Siesta Key Vacation Rentals

(204 rentals)
Casa De Mariposa

Casa De Mariposa

6 BR | 6 BA | Sleeps 16 | Quick View

$396

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Beachfront
  • Communal Pool
  • Free WiFi

About this property

Welcome to Casa de Mariposa! This gorgeous property is comprised of two units, Monarch and Peacock Villa which are both mirror images of one another. Each unite features a 3 bedroom, 3 bathroom configuration with their very own common space to include ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Honey Mango Cabana

Honey Mango Cabana

2 BR | 1 BA | Sleeps 6 | Quick View

$136

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen

About this property

Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Honey Mango Cabana can be reserved alone or along with Juicy Mango Cabana for big families or groups. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Latitude Adjustment

Latitude Adjustment

4 BR | 4 BA | Sleeps 10 | Quick View

$286

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

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, ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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"Everglades" 378 Canal Rd.

"Everglades" 378 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager

About this property

2 Bd/2 Bath, King Bed, Two queen beds, Open Deck, ground floor. Pool Access, WIFI, *W&D access, and ground floor.Local free shuttles so no need for a car.Located on the Voted number “#1 Beach in America” popular Siesta Key in Sarasota, ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Sophie’s Quartier

Sophie’s Quartier

6 BR | 5 BA | Sleeps 16 | Quick View

$586

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Free WiFi

About this property

Welcome to Sophie’s Quartier, a waterfront compound consisting of two homes right near Siesta Key Beach! This is a perfect retreat for huge family and friends’ get togethers! Enjoy a heated pool, one hot tub, two docks overlooking The Grand ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Renovated 2 Bdrm/2 BA, Ground Floor with W/D, WIFI

Renovated 2 Bdrm/2 BA, Ground Floor with W/D, WIFI

2 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 0.2 miles to World Renowned Siesta Key Beach/Crescent Beach

$121

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Managed by Property Manager

About this property

Siesta Key 611 rents Saturday to Saturday, for a one week MINIMUM. It sleeps 4 people maximum. For available dates, please scroll down to the calendar or contact me.Siesta Key 611 is a renovated 2-bedroom condo with 2 FULL bathrooms on the beautiful ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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The Nautilus

The Nautilus

8 BR | 6 BA | Sleeps 24 | Quick View

$102

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Siesta Key home perfect for groups up to 24! The Nautilus, a combo of the Casa Tegula and Casa Stolida homes, is walking distance to the beach. Each cottage has 4 bedrooms, 3 bathrooms, their own heated pool and private cabanas. Welcome to The Nautilus! ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Isla Amor – Stunning 5 BR/3BA Heated Pool Home on The Grand Canal

$232

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool

About this property

Welcome to Isla Amor. An absolute one of kind, limited edition home located in the "heart of the Siesta Key" on the prestigous Palm Island (the island within the island). Featuring a private heated pool, near America's #1 Beach, on the Grand ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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SANDPIPER

SANDPIPER

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$115

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed

About this property

VOTED #1 BEACH IN AMERICA! JUST MINUTES TO YOUR DOOR WAY. THREE POOLS, SHUFFLE BOARD COURT, GRILLS, PRIVATE BEACH AREA, LAUNDRY FACILITIES, PATIO FOR COOKING AND EATING OUT DOORS. SHORT WALK TO SOUTH VILLAGE WITH RESTURANT'S, GROCERY STORE, NIGHT CLUBS, ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Coconut Grove – 6BR/6BA Private Heated Pool in the heart of Siesta Village

$396

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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MAGNOLIA 317-319

MAGNOLIA 317-319

4 BR | 4 BA | Sleeps 12 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

Distance to beach: 0.3 miles to SIESTA KEY BEACH

$151

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager

About this property

PRICE PER INDIVIDUAL UNIT. DUPLEX: 1 UPSTAIRS UNIT AND 1 DOWNSTAIRS UNIT. SHORT WALK TO VILLAGE, OR BEACH. PRIVATE HEATED POOL, TIKI HUT, GRILL, EACH UNIT HAS OWN WASHER AND DRYER IN UNIT, FULL KITCHENS, WALK TO GROCERY STORE, GIFT SHOPS, RESTURANT'S, ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Apartment

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Casa Costero

Casa Costero

3 BR | 3 BA | Sleeps 9 | Quick View

$206

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Free WiFi

About this property

Casa Costero - luxury 3-level townhouse features an open floor-plan with 3 bedrooms and 3.5 baths, plus a private elevator! Just 1 block from the beach & the north Village, the vacation home also has a gourmet kitchen and covered lanai. Welcome to ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Sea Esta – 5319 (L)

Sea Esta – 5319 (L)

3 BR | 2 BA | Sleeps 8 | Quick View

$206

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Villa Vista Mare

Villa Vista Mare

3 BR | 3 BA | Sleeps 10 | Quick View

1

$326

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Beachfront
  • Oceanfront
  • Communal Pool
  • No Pets Allowed
  • Free WiFi

About this property

Welcome to Villa Vista Mare! This beautiful and luxurious 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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Town Home

"Best ever..."
Reviewed May 27, 2018

This was the first time we have ever rent without see the property or at least know the owner. I was very nervous about the whole situation, as you can imagine. We were in Siesta Key for our daughters ...

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Closest Condo to the Gulf of Mexico on Siesta Key - Direct Oceanfront

Closest Condo to the Gulf of Mexico on Siesta Key - Direct Oceanfront

2 BR | 2 BA | Sleeps 6 | Quick View

10

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

$164

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Beachfront
  • Oceanfront
  • Communal Pool
  • Kid Friendly

About this property

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

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

"A relaxing "Siesta""
Reviewed October 31, 2018

We found this condo while doing a search for somewhere quiet and relaxing; away from the hustle bustle of the commercialized areas. We were not disappointed. The unit was a mirror image of the photos ...

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The Sun Dial

The Sun Dial

4 BR | 4 BA | Sleeps 12 | Quick View

$550

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool

About this property

Welcome to The Sun Dial! An absolute one of kind, limited edition home located in a beautifully secluded private neighborhood only minutes from Siesta Key's main beach access. Featuring a private heated pool, near America's #1 Beach, on the canal with ...

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Location Information

Siesta Key, Florida, USA

Property Type

Apartment

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Tranquil Townhouse Next to Pool and Siesta Key Beach

$206

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Non-Smoking
  • No Pets Allowed
  • Managed by Owner
  • Managed by Property Manager

About this property

Directly across the street from the world famous white sands -Siesta Key Public Beach!

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Sea Wave Casita

Sea Wave Casita

2 BR | 2 BA | Sleeps 6 | Quick View

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

The Sea Wave Casita of Villa Brisa Marina is one of two beautiful casitas, uniquely configured, featuring two bedrooms, 2 full bathrooms, a gourmet kitchen and a heated pool. One of 2 homes (along with Sea Shell Casita) that are Villa Brisa Marina.The ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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The Canopy Cottage

The Canopy Cottage

4 BR | 3 BA | Sleeps 9 | Quick View

$214

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen

About this property

Welcome to The Canopy Cottage! Nestled deeply into a beautiful neighborhood canopied by Florida's oldest trees, this lovely 4/3 home that sleeps 9 features a heated pool/spa under a screened in lanai just a few minutes from America's #1 Beach! Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Cottage

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"Village Resort" 320 Canal Rd.

"Village Resort" 320 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

(downstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Villa De Paradisio

Villa De Paradisio

4 BR | 2 BA | Sleeps 12 | Quick View

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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

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

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT ! PLEASE CONTACT US FOR RATES.

$103

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager
  • Free WiFi

About this property

1 Bedroom, King Bed & Queen Sleeper, Ground level, Screen Porch. Pool Access, WIFI *W&D access, and ground floor. Across from Canal

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Location Information

Siesta Key, Florida, 34242

Property Type

Apartment

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The Solaster

The Solaster

6 BR | 6 BA | Sleeps 20 | Quick View

$396

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

The Solaster is a combination of two units (Casita Morning Star and Casita Sun Star) within walking distance of Point of Rocks Beach. Each unit has 3 bedrooms, 3 bathrooms, their own heated pool & a private screened in lanai. Ideal for large groups! Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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A special SECRET retreat...#26

A special SECRET retreat...#26

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 100 yards to Crescent Beach

$128

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed 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 Air Dream sofa sleeper for separate sleeping ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Casita Playa

Casita Playa

2 BR | 1 BA | Sleeps 4 | Quick View

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

Welcome to Casita Playa of Playa y Blanca. This single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimming ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Seaside Cottage

Seaside Cottage

4 BR | 3 BA | Sleeps 10 | Quick View

1

$286

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Welcome to Seaside Cottage! A 4 bedroom, 3 bathroom vacation home with a heated pool is across the street from the No. 1 beach in the world! Hop on the trolley or a bike for easy access to Siesta Village. Enjoy the best of island living! Welcome to Seaside ...

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Location Information

Siesta Key, Florida, 34242

Property Type

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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Seahorse Cabana

Seahorse Cabana

3 BR | 3 BA | Sleeps 8 | Quick View

$186

per night

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Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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The Seagull – 2/2 Condo with Heated Shared Pool in Heart of Siesta Key Village

$176

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Free WiFi

About this property

Welcome to The Seagull, a 2BD/2BA private condo perfectly located only 1/2 mile from Siesta Beach and located in the heart of Siesta Key Village. This spaciously designed open floorplan comfortably sleeps 8! JUST WAIT TO SEE IT! NEWLY UPDATED FURNITURE ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

"Siesta Key"
Reviewed October 23, 2018

Super place and had easy access to the Village.....would go back for sure!

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"Fiji" 378 Canal Rd.

"Fiji" 378 Canal Rd.

1 BR | 1 BA | Sleeps 4 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT ! PLEASE CONTACT US FOR RATES.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Private Pool
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed
  • Managed by Property Manager

About this property

1 Bedroom King Bed, queen sleeper, screened porch. Pool Access, WIFI *W&D access, and ground floor.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Peacock Villa

Peacock Villa

3 BR | 3 BA | Sleeps 9 | Quick View

$206

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Communal Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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"Village Resort" 318 Canal Rd.

"Village Resort" 318 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

About this property

(upstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Playa y Blanca

Playa y Blanca

4 BR | 2 BA | Sleeps 10 | Quick View

$266

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

Welcome to Playa y Blanca! A combo of Casita Blanca & Casita Playa, the 4 bed/2 bath home sleeps up to 8, or you can book the 2 units separately. Surrounded by lush gardens with a private spa & beach access, there's also a shared heated pool. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Siesta Dream House

Siesta Dream House

4 BR | 3.5 BA | Sleeps 12 | Quick View

$286

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Kid Friendly
  • Non-Smoking
  • Free WiFi

About this property

Welcome to the Siesta Dream House!Hidden within Siesta Key lies a luxurious villa in all of it's splendor. Just after you cross the North Bridge from the mainland in the coveted northern part of the Island, among some of Siesta’s wealthiest ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Sea Grape Cottage

Sea Grape Cottage

5 BR | 3.5 BA | Sleeps 12 | Quick View

2

$286

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

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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Siesta Key Beachfront Condo with Gulf View!

$135

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Beachfront
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • No Pets Allowed

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

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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The Seascape – 8BR/9BA Beachfront, Heated Shared Pool, Private Access to Beach

$1100

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Communal Pool
  • Free WiFi

About this property

Welcome to The Seascape! The Seascape is the combination of two massive gulf front penthouses located right on Siesta Beach in a newly constructed building. With amazing views, a heated pool, and enough room to sleep up to 16, it is the only way to experience ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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La Contento Casa

La Contento Casa

3 BR | 2 BA | Sleeps 8 | Quick View

$179

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

About this property

Welcome to the completely remodeled, and newly furnished La Contento Casa! This lovely 3 bedroom, 2 bath home comfortably sleeps 6 in beds, with ultra deluxe rollaway beds for an extra 2. Enjoy the peacefulness of a large heated pool with beautiful and ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Casa Stolida

Casa Stolida

4 BR | 3 BA | Sleeps 8 | Quick View

$326

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Welcome to Casa Stolida! Our newest south Siesta Key luxury cottage has all the amenities your large group - up to 12. Enjoy a private heated pool & nearby beach access. When reserved with Casa Tegula to become The Nautilus, you can sleep up to 24. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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The Palms Cottage

The Palms Cottage

4 BR | 2 BA | Sleeps 10 | Quick View

$232

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Welcome to The Palms Cottages! A gorgeous 4 bed/2 bath Siesta Key vacation home with heated pool, spa, covered lanai and views of the canal. Tropical landscape with large trees, mangroves & sea grapes. Walking distance to beach and Siesta Village! Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Siesta Key Beachfront 3 Bedroom Private Home

Siesta Key Beachfront 3 Bedroom Private Home

3 BR | 3 BA | Sleeps 7 | Quick View

1

Distance to beach: 300 feet to Siesta Beach

$395

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen

About this property

This home has private Siesta Key beach frontage on the prime section of beach, there are no streets to cross or homes between you and the beach. Nearly every room has a full view of the beach and Gulf of Mexico. The entire back of this house opens with ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

"Most amazing house and location!"
Reviewed May 14, 2018

We took our family here for vacation! We had a 1 year old granddaughter also. The house was meticulous and the most modern upscale appliances and amenities! The porches with views of beach-Beach supplies! ...

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The Pearl by the Sea

The Pearl by the Sea

4 BR | 3 BA | Sleeps 12 | Quick View

$232

per night

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Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Welcome to The Pearl by the Sea. An absolute one of kind, limited edition home located on prestigous Siesta Key featuring a private heated pool and spa, near America's #1 Beach, on the Grand Canal with intracoastal bay access and a boat dock. You have ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Casa Tegula

Casa Tegula

4 BR | 3 BA | Sleeps 12 | Quick View

$326

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Free WiFi

About this property

Welcome to Casa Tegula! Our newest south Siesta Key luxury cottage has all the amenities your large group - up to 12. Enjoy a private heated pool & nearby beach access. When reserved with Casa Stolida to become The Nautilus, you can sleep up to 24. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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West Shore - 4BR/4.5BA Beach Front Condo, Heated Pool, With Private Beach Access

$550

per night

View Details

Key Amenities

  • Private Pool
  • Communal Pool
  • Free WiFi

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Mango Manor

Mango Manor

4 BR | 3 BA | Sleeps 12 | Quick View

$266

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Free WiFi

About this property

Welcome to the Mango Manor! A beautiful and vibrant 4 bedroom, 3 bathroom vacation home with a heated pool accommodates up to 12 people. The attractive property, a combination of Honey Mango Cabana & Juicy Mango Cabana, is perfect for large families. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Siesta Key Condo 1/1 with 2 Queen Beds, Walk to Beach!

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking
  • Managed by Owner

About this property

Charming Siesta Key Condo fully furnished and ready for your visit. Bring your bathing suit and flip flops. We’ve got beach chairs and beach towels for you. Two queen beds in spacious bedroom and the living room sofa easily converts to an adult ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa

5 BR | 4 BA | Sleeps 13 | Quick View

Distance to beach: 400 feet to Siesta Beach

$395

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Pet Friendly
  • Kid Friendly

About this property

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

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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"Village Resort" 316 Canal Rd.

"Village Resort" 316 Canal Rd.

2 BR | 2 BA | Sleeps 6 | Quick View

Owner special: FALL SPECIAL 20% DISCOUNT! PLEASE CONTACT US FOR RATES.

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Kid Friendly
  • Non-Smoking
  • Managed by Property Manager

About this property

(downstairs) - 2 bed/ 2 bath- 1 king, 1 queen, queen sleeper, private laundry room, full kitchen including DW, heated pool, great back yard for BBQ and gathering.

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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

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

1 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 20 yards to Siesta Key Beach

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Private Pool
  • Pet Friendly
  • Communal Pool
  • Kid Friendly
  • Non-Smoking

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 ...

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Location Information

Siesta Key, Florida, 34242

Property Type

Condo

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Juicy Mango Cabana

Juicy Mango Cabana

2 BR | 2 BA | Sleeps 6 | Quick View

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Linens Provided
  • Full Kitchen
  • Pet Friendly
  • Communal Pool
  • Free WiFi

About this property

Welcome to the Juicy Mango Cabana! This beautiful and vibrant 2 bedroom, 2 bathroom vacation home accommodates up to 6 people. Part of Mango Manor, Juicy Mango Cabana can be reserved alone or along with Honey Mango Cabana for big families or groups. Welcome ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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The Grand Canal Cottage

The Grand Canal Cottage

5 BR | 4 BA | Sleeps 12 | Quick View

$500

per night

View Details

Key Amenities

  • Air Conditioning
  • Hot Tub
  • Linens Provided
  • Full Kitchen
  • Waterfront
  • Private Pool
  • Free WiFi

About this property

The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal-front private luxury home featuring a heated pool with sun shelf and a separate 8-person spa. It is situated on Siesta Key on the beach ...

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Location Information

Siesta Key, Florida, 34242

Property Type

House

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Siesta Key Vacation Rentals

Local 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°
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JUNE
Ocean 8228°
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JULY
Ocean 8530°
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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!