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Lil John Coastal Cottage near Siesta Key Beach

Book your Summer 2026 Sarasota getaway-30% off stays of 28+ nights. Welcome to Robinhood's, pet-friendly Lil John Coastal Cottage is a cozy private guesthouse, located on a quiet cul-de-sac street near #1 ranked Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy smart-lock self check-in, T-Mobile 5G Wi-Fi, coffee essentials, a comfortable bedroom, sleeper sofa, a screened in porch area, outdoor dining table & umbrella for 4, & shared outdoor spaces, a fire pit, in a fenced yard.

AMI/IMG/Boat/Bikes/Golf/Hottub/Kayak/Beach/pool

Welcome to the Paradise Fun House, the ultimate spot for your dream bash! Our Airbnb oasis is packed with tons of fun and activities for an epic stay. Cruise around on free bikes or kayaks, fish with top-notch gear, challenge friends to mini-golf, chill in the hot tub, or enjoy our game collection. Golf clubs and beach gear are ready to roll. Our spacious layout is perfect for partying all night long. Book now for the ultimate fun or relaxing experience! Boat/Dog-sitting/cleaning are available

Blue Tide Bungalow

Relax & Play in Paradise – Family Retreat with Pool & Hot Tub and firepit in Bradenton, FL Welcome to your Bradenton getaway! Whether you’re here for the beaches, the ballfields, or simply a warm-weather escape, you’ll feel right at home the moment you arrive. This stylishly furnished 4-bedroom, 3-bath home comfortably sleeps 8–10 guests and offers everything you need for a relaxing and memorable stay. From coffee by the pool to sunset cocktails around the fire pit, no detail is overlooked.

Bermuda Bay Club 1427 by Duncan Real Estate

Welcome to the Bermuda Bay Club!This 3 bedroom/2.5 bath townhome is conveniently located in the Bermuda Bay Club complex with water views from the upstairs balcony. The Bermuda Bay Club community stretches from Gulf to Bay and is just a flip flop walk across the street to the white sandy beaches of Bradenton Beach. The complex has a large, heated pool to swim a few laps and a hot tub to relax. From the pool area, you can stroll down the mangrove lined boardwalk to the Bay where you can try ...

A Piece Of Sunshine to Enjoy!

Beautiful two bedroom, two bathroom home on a dead end road completely fenced and gated it has a pull out couch, full kitchen, dining room, laundry room, and plenty of space to spread out. Located just 10 miles from Bradenton beach and minutes to Anna Marie island from there. 15 miles to Siesta Key Beach. Sarasota airport is 5 miles away, and Tampa Airport is 47 miles away. There are plenty of places to dine out and plenty of places to visit locally. Ideal space for enjoying time with family.

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

Apollo Beach is your getaway destination!

Receive a $25 gift card when you book this Tampa luxury private retreat. Just minutes from Apollo Beach Nature Reserve, Manatee Viewing Center, Downtown, Riverwalk, Busch Gardens, Florida Aquarium, & more! The perfect spot for family & friends, to relax or if you just want to enjoy a great chartered fishing trip sightseeing shopping and let's not forget our beautiful beaches Apollo Beach is just minutes from the interstates for quick easy access for whichever direction you want to travel

SIP & RELAX SPECTACULAR SUNSETS CLOSE TO SIESTA

Walk the No 1 beach in America, watch dolphins, wake up to sunny blue skies and the breeze from the bay. Watch spectacular sunsets daily whilst sipping your cocktail. Host your destination wedding - additional arrangements & cost. Located on the inter coastal waterway, a peaceful cul da sac & neighborhood close to Siesta Key. Gaze at the water & garden, spot the dolphins & birdlife. Close proximity to fabulous restaurants, boat/kayak rentals, Siesta Key, Downtown, & St Armands Circle.

LJ's Cottage 2

STEPS TO THE SAND - Welcome to your tranquil oasis on Siesta Key at our first floor 2 bedroom, 2 bathroom beach bungalow style cottage unit with plenty of room for family and friends. Enjoy the Siesta Key sands and famous Point of Rocks beach access just steps away. Relax in our expansive living/dinning room while watching large 60in TV's, perfect after a long day at the beach. The properties amenities boast private balconies, tiki hut, pool, hot tub, grill, and parking.

The Guest House at Riverbend Retreat Fla.

True Florida-style living under the oaks and palms on the Alafia River with beautiful views and comfortable beds. We include use of the pool, spa, fire pit, hammock, putting green, yard games, BBQ and dock area. There are additional bedrooms in the adjoining house for larger groups. Fisherman can cast into the river with expectations of catching Sheepshead, Red Snapper, Speckled Trout, Snook, Spotted Bass and Florida Gar off the dock. We also catch blue crabs.

Trophy Fish at the Oasis

Trophy Fish at the Oasis is where your group actually lives outside. Heated saltwater pool and spa, full outdoor kitchen, putting green, fire pit, cornhole, and a 75" smart TV under a covered pavilion. Sonos sets the soundtrack inside and out. The yard is professionally misted for mosquitos — you're genuinely comfortable in Florida. Four bedrooms sleep 10. 45 minutes to Anna Maria Island and Siesta Key and 25 min to St. Pete!

The Boho | Walk to Gulfport Beach & Restaurants

Boho inspired cottage in the heart of the Gulfport Waterfront District. Steps away from Gulfport beach, restaurants, and nightlife. Enjoy strolling along Beach Boulevard where you'll find local coffee shops, ice cream parlors, Gulfport brewery, and eclectic shops. Relax in the comfort of your backyard oasis or enjoy some fun in the sun with the best Gulfport has to offer right outside your back door.