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Southwest Florida >
Siesta Key >
Holiday homes

Vacation Rentals Siesta Key, Vacation Rentals

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Commonwealth On The Key

4947 Commonwealth Drive, Hotel in Siesta Key, United States

5120 Sandy Shore Ave

5120 Sandy Shore Avenue, Hotel in Siesta Key, United States

Sea Dream - 171

104 Avenida Veneccia, Hotel in Siesta Key, United States

1623 US$

min. price/night

Golden Set

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

3074 US$

min. price/night

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

104 Avenida Veneccia, Hotel in Siesta Key, United States

Siesta Key Beach Waterfront Home With Kayaks And Bikes

1038 Contento Street, 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

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

Coastal Elegance Pool Home In Sarasota

430 Island Circle, Hotel in Siesta Key, United States

Vista Hermosa - 302C

116 Vista Hermosa Circle, Hotel in Siesta Key, United States

540 US$

min. price/night

Happy Blue Coconuts - North

650 Beach Road, Hotel in Siesta Key, United States

Sundown Sanctuary

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

Serious Leisure

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

1806 US$

min. price/night

Bay Oaks - E01

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

Gulfside Green Estate

459 Beach Road, Hotel in Siesta Key, United States

Serene Bay Front Condo On Siesta Key - 2 Heated Pools, Pickleball And Tennis, Private Beach Access

1368 Siesta Bayside Drive, Hotel in Siesta Key, United States

Crescent Royale Condominiums 400

757 Beach Road, Unit 400, Hotel in Siesta Key, United States

The Big Dipper

3810 Flamingo Ave, Hotel in Siesta Key, United States

Sol Y Mar

1137 Sun N Sea Dr, Hotel in Siesta Key, United States

Beach Walk Cottage - 451

451 Island Cir, Hotel in Siesta Key, United States

Crescent Royale Condominiums 4D

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

6415 Midnight Pass #805

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

Villa De Paradisio - 347

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

Anchorage Resort 5Th Floor 2 Bedroom Condo With Beach Access 0888

6415 Midnight Pass Road #506, Hotel in Siesta Key, United States

Paradise Palms

710 Birdsong Lane, Hotel in Siesta Key, United States

Tidal Wave - In Siesta Key Village, Pet Friendly, Private Pool!

303/305 Canal Rd, Hotel in Siesta Key, United States

Vitamin Sea

306 Beach Road, Hotel in Siesta Key, United States

Crescent Royale Condominiums 307

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

Casa Playa

3508 La Paloma Ave, Hotel in Siesta Key, United States

Crescent Royale Condominiums 3C

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

611 Venice Lane

611 Venice Lane, Hotel in Siesta Key, United States

Crescent 206

6512 Midnight Pass Road, 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

Excelsior 401

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

Bay Oaks C Ground Floor

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

298 US$

min. price/night

Mainsail

1245 Big Oak Ln, Us, 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

Crescent Royale Condominiums 3E

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

Villa 38 - Aloha Kai Vacation Villas

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

Villa 2 - Aloha Kai Vacation Villas

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

The Oasis

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

2013 US$

min. price/night

Villa 54 - Aloha Kai Vacation Villas

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

Blue Paradise

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

2574 US$

min. price/night

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

Casa Blanca

5235 Siesta Cove Dr, 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

Bay Oaks G-22

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

Relaxing Siesta Key Condo With Private Beach Access

1374 Siesta Bayside Drive, Hotel in Siesta Key, United States

Siesta Bayside 2Nd Floor Townhome

1334 Siesta Bayside Dr, Hotel in Siesta Key, United States

352 US$

min. price/night

Gulf Birdie - 5551

5551 Contento Drive, Hotel in Siesta Key, United States

858 US$

min. price/night

Dry Dock

515 Canal Rd, Unit B, Us, Hotel in Siesta Key, United States

655 US$

min. price/night

Luxe Lagoon - 119

119 Avenida Messina, Hotel in Siesta Key, United States

3121 US$

min. price/night

New Listing! Spacious, 100 Percent Private, Near The Siesta Key Beach And Village!

5156 Siesta Woods Drive, Hotel in Siesta Key, United States

Crescent 505

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

Happy Blue Coconuts

650 Beach Road, Hotel in Siesta Key, United States

Edgemere

738 Edgemere Lane, Hotel in Siesta Key, United States

2Br Siesta Key Downtown Condo Walk Everywhere

5108 Calle Minorga, Hotel in Siesta Key, United States

112 Columbus Blvd

112 Columbus Boulevard, Hotel in Siesta Key, United States

Villa 22 - Aloha Kai Vacation Villas

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

Palm Shade Cottage - 606A

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

Copacabana

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

Casa Leone - 3446

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

484 US$

min. price/night

Villa 59 - Aloha Kai Vacation Villas

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

Midnight Cove II 731F

1300 Cove II Place, Unit 731F, Hotel in Siesta Key, United States

Crescent Royale Condominiums 403

797 Beach Road, Unit 403, Hotel in Siesta Key, United States

366 US$

min. price/night

Our House At The Beach W-Tower 5Th Fl

1001 Beach Rd, Hotel in Siesta Key, United States

Villa 61 - Aloha Kai Vacation Villas

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

Chasin' Waves

4923 Commonwealth Drive, Hotel in Siesta Key, United States

Cape Aqua Retreat

5640 Cape Leyte, Hotel in Siesta Key, United States

Crescent Royale Condominiums 6A

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

Siesta Sunset Sanctuary

156 Givens St, Hotel in Siesta Key, United States

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

Siesta Dreamin

5536 Contento Dr, Hotel in Siesta Key, United States

6415 Midnight Pass #608

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

Villa 53 - Aloha Kai Vacation Villas

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

Excelsior 302

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

Sea Club II 5955 #8E

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

382 US$

min. price/night

Beach Dream

657 Beach Road, Hotel in Siesta Key, United States

2140 US$

min. price/night

Peacock Villa - 5540 E

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

728 US$

min. price/night

Beachfront Sarasota Resort Condo: Siesta Key View!

Siesta Key, FL, 34242, Hotel in Siesta Key, United States

359 US$

min. price/night

Bay View Siesta Key Condo With Private Beach Access

1343 Siesta Bayside Drive, 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

Southern Exposure

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

1323 US$

min. price/night

Casita West

1139 Sun And Sea Dr, West Unit, Hotel in Siesta Key, United States

Midnight Cove II - 137

6327 Midnight Pass Rd, Bldg 1, Unit 137, Hotel in Siesta Key, United States

Crescent Royale Condominiums 115

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

Siesta Beach House - 204

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

Crescent Royale 405

797 Beach Road, Unit 405, Hotel in Siesta Key, United States

Crescent Royale Condominiums 208

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

Harbor Towers- 420

5855 Midnight Pass Rd, Unit 420, Hotel in Siesta Key, United States

Villa 32 - Aloha Kai Vacation Villas

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

Coastal Cottage

552 Beach Rd, Hotel in Siesta Key, United States

Charming 2Br Siesta Key Condo With Beach Access

1338 Siesta Bayside Drive, Hotel in Siesta Key, United States

Crescent Royale Condominiums 7E

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

655 US$

min. price/night

Siesta Bayside With Bay And Dock Views

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

420 US$

min. price/night

Gertrudes Siesta Village Properties - Short Walk To Best Beaches!

5233 Avenida Navarra, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

Siesta Beach House - 310 Come N' Beach It

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

Crescent Royale 1E

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

Crescent Royale Condominiums 106

757 Beach Road, Unit 106, Hotel in Siesta Key, United States

283 US$

min. price/night

Siesta Key Bungalows, The Poolside Complex, 3-Bungalows

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

6415 Midnight Pass #202

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

6415 Midnight Pass #409

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

245 US$

min. price/night

Beach Life! It Doesn

6020 Midnight Pass Road Unit 28, Hotel in Siesta Key, United States

Sugar Sand Cottage

105 Beach Rd, Us, Hotel in Siesta Key, United States

1555 US$

min. price/night

Beautiful 3Br Siesta Key Condo - Private Beach Access

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

Sunset West - 3360

3360 Higel Ave, Hotel in Siesta Key, United States

Gulf-Front Charm, Guest House Suite, Direct Beach Access On Siesta Key

6920 Point Of Rocks Rd, 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

Exclusive Complex - Private Heated Pool - 100 Steps To Beach - Village 5 Minute Walk

5316 Calle De La Siesta, Siesta Key, Fl 34242, Usa, 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

Crescent Royale Condominiums 3D

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

Anchorage Resort 2 Bedroom Condo 2Nd Floor Community Pool 0883

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

A Charming Beach Cottage By Beachside Management

5408 Plaza De Las Palmas, Hotel in Siesta Key, United States

House Of The Sun

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

Sandbar Social

64 Avenida Veneccia, Hotel in Siesta Key, United States

2890 US$

min. price/night

Anc903 Anchorage Resort

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

The Lookout

5507 Calle Invierno, Hotel in Siesta Key, United States

2899 US$

min. price/night

Luxe Siesta Key Home Pool Hot Tub Near Beach

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

High Tide - Pool, Grill, Pet Friendly, Located In The Heart Of Sk!

305 Canal Rd, Hotel in Siesta Key, United States

Crescent Royale Condominiums 5D

777 Beach Road, Unit 5D, Hotel in Siesta Key, United States

Bay Tree Club 103A

8630 Midnight Pass Rd. #103A, Hotel in Siesta Key, United States

Surf View

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

3034 US$

min. price/night

Honeysuckle - L

5251 Calle Menorca, Hotel in Siesta Key, United States

1171 US$

min. price/night

Luxury Beachfront Condo In Siesta Key

5780 Midnight Pass Road, Hotel in Siesta Key, United States

Anchorage Resort

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

Crescent Royale Condominiums 104

757 Beach Road, Unit 104, 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

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

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

104 Avenida Veneccia, Hotel in Siesta Key, United States

Crescent Royale Condominiums 4A

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

Unveiling Joyful Beachside Moments - Aloha Kai #62 - Roelens

6020 Midnight Pass Road Unit 62, Hotel in Siesta Key, United States

Anchorage Resort 2Nd Floor 2 Bedroom Condo Facing Intracoastal Waters 0884

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

Retreat Half-Mile To Beachandsiesta Key Village

605 Calle De Peru, Hotel in Siesta Key, United States

203 US$

min. price/night

Casa Tegula - 1028U

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

1514 US$

min. price/night

Blue Mermaid On Siesta Key

Siesta Key, United States

239 US$

min. price/night

Blu Sky Cottage - 5037

5037 Higel Ave, Hotel in Siesta Key, United States

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

104 Avenida Veneccia, Hotel in Siesta Key, United States

Del Norte Retreat

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

Siesta Sands 411

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

Crescent 204

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

Coral Breeze - 4576

4576 Higel Ave, Hotel in Siesta Key, United States

239 US$

min. price/night

Minorga On The Gulf

5144 Calle Minorga, Hotel in Siesta Key, United States

324 US$

min. price/night

Villa 52S - Aloha Kai Vacation Villas

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

Talk To The Sand

5219 Calle Menorca, Hotel in Siesta Key, United States

The Pool House

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

1327 US$

min. price/night

Double Your Beachside Fun - Aloha Kai #34 & #55 - Roelens

6020 Midnight Pass Road Unit 34 & 55, Hotel in Siesta Key, United States

Pelicans Place - 117

117 Beach Road, Hotel in Siesta Key, United States

996 US$

min. price/night

Blue Wave

5520 Avenida Del Mare, Hotel in Siesta Key, United States

Palm Bay Club #97

5960 Midnight Pass Road, Hotel in Siesta Key, United States

Siesta Key Village - Townhouse Fourplex - Private Heated Pool - Beach Walkable

5239 Calle Menorca, Siesta Key, Fl 34242, Usa, Hotel in Siesta Key, United States

Jamaica Royale 101

5830 Midnight Pass Road, Hotel in Siesta Key, United States

Crescent Royale Condominiums 6E

777 Beach Road, Unit 6E, 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

2Nd Floor Bayfront Siesta Key Condo With Private Beach Access

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

Harbor Towers-Ground Floor

Siesta Key, United States

194 US$

min. price/night

Sunset View

547 Beach Rd, Us, 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

Villa 31 - Aloha Kai Vacation Villas

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

Excelsior 309

6267 Midnight Pass Road, Hotel in Siesta Key, United States

Crescent Royale Condominiums 111

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

Seagull Studio - 117B

117 Beach Road, Hotel in Siesta Key, United States

908 US$

min. price/night

The Windward House

5022 Windward Avenue, Hotel in Siesta Key, United States

Golden Springs Estate

1142 Windsong Lane, Hotel in Siesta Key, United States

Crescent Royale Condominiums 6C

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

Luxury Top-Floor Retreat - Siesta Key

1144 Windsong Ln, Hotel in Siesta Key, United States

Central - Edgemere 738

738 Edgemere Lane, Hotel in Siesta Key, United States

433 US$

min. price/night

Happy Blue Coconuts - South

652 Beach Road, Hotel in Siesta Key, United States

Harbor Towers Ocean View Escape

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

Crescent Royale Condominiums 315

797 Beach Road Unit 315, Hotel in Siesta Key, United States

Bayside Pointe 3 - 1302

1302 Siesta Bayside Drive, Hotel in Siesta Key, United States

Casa De Mayo

601 Avenida De Mayo, 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

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

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

6415 Midnight Road #709

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

302 US$

min. price/night

Extraordinary Bay Views - Siesta Key

1385 Siesta Bayside Drive, Hotel in Siesta Key, United States

Villa 48 - Aloha Kai Vacation Villas

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

Bay Oaks E-92

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

Crescent Royale Condominiums 407

797 Beach Road, Unit 407, Hotel in Siesta Key, United States

Lulu'S Key House - Entire 4-Unit Complex

5247 Calle Menorca, Hotel in Siesta Key, United States

Bikini Tini Time

5577 Contento Drive, 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

Gulf And Bay - Bayside 1223D

Siesta Key, United States

Crescent Royale Condominiums 1C

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

Crescent Royale Condominiums 205

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

Crescent Royale Condominiums 303

797 Beach Road, Unit 303, Hotel in Siesta Key, United States

Cozy 2Br Siesta Key Condo - 2 Heated Pools, Tennis And Pickleball, Private Beach Access

1364 Siesta Bayside Drive, Hotel in Siesta Key, United States

Vantage Point

655 Beach Road, Hotel in Siesta Key, United States

Sandy Rocks

1104/1106/1034 Crescent St, Hotel in Siesta Key, United States

Siesta Key Coastal Getaway - Steps To The Beach

1144 Windsong Ln, Hotel in Siesta Key, United States

Siesta Key Waterfront Oasis - Heated Pool, Dock, Walk To Village & Beach

329 Avenida Leona, 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

The Rooftop

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

2329 US$

min. price/night

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

104 Avenida Veneccia, Hotel in Siesta Key, United States

The Hummingbird

5251 Calle Menorca, Hotel in Siesta Key, United States

1553 US$

min. price/night

Villa 63 - Aloha Kai Vacation Villas

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

The Mangrove House On Siesta Key

651 Mangrove Point Road, Hotel in Siesta Key, United States

Sunkissed Pool Home

5005 Commonwealth Dr, Hotel in Siesta Key, United States

368 US$

min. price/night

Siesta Springs

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

2022 US$

min. price/night

Crescent Royale Condominiums 501

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

Our House At The Lake House C113 By Beachside

1129 Lake House Circle, Hotel in Siesta Key, United States

413 US$

min. price/night

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