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Sarasota Area >
Siesta Key >
Holiday homes

Vacation Rentals Siesta Key, Vacation Rentals

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456 Canal Rd

456 Canal Road, Hotel in Siesta Key, United States

Crescent Royale Condominiums 1C

777 Beach Road Unit 1C, Hotel in Siesta Key, United States

Lulu'S Key House Kemp Ridley 1/1 Downstairs

5247 Calle Menorca, Hotel in Siesta Key, United States

279 US$

min. price/night

6415 Midnight Pass #Ph8

6415 Midnight Pass Road, Hotel in Siesta Key, United States

209 US$

min. price/night

Excelsior 401

6265 Midnight Pass Road, Hotel in Siesta Key, United States

Central - Edgemere 738

738 Edgemere Lane, Hotel in Siesta Key, United States

433 US$

min. price/night

Casa De Siesta

312/314 Canal Road, Hotel in Siesta Key, United States

51 Beach Rd

51 Beach Road, Hotel in Siesta Key, United States

Anchorage Resort 7Th Floor 2-Bedroom Condo W Private Balcony Beach Access 0893

6415 Midnight Pass Road #709, Hotel in Siesta Key, United States

Siesta Sea Life

5319 Calle De La Siesta, Hotel in Siesta Key, United States

1542 US$

min. price/night

Island Time East

355 Calle Miramar, Us, Hotel in Siesta Key, United States

627 US$

min. price/night

Shaker Of Salt

6525 Sabal Dr., Hotel in Siesta Key, United States

Bikini Tini Time

5577 Contento Drive, Hotel in Siesta Key, United States

Sundown Sanctuary

4408 Midnight Pass Rd, Hotel in Siesta Key, United States

Casa Tegula - 1028U

1028 Point Of Rocks Road, Hotel in Siesta Key, United States

1514 US$

min. price/night

Crescent Royale Condominiums 307

797 Beach Rod, Unit 307, Hotel in Siesta Key, United States

Vantage Point

655 Beach Road, Hotel in Siesta Key, United States

6415 Midnight Pass #210

6415 Midnight Pass Road, Hotel in Siesta Key, United States

Penthouse Paradise

1308 Old Stickney Point Rd #Wp1, Hotel in Siesta Key, United States

Summer House

99 Avenida Messina, Us, Hotel in Siesta Key, United States

1826 US$

min. price/night

Siesta Key Condo Close Proximity To Beach

Midnight Pass Road 5855, Hotel in Siesta Key, United States

362 US$

min. price/night

Crescent Royale Condominiums 312

757 Beach Road, Unit 312, Hotel in Siesta Key, United States

Crescent Royale 1E

777 Beach Road, Unit1E, Hotel in Siesta Key, United States

Sunset Lagoon Estate

1140 Windsong Lane, Hotel in Siesta Key, United States

Siesta Key - Pet Friendly - Private Pool - Garage - Aylees Private Beach House

5346 Calle Florida, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

1398 US$

min. price/night

Anc903 Anchorage Resort

6415 Midnight Pass Road, Hotel in Siesta Key, United States

Villa 56 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

225 US$

min. price/night

Crescent Royale Condominiums 205

797 Beach Road, Unit 205, Hotel in Siesta Key, United States

Crescent 204

6512 Midnight Pass Road, Hotel in Siesta Key, United States

Crescent Royale Condominiums 6C

777 Beach Road Unit 6C, Hotel in Siesta Key, United States

Siesta Bayside With Bay And Dock Views

1355 Siesta Bayside Dr, Hotel in Siesta Key, United States

420 US$

min. price/night

Honeysuckle - L

5251 Calle Menorca, Hotel in Siesta Key, United States

1171 US$

min. price/night

Tarpon Villa

340 Canal Rd, Us, Hotel in Siesta Key, United States

Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1 Mile And Crescent Beach 2 Miles, 1Bdr

8212 Midnight Pass Rd, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

Luxury Top-Floor Retreat - Siesta Key

1144 Windsong Ln, Hotel in Siesta Key, United States

Charming Siesta Key Condo With Beach Access

1346 Siesta Bayside Drive, Hotel in Siesta Key, United States

Anc605

6415 Midnight Pass Road, Hotel in Siesta Key, United States

Salty Oak

6540 Peacock Rd., Hotel in Siesta Key, United States

3298 US$

min. price/night

Siesta Key Village Heated Pool

5245 Calle Menorca, Hotel in Siesta Key, United States

1851 US$

min. price/night

611 Venice Lane

611 Venice Lane, Hotel in Siesta Key, United States

Sea Spray

538 Canal Rd, Us, Hotel in Siesta Key, United States

1599 US$

min. price/night

Harbor Towers, 4Th Floor, Modern With Den

5855 Midnight Pass Road #203, Hotel in Siesta Key, United States

252 US$

min. price/night

Keylime Retreat

446 Canal Rd #5, Hotel in Siesta Key, United States

The Windward House

5022 Windward Avenue, Hotel in Siesta Key, United States

The Rooftop

329 Beach Road, Unit A, Hotel in Siesta Key, United States

2329 US$

min. price/night

Siesta Key, Heated Pool, Dock On Lagoon, Turtle Beach 1 Mile And Crescent Beach 2 Miles, 1Bdr

8212 Midnight Pass Rd, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

Golden Set

1142 Windsong Lane, Unit B, Hotel in Siesta Key, United States

3074 US$

min. price/night

Casa De Mariposa

5542/5540 Calle Del Invierno, Hotel in Siesta Key, United States

Villa 48 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Villa 52N - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

590 US$

min. price/night

Crescent Royale Condominiums 201

797 Beach Rd, Unit 201, Hotel in Siesta Key, United States

Excelsior Beach To Bay-Bayside

6263 Midnight Pass Rd, Hotel in Siesta Key, United States

297 US$

min. price/night

Siesta Beach House - 310 Come N' Beach It

5950 Midnight Pass Road, Hotel in Siesta Key, United States

Blu Sky Cottage - 5037

5037 Higel Ave, Hotel in Siesta Key, United States

White Sands Walk To Siesta Beach

Siesta Key, United States

137 US$

min. price/night

Bay Oaks E-12

6157 Midnight Pass Road, Hotel in Siesta Key, United States

Crescent Royale Condominiums 412

757 Beach Road, Unit 412, Hotel in Siesta Key, United States

Harbor Towers 220

5855 Midnight Pass Road, Hotel in Siesta Key, United States

Beachside Escape With Grill, Dining & Views - Perfect For Two! - Aloha Kai #24N

6020 Midnight Pass Road Unit 24N, Hotel in Siesta Key, United States

Villa 36 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Bay View Siesta Key Condo With Private Beach Access

1343 Siesta Bayside Drive, Hotel in Siesta Key, United States

Crescent Royale Condominiums 509

797 Beach Road, Unit 509, Hotel in Siesta Key, United States

Siesta Springs

1142 Windsong Lane, Unit A, Hotel in Siesta Key, United States

2022 US$

min. price/night

Crescent Royale Condominiums 6D

777 Beach Road, Unit 6D, Hotel in Siesta Key, United States

White Sands Near The Beach

5661 Midnight Pass Rd, Hotel in Siesta Key, United States

209 US$

min. price/night

Crescent Royale Condominiums 411

797 Beach Road, Unit 411, Hotel in Siesta Key, United States

New Updated Siesta Key Vacation Rental With Heated Pool Access

6157 Midnight Pass Road, Hotel in Siesta Key, United States

166 US$

min. price/night

Crescent Royale Condominiums 115

797 Beach Road, Unit 115, Hotel in Siesta Key, United States

Charming Beachside Retreat - Aloha Kai #18 - Roelens

6020 Midnight Pass Rd. Unit 18, Hotel in Siesta Key, United States

100 Percent Private - Pool, Oceanviews, Village, Beaches!

113 Columbus Blvd, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

3923 US$

min. price/night

The Oasis

105 Columbus Blvd., Hotel in Siesta Key, United States

2013 US$

min. price/night

Villa 9 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Minorga On The Gulf

5144 Calle Minorga, Hotel in Siesta Key, United States

324 US$

min. price/night

2Nd Floor Bayfront Siesta Key Condo With Private Beach Access

1373 Siesta Bayside Drive, Hotel in Siesta Key, United States

Villa 12 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Moonmist Circle-Steps To Heated Pool

1223 Moonmist Cir, Hotel in Siesta Key, United States

192 US$

min. price/night

Off The Hook - B

328 Calle Miramar - B, Hotel in Siesta Key, United States

Siesta Sands 411

1001 Point Of Rocks Road, Hotel in Siesta Key, United States

Relaxing Siesta Key Condo - Pickleball, 2 Heated Pools, Beach Access

1344 Siesta Bayside Drive, Hotel in Siesta Key, United States

Villa 31 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Crescent Royale Condominiums 408

757 Beach Road, Unit 408, Hotel in Siesta Key, United States

Over The Top

1060 Windsong Lane, Hotel in Siesta Key, United States

Gulf And Bay - Bayside 1223D

Siesta Key, United States

Beachside Haven - 650C

650 Calle Del Ontono #C, Hotel in Siesta Key, United States

754 US$

min. price/night

Entire Siesta Key Beach House - 6 Bedroom Pool & Ocean Access

1144 Windsong Ln, Hotel in Siesta Key, United States

2853 US$

min. price/night

Beach Dream

657 Beach Road, Hotel in Siesta Key, United States

2140 US$

min. price/night

Peaceful Siesta Key Condo - Short Stroll To #1 Beach

1219 Siesta Bayside Drive, Hotel in Siesta Key, United States

Hidden Treasure - 622

622 Treasure Boat Way, Hotel in Siesta Key, United States

Siesta Avenida

5208 Avenida De Cortez, Hotel in Siesta Key, United States

Crescent Royale Condominiums 311

797 Beach Road, Unit 311, Hotel in Siesta Key, United States

Happy Blue Coconuts - North

650 Beach Road, Hotel in Siesta Key, United States

Happy Blue Coconuts

650 Beach Road, Hotel in Siesta Key, United States

Siesta Key Bungalows, The 3-Bungalow Complex

8212 Midnight Pass Rd, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

Bay Oaks E-43

6157 Midnight Pass Road, Hotel in Siesta Key, United States

Coastal Condo, Water Views, Fishing Dock & 0.6 Miles To Siesta Beach

6157 Midnight Pass Rd, Hotel in Siesta Key, United States

Siesta Sunset Sanctuary

156 Givens St, Hotel in Siesta Key, United States

Palm Shade Cottage - 606A

606 Calle Del Otono, Hotel in Siesta Key, United States

Serious Leisure

144 Avenida Veneccia #B, Hotel in Siesta Key, United States

1806 US$

min. price/night

Dockside Getaway On Avenida

615 Avenida Del Norte, Hotel in Siesta Key, United States

Anchorage Resort 3 Bedroom 3Rd Floor Condo With Balcony 0886

6415 Midnight Pass Road #311, Hotel in Siesta Key, United States

Watch Dolphins From Your Lanai In This Bayfront Siesta Key Condo

1365 Siesta Bayside Drive, Hotel in Siesta Key, United States

Harbor Towers- 514

5855 Midnight Pass Rd, Unit 514, Hotel in Siesta Key, United States

Crescent Royale Condominiums108

757 Beach Road, Unit 108, Hotel in Siesta Key, United States

House Of The Sun

5216 Calle De Costa Rica, Hotel in Siesta Key, United States

Crescent Royale Condominiums 505

797 Beach Road, Unit 505, Hotel in Siesta Key, United States

Crescent Royale Condominiums 409

797 Beach Road, Unit 409, Hotel in Siesta Key, United States

Crescent Royale Condominiums 102

757 Beach Road, Unit 102, Hotel in Siesta Key, United States

Carefree Coconut

116 Vista Hermosa Cir #210C, Hotel in Siesta Key, United States

Crescent 502

6512 Midnight Pass Road, Hotel in Siesta Key, United States

Bayside Endless Summer - 1239C

1239 Siesta Bayside Dr #1239-C, Hotel in Siesta Key, United States

Canal 315 - Right In Siesta Key Village!

315 Canal Road, Hotel in Siesta Key, United States

237 US$

min. price/night

Luxe Lagoon - 119

119 Avenida Messina, Hotel in Siesta Key, United States

3121 US$

min. price/night

Bahama Mama

5227 Calle Menorca, Us, Hotel in Siesta Key, United States

1893 US$

min. price/night

Gulf Birdie - 5551

5551 Contento Drive, Hotel in Siesta Key, United States

858 US$

min. price/night

Family-Friendly Beach Escape With Pool, Porch & Sun-Filled Fun - Aloha Kai #24

6020 Midnight Pass Road Unit 24, Hotel in Siesta Key, United States

Blue Paradise

5234 Avenida Navarra, Us, Hotel in Siesta Key, United States

2574 US$

min. price/night

Coastal Charm

313 Avenida Leona, Hotel in Siesta Key, United States

Crescent Royale Condominiums 111

797 Beach Road, Unit 111, Hotel in Siesta Key, United States

Crescent Royale Condominiums 204

757 Beach Road, Unit 204, Hotel in Siesta Key, United States

5125 Oakmont Place

5125 Oakmont Place, Hotel in Siesta Key, United States

Crescent Royale Condominiums 208

757 Beach Road, Unit 208, Hotel in Siesta Key, United States

Crescent Royale Condominiums 3C

777 Beach Road Unit 3C, Hotel in Siesta Key, United States

100 Percent Private, Tiki-Bar, 250Steps To Beach And Village!

360 Canal Road , Siesta Key, Florida 34242, United States, Hotel in Siesta Key, United States

4621 US$

min. price/night

Island House

344 Canal Rd, Us, Hotel in Siesta Key, United States

1056 US$

min. price/night

2Nd Floor Lakeview Condo In Siesta Key With Private Beach Access

1275 Siesta Bayside Drive, Hotel in Siesta Key, United States

Sk Canal Pool Home Near Village

627 Avenida Del Norte, Hotel in Siesta Key, United States

Villa 61 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Anchorage Resort Siesta Key 6Th Floor 2 Bedroom Condo Beach Access 0890

6415 Midnight Pass Road, Hotel in Siesta Key, United States

Harbor Towers- 417

5855 Midnight Pass Rd, Unit 417, Hotel in Siesta Key, United States

Siesta Key Luxury Retreat - Steps From Crescent Beach

1001 Crescent St, Siesta Key, Fl, Hotel in Siesta Key, United States

Harbor Towers End Unit, 4Th Fl Pool & Bay Views

5855 Midnight Pass Rd, Hotel in Siesta Key, United States

165 US$

min. price/night

Crescent Royale Condominiums 1B

777 Beach Road Unit 1B, Hotel in Siesta Key, United States

Aloft On Canal

542 Canal Rd, Us, Hotel in Siesta Key, United States

2028 US$

min. price/night

Crescent Royale Condominiums 300

757 Beach Road, Unit 300, Hotel in Siesta Key, United States

Anchorage Resort 3Rd Floor 2 Bedroom Condo South West Balconies 0885

6415 Midnight Pass Road #304, Hotel in Siesta Key, United States

Midnight Cove II - Doveplum

6327 Midnight Pass Road, Hotel in Siesta Key, United States

Unleash Island Bliss - Aloha Kai #34 & #37 - Roelens

6020 Midnight Pass Road Unit 34 & 37, Hotel in Siesta Key, United States

Palm Island Life - Heated Pool, Canal Front, Fire Pit, Walk To Siesta Beach

208 Island Circle, Hotel in Siesta Key, United States

The Big Dipper

3810 Flamingo Ave, Hotel in Siesta Key, United States

Holiday House 4

1015 Crescent Street, Hotel in Siesta Key, United States

Crystal Sands 1101

6300 Midnight Pass Road, Hotel in Siesta Key, United States

Siesta Beach House - 202

5950 Midnight Pass Road, Hotel in Siesta Key, United States

1106 US$

min. price/night

Anchorage Resort 2 Bedroom Condo 2Nd Floor Community Pool 0883

6415 Midnight Pass Road, Hotel in Siesta Key, United States

Peaceful Lakefront Condo On Siesta Key - Private Beach Access, 2 Pools, Tennis And Pickleball Courts

1230 Siesta Bayside Drive, Hotel in Siesta Key, United States

Beachfront Bliss For 4 With Sunroom & Pool Access On Siesta Key - Aloha Kai #34

6020 Midnight Pass Road Unit 34, Hotel in Siesta Key, United States

Bay Oaks C-12

6157 Midnight Pass Road, Hotel in Siesta Key, United States

Bali Hai House - 5041

5041 Sandy Shore Avenue, Hotel in Siesta Key, United States

6415 Midnight Pass #506

6415 Midnight Pass Road, Hotel in Siesta Key, United States

Bay Oaks E-93

6157 Midnight Pass Rd, Unit E-93, Hotel in Siesta Key, United States

Crescent Royale Condominiums 7A

777 Beach Road Unit 7A, Hotel in Siesta Key, United States

Stunning Lakefront Condo On Siesta Key With Private Beach Access

1315 Siesta Bayside Drive, Hotel in Siesta Key, United States

45 Beach Rd

45Beach Road, Hotel in Siesta Key, United States

Sunset West - 3360

3360 Higel Ave, Hotel in Siesta Key, United States

Casa Leone - 3446

3446 W Anglin Drive, Hotel in Siesta Key, United States

484 US$

min. price/night

Crescent Royale Condominiums 4A

777 Beach Road Unit 4A, Hotel in Siesta Key, United States

Bayfront 3Br 2Nd Floor Siesta Key Condo With Private Beach Access

1389 Siesta Bayside Drive, Hotel in Siesta Key, United States

Silver Shore - 657B

657B Beach Road, Hotel in Siesta Key, United States

693 US$

min. price/night

Coastal Comfort Steps From Crescent Beach Paradise - Aloha Kai #63 - Roelens

6020 Midnight Pass Road Unit 63, Hotel in Siesta Key, United States

Beachside Bliss Awaits - Aloha Kai #55- Roelens

6020 Midnight Pass Rd. Unit 55, Hotel in Siesta Key, United States

Harbor Towers 3Rd Fl 2 Bedroom

5855 Midnight Pass Rd, Hotel in Siesta Key, United States

Villa De Paradisio - 347

347 Avenida De Paradisio, Hotel in Siesta Key, United States

4931 Oxford Drive

4931 Oxford Drive, Hotel in Siesta Key, United States

Gulf Holiday Unit 7

73 Avenida Messina, #7, Hotel in Siesta Key, United States

Village Breeze - Heated Pool, Private Patio, Village And Beach!

5140 Calle Minorga, Hotel in Siesta Key, United States

6415 Midnight Pass #304

6415 Midnight Pass Road, Hotel in Siesta Key, United States

180 US$

min. price/night

Crystal Sands 1106

6300 Midnight Pass Road, Hotel in Siesta Key, United States

Villa 40 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Sand Dollar Cottage - 910

910 Contento St, Hotel in Siesta Key, United States

The Sun Dial - 827

827 Paradise Way, Hotel in Siesta Key, United States

1101 US$

min. price/night

Anchorage Resort 3 Bedroom Luxury Condo W Balcony Pool Table Near Beach 0891

6415 Midnight Pass Road #611, Hotel in Siesta Key, United States

Siesta Heron 5 Key Lime

8254 Midnight Pass Road, Hotel in Siesta Key, United States

Casa De Mayo

601 Avenida De Mayo, Hotel in Siesta Key, United States

Villa 59 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Paradise Palms

710 Birdsong Lane, Hotel in Siesta Key, United States

Villa 39 - Aloha Kai Vacation Villas

6020 Midnight Pass Rd, Hotel in Siesta Key, United States

Wild Lime Cottage

1105 Point Of Rocks Rd, Hotel in Siesta Key, United States

309 US$

min. price/night

Sea Club II 5955 #8E

5955 Midnight Pass Road, Hotel in Siesta Key, United States

382 US$

min. price/night

Bayfront Siesta Key Condo With Amazing Views

1391 Siesta Bayside Drive, Hotel in Siesta Key, United States

Bay Oaks - E53

6157 Midnight Pass Road, Hotel in Siesta Key, United States

Peppertree Penthouse #803

1125 W Peppertree Dr #803, Hotel in Siesta Key, United States

Crescent Royale Condominiums 309

797 Beach Rd Unit 309, Hotel in Siesta Key, United States

Sea Coast - Pet Friendly, Located In Siesta Key Village, Steps To Siesta Key Beach!

104 Avenida Veneccia, Hotel in Siesta Key, United States

On The Rocks

309 Calle Miramar, Us, Hotel in Siesta Key, United States

Peppertree Paradise #507

1055 W Peppertree Dr #507Aa, Hotel in Siesta Key, United States

Crescent 206

6512 Midnight Pass Road, Hotel in Siesta Key, United States

Crescent Royale Condominiums 404

757 Beach Road, Unit 404, Hotel in Siesta Key, United States

285 US$

min. price/night

Crescent Royale Condominiums 501

797 Beach Road, Unit 501, Hotel in Siesta Key, United States

Beautiful 3Br Siesta Key Condo - Private Beach Access

1350 Siesta Bayside Drive, Hotel in Siesta Key, United States

Crescent Royale Condominiums 7C

777 Beach Road, Unit 7C, Hotel in Siesta Key, United States

Two Units! Pool, Jacuzzi, Sunsets, Bars, Snorkeling & Paddling. 1-Min To Path Of Siesta Beach!

1020 Sun And Sea Dr #206B, Hotel in Siesta Key, United States

1870 US$

min. price/night

Crescent Royale Condominiums 7E

777 Beach Road, Unit 7E, Hotel in Siesta Key, United States

655 US$

min. price/night

Crescent Royale Condominiums 105

797 Beach Rd Unit 105, Hotel in Siesta Key, United States

The Pool House

98 Avenida Messina, Us, Hotel in Siesta Key, United States

1327 US$

min. price/night

Waters Edge - 5049

5049 Higel Avenue, Hotel in Siesta Key, United States

Gulf And Bay Club- C607

5770 Midnight Pass Rd, Unit C607, Hotel in Siesta Key, United States

Coastal Elegance Pool Home In Sarasota

430 Island Circle, Hotel in Siesta Key, United States

Luxury, Exclusive Building, Ocean Views, And Private Rooftop Sundeck

228 Beach Rd, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

Sandbar Social

64 Avenida Veneccia, Hotel in Siesta Key, United States

2890 US$

min. price/night

High Tide

141 Avenida Veneccia, Us, Hotel in Siesta Key, United States

2221 US$

min. price/night

Gulf And Bay Club- B408

5780 Midnight Pass, Hotel in Siesta Key, United States

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