by owner

About this property

THE BEACH IS CALLING AND I MUST GO!! *We invite you to come stay with us in the Crescent Arms South Tower--Condo 601S--directly on the #1 famous Crescent Beach with a FULL view of the Gulf on a private 32 foot lanai.*Decorated in a "beachy motif" with granite counter tips in the kitchen ...

View all property information

Property Type

Siesta Key Condo

"Wonderful week at Crescent Arms 601S!"

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

See all reviews

Show less

2 BR | 1 BA | Sleeps 6 | Quick View

$225

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

This newly furnished and decorated 2 bedroom villa with a brand new king mattress, and sleeper sofa, accommodates up to 6 guests. The master bedroom offers a king bed, private bath and cable TV. The guest bedroom offers 2 twin beds and cable. Villa B4 offers HD TV, DVD, movie choices, surround sound, ...

View all property information

Property Type

Siesta Key Villa

Show less

$356

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

View all property information

Property Type

Siesta Key Condo

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

$255

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen

About this property

This villa is one of the large villas and closest to the beach area. It has a 55 inch Samsung plasma TV and a blue ray Samsung smart DVD player with WiFi. The TV has a high definition connection with Comcast. There is also private Comcast WiFi with Password provided. The patio has a large ...

View all property information

Property Type

Siesta Key Villa

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$351

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

View all property information

Property Type

Siesta Key Condo

Show less

Map
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°

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

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

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

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

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

Siesta Key, Florida Travel Tips

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

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

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

How to Spend Your Vacation to Siesta Key House Rentals

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

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

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

Best Eats Near Siesta Key Rentals

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

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

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


FAQ

How many vacation rentals are there in/around Siesta Key?

There are 312 Siesta Key vacation rentals available on FloridaRentals.com. From condo rentals to house rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Siesta Key?

There are vacation rentals available in Siesta Key for as low as $140 per night with an average price per night of $304.

Can I find a vacation rental in Siesta Key?

Yes, you can find vacation rentals in Siesta Key close to Sieta Beach, Turtle Beach and Crescent Beach. Don't forget to stop in to Point of Rocks or Siesta Farmer's Market.

Do any vacation rentals in Siesta Key have a pool?

Yes, there are 68 vacation rentals with a pool in Siesta Key on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Siesta Key vacation rentals on the ocean?

There are 52 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!