Holiday rentals with lake access in Siesta Key

Bayside Escape-Condo w/ Dock, Pool, and Near Beach

This 2 bedroom/ 2 bath condo is right on the waterfront in Siesta Key! It is the upper condo of a two story complex that has a perfect view and feels like your own personal getaway! It comes with a full kitchen, living room w/ a sofa-bed, and two decks. Part of what makes it amazing is the private dock on the Pass. Perfect for kayaking and exploring! Or maybe you'd like to just relax and take a dip in the heated pool? Located in the quiet end, you can enjoy the calm, or head to Siesta Village!

The Ibis Cottage

Freshly renovated, The Ibis Cottage is a cozy studio on a beautiful property overlooking a small lake. It is a 5 minute drive to Nokomis Beach, Siesta Beach and Venice Beach are within easy reach, and a block away to the Legacy Trail bike path (Sarasota to Venice). Enjoy seeing a variety of birds on the property including the ibis, heron, and snowy egret. The cottage is conveniently located between Sarasota and Venice. The perfect location for enjoying the Gulf coast and outstanding beaches.

NEW! Sea Haven~Heated Pool~Fishing from back yard!

Sea Haven AMI Retreat, a charming canal front home just a five-minute walk from Holmes Beach’s pristine beaches! This beautifully remodeled retreat (2025) offers three spacious bedrooms and three bathrooms, ideal for families or groups seeking relaxation, outdoor fun, & waterfront adventures. Ping Pong & Life size Connect 4! With your own private dock, fishing right from your backyard, & pet-friendly accommodations, Sea Haven is the perfect sanctuary for creating unforgettable island memories!

LUXE! Heated Salt POOL! Close to Town, Beach, IMG

Beautifully updated coastal farmhouse home in a quiet cul de sac with a private pool oasis in the back. The salt water pool is completely screened in so you can stay in the pool all day and night long without worrying about flies or mosquitos. Kitchen is fully stocked and ready for you to cook up a storm! Or if you prefer, downtown Sarasota is only a short 15 minute drive away with plenty of eating options. Siesta key beach is rated the number one beach in the USA and it’s only 30 minutes away!

Peaceful Braden River Oasis: Cottage

Come get away to this river retreat just outside of Lakewood Ranch. This property has three separate rental units on it including this charming single bedroom cottage with access to the river. It comes with everything you need to enjoy a wonderful vacation! The other units on this property are the Guest House, a larger studio unit 1 bed/1 bath sleeps 2 (Search Peaceful Braden River Oasis: Guest House) and the Main House, a 2 bed/2 bath sleeps 7 (search Peaceful Braden River Oasis: Main House).

Siesta Key home 5 min from beach

Only 1 booking allowed in a 30 day period. You will be close to everything when you stay at this centrally-located house. It's a 2 min drive to Siesta Key village restaurants and shops. A 5 min drive or 20 min walk to the #1 beach in US. Stocked with beach chairs, umbrellas, cooler, and floats The pool area has a bbq, bar, TV and dining set for 8. There is a high chair, pack and play, puzzles, books and toys. There is a trolly stop around the corner. You will certainly enjoy your stay here!

Near beach. Pool view. King bed. Daily rentals

The ‘pool view’ overlooks the swimming pool & has a private covered open porch for shade 1 bed 1 bath w/ private entrance. The bedroom has a king sized mattress bed. The living room has a kitchenette area with a fridge, freezer, microwave, coffee maker and the essentials. There is a Smart TV. Separate bedroom with King size bed 3 mins walk to Crescent beach access #12 You can walk to a great choice of places to eat and drink Max 2 guests No smoking, No Pets, Great Location, Good Value.

@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)

Heated Pool, Dock, Kayaks, 1-mile to Turtle Beach

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 king-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 queen sofa-bed allows accommodations for three guests.

STEPs to BEACH! /Heated Salt Pool/Sunsets/5 STAR!

Less than a 2 min WALK to the white sand beaches of the Gulf, this 4 BR home comfortably sleeps 8. Large bedrooms & a spacious floor plan (the kitchen, dining and living rooms flow together), the house is perfect for families. The bedrooms are split 2+2 & paired with bathrooms on opposite ends of the house (a pocket door adds privacy). Private heated saltwater pool sits amidst the tropical yard. Hop on the free trolley and explore Florida's gorgeous Anna Maria Island.

Minutes to Siesta Key, heated pool & tiki on water

Coral Harbor is conveniently located in Gulf Gate Estates, just 3 miles to the beach. The 1 acre property sleeps up to 12, with a private heated salt water pool, mature trees, lanai, sun deck, and bonus "Tiki" bar. You'll love the deck overlooking the lake to feed the turtles! The home has all the modern amenities you would expect from a vacation home. Minutes to Siesta Key, easy access to Venice Beach, Lido Beach, downtown Sarasota, AMI & more!

The Seashell Cottage with peaceful water views!

Hello and welcome to my beautiful Seashell Cottage! I have completely renovated and remodeled this townhome for you! It has a new kitchen and bathroom, new vinyl plank flooring upstairs, new furniture and bedding throughout, and is freshly painted. Decorated in a turquoise beachy decor, it gives you a sense of peace and tranquility the moment you step inside! There are gorgeous water views of the lake from both the first and second floor.