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Siesta Key Vacation Rentals

(169 rentals)
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

1 BEDROOM, 1ST FLOOR CONDO W/ PRIVATE SCREENED LANAI, NEW PERGO FLOORS, NEW KITCHEN, WASHER/ DRYER IN UNIT. LOCATED ONLY 1 BLOCK FROM THE SHOPS AND RESTAURANTS IN THE VILLAGE, 1 BLOCK TO THE BEACH, SEPARATE DINING ROOM, HIGHSPEED INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT). POOL ...

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$221
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...

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$127
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

SPECTACULAR VIEWS FROM THIS 2 BEDROOM / 2 BATH BEACHFRONT, GROUND FLOOR UNIT LOCATED IN THE CASA MAR COMPLEX WITH THE WORLD FAMOUS SIESTA KEY BEACH JUST A FEW FEET AWAY. THE CASA MAR COMPLEX OFFERS 2 POOLS, TENNIS, WIFI, (SIESTA 4- RENT DOES NOT OFFER TECH SUPPORT), COMMUNITY LAUNDRY ROOM, AND 1 COVERED ...

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$383
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

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

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Best beachfront view on Siesta Key from remodeled two bedroom and two bathroom beachfront condo. Stay for the unbelievably beautiful beachfront balcony views. Enjoy the modern open floor plan with beach views from most rooms. Beautifully furnished apartment you will be proud of.Upgraded, secure WiFi.Spectacular ...

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Featured review

"Any last minute availability for February"

Hello I was looking to see if you had any last minute availability for February ? Sorry to contact through the review I could not find an email address to send a request. Thank you for your time best Joann

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$353
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
12 reviews

Distance to beach: 200 feet to across street

Key Amenities

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

About this property

2 bedroom gorgeous condo overlooking Siesta Key Beach and Gulf of Mexico. Complex with large community pool, sauna, covered parking, secure gated area. Gas grills, party room, beautiful property. 2 full bathrooms with granite walk in showers and basin, etc. King bed in master with ensuite full bath, ...

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Featured review

"Crescent Royale 4b Siesta Key,FL"

We had a great time. Condominium was wonderful. It had everything we needed. The owners were very helpful.

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$216
avg per night

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Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"Super convenient spot!"

We thoroughly enjoyed our time at this condo. You are literally steps from a pool, the grills and the beach! The condo had everything we needed and more. We are definitely renting here again!

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$260
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

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

About this property

Our gorgeous condo is surrounded by water with the Gulf of Mexico on one side and Blind Pass Lagoon on the other side and Sarasota Bay within kayak range! Such a unique setting, sitting at the southern and most private end of Siesta Key. A306 is on the third floor and the views are stunning! Our community ...

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Featured review

"Excellent Condo A306"

We stayed at A306 the third week of April 2023. Our stay was well beyond expectation and this location & Unit is the best overall rental we’ve experienced in 25+ years of Florida vacationing. Everything ...

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$289
avg per night
Siesta Key Condo
Sleeps 3, 1 bedroom, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

Enjoy spectacular views of the Gulf from all levels of this freshly remodeled, coastal contemporary townhouse featuring a master Bedroom with a den and luxurious bathrooms. The beach is just steps away and a block from Siesta Village offering restaurants, shopping and nightlife. This three-story unit ...

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$350
avg per night
Siesta Key Condo
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

This lovely penthouse condo is in one of Siesta Key's newest complexes (built in 2006). The Crescent offers luxury living at its finest. Bask in the spectacular view of the world famous Crescent beach on Siesta Key from this three (3) bedroom, three (3) bath beach front condominium's open air ...

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$811
avg per night
Special Offer
Siesta Key Condo
Sleeps 4, 2 bedrooms, 1.5 bathrooms
33 reviews

Distance to beach: 200 yards to Crescent Siesta Key Beach

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

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 ...

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Featured review

"Great stay at a great condo!!!"

Sandy, the owner was excellent with communication! I appreciated how immaculate and comfortable the condo was. The condo lacked nothing! Home away from home! The location of the condo provided a peaceful ...

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$183
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Beautiful 1 Bedroom w/ den in Bayside community of Bay Oaks. 3 TV's, 1st floor unit. Sleeps 4, King in the master bedoom. The den has a twin bed and the livingroom has a sleeper sofa. No cable, Streaming only. Highspeed internet. (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT).1 week min. CLEANING ...

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$112
avg per night
Siesta Key Condo
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

3 Bedroom/ 3 Bath Beachfront Townhome in Siesta Village, offering beautiful sunsets from your 2 balconies. Note that the beach directly in front of the property is private and may not allow access. Public beach access is always available just a few steps away. Go a block behind the unit to all the restaurants ...

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$626
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

4TH FLOOR BAYSIDE, 2 BEDROOM / 2 BATH CONDO LOCATED IN THE CAPRI BUILDING OF THE EXCELSIOR COMPLEX. THE COMPLEX HAS 2 POOLS (ONE ON BEACHSIDE AND ONE ON BAYSIDE) WITH HOT TUB, 3 LIGHTED TENNIS COURTS, OUTDOOR BARBECUE / PICNIC AREA AND BEACH ACCESS. UNIT OFFERS WASHER / DRYER, HIGH SPEED INTERNET SERVICE, ...

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Featured review

"2 hurricanes"

We were due to stay for 2 weeks from 26th sep unfortunately due to hurricane helene we weren't able to stay .siesta rentals returned all our sad but we will come ahain

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$166
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is a Gem, 2nd/3rd floor Bayfront townhome, Living area on second floor and interior stairs lead to bedrooms on 3rd floor. Top of the line unit, offering travertine floors, new kitchen and baths, leather furnishings, 1/2 bath on the 2nd floor and 2 baths on the 3rd floor. Unit offers highspeed internet ...

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$145
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME RELAX IN THIS QUIET BAYSIDE COMPLEX THAT IS SURROUNDED BY WHISPERING OAKS. UNIT LOCATED ON THE 2ND FLOOR AND IS A 2 BEDROOM / 2 BATH REMODELED UNIT. COMPLEX OFFERS A NEWLY RENOVATED POOL AND POOL DECK, TENNIS, COMMUNITY ROOM AND A SMALL PIER. UNIT HAS TILE IN THE MAIN TRAFFIC AREAS WITH CARPET IN ...

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$127
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

ENJOY THIS 4 BEDROOM, 3 BATH PRIVATE HOME LOCATED ON A CANAL IN BEAUTIFUL SIESTA ISLES. OPEN FLOOR PLAN WITH LOTS OF SPACE, HARD WOOD FLOORS, WITH STUNNING VIEWS FROM EVERY ANGLE. LAUNDRY ROOM WITH FULL SIZE WASHER / DRYER AND WIRELESS INTERNET ACCESS, (SIESTA 4 RENT IS NOT RESPONSIBLE FOR TECH SUPPORT.) ...

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$284
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Experience luxurious living in one of the largest units on Siesta at this stunning 2 bedroom, 2 bathroom condo. This immaculate condo features porcelain tile flooring in the living areas, brand new plush carpeting in both bedrooms, and beautiful crown molding throughout. The kitchen is a chef's dream, ...

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$193
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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, FLCrescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront ...

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$285
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks - UpscaleLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may be some ongoing construction ...

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Featured review

"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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$263
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Spectacular, modern 1 bedroom , 2nd Floor unit in Siesta Key Village offers great location 2 buildings from the beach, 1 block into the village with restaurants and shopping. The unit offers, central air, leather furniture, updated kitchen, 1 flat screen TV. Complex offers heated community pool and laundry ...

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$143
avg per night
Siesta Key House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

***Fresh remodel in 2025*** Tucked away amid the tropical tranquility of Siesta Keys Grand Canal, this ranch style home delivers on location and lifestyle. Featuring three bedrooms and two baths and a one-car garage, laundry room with washer and dryer. Gorgeous heated pool looks out to the grand canal, ...

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Featured review

"Beautiful!"

Siesta 4 rent was very accommodating and responsive. It was very clean and great location. Would definitely rent again! Thank you!

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$282
avg per night
Siesta Key Condo
Sleeps 2, 1 bedroom, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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. ...

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Featured review

"March Getaway!"

Siesta Key was very beautiful and a great place to visit. The accommodations were very nice, clean and comfortable. We hope to visit this area again next year.

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$135
avg per night
Siesta Key House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Very private - empty lot across the canal and fenced in. Walk to the islands best restaurants, bars, shops and ice cream parlors. The beach is a short stroll (8 min), use free golf cart taxi or ride provided bikes with tow behind cart! Siesta is well known for its #1 beach in the USA!

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$399
avg per night
Siesta Key Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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, FLRe-opening of 2nd and 3rd floor units on 6/28/25. Property restoration from Hurricane Helene has not been completed and there may ...

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$307
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
11 reviews

Key Amenities

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

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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Featured review

"Amazing"

This unit offers an amazing view of the ocean and sunsets. Perfect get away spot, great location, clean and has everything you need to enjoy your stay. We will be back in 2014!

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$284
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
7 reviews

Key Amenities

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

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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Featured review

"Loved our stay!"

Property was as described and exactly what we were looking for as a base for our week on Siesta Key and surrounding area! Beautiful condo, beach was perfect, and location was ideal for activities and restaurants. ...

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$366
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Distance to beach: 0.1 miles to Crescent Beach Siesta Key

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to The Anchorage Yacht and Tennis Club across from the beautiful sands of Crescent Beach on Siesta Key. Sitting directly on the intercoastal waterway where you can park your boat, jet ski, kayak, and paddleboard. This complex has an olympic size pool, new state of the art pickleball and tennis ...

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Featured review

"Unit 403"

The place is absolutely beautiful. Great views and amenities! Close to walking distance to most things. Would definitely stay here again!

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$197
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

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 ...

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Featured review

"Wonderfully Relaxing"

Staff, wonderful, front desk also wonderful. Snythyou need is a call away. Condo comfortable and clean

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$314
avg per night
Siesta Key House
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

WELCOME TO PARADISE! COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH GRAND CANAL HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES., WALKING DISTANCE TO THE BEACH. THIS FABULOUS REMODELED HOME FEATURES A CUSTOM GOURMET KITCHEN AND OPEN FLOOR PLAN PERFECT FOR ENTERTAINING. HIGH-SPEED INTERNET AVAILABLE, ...

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Featured review

"522 Canal Rd"

Great vacation rental home with tile floors throughout making it a perfect beach home. The house has four bedrooms three of which have their own private, full bathroom. Siesta-4-Rent Management was great ...

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$241
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

BEAUTIFUL BEACHFRONT CONDO WITH VIEWS FROM LIVING ROOM AND BOTH BEDROOMS. BEACH CHAIRS PROVIDED ON THE BEACH. LARGE LANAI RUNS ENTIRE WIDTH OF UNIT. LEATHER FURNITURE, ONE OF OUR MOST POPULAR UNITS. BIG SCREEN TV, VCRand DVD, TV IN EACH BEDROOM. WASHER and DRYER IN UNIT. HIGH SPEED INTERNET ACCESS. (SIESTA ...

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$413
avg per night
Siesta Key House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
9 reviews

Key Amenities

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

About this property

Hurricane Update: We lucked out! Hurricane Helene did not flood our beach house except for the carport. We need to replace the hot water heater, the washer and dryer, and some walls and doors made of wood. Hurricane Milton damaged some soffits but they have already been repaired.A front row seat ...

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Featured review

"Perfect location! Wonderful accommodations!"

Booked this spot for the first time and spent a wonderful week there with my three sisters for a birthday celebration. The weather was great and the beach and water were everything we had hoped it would ...

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$770
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Luxury at its finest in this 1600 sq. ft. 2006 built Crescent condo complex. This Unique 2 Bedroom 2 Bath on the 2nd floor of the complex is a quiet and peaceful setting and opens up directly to one of the two pools through an additional large outside dining patio with gas grill.The newly furbished pool ...

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$497
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

BREATHTAKING, DIRECT OCEANFRONT, 2 BEDROOM / 2 BATH UNIT WITH PANORAMIC VIEWS OF THE BEACH AND SARASOTA SKYLINE. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S ( 65 LIV ROOM) I-POD DOCKING STATION, WASHER / ...

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Featured review

"Great condo"

Location and condition and furnishings of condo are the best, the only suggestion we have (and it's not a deal breaker ) is a recliner or two would be great.

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$310
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Harbor Towers 2nd floor unit located a few blocks south of the Siesta Public beach. Beautiful property located on the intercoastal. Pool and tennis, propane grills and coin laundry on each floor and elevator. NO smoking in unit and NO pets. Units sleeps 4, 1 King and 2 twins. 2 Week min. CLEANING FEE ...

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$153
avg per night
Siesta Key House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

TRULY THE BEST OF BOTH WORLDS- BEAUTIFUL CANAL HOME JUST TWO BLOCKS TO WORLD-FAMOUS SIESTA KEY BEACH. COME RELAX IN THIS BEAUTIFUL 3 BEDROOM / 2 BATH HOME LOCATED IN THE QUIET NEIGHBORHOOD OF SIESTA ISLES WITH A GORGEOUS POOL. (NOTE POOL CAGE SHOWN IN SOME PHOTOS IS NO LONGER THERE.) THIS FABULOUS REMODELED ...

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$386
avg per night
Siesta Key Condo
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

**Any advertised discounts on website do not apply to this unit*** THIS 2ND FLOOR LUXURY CONDO HAS ONCE AGAIN BEEN UPDATED WITH DESIGNER FURNITURE AND FURNISHINGS. ALL BEDS NOW HAVE 800 COUNT VERA WANG COTTON HOTEL STYLE SHEETS. THIS UNIT ALSO HAS A FULLY RESTOCKED COOKS KITCHEN, GRANITE COUNTERTOPS, ...

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$790
avg per night
Siesta Key House
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

PRIVATE 3 BEDROOM / 2 BATH HOME LOCATED IN A BEAUTIFUL RESIDENTIAL NEIGHBORHOOD. 1 MILE FROM THE WORLD FAMOUS SIESTA KEY BEACH. FULLY RENOVATED AND NEWLY FURNISHED FOR YOUR ENJOYMENT WITH AN OPEN FLOOR PLAN WITH LOTS TO OFFER. KITCHEN W/ STAINLESS STEEL APPLIANCES AND LARGE PANTRY. 3 LCD SMART TVS, DVD. ...

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$212
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
10 reviews

Key Amenities

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

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 ...

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Featured review

"All about the location"

We stayed on Holmes Beach in early March. Our condo was directly on the beach. Location could not be beat. There was plenty of room in this two bedroom unit with two full bathrooms. There was plenty ...

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$286
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Completely Remodeled Beachfront 11th Floor unit at Crystal Sands. Gulf views from each bedroom and living room south on Crescent beach. (The view in picture #3) is the view from your screened lanai. Elevator down to Pool located on the white sands of Crescent Beach, beach chairs provided by Crystal Sands. ...

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$315
avg per night
Siesta Key Condo
Sleeps 3, 0 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool

About this property

GROUND FLOOR STUDIO LOCATED IN THE MIDDLE OF THE CASA MAR COMPLEX. SHORT DISTANCE FROM THE BEACH AND POOLS. UNIT OFFERS A BRAND NEW QUEEN MURPHY BED, 32" LCD FLAT SCREEN TV, DVD / VCR AND CD PLAYER. 1 COVERED PARKING SPACE. COMPLEX OFFERS 2 POOLS, TENNIS, SHUFFLE BOARD AND BEACH CHAIRS. COMPLEX ALSO ...

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$143
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Awesome 1st Floor Beachfront! Just outside your sliding doors is the #1 rated Crescent Beach. Condo features sweeping ocean view and super easy access to the beach while maintaining privacy of corner unit. Two bedrooms, two baths. Washer/dryer, Flat screen TVs in bedrooms 60" Ultra High Def 4k TV ...

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$305
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
11 reviews

Distance to beach: 0.2 miles to Siesta Key Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Our adorable unit – Casita Siesta - is located at Gulf & Bay Bayside on Siesta Key, on the bay just south of Sarasota and with private beach access to world-famous Siesta Key Beach. It is a lovely 2 bdr/2 bath unit with a spacious living room and sunny lanai. The master bedroom has full bathroom ...

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Featured review

"Mullins review"

The place was very clean. The location was perfect for beach trips and trolleys for visiting the village.

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$237
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • WiFi

About this property

BREATHTAKING GULF FRONT, 2 BEDROOM / 2 BATH UNIT IN THE BEAUTFUL CRYSTAL SANDS COMPLEX. GRANITE COUTERTOPS, TILE FLOORS IN KITCHEN, BATHS and LIVING ROOM, AND WOOD FLOORING IN BEDROOMS. LEATHER FURNITURE, 3 FLAT SCREEN T.V.'S, WASHER / DRYER AND SCREENED LANAI OFF ALL ROOMS WITH DIRECT ACCESS. HIGH ...

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$310
avg per night
Siesta Key Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

Distance to beach: 100 feet to Crescent Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Relax and listen to the waves while sitting on your private lani. You're on the top floor (6th) of the Siesta Breakers Condominium, a private, gated facility with direct access to Crescent Beach, the #1 Top Rated beach in the USA.This luxury 2 bedroom 2 bath apartment, has been kept up to date ...

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Featured review

"Siesta Key"

The area: The general area of the condo was a fun place to visit. Plenty of stores within walking distance (just across the street). More than ample restaurants from which to choose. If you are heading ...

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$375
avg per night
Siesta Key Condo
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • Rentals by owner
  • WiFi

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 ...

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Featured review

"Just what we wanted."

Just returned from a week in Karen’s condo. Her place is perfect. The balcony and view were wonderful. Sitting and looking at the beach was so relaxing. The condo was great. Gave you a beach feeling. ...

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$189
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Distance to beach: 0.2 miles to Siesta Key

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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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Featured review

"Great place!"

This was our first time back to Siesta Key in 20 years and we loved this condo! The location is right between the two villages, so super easy to grab a trolly to dine or shop. The beach is a pretty short ...

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$203
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This is located on the 3rd floor of the clubhouses located on the beachside of Palm Bay Resort, just steps from the beach. Custom cabinets, granite counters, stainless kitchen appliances, screened lanai, 3 LCD TV's, stackable washer/ dryer in unit, and Wi fi. (Siesta 4 Rent does not offer tech support). ...

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$227
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

2ND FLOOR, 2 BEDROOM / 2.5 BATH TOWNHOME LOCATED IN THE QUIET COMPLEX OF BAY OAKS. UNIT NICELY FURNISHED WITH LOTS OF SPACE. UNIT OFFERS TILE FLOORING FOR KITCHEN, DINING ROOM AND LIVING ROOM, 2 TV'S, WASHER / DRYER INSIDE UNIT, 2 SCREENED LANAI’S, SMALL BALCONY AND A FULL KITCHEN. WIRELESS ...

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$127
avg per night
Siesta Key Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
3 reviews

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

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

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 ...

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Featured review

"Siesta Sand Dollar"

We had an amazing stay at Maria's place at Siesta Harbor. Everything had just been updated and was very modern and beautiful. We would highly recommend her unit and we are looking forward to going back ...

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$137
avg per night
Siesta Key Condo
Sleeps 6, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

COME RELAX IN THIS 3RD FLOOR, FIRETHORN UNIT LOCATED IN MIDNIGHT COVE I, BAYSIDE. COMPLEX OFFERS 2 POOLS, BEACH CHAIRS PROVIDED BY ASSOCIATION, 2 TENNIS COURTS AND BEACH ACCESS THROUGH THE GULF SIDE. (NO BEACH CHAIRS OR EQUIPMENT PROVIDED) 3RD FLOOR UNIT, (NO ELEVATOR) HAS OPEN BALCONY WITH VIEW OF CANAL, ...

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$165
avg per night
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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°

FAQ

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

There are 169 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 $67 per night with an average price per night of $263.

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 47 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 50 oceanfront rentals in Siesta Key available on FloridaRentals.com. Use our filters to search and book yours today!