Vacation 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!

Heated saltwater pool home - turf putting green

Private 3 bedroom single family home 4 miles to white sand gulf beaches Longboat Key and Anna Maria Island. HEATED SALTWATER POOL home with access to ride bikes to the beach. Spread out in the oversized backyard with your own private pool and sitting area, featuring artificial turf yard and putting green, and beautiful landscaping. All hurricane damage has been repaired. The fence is fixed and the backyard is again completely private. The pergola pictured in photos was lost in the storm.

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.

Frangipani | Amazing Pool, Game Room, Hot Tub

Property Highlights • 5 Minute Walk to Beach (800ft) 5-10 Minutes to Village • Shared Heated Resort style Pool, Water Feature & Garden • 1 Bedroom, Bathroom, Living Room & Full Kitchen • 1 Queen Bed & Queen Sleeper Sofa (sleeps 4) • Outdoor Lounge Dinning Table for 8, Fire Table, Ice Maker, 2 Kayaks
 • Clubhouse 1 w Ping Pong, Pool, Foosball, Pac-Man, Games • Starter Kit of Toiletry & Home Essentials • Free Private Parking, Laundry & Beach Essentials (Towels, Chairs, Cart, 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.

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

Welcome to our Mid Century Modern waterfront getaway on the highly sought after Curry Creek. Perfectly situation between Nokomis Beach (2 miles) and Venice Beach (3 miles). Enjoy spending time fishing on the private dock or getting out on the water with our 4 kayaks and slip. We're located a half mile away from The Legacy Bike Trail (we have 6 bikes for guest use). large firepit, charcoal grill, cornhole, tons of supplies for shark teeth hunting and days spent at the beach

Vintage Coastal

Enjoy Siesta Key to is't fullest with this well appointed house. This house sits right on a canal with water access so you can enjoy kayaking and paddle boarding at your leisure. Also outside is and outdoor fire pit and a screened in pool that is heated so you can enjoy year round. Once you step inside this beautiful house you are greeted with a bright and airy beach theme that extending into the kitchen with white cabinets and marble countertops.

Bayfront Beauty: Heated Pool, King size Bed

Conveniently located near plenty of Sarasota's shopping and dining areas, your new home away from home is nice and isolated, surrounded by gorgeous views and just a quick walk from the waters of Sarasota Bay. You will have whole house except two rooms which will be locked and no one will be there. One bedroom with a king size bed. Full size kitchen, family room, pool and gorgeous view on the salty bay for nature lovers.

2/2 Beach House Apt on Siesta Key

Siesta Key Waterfront Apartment. Sleeps 6. Split plan 2 bedroom, 2 full bathroom “Beach House” w/ a full kitchen & recently updated! Bedroom 1: King. Bedroom 2: Queen. Living room: Sleeper sofa. 75” smart TV in the living room. A private screened lanai overlooking canal to Sarasota Bay. This is located in a super cute, quaint resort w/ other units. FREE KAYAKS & SUPs FOR GUESTS!