Holiday rentals with a kayak near Siesta Beach

Charming Florida Cottage - Kayaks Included

Welcome to the Spanish Point Cottage! Our Old Florida style cottage is conveniently located within steps of some of Sarasota's most historic sites making it the ideal place to experience true Florida. Enjoy exploring Historic Spanish Point, kayaking to a secluded beach, walking to Historic Bay Preserve, watching the sunset over the Bay, fishing at Osprey Fishing Pier, walking to dinner all from your well appointed and peaceful oasis. There is no better place to experience true Florida living!

WOW-King Bed w/86° Pool, Turf Golf green, Beaches

Location! Have fun with the whole family at this stylish home. Just minutes to Anna Maria Island beaches. This incredible newly built home sets the highest standards of luxury living. It’s the ideal retreat with its expansive views of the outdoors from the moment you enter. Open concept with large French doors throughout the home creates the perfect indoor-outdoor lifestyle. Spend the day lounging by the heated pool with a cold drink in your hand. Fun turf yard area with games and putting green

Lagoon, pool, the Pineapple, Siesta Key Bungalows

The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. Featuring a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a queen-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.

@Shellmateisland |tiny home| island| bikes| kayaks

⭑Octagonal 320ft² tiny home sitting on a private 1.5-acre island!⭑ ✯ Lake access ✯ Walk to dining, nightlife, and shopping ✯ Fully equipped + stocked kitchen ✯ Free bikes + kayaks +beach gear ✯ Backyard fire pit + BBQ ✯ Screened-in outdoor lounge w/ hammocks ✯ Smart TV w/ Netflix ✯ Memory foam bed ✯ 426Mbps wifi Ask which fruit trees are in season for a homegrown treat! 3 min → Siesta Key Beach 7 min → Downtown SRQ 12 min → Myakka River State Park (river kayaking + wildlife viewing)

Quick and Easy Walk Downtown - Tons of Amenities

Are you coming to Sarasota on vacation or perhaps considering moving here? If yes, then the Carriage House is the perfect place to use as a base camp while you explore the area and experience the best Sarasota has to offer. Quick and easy walk to dozens of casual restaurants, cool bars and unique shops. 5 minutes to Selby Gardens. 10 minutes to the Sarasota Bayfront. Main street is half a mile away. We provide tons of amenities including bikes, kayaks, beach chairs and umbrella.

The Shore House Private Dock Hot Tub

This Three bedroom two bathroom property is located in a quiet neighborhood, just a short walk or bike ride to the heart of Siesta Key Village, a quaint beachfront neighborhood that offers plenty of restaurants, shops and entertainment. It’s also just a short walk from the beautiful white sand beaches of Siesta Key. The house has been thoughtfully designed and furnished to emphasize style, comfort, and convenience. The energy of this home is so soothing its truly a relaxing oasis.

Sea Gem | Waterfront w/ Pool, Dock + Paddle/Kayaks

BNB Breeze Presents: Sea Gem! This stunning waterfront haven in the heart of the Sunshine State is going to blow you away! Located just 30 minutes away from Siesta Key Beach, this beautiful and entertaining home includes: ✔ Private Dock on the Canal w/ String Lights! ✔ Heated Saltwater Pool ✔ Rooftop Deck w/ Picturesque Views! ✔ Kayaks + Paddle Boards ✔ Outdoor Kitchen! ✔ Dolphin Sightings From the Dock! ✔ An Outdoor Grill + Wine Cooler!

Waterfront Home by Ralph Twitchell

Beautiful midcentury waterfront home on Phillipi Creek close to all that Sarasota has to offer. 5 miles to America's number 1 beach Siesta Key, and only a few short blocks from stores, nightlife, & other beaches. This quaint ​​getaway includes a kayak to enjoy the pure bliss of the calm ​​​​​waters of ​​Phillipi Creek as well as a game room including a pool table, foosball table, and a fireplace to lounge around and chat.​

Avanti Villa | Siesta Beach Views, Walk to Beach!

Exclusive Amenities Include: • Short Walk to Siesta Key Village & Beach • Breathtaking Views of Siesta Beach • 3 Bedroom, 3 Full Bath • Rooftop Balcony • Two Balconies With Seating Areas • Private Garage • Free WiFi • Regular & Keurig Coffee Maker, Washer & Dryer, and Kitchen Essentials Provided • Beach Essentials Provided • Gas Grill • Enhanced cleaning protocols provided by our CottageClean Team • Island Shuttle Transp.