Siesta Key Vacation Rentals

(245 rentals)
booking message booking message

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

"Favorite unit yet!"

The one thing that surpassed the perfection of this Fisherman Cove unit was the friendly service from Dina and Russell and Rhonda. Each call , text or email was promptly returned with " that's no problem" ...

See all reviews

Show less

Key Amenities

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

About this property

Enjoy our 2br 2 bathroom ground floor condo. 30’ to the pool, tennis courts, Weber gas grills, and picnic table . Or cross the street to private deeded beach access on the #1 beach in the US. Enjoy bayside fishing on the fishing deck. 1280 square feet of living space. Roku tv’s and ...

View all property information

Property Type

Siesta Key Condo

"Cold escape"

We always enjoy our stay at Gulf and Bay Bayside!!! Condos are perfect! We always meet new people who have become friends and can’t wait to see them again next year!!!

See all reviews

Show less

2 BR | 1 BA | Sleeps 6 | Quick View

$251

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

2 bedroom / 1 bath with private patio, spacious kitchen and living room. Enjoy eating outside on your private patio. Every bedroom and the living room have flat screen televisions; this is true for every unit at Sea Spray Resort! One of our favorite 2 bedroom units and one of the closest to the beach ...

View all property information

Property Type

Siesta Key Apartment

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$251

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

1 bedroom / 1 bath has a full kitchen, private patio off bedroom and lovely walkway to pool. The world will never find you in this sultry hideaway located on our tropical, brick paver walkway just steps from the pool or the beach!

View all property information

Property Type

Siesta Key Apartment

Show less

$326

avg/night

View Details

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

"After Holiday Family Getaway"

Escaped the cold from Chicago in this great 2bed/2bath condo..Walk out of the unit and had sand on my toes in minutes. Left the doors open and fell asleep to the waves.. Perfect sized unit for our family. ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$237

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath on first floor with private front patio (“no baking oven” discount). Open kitchen and dining area, and like all our units, turn-key furnished, including beach towels. You will like this one! First floor and very spacious! Nice private patio at front door and back door leads ...

View all property information

Property Type

Siesta Key Apartment

Show less

Key Amenities

  • Air conditioning
  • Beachfront
  • 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

"Peaceful"

Really enjoyed staying at this quieter end of the island. It was a much needed break. Carrie is very sweet and easy to deal with. Will definitely be returning again.

See all reviews

Show less

3 BR | 2 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$317

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

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

4 BR | 4 BA | Sleeps 12 | Quick View

9

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$305

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

2 BR | 2 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$271

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

1 BR | 1 BA | Sleeps 4 | Quick View

5

Distance to beach: 100 yards to Crescent Beach

$204

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • 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 memory foam sofa sleeper for separate sleeping area if needed Unit includes a full kitchen for ...

View all property information

Property Type

Siesta Key Condo

"Fabulous"

We stayed at La Siesta in Siesta Keys. This was our sixth time at this resort and have loved it each time. This time we stayed for three weeks and just loved it. We did not rent a car, but used the local ...

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

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

"Beach west side"

The place was very clean. The kitchen was well equipped Liked the the decks on both levels. The place is close to the beach. One caveat- time for new living room furniture.- the sofa has its day.

See all reviews

Show less

$317

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

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

"What a wonderful two weeks in a perfect condo!"

We’ve spent time at Fisherman’s Cove before but this was our first time in unit A108. What a delight! The unit is well done with all the amenities anyone could want. The location is ideal. Out the ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

2

Distance to beach: 30 feet to Turtle Beach

$284

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront

About this property

Within just a few feet of the beach, our condominium home features a well equipped kitchen with granite counter tops, luxury vinyl flooring, a leather sectional couch, recliner chairs, teak furnishings, ceiling fans in all rooms, a 55 inch smart TV in the living room and a flat screen TV in each bedroom ...

View all property information

Property Type

Siesta Key Condo

"Oldie but Goodie"

We’ve traveled many places in our lives ( especially all over Florida) and this is one of our favorites. From the moment we requested more info on Bill and JoAnn’s condo until today at check out the ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

1

$322

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Private pool

About this property

RENOVATED 2020!!! From the lanai and your private patio, you are directly on the beach where it is easy to keep an eye on the children playing, or walk down to the Gulf of Mexico for a swim. Located on Turtle Beach, Siesta Key's quiet south end - this lovely Gulf front first floor unit with large washer ...

View all property information

Property Type

Siesta Key Condo

"Beautiful Condo!"

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

Key Amenities

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

About this property

Our Condo is on beautiful Turtle Beach at the southern and most private end of Siesta Key directly on the Gulf of Mexico. When we say directly, we mean directly and not merely a Gulf “View” or a long car ride or a long walk to the Gulf. We call it “Paradise” and you could not ...

View all property information

Property Type

Siesta Key Condo

"Paradise Found!!"

We were excited to spend a week in Florida. The condo made our vacation the ultimate paradise getaway!! This condo was very clean and beautifully decorated! Eating our meals in the lanai with that view ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

This is a 3rd floor walk-up with 1 bedroom / 1 bath. It is turn-key furnished with everything you need — except “baking oven”…you will have to hold off on baking until you return home! A balcony off the bedroom overlooks the lush grounds. You can enjoy total privacy in your 3rd ...

View all property information

Property Type

Siesta Key Apartment

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

"GREAT!!"

These people are great , have stayed there before and will again.clean good service nice pool right on the gulf.

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This is a 3rd floor, 1 bedroom / 1 bath furnished unit with kitchen area but no “baking oven.” (You’ll have to save baking for another time!) However, you will find everything else you need in your unit, including your very private 3rd floor balcony off the living room. This is a great ...

View all property information

Property Type

Siesta Key Apartment

Show less

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

"good place"

Comfortable and quiet at that time. I recommend it to everybody.. Please have more explanation to find the place to unlock the gate

See all reviews

Show less

2 BR | 1 BA | Sleeps 6 | Quick View

$251

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Our guests always comment on how clean our units are and we take pride in this.2 bedroom / 1 bath with direct access to pool through back door, one of our favorites for families! 1 King Bed + 1 Queen Bed

View all property information

Property Type

Siesta Key Apartment

Show less

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

The Siesta Key vacation condo rental is a one bedroom / one bathroom individually owned condominium at the Gulf and Bay Club Bayside and is furnished with the basic household items necessary for normal living. This unique Old Key West style condo is fully equipped with an emphasis on vacation living. ...

View all property information

Property Type

Siesta Key Condo

"Bay side"

Great townhouse great location very cleanIt had all the amenities for the beach pools were very nice walk to the beach

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 0.1 miles to Siesta Key Beach

$224

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

"Beach, Pool, Great Condo amazing owner"

This rental was beautiful, clean and location was primo. Kitchen was well stocked. I mentioned to the owner that I cooked most evenings and asked if they had a slow cooker, she said they did not but she ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 7 | Quick View

1

Distance to beach: 0.0 miles to Cresent Beach

$210

avg/night

View Details

Key Amenities

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

About this property

Siesta Key condo with heated pool. One of the best locations in Siesta Key. Updated with fun designs, feature walls, smart TVs, functional kitchen. Minutes’ walk to white sands of Siesta Beach ranked #2 beach in the US and #14 in the world. Walk to Tiki bar, Captain Curt’s, bike, boat, kayak, ...

View all property information

Property Type

Siesta Key Condo

"Perfect Getaway!"

This condo has it ALL! It's all about location in Siesta Key & this condo is a very short walk to the beach, stores & restaurants! I loved walking down the lush path to see the picture perfect sunsets on ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.1 miles to Crescent Beach on Siesta Key

$150

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

This 2nd floor, completely renovated 2 bedroom, 2 full bath condo in Siesta Harbor with private beach access and overlooking its own private harbor is the perfect getaway to the #1 beach on Siesta Key in Sarasota, Florida. This unit is located near the community pool and hot tub along with guest grilling ...

View all property information

Property Type

Siesta Key Condo

"Great condo for relaxing"

This was our first stay in the Siesta Key area and this condo set the bar quite high. It is set in an over 55 complex with a pool, covered parking and across the street access to the beautiful beach. Captain ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: -100.0 feet to Crescent Beach -- we are located on the beach

$204

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Sea Crest on Siesta Key is a small 40-unit condominium complex at 1129 Seaside Drive consisting primarily of one-bedroom units with separate bedroom, one efficiency, and one two-bedroom, two-bathroom unit. A true old style Floridan resort. Enjoy our one bedroom condo just a few steps to our private ...

View all property information

Property Type

Siesta Key Condo

"Great family vacation"

I was supposed be there Oct 1 to 29th, but hurricane Ian had other plans for me, Jeffrey the manager was very acommodating in making all the necessary changes to make my stay wonderfull. I ended going the ...

See all reviews

Show less

2 BR | 1.5 BA | Sleeps 4 | Quick View

26
Owner special: We still have opening this summer!

Distance to beach: 200 yards to Crescent Siesta Key Beach

$191

avg/night

View Details

Key Amenities

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

About this property

Located in beautiful Siesta Key, Fl (consistently ranked #1 beach in the US!!) in Midnight Cove 1, this bayside condo spoils its occupant with all the amenities and luxuries needed for a relaxing, tropical vacation. Nestled amid lush landscaping in this gated community, our unit is newly remodeled and ...

View all property information

Property Type

Siesta Key Condo

"Breath taking"

The Condo was everything that was described. Very cozy and comfortable. Could live that life year round. Pools were nice. Beach service was very convenient. The office was nice to answer any questions. ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath on ground floor with patio off bedroom (“no baking oven” discount). This is a first floor unit with a patio off the bedroom. From your patio it is just steps to pool area where you can grill, kick back in the hammock, relax by the pool, or later in the evening have a campfire….you ...

View all property information

Property Type

Siesta Key Apartment

Show less

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach(Two Bedroom Beachview 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

"Nice beach, bad red tide"

Unit was clean and close to the beach. Sufficient kitchen supplies, however, frying pans scratched up , wouldn’t use them. Linens and towels clean. Dishwasher and refrigerator clean and in working condition. ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

$251

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

2 bedroom / 2 bath unit with direct back door access to main pool! There you can grill on one of the barbeques, relax in the hammock, swim in the pool and later in the evening have a campfire and enjoy the starry night sky! 1 King Bed + 1 Queen Bed

View all property information

Property Type

Siesta Key House

Show less

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

"Vaca 2023 unit B309"

I just want to say thank you so very much Dina for allowing us to rent your condo for 1week we had the very best vacation ever as a couple! The condo is absolutely beautiful and was very clean and stocked ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 5 | Quick View

13

Distance to beach: 400 yards to Crescent Beach

$272

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

The Sand Dollar is a private villa located at the quiet, well run and exceedingly clean "beach to bay" community of Horizons West. A maximum of 50% of Horizons West properties are rented so the community has a more residential feel than many others on the island. The villa has been recently ...

View all property information

Property Type

Siesta Key Villa

"1st time on Siesta Key"

This was my first time on Siesta. Beautiful place! From my first inquiry to my last day Chris was the ultimate host! He texted to see that I had arrived and everything was ok. When we had ac issue he ...

See all reviews

Show less

2 BR | 1.5 BA | Sleeps 6 | Quick View

4

Distance to beach: 200 yards to Siesta Key/ Crescent Beach

$228

avg/night

View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Villa

"Wonderful!"

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

See all reviews

Show less

Key Amenities

  • Air conditioning
  • 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

"Jamaica Royal"

We loved our stay here. Right on the beach and great pool close to our condo. Clean and spacious. Maybe could use a few updates but we were mainly here at night for sleeping so it worked well for us.

See all reviews

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

"Beautifully renovated beach condo"

The condo contained anything and everything need to have a wonderful vacation. The view of the ocean was spectacular.

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$222

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 bedroom / 1 bath with full kitchen and walled private patio off living room…one of our largest 1 bedroom units with a very private, walled patio with table/chairs/umbrella for morning breakfast or evening dinner on the patio! Just steps to the pool, grills, hammock…a great unit! 1 King ...

View all property information

Property Type

Siesta Key Apartment

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$309

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

1 BR | 1 BA | Sleeps 4 | Quick View

$202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

This second floor 1 bedroom / 1 bath is beautifully furnished with everything you need, including beach towels. Kitchen has everything except “baking oven”…think you can make it without baking a turkey while you relax in paradise? Private patio for romantic setting while enjoying drinks ...

View all property information

Property Type

Siesta Key Apartment

Show less

3 BR | 3 BA | Sleeps 6 | Quick View

8

Distance to beach: 0.3 miles to Crescent Beach

$339

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Pool

About this property

Looking for the perfect vacation spot? Look no further! This beautiful condominium in Siesta Key is just a short 3 minute walk away from the stunning Crescent Beach. Enjoy a day out in the sun, swimming, and relaxing on the sandy shore before returning to your own private oasis. The condominium comes ...

View all property information

Property Type

Siesta Key Townhome

"Paradise!"

The place was immaculate and had everything we needed. It was so nice to have beach towels, chairs, and sand toys provided. The location is perfect. It's a very short walk to the beach. Some restaurants ...

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.2 miles to Siesta Key

$203

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

3 BR | 2 BA | Sleeps 6 | Quick View

1

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

$393

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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

"Stunning Condo"

My family stayed in this stunning condo and absolutely loved it. Beautiful views, fabulous modern furniture, high tech TVs and sound system, awesome high end kitchen and baths.

See all reviews

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

52

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

$306

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

"Our Stay at Fisherman's Cove"

We thoroughly enjoyed our stay in unit 309A at Fisherman's Cove. Loved having 2 bedrooms, 2 full bathrooms and a washer/dryer in the unit. The view was awesome and it was great being able to walk right ...

See all reviews

Show less

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 2 miles to siesta key

$750

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

LaVida Vacations presents a wooded property is unreal and our 5 star ratings agree! 1 acre on the water for your entire family or group to relax and enjoy. Go swimming in the huge heated private pool or go to the water and enjoy paddle boarding or kayaking to the Gulf of Mexico! After a long day at the ...

View all property information

Property Type

Siesta Key House

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

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

$286

avg/night

View Details

Key Amenities

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

About this property

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

View all property information

Property Type

Siesta Key Condo

Show less

2 BR | 2 BA | Sleeps 6 | Quick View

9

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

$158

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

View all property information

Property Type

Siesta Key Condo

"Repeat visitor"

We have visited at the condo numerous times. Every visit has been fun and relaxing. Clean and comfortably furnished.. With the beach, restaurants and shops close by, having a beautiful view of the causeway ...

See all reviews

Show less

1 BR | 1 BA | Sleeps 4 | Quick View

$212

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

1 Bedroom/1 bath with full kitchen, pool view and private patio area adjacent to the pool. This 1 bedroom unit has a comfy king bed as well as a pull-out sofa bed in the living room. Enjoy a mid-day refreshment on your private patio with table, chairs, and umbrella for your comfort and relaxation. An ...

View all property information

Property Type

Siesta Key Apartment

Show less

1 BR | 1 BA | Sleeps 3 | Quick View

8

Distance to beach: 0.5 miles to Siesta Key Main Beach

$91

avg/night

View Details

Key Amenities

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

About this property

Sweet and spacious one bedroom condo in a Siesta Key Luxury Resort Building - Harbor Towers Yacht & Racquet Club. Great view of the historic waterfall in front of building, Palm Trees and Blue Skies and Great Sun Sets. 2 Pools (1 for kids), Fitness Room, , 3 lighted Tennis courts, boat marina, gazebo, ...

View all property information

Property Type

Siesta Key Condo

""Wonderful two weeks at the Harbor Towers in Siesta Key!""

We thoroughly enjoyed our Sweet Siesta Key Condo located in the Harbor Towers facility in Siesta Key. The resort was well maintained and beautifully decorated. Our condo was minutes from the beautiful Siesta ...

See all reviews

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 245 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 $75 per night with an average price per night of $298.

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 64 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 44 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!