Holiday rentals with a kayak in Sarasota

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

Large and Beautiful, Steps from Bay, Ringling!!

Tropical Paradise by the Bay – Walk to Ringling Museum, Asolo Theatre! Nestled between two university campuses and just a 5-minute walk to Sarasota Bay, this 2,200 sq ft tropical retreat beacons you to unwind. Enjoy 3 very private bedrooms, an office area, spacious living room, and a huge fenced-in backyard perfect for kids and pets—all less than 15 minutes from Lido Beach and café-lined St. Armands Circle. Kayaks, hammock, grill, foosball, sandbox, basketball hoop, and more await your stay!

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.

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.

Rita Retreat - Beautiful 2/2 with private pool

Welcome to your dream vacation home! This charming rental offers a private pool and a lush green area for relaxation and fun. Situated just 4.6 miles away from the stunning Siesta Key beach, you'll have easy access to sun-kissed sands and sparkling waters. Seafood lovers will be delighted to find the renowned Phillippi Creek Oyster Bar nearby, offering some of the best seafood in town. Embrace the Florida lifestyle and make cherished memories in this wonderful retreat!

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.​

Stunning Home, Heated Pool and Boat Dock

Be among the initial guests to relish in the splendor of this charming 3-bed, 2-bath abode overlooking Phillippi Creek, with a rejuvenating pool and fresh, deluxe furnishings. It offers all you need for an unforgettable escape, featuring a well-equipped open kitchen, 2 fun large Roku smart TVs in the living spaces, and a 50" Roku Smart TV in the master bedroom. Essential bathroom amenities are provided for your comfort.

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.