Siesta Key Vacation Rentals

(278 rentals)
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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 ...

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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. ...

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1 BR | 1 BA | Sleeps 3 | Quick View

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

$287

avg/night

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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 ...

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Property Type

Siesta Key Condo

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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 ...

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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.

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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 200 yards to Siesta Key Crescent Beach

$170

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

JANUARY SPECIAL - 15% OFF THE PUBLISHED RATE FOR STAYS 7 NIGHTS OR MORE FROM JANUARY 7 - FEBRUARY 4We invite you to stay in our spacious 2 bed 2 bath condo, 'Siesta Chillin', across from the beautiful crystal sands of Crescent Beach on Siesta Key. Siesta Chillin has been recently updated and has all ...

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Property Type

Siesta Key Condo

"Siesta Central - The Anchorage!!"

We stayed at the Anchorage in unit 305. It faces the city and the inner coastal lagoon. We were treated to a dolphin show one evening when they entered the lagoon searching for food!! This location ...

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2 BR | 1.5 BA | Sleeps 6 | Quick View

5

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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 ...

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Property Type

Siesta Key Villa

"#livingdreaming"

So relaxing. Stocked for everyday needs. Very clean. Very comfortable. Perfect size. People were very nice. Clean pool.

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1 BR | 1 BA | Sleeps 4 | Quick View

$222

avg/night

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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 ...

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Property Type

Siesta Key Apartment

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2 BR | 2 BA | Sleeps 6 | Quick View

4

$290

avg/night

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Key Amenities

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

About this property

This colorful custom2rd floor unit has a commanding view of the Gulf of mexico.This special unit has been decorated by a pro, and shows it! unit, perfect for people who can take excellent care of things and appreciate the fine nature of this unit.From the modern kitchen, you will enjoy Siesta ...

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Property Type

Siesta Key Condo

"AMAZING view!"

This condo has it all! This is the first condo I have ever stayed at that had ALL the kitchen utinsels you could ever need (minus and Instant Pot, but it does have a crockpot)! The view makes it seem ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$202

avg/night

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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 ...

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Property Type

Siesta Key Apartment

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2 BR | 1 BA | Sleeps 6 | Quick View

$251

avg/night

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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 ...

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Property Type

Siesta Key Apartment

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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 ...

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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.

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2 BR | 2 BA | Sleeps 6 | Quick View

4.6 rating on other travel sites

$310

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 ...

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Property Type

Siesta Key Condo

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2 BR | 2 BA | Sleeps 6 | Quick View

3

Distance to beach: 0.2 miles to Siesta Key

$203

avg/night

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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 . ...

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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!

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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 ...

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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.

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2 BR | 1 BA | Sleeps 4 | Quick View

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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.

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Property Type

Siesta Key Villa

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1 BR | 1 BA | Sleeps 4 | Quick View

$237

avg/night

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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 ...

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Property Type

Siesta Key Apartment

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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 ...

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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 ...

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2 BR | 1 BA | Sleeps 6 | Quick View

1

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

2 Bedroom/ 1 Bath Private Villa, Close to Pool, Clubhouse, and Laundry. A few Steps to our Private Beach.Completely remodeled, spacious two bedroom villa with room for the whole family. Sleeps six with pullout couch. Brand new kitchen, flooring, paint and bedroom carpeting. Open floor plan is perfect ...

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Property Type

Siesta Key Villa

"Great time"

Loved our stay!! The bed was comfortable, pool was perfect, proximity to the beach was fantastic! Wish there was room for food storage in the kitchen and water pressure in the sink was poor.We would ...

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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)! ...

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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.

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2 BR | 2 BA | Sleeps 6 | Quick View

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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. ...

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Property Type

Siesta Key Villa

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4 BR | 2.5 BA | Sleeps 8 | Quick View

6
LAST MINUTE DEAL 4/29 - 4/29: New week available. Starting Saturday, April 29. 15% Discount. Also 5 nights May 22-27.

$786

avg/night

View Details

Key Amenities

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

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Property Type

Siesta Key House

"Family Time"

We are a family of 8, including a 9 yo & 2 yo. Staying in this beautiful home was a dream come true! Direct beachfront, lovely patio with nice furniture, an umbrella for enjoying the afternoon sunshine, ...

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DEAL

2 BR | 2 BA | Sleeps 4 | Quick View

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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 ...

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Property Type

Siesta Key Villa

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1 BR | 1 BA | Sleeps 3 | Quick View

8

Distance to beach: 150 yards to Crescent Beach

$288

avg/night

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Key Amenities

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

About this property

1 Week Minimum Stay Required except during Feb 1 to the first Saturday after Easter when 2 weeks are required. Newly Upgraded 1BR/1 BA condo with full sleeper sofa and twin sleeper chair in LR. Updated Kitchen fully remodeled with premium appliances. Top of the Line King Size Bed will give you a great ...

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Property Type

Siesta Key Condo

"Georgious Siesta Key Condo"

This condo is perfectly located in the middle of Siesta Key, on the beach. It is a short distance to Siesta Key Village, that has shopping and restaurants. The condo is very comfortable, with up to date ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$278

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath with its own private pool walled in for complete privacy. Vaulted ceilings — spacious inside and out, with flat screen TVs in bedroom and living room. Great get-away unit…with pull-out sofa, great for families or even two couples. Pool and patio area is entirely ...

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Property Type

Siesta Key Apartment

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2 BR | 2 BA | Sleeps 6 | Quick View

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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 ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 6 | Quick View

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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.

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 5 | Quick View

13

Distance to beach: 400 yards to Crescent Beach

$272

avg/night

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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 ...

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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 ...

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2 BR | 2 BA | Sleeps 6 | Quick View

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

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

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Property Type

Siesta Key Villa

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

NEWLY RENOVATED IN 2023!!VERY SPACIOUS 4 BEDROOM 2 BATHROOM DETACHED VILLA IN HIGHLY SOUGHT AFTER POLYNESIAN GARDENS COMMUNITY ON BAY SIDE OF THE ROAD. PUBLIC BEACH ACCESS AT CRESCENT BEACH AND ACCESS TO HEATED POOL AND COMMUNITY CENTER. WIRELESS INTERNET ACCESS,VILLA SLEEPS 8, 1 KING, 1 QUEEN, ...

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Property Type

Siesta Key Villa

"Family vacation 22"

The place was very roomy for all 7 of us. Location is perfect with a lot of eating place that have been in business over the 30 years I lived in Sarasota. We had one issue and it was handled right away. ...

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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 ...

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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!!!

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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

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Property Type

Siesta Key House

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$318

avg/night

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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 ...

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Property Type

Siesta Key Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

4.9 rating on other travel sites

$318

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, ...

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Property Type

Siesta Key Condo

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 plus pull-out sofa (in all units); from your doorway you can see the beach access just across the street – it’s that close! Flat screen televisions in each bedroom and the living room (in all units at Sea Spray Resort). Dine on your private patio! All ...

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Property Type

Siesta Key Apartment

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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 ...

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Property Type

Siesta Key Condo

"Paradise"

Our vacation experience in Siesta Keys was amazing. The condo owner was so communicative, provided a rental agreement after my inquiry, and all the needed to know info about the unit and area closer to ...

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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 ...

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Property Type

Siesta Key Apartment

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 0.4 miles to Crescent Beach

$250

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 ...

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Property Type

Siesta Key Apartment

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1 BR | 1 BA | Sleeps 4 | Quick View

1

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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. ...

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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. ...

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2 BR | 2 BA | Sleeps 6 | Quick View

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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 ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 4 | Quick View

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Key Amenities

  • Air conditioning
  • Kitchen

About this property

Welcome to one of the closest villas to the beach! Technology upgrades include dedicated WiFi. The living room features a home theater 55" HD flat screen TV with DVD player and HBO provided compliments of the owner. Each bedroom has its own flat screen TV while the master bedroom also has a ...

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Property Type

Siesta Key Villa

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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!

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Property Type

Siesta Key Apartment

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2 BR | 2 BA | Sleeps 4 | Quick View

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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 ...

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Property Type

Siesta Key Villa

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2 BR | 2 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$272

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 ...

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Property Type

Siesta Key Condo

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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 ...

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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.

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$318

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 ...

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Property Type

Siesta Key Condo

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1 BR | 1 BA | Sleeps 4 | Quick View

$202

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Second floor 1 bedroom / 1 bath turn-key furnished with no “baking oven” discount but everything else is there for your kitchen needs…what a way to “rough it” at the beach! There is a lovely balcony off the bedroom for romantic drinks at night and coffee in the morning. ...

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Property Type

Siesta Key Apartment

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4 BR | 4 BA | Sleeps 12 | Quick View

9

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$306

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. ...

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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!

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1 BR | 1 BA | Sleeps 4 | Quick View

5

Distance to beach: 100 yards to Crescent Beach

$204

avg/night

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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 ...

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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 ...

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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 ...

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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 ...

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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 ...

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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 ...

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1 BR | 1 BA | Sleeps 4 | Quick View

$229

avg/night

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

1 Bedroom / 1 bath with TWO private patios, one off the dining/living room and the other off the bedroom. Both patios are walled for privacy. With a pull-out sofa on one end of the unit and the bedroom on the other side it makes a great unit for up to four people, even though it is a one bedroom unit. 1 ...

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Property Type

Siesta Key Apartment

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Siesta Key Vacation Rentals

Siesta Key Weather

 | 

7122°  5111°
JANUARY
Ocean 6418°
7423°  5412°
FEBRUARY
Ocean 6518°
7725°  5814°
MARCH
Ocean 6719°
8127°  6217°
APRIL
Ocean 7323°
8630°  6820°
MAY
Ocean 7826°
8932°  7323°
JUNE
Ocean 8228°
9133°  7423°
JULY
Ocean 8530°
9133°  7524°
AUGUST
Ocean 8730°
8932°  7323°
SEPTEMBER
Ocean 8529°
8529°  6719°
OCTOBER
Ocean 8228°
7926°  6016°
NOVEMBER
Ocean 7524°
7423°  5412°
DECEMBER
Ocean 6921°

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 278 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 $284.

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