Siesta Key Vacation Rentals

(222 rentals)
Casa Ohana

4 BR | 3 BA | Sleeps 12 | Quick View

2

$288

per night

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Key Amenities

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

About this property

Welcome to Casa Ohana! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy ...

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Property Type

Siesta Key House

"Fantastic Florida Rental"
Reviewed June 22, 2019

Casa Ohana was terrific. Family friendly, close to the beach and main attractions of Siesta Key. Will definitely be returning!

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Siesta Key Condos - Gulf & Bay Club Bayside Condo

1 BR | 1 BA | Sleeps 2 | Quick View

1
Owner special: 10/26 - 11/23: $700 per week plus tax or $100 per night plus tax, minimum stay 1 week.

$111

per night

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Key Amenities

  • Air Conditioning
  • Full 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. ...

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Property Type

Siesta Key Condo

"Fabulous"
Reviewed September 7, 2019

A beautiful complex with a beach house feel ! A very welcoming unit with a generous space. Making the best of the intercostal and gulf !

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"Fiji" 378 Canal Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

1
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool
  • Private Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!1 Bedroom King Bed, screened porch. Pool Access, WIFI *W&D access, 2 flat screen TV's, and ground floor.

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Property Type

Siesta Key Condo

"Banyan Tree"
Reviewed June 10, 2019

Great little place to stay, close to beach, restaraunts and bars .Everything you need in the appartment and quiet little pool area..However our stay was marred by a group who hired the house next door and ...

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Coconut Grove

6 BR | 6 BA | Sleeps 16 | Quick View

$404

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Coconut Grove! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 16, a private heated pool, and quite literally in the heart of Siesta Village!Coconut Grove features a unique combination of two ...

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Property Type

Siesta Key House

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25% discount Hour is NOW. #1 USA BEACH SIESTA KEY ISLAND GLASS HOUSE

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.5 miles to SIESTA KEY BEACH, EASY ACCESS

$168

per night

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Key Amenities

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

About this property

******PRICE OF A HOTEL OFF THE ISLAND IS 165.00 A NIGHT.******PRICES SUBJECT TO CHANGE WITHOUT NOTICE! ..........BOOK NOW! *PRICE LISTED IS DISCOUNTED PRICE. -------------------------IMPORTANT------------------------------------------------------------ * YOU WILL NOT BE ...

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Property Type

Siesta Key House

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BEAUTY AT THE BEACH--Full front Gulf view!! Crescent Arms 601S

$214

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full 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

"Beautiful beach and condo!!"
Reviewed July 25, 2018

The beach and condo were perfect. The sand was so soft and cool. The condo was decorated beautifully. There were 4 people staying in the condo and it had enough room for a couple more. We will be returning ...

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Admirals Watch

3 BR | 3 BA | Sleeps 8 | Quick View

1

$354

per night

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Key Amenities

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

About this property

Welcome to Admirals Watch! This beautiful, luxurious and modern 3 bedroom, 3 bathroom, heated pool, townhome boasts the best views of the world famous No. 1 Siesta Key Beach Access! With absolutely unobstructed views, this home is part of only a handful of private residences that can claim such gorgeous ...

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Property Type

Siesta Key Condo

"Wonderful Stay"
Reviewed July 1, 2019

Admirals Watch, Siesta Key was a great place to stay with an amazing view! Everything is just like the picture. The rental company "The Cottages on the Key" checked in with us a couple of times to make ...

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"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

4
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$143

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!2 Bed/2 Bath unit with King Bed, Two queen beds, Open Deck, ground floor. Pool Access, WIFI, *W&D access.Local free shuttles so no need for a car.Located on the Voted number “#1 Beach in America” popular Siesta ...

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Property Type

Siesta Key House

"Perfection in Paradise"
Reviewed June 18, 2019

We stayed in this lovely condo for 10 nights, and enjoyed every minute.The condo was spotless when we arrived, and had all the amenities we needed with ample space.Right outside is the heated pool ...

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2BR2BA 2nd Floor 800sqft Condo Siesta Key Crescent Beach + WiFi No Road to Cross

2 BR | 2 BA | Sleeps 7 | Quick View

3
Owner special: Last Minute Openings (Some with Discounts): Dec 8-21; Apr 11-18... ...

Distance to beach: 120 yards to Siesta Key Crescent Beach

$100

per night

View Details

Key Amenities

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

About this property

Last Minute Openings (Some with Discounts): Dec 8-21; Apr 11-18... ... ...YouTube Video-- ask!! ... Dr. Beach names Siesta Beach Best Beach in US - just Google 'dr beach names siesta beach best beach in us' and find out why. We have a new 360 degree picture layout of all rooms, similar to Real Estate ...

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Property Type

Siesta Key Condo

"Perfect Beach Stay"
Reviewed June 21, 2019

The condo was great! I couldn't have asked for a better fit for our family vacation. Very clean and quiet! Great proximity to the Private Beach! There are even loungers and chairs at the beach for ...

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Casa Stolida

4 BR | 3 BA | Sleeps 8 | Quick View

$257

per night

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Key Amenities

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

About this property

Luxurious 4BR/3BA villa features a private heated pool and cabana room. Casa Stolida is just steps from prestigious Crescent Beach and is centrally located in close proximity to Siesta Key Beach, voted the #1 beach in the USA!Once inside the home, you will see that Casa Stolida is the definition ...

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Property Type

Siesta Key House

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Ocean View right on the beach!

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 70 feet to Creasent Beach

$238

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool

About this property

Fabulous condo on Creasent Beach with great ocean view.Relax and enjoy the views of the beach and gulf from the balcony and throughout the condo with the open floor plan; from the Kitchen, Living Room along with the Master Bedroom. Take in the spectacular sunsets!The condo is fully updated and ...

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Property Type

Siesta Key Condo

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"Key West" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

1
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$151

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!2 BEDROOM/2 bath, Large Deluxe unit, King bed, Queen bed and Queen sleeper sofa, 3 TVs, large deck with awning, small screened porch, an upstairs accommodation. Pool Access, WIFI, private W&D. Local free shuttles so no need for a ...

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Property Type

Siesta Key House

"Best and thoughtful rental company with beautiful beach"
Reviewed June 12, 2019

We have been visiting Siesta Key for the past 10 and renting from the same company. There accommodating attention to their guests has us coming back year after year. We never consider renting with any ...

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Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$254

per night

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Key Amenities

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

About this property

One of Siesta Key's most alluring homes, with private heated pool & spa! Siesta Dream House is perfect for family get togethers and romantic getaways alike.Welcome to Siesta Dream House! This enchanting 4-bedroom/3.5-bathroom home is located in Siesta’s North Key and is close to Siesta Key ...

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Property Type

Siesta Key House

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Dolphin" 378 Canal Rd. Just a short walk to the beach and Village

1 BR | 1 BA | Sleeps 4 | Quick View

2
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$103

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pool

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNTED RATES!1 Bedroom, King Bed, Queen sleeper sofa, Ground level, Screen Porch. Pool Access, WIFI *W&D access, and ground floor. Across from Canal

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Property Type

Siesta Key Apartment

"Great "Old Village" Rental Experience"
Reviewed June 13, 2019

We are lucky to have found this rental property in Siesta Key Village! A well maintained unit, it is ideally located a short walk from the beach and a five minute walk to the village for dining, shopping, ...

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The Palms Cottage

4 BR | 2 BA | Sleeps 10 | Quick View

$385

per night

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Key Amenities

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

About this property

This charming recently updated four-bedroom, 2-bathroom home is just a short walk to Siesta Key Village and minutes from Siesta Key Beach, voted the # 1 beach in the USA! This home is ideal for families and couples looking for their perfect tropical getaway.The Palms Cottage can accommodate up to ...

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Property Type

Siesta Key House

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Latitude Adjustment

4 BR | 4 BA | Sleeps 10 | Quick View

$294

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Latitude Adjustment! This breathtaking 4 bedroom, 4 bathroom home is perfectly situated between America's #1 beach in the world and Siesta Key's famous North Village! You will not be able to ask for more as you drive up to this tropical oasis, covered with vibrant hot pink bougainvillea flower ...

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Property Type

Siesta Key House

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The Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

2

$514

per night

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Key Amenities

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

About this property

This luxurious 8 bedroom/six bathroom home is a unique combination of two units: “Casa Stolida” and “Casa Tegula” (4000 sq. ft. total). Each unit features a 4 bedroom/3 bathroom configuration, each with their own cabana room, separate living areas, private elevators and your very ...

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Property Type

Siesta Key House

"Beautiful Home"
Reviewed June 19, 2019

The Nautilus was a fantastic home on Siesta Key. Short walk to the beach and we had our own pool. House was well appointed and very comfortable and clean. We will be back and definitely recommend renting ...

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Caribbean Sol – 6900

5 BR | 5 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta Key Beach

$523

per night

View Details

Key Amenities

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

About this property

Welcome to Caribbean Sol, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 5-bedroom/5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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Property Type

Siesta Key House

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Siesta Key Gulf View Palm Bay Club in the Tower

$179

per night

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Key Amenities

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

About this property

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

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Property Type

Siesta Key Condo

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SIESTA KEY DIRECT GULF FRONT CLEAN/NEAT WKLY RENTALS SECURE WEB

$243

per night

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Key Amenities

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

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Property Type

Siesta Key Condo

"Great beachfront"
Reviewed February 4, 2019

Terrific location on Crescent Beach - just as beautiful as Siesta Beach but less busy. Comfortable and clean condo in secure building and complex. Even when evenings were cool or too windy, we enjoyed gorgeous ...

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Beach Haven 5858

2 BR | 2 BA | Sleeps 4 | Quick View

$116

per night

View Details

Key Amenities

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

About this property

Siesta Key Beach only 20 steps out the back sliding door. Come feel the powdery white sand that never gets hot from the sun!! This 2 bedroom 2 full bathroom villa is on the great Siesta Key Beach, come enjoy this 2 bedroom 2 bathroom with a walk-in shower and a carport for your vehicle. Sit out on ...

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Property Type

Siesta Key Villa

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Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

$287

per night

View Details

Key Amenities

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

About this property

Explore Playa y Blanca, a charming 4BR/2BA beach bungalow located steps from Crescent Beach. This home is the perfect beach escape for small families and couples alike!Welcome to Playa y Blanca! This uniquely configured 4BR/2BA villa is a combination of two units: “Casita Blanca” and “Casita ...

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Property Type

Siesta Key House

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Monarch Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

Welcome to Monarch Villa, a beautiful 3 bedroom, 3 bathroom townhome just steps from the beach. Along with its sister property Peacock Villa, reserve Casa de Mariposa for the ultimate corporate retreat, family reunion or destination wedding setting! Welcome to Monarch Villa! The luxurious three (3) bedroom, ...

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Property Type

Siesta Key House

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Sophie’s Cottage

2 BR | 2 BA | Sleeps 8 | Quick View

$330

per night

View Details

Key Amenities

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

About this property

Welcome to one of Siesta Key’s most charming canal-front cottage, with private heated pool and boat dock! Sophie's Cottage is located close to shops/restaurants and is just a 5 minute walk to world famous Siesta Key Beach!This Picturesque 2 bedroom/2 bathroom water-front cottage features a ...

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Property Type

Siesta Key House

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Honeysuckle

3 BR | 3 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

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

About this property

Welcome to Honeysuckle, one of Siesta Key's most inviting homes with heated pool! This home is a unique combination of two units: Lantana and Mimosa. This home is ideal for families and small groups.This inviting 3 bedroom/3 bathroom home is located right in the heart of Siesta Key Village and just ...

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Property Type

Siesta Key House

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Sea Grape Cottage

5 BR | 3.5 BA | Sleeps 12 | Quick View

2

$271

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Sea Grape Cottage! The luxurious tri-level Siesta Key home features gourmet kitchen, heated pool with a sloped beach entry, hot tub, covered lanai with outdoor kitchen & 2-car garage. Perfect for a dream beach vacation for up to 12! Built in June 2017, this tri-level home completely captures ...

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Property Type

Siesta Key House

"Family vacation"
Reviewed July 14, 2018

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

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Seahorse Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$142

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to the Seahorse Cabana!The Seahorse Cabana is one half of the uniquely configured private homes called the Sandy Seahorse Cottage and it is the perfect escape in the tropics of Siesta Key. This property can be rented separately or combined to accommodate a large party! This side of the gorgeous ...

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Property Type

Siesta Key House

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Villa De Paradisio

4 BR | 2 BA | Sleeps 12 | Quick View

$385

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to the beautiful Villa De Paradisio! This gorgeous waterfront cottage is a very luxurious and large four [4] bedroom canal front heated pool home with two bathrooms in approximately 1,800SF of air conditioned living space with a heated pool overlooking the dock and canal. This home has been completely ...

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Property Type

Siesta Key House

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The Lily Patch Bungalow - MONTHLY RENTAL

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.4 miles to Beach access 10 of Siesta Beach

$80

per night

View Details

Key Amenities

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

About this property

Situated in the quiet and secluded neighborhood of Palm Island, the Lily Patch is a cozy pecky cypress bungalow with two bedrooms and two bathrooms. Hardwood floors throughout add to its charm. Double sets of double French doors lead from the living and dining rooms onto the large private Mexican tiled ...

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Property Type

Siesta Key Bungalow

"The Lily Pad...a piece of paradise to cherish"
Reviewed February 26, 2019

The location offers you incredible privacy and easy access to the Siesta Key village and Sarasota proper.This is a great family-friendly bungalow that allows you to bring the family dog with added room ...

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Casa Mahalo

4 BR | 3 BA | Sleeps 12 | Quick View

$288

per night

View Details

Key Amenities

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

About this property

Welcome to Casa Mahalo! Our newly constructed luxury cottage (completion date of June 2017) has all the amenities your large group [up to 12!!!] can fathom. The location is THE premier location in the heart of Siesta Key Village, just behind Gilligan's and Lelu's Coffee Shop! Inside you’ll enjoy ...

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Property Type

Siesta Key House

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Tropical Gardens on Secluded Harbor

$200

per night

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Key Amenities

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

About this property

About the PropertyWelcome to TROPICAL GARDENS ON SECLUDED HARBOR, one of Siesta Key's truly secluded and very special locations! Located just five minutes from Siesta Key Beach, voted the # 1 beach in the USA! Siesta Key Village with its excellent restaurants and many eclectic bars, shops and cafes ...

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Property Type

Siesta Key House

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"Village Resort" 322 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

2
Owner special: Fall discount 20% off any one week booking until Dec 21! Please contact us for special rates.

$151

per night

View Details

Key Amenities

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

About this property

PLEASE CONTACT US FOR FLORIDA RENTALS SPECIAL DISCOUNT RATES!322 Canal Rd - Village Resort Just steps to #1 voted beach, restaurants, grocery’s, shops, bars & ice cream! (upstairs) - 2 bed/ 2 bath-dishwasher, heated pool, great back yard for BBQ and gatherings. Combine all four units ...

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Property Type

Siesta Key Condo

"Great location for a relaxing stay!"
Reviewed June 6, 2019

Rental was very clean and well stocked with towels, kitchen items, and even beach towels and folding beach chairs. Location is great for a relaxing and walking to the beach and village. Enjoy seeing ...

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Sand Dollar Cottage

3 BR | 2 BA | Sleeps 8 | Quick View

$385

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sand Dollar Cottage! This lovely 3 bedroom, 2 bath north Siesta Key vacaiton home comfortably sleeps 6 in beds, with a soft ultra plush sofa sleeper in the living room for an extra 2. Enjoy heated pool and waterview of Intracoastal canal. Welcome to the completely remodeled, and newly furnished ...

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Property Type

Siesta Key House

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Tropical Escape 2 Br/2 B Siesta Key Inn #226

$265

per night

View Details

Key Amenities

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

About this property

Welcome to our Beach Get-away...where we invite you to relax, unwind and enjoy our casual Siesta Key way of life. Resting just yards from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our Tropical Siesta Key Inn. With no busy streets to cross, it's a leisurely stroll ...

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Property Type

Siesta Key Condo

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Casita Blanca

2 BR | 1 BA | Sleeps 4 | Quick View

$143

per night

View Details

Key Amenities

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

About this property

Explore Casita Blanca, a cozy 2BR/1BA bungalow located minutes from prestigious Crescent Beach. This home is the perfect beach retreat for small families and couples alike!This inviting beach bungalow is just a short walk to prestigious Crescent Beach and close to world famous Siesta Key Beach, continually ...

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Property Type

Siesta Key House

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Vinca – 5251D

1 BR | 1 BA | Sleeps 2 | Quick View

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

$71

per night

View Details

Key Amenities

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

About this property

Welcome to Vinca, a charming 1BR/1BA home with heated pool located in the heart of Siesta Key Village and just steps from world famous Siesta Key Beach! This home is perfect for small families and groups.This adorable 1 bedroom/1 bathroom home is a unique combination of 4 units that can be rented ...

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Property Type

Siesta Key Cottage

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Sea Esta – 5319 (L)

3 BR | 2 BA | Sleeps 8 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to Sea Esta! This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? The Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea Esta offers a shared heated pool with ...

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Property Type

Siesta Key House

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West Shore

4 BR | 4 BA | Sleeps 8 | Quick View

$550

per night

View Details

Key Amenities

  • Pool
  • Private Pool

About this property

Welcome to West Shore! A massive gulf front penthouse located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 8, it is the only way to experience Siesta Key!West Shore is a luxuriously appointed penthouse in an extremely private ...

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Property Type

Siesta Key Condo

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Peacock Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Peacock Villa, a beautiful 3 bedroom, 3 bathroom townhome just steps from the beach. Along with its sister property Monarch Villa, reserve Casa de Mariposa for the ultimate corporate retreat, family reunion or destination wedding setting!The luxurious three (3) bedroom, three (3) bathroom ...

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Property Type

Siesta Key House

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The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$330

per night

View Details

Key Amenities

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

About this property

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

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Property Type

Siesta Key House

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Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Welcome to Honey Mango Cabana, one of Siesta Key’s most tropical beach bungalows with heated pool. When combined with its sister property Juicy Mango Cabana, both units make up Mango Manor.This tropical 2 bedroom/1 bathroom cottage is just a five minute walk to Crescent Beach and a short drive ...

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Property Type

Siesta Key House

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Casita Bayou

2 BR | 1 BA | Sleeps 6 | Quick View

$142

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool

About this property

Welcome to Casita Bayou!Casita Bayou is the larger half of this uniquely configured private home called the Coconut Bayou Cottage and it is the perfect escape for you and your guests. This side of the gorgeous home has recently been updated with new furnishings and completely renovated on the interior. ...

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Property Type

Siesta Key House

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

$508

per night

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Key Amenities

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

About this property

December 2017 renovation expands fantastic views of beach, gulf and sunsets New windows, doors, bathrooms, floors, paint and landscaping 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 ...

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Property Type

Siesta Key House

"Doesn't get much better!"
Reviewed May 25, 2019

This amazing duplex is absolutely perfect for a family getaway! From the cute quiet brick street leading to the house, to the towels embroidered w/colorful fish, you won't be disappointed in the details ...

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Couples and Family Friendly. Some pet friendly units are available too.

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 20 yards to Siesta Key Beach

$171

per night

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Key Amenities

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

About this property

We are full turnkey condos. Our laundry facilities, gas grills around the pool, in unit cleaning supplies and dishwasher detergent are complementary. We are easily within walking distance to the Main Siesta Key beach (100 ft & across beach road to access #10) and the "Village"(most of the ...

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Property Type

Siesta Key Condo

"Awesome Rental"
Reviewed May 27, 2019

We stayed at Sea Spray rentals for a week April 2019. This is the nicest, cleanest rental we have ever stayed at and management was very accommodating.

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Siesta Key Beachfront Condo with Gulf View!

$135

per night

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Key Amenities

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

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Property Type

Siesta Key Condo

"Beautiful view of a world-class beach!"
Reviewed November 16, 2018

The tidy condo was well located on the 4th floor allowing for a magnificent view of the beach from the lanai. Great place to take our coffee in the morning before our morning walk; or a glass of wine in ...

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Ground Floor 550sqft 1BR Condo Siesta Key Crescent Beach + WiFi No Road to Cross

1 BR | 1 BA | Sleeps 4 | Quick View

3
Owner special: Last Minute Openings (Some with Discounts): Oct 27 - Nov 6; Nov 17 - Dec 25; Jan 1-19; Apr 11-19....

Distance to beach: 250 yards to Siesta Key Crescent Beach

$86

per night

View Details

Key Amenities

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

About this property

… Aug 2019 … New Paint and New Furnishings ... Last Minute Opening (Some with Discounts): Oct 27 - Nov 6; Nov 17 - Dec 25; Jan 1-19... ... Dr. Beach names Siesta Beach Best Beach in US - just Google 'dr beach names siesta beach best beach in us' and find out why. We have a new 360 ...

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Property Type

Siesta Key Condo

"Siesta Key Holiday"
Reviewed October 11, 2019

The location was perfect with a short walk straight on to the beach.I have to mention the beach equipment which is supplied free of charge by Beach House is a novel idea as well as being a great saver. ...

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The Hummingbird

6 BR | 6 BA | Sleeps 12 | Quick View

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

$286

per night

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Key Amenities

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

About this property

Welcome to The Hummingbird, a delightful 6BR/6BA home with private heated pool! Located just steps from world famous Siesta Key Beach and Siesta Key Village This home is perfect for families and small groups.This private six bedroom/six bathroom home is a unique combination of four units: Lantana, ...

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Property Type

Siesta Key House

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The Hidden Gem – 5290L

2 BR | 1 BA | Sleeps 6 | Quick View

Distance to beach: 0.3 miles to Siesta Key Beach (Access # 2)

$143

per night

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Key Amenities

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

About this property

Welcome to The Hidden Gem, one of Siesta Key’s newest and coziest 2BR/1BA beach bungalows with heated pool and located in the heart of Siesta Key Village!This charming 2BR/1BA cottage is located in the heart of Siesta Key Village and is just minutes from world famous Siesta Key Beach, continually ...

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Property Type

Siesta Key Cottage

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Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$294

per night

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Key Amenities

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

About this property

Welcome to Seaside Cottage, one of Siesta Key's most dazzling 4BR/3BA homes, with private heated pool. Steps from world famous Siesta Key beach and just minutes so Siesta Key Village!! This remarkable 4 bedroom/3 bathroom home features a private heated pool. With its location less than a mile from Siesta ...

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Property Type

Siesta Key Cottage

"Wonderful"
Reviewed May 3, 2018

Great place, very comfortable beds, all the items you need - kitchen equipped with great tools. Very clean.

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Turtles Watch – 6925

4 BR | 4 BA | Sleeps 12 | Quick View

Distance to beach: 1 miles to Siesta key Beach

$468

per night

View Details

Key Amenities

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

About this property

Welcome to Turtles Watch, one of Siesta Key's premier luxury townhomes with private heated pool and spa! Located just five minutes from Siesta Key Beach and Village!This massive and decadent 4-bedroom/4.5-bathroom townhome is located near Siesta Key Village and just five minutes from Siesta Key Beach, ...

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Property Type

Siesta Key House

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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°

Siesta Key condo rentals in gulf coast Florida's top barrier island

Siesta Key is a barrier island in the Gulf of Mexico, off the coast of Sarasota, Florida. It’s known for its sandy beaches and friendly locals. Fine white sand and gentle gulf breezes keep visitors coming back year after year. An ideal escape for a couple looking for romance, or a family looking to escape the Disney or Panama City crowds.

Siesta Key has amazing beach front with available rentals for you. When staying in one of our Siesta Key vacation rentals instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Use the filters to narrow down your choices and choose the rental that calls to you.

Climate

Prevalent sunshine and gentle coastal breezes should be expected daily. Sounds incredible, right? Well, it is. With well over 300 sunny days per year, you’d be hard pressed to visit Siesta Key at a “bad time”. Low humidity makes the area comfortable, as well as warm. Bring your sunblock to protect against UV rays and don’t forget a few pairs of swim trunks, as the warm gulf waters are perfect for boogie boarding and bodysurfing.

Getting around

From November to September the Siesta Key Trolley will take you from the southernmost part of the island to the north end. The 3 open air trolleys run 7 days a week from 8-Midnight between Turtle Beach to Siesta Village. They will pass by about every 20-30 minutes. So don’t worry too much about getting around this small barrier island. Plus, bike or scooter rentals are everywhere -- so you can exercise while you move from beach to beach.

For those who drive, two bridges link the island to the mainland. The north bridge, Siesta Drive, is within the City of Sarasota and provides convenient access to the city, its business and arts districts, and to the Sarasota/Bradenton International Airport via US Highway 41. The south bridge, Stickney Point Road, provides access to south Sarasota County and a direct route to Interstate 75.

Top activities and attractions

Let’s be serious: you’re visiting Siesta Key for the pristine beaches along the 35 miles of coastline. Here are the names to remember: Siesta Beach, Turtle Beach, and Crescent Beach. Each features soft quartz sand and warm gulf seas. The sand is cool on your feet, so you can take an extended walk by the ocean without fear.

Siesta Beach has relatively shallow waters and it is monitored by lifeguards year-round. Plus, there’s plenty of room to spread out and enjoy a long, relaxing day. Turtle Beach is the most active (think volleyball net and horseshoe pits) while Crescent Beach is known for its seclusion and relaxed atmosphere.

Just off the southern tip of Crescent Beach is Point of Rocks, one of the best places for snorkeling and underwater exploration along the Gulf Coast beaches. It is made up of large chunks of limestone covered with coral and sponges and a range of sea life inhabit these underwater formations.

Bring your clubs here, too. With over 100 golf courses in the area you’ll want to take advantage of the sunny days out on the links. There’s ample opportunity for water sports for those who shun dry land. Visitors can find companies offering kayaking, paddle boarding, deep sea fishing and much more.

Just north of Siesta Beach, Siesta Key Village has many stores ranging from hip and funky to high-end boutiques and, of course, we wouldn't be a beach town without the beach accessory and souvenir shops.

Events 

If you love carefully constructed creations, visit in May for the sand castle competition. Local sand artisans and amateurs try their hand at creating jaw-dropping scenery out of sand.

Every Sunday there’s the Drum Circle featuring a cacophony of sound from various instruments performed by locals and tourists. Enjoy a stroll through the galleries of Palm Avenue on the first Friday of every month. In addition to fine galleries, this area along lower Main Street is known for its unique variety of shops and restaurants.

In April, the aptly named Siesta Fiesta takes place. Stroll along the beach while enjoying fine art and handmade crafts from 200 of the nation’s most talented artists and crafters. Showcasing an extensive collection of work ranging from life-size sculptures, spectacular paintings, one-of-a-kind jewels, photography, ceramics and more, this show truly has something for anyone. Complete with an additional green market, this spectacular show also features plants, body products, and tasty dips.

Siesta Key house rentals on FloridaRentals.com

Booking a condo for rent in Siesta Key on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!