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Holiday Apartments in Siesta Key

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938 rentals in Siesta Key.
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Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!, holiday rental in Siesta Key

Gorgeous Direct Gulf/Beach Front 2 Bedroom Condo on Siesta Key, Amazing views!

2 bedrooms
2 bathrooms
Sleeps 6
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Siesta Key-#1 Beach,  2017 Renovation w/ private entrance,  Intracoastal/Marina, holiday rental in Siesta Key

Siesta Key-#1 Beach, 2017 Renovation w/ private entrance, Intracoastal/Marina

2 bedrooms
2 bathrooms
Sleeps 4
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CHATEAU du SOLEIL         10% DISCOUNT Dec 5-19, holiday rental in Siesta Key

CHATEAU du SOLEIL 10% DISCOUNT Dec 5-19

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale, holiday rental in Siesta Key

Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale

3 bedrooms
3 bathrooms
Sleeps 8
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WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY, holiday rental in Siesta Key

WHAT A VIEW !! 2 BED BAYSIDE CONDO ON SIESTA KEY

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Beachfront Getaway in Siesta Key, holiday rental in Siesta Key

Beachfront Getaway in Siesta Key

1 bedroom
1 bathroom
Sleeps 4
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Cathy's Crescent Condos-Siesta Key,  FL GULF FRONT, holiday rental in Siesta Key

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*, holiday rental in Siesta Key

Siesta Breakers #603 in Siesta Key, FL- Sun, Sand & *Save 10% to 25% per Week*

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key, holiday rental in Siesta Key

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Siesta Key Inn - 1Br/1B Sabal Palm #2A, holiday rental in Siesta Key

Siesta Key Inn - 1Br/1B Sabal Palm #2A

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Key Beach Cottages on Crescent, holiday rental in Siesta Key

Siesta Key Beach Cottages on Crescent

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY, holiday rental in Siesta Key

WE LIKE BLUE, SIESTA BLUE! 2 BED BAYSIDE CONDO ON SIESTA KEY

2 bedrooms
1 bathroom
Sleeps 4
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Siesta Villa Coralline, holiday rental in Siesta Key

Siesta Villa Coralline

2 bedrooms
1 bathroom
Sleeps 5
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Siesta Key Beachfront Condo with Gulf View!, holiday rental in Siesta Key

Siesta Key Beachfront Condo with Gulf View!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops, holiday rental in Siesta Key

New Listing! Charming Island Getaway - Steps to Sand, Walk to Dining & Shops

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Luxury Romantic Oceanfront Siesta Beach Condo #304, holiday rental in Siesta Key

Luxury Romantic Oceanfront Siesta Beach Condo #304

1 bedroom
1 bathroom
Sleeps 4
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Newly discounted rates! Gorgeous one bedroom across from beach, near village!, holiday rental in Siesta Key

Newly discounted rates! Gorgeous one bedroom across from beach, near village!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Siesta Key Inn 1Br/1B Pineapple Palm #2D, holiday rental in Siesta Key

Siesta Key Inn 1Br/1B Pineapple Palm #2D

1 bedroom
1 bathroom
Sleeps 4
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Island House Beach Resort 15N, holiday rental in Siesta Key

Island House Beach Resort 15N

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Island House Beach Resort V27, holiday rental in Siesta Key

Island House Beach Resort V27

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning 2 Bedroom/ 2 Bath by Siesta Key Beach, Sunlight Sensation!!, holiday rental in Siesta Key

Stunning 2 Bedroom/ 2 Bath by Siesta Key Beach, Sunlight Sensation!!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly Listed... NEW Decor by Jan 10th 2021!  Walk to SK Beach, 2 Heated Pools, W, holiday rental in Siesta Key

Newly Listed... NEW Decor by Jan 10th 2021! Walk to SK Beach, 2 Heated Pools, W

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Location. 3 bedroom cottage block from beach and two blocks from Siesta Village, holiday rental in Siesta Key

Location. 3 bedroom cottage block from beach and two blocks from Siesta Village

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Siesta Key Village  Unbeatable Location, holiday rental in Siesta Key

Charming Siesta Key Village Unbeatable Location

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach, holiday rental in Siesta Key

Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!, holiday rental in Siesta Key

Very Clean! 2 min. drive to Siesta Key! Stay a few nights or a month!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Island House Beach Resort 8N, holiday rental in Siesta Key

Island House Beach Resort 8N

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Bright & Beachy - Steps to the Water!, holiday rental in Siesta Key

Bright & Beachy - Steps to the Water!

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Peaceful Haven on Siesta Key with Beach Access, holiday rental in Siesta Key

Peaceful Haven on Siesta Key with Beach Access

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Siesta Beach Zen Den, holiday rental in Siesta Key

Siesta Beach Zen Den

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Siesta Beach House #211 Beautiful Updated Unit, holiday rental in Siesta Key

Siesta Beach House #211 Beautiful Updated Unit

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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2 BR, 2 Bath, Siesta Key Village Condo with Pool, holiday rental in Siesta Key

2 BR, 2 Bath, Siesta Key Village Condo with Pool

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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GULF FRONT ON #1 Beach! Siesta Dunes (by owner), holiday rental in Siesta Key

GULF FRONT ON #1 Beach! Siesta Dunes (by owner)

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach, holiday rental in Siesta Key

A Siesta Tropical Retreat - Island Pool Oasis -super close to Village & #1 beach

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Quiet and Comfortable Condo Near Turtle Beach, holiday rental in Siesta Key

Quiet and Comfortable Condo Near Turtle Beach

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Siesta Key Old Florida Cottage, Great Location at a Great Price, holiday rental in Siesta Key

Siesta Key Old Florida Cottage, Great Location at a Great Price

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Excelsior- 102 G-great Gulf side location!- 1 WEEK MIN RENTAL, holiday rental in Siesta Key

Excelsior- 102 G-great Gulf side location!- 1 WEEK MIN RENTAL

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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4 Bedroom with Gulf View Siesta Key FL Beach Fun, holiday rental in Siesta Key

4 Bedroom with Gulf View Siesta Key FL Beach Fun

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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SHARK UNIT-THE BEST SPOT ON SIESTA KEY BEACH & VILLAGE! !, holiday rental in Siesta Key

SHARK UNIT-THE BEST SPOT ON SIESTA KEY BEACH & VILLAGE! !

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Ground floor unit with quick access to Siesta Beach Amenities, holiday rental in Siesta Key

Ground floor unit with quick access to Siesta Beach Amenities

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!, holiday rental in Siesta Key

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN, UPDATED KITCHEN!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Crescent Beach on Siesta Key One of the, holiday rental in Siesta Key

Beautiful Crescent Beach on Siesta Key One of the

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Direct Gulf-Front / End Unit Fisherman's Cove A201, holiday rental in Siesta Key

Direct Gulf-Front / End Unit Fisherman's Cove A201

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sandy Toes Town Home, holiday rental in Siesta Key

Sandy Toes Town Home

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chinaberry 911 at Midnight Cove Siesta Key, FL., holiday rental in Siesta Key

Chinaberry 911 at Midnight Cove Siesta Key, FL.

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chinaberry 953 at Midnight Cove Siesta Key, FL., holiday rental in Siesta Key

Chinaberry 953 at Midnight Cove Siesta Key, FL.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Doveplum 624 at Midnight Cove Siesta Key, FL., holiday rental in Siesta Key

Doveplum 624 at Midnight Cove Siesta Key, FL.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Buttonwood 462 at Midnight Cove Siesta Key, FL., holiday rental in Siesta Key

Buttonwood 462 at Midnight Cove Siesta Key, FL.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun, holiday rental in Siesta Key

Perfect Local In Village,1 1/2 Block From #1 Beach In USA, Pool, Wifi, Sun & Fun

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Newly renovated condo with premium features on Siesta Key, holiday rental in Siesta Key

Newly renovated condo with premium features on Siesta Key

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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