Holiday rentals with a kayak in Lemon Bay

Dockside Delight:Waterfront/Gulf Access/4minsbeach

Canal-Front, Direct Gulf Access & Private Dock Stylish home w/ hotel-grade amenities Prime Location: Just 2-5 minutes from Englewood's vibrant dining, shopping, and entertainment on Dearborn Street. Outdoor Fun & Watersports: Guests can enjoy scenic paddles with our complimentary kayaks or unwind in style with lounge chairs, a hammock, firepit, BBQ, games and cozy ambiance —perfect for day or night relaxation Manasota Key's breathtaking beaches - 2 miles away for the ultimate coastal escape.

Relax & Play • Pool • Family-Friendly • Near Beach

Looking for a list of local recommendations? Shoot me a message! Welcome to 🍍Pineapple in Paradise Luxurious oasis is nestled close to the historic charm of Dearborn Street and the pristine beauty of the beach. 🏖️ 🌟Prime Location: .5 Miles to Dearborn Street 10 Miles to Wellen Park 11 Miles to Historic Downtown Venice Beaches: 🌴🍹🍉⛱️🥥 4 Miles to Englewood Beach 6 Miles to Manasota Key Beach 13 Miles to Boca Grande Causeway (GIBA Bridge Pass included in your stay, $6/value per day)

Beach Retreat, Families, Bachelorette, Pool, Kayak

Your dream beach getaway awaits at Sunset Beach Retreat, on Manasota Key— 2 blocks from the beach! Whether you’re planning a family vacation or a girls’ weekend, this retreat has everything you need for relaxation, adventure, and unforgettable memories. Unwind and recharge with our heated pool, 5-person infrared sauna, and cold plunge. For those who love to stay active, enjoy our kayaks, kids play set, bicycles, putting green, or rent our 6-person golf cart to explore the island in style.

Spacious 4 BR Across From Beach w/ Heated Pool

Enjoy the ocean view from our renovated 4 bedroom haven on the coveted Manasota Key. With a new pool and deeded private beach. Relish in the breathtaking views, idyllic beaches and stunning sunsets. This home is perfect for families, providing versatile sleeping arrangements. The screened in lanai boasts ping-pong, cornhole and paddle boards. Nestled just a short bike ride or drive from the vibrant restaurants and shops on Manasota Key, where nightly live music adds a touch of local charm.

The Manatee Flat at ManasotaKeyHouse 2bed/2bath

* Due to hurricanes in Sept. 2024, Manasota Key sustained heavy damage. We have completed repairs and are excited to be renting again, but other businesses and home owners are working hard to recover/rebuild. Things are constantly changing on the island, with some closures. What is mentioned/pictured in our listing may not be exact due to the constant changes. We will do our best to keep our guests up to date. The beaches are open and as beautiful as ever! Most restaurants have reopened.

Peaceful Waterfront Orchard 1

bring the whole family including your pets to this peaceful orchard and garden oasis. the action packed backyard of this duplex proudly boasts over 40 fruit trees of various varieties including banana, orange, lemon, fig, mango, papaya... and many more! choose to fish from the dock in the backyard canal, go exploring with the kayaks or paddleboards, play in the sandbox, try out the slackline, or even say hi to the chickens in the coop (maybe even grab a few fresh eggs for breakfast).

Blue Cottage Suite- Peaceful Old Englewood Charm!

This charming rental is in historic Old Englewood right at the edge of Lemon Bay. The Blue Cottage is in a quiet neighborhood just 4 blocks from Dearborn Avenue with all great entertainment, eclectic shopping and restaurants, live music, and more. The Front porch pictured is part of the main house and is NOT included for use while renting the Blue Cottage Suite. IF the main home is vacant during your stay, I will let you know and it can be used during that time.

Peaceful waterfront home

Take it easy at this unique and tranquil getaway. Nestled alongside a serene canal, our home is a sanctuary of tranquility and natural beauty. From the moment you step onto the property, you are met with charm and allure that only canal front residence can offer. For those who enjoy outdoor activities, the canal provides a perfect venue for kayaking, fishing and lounging in the pool and hot tub. Surrounding sliding glass doors opens up to 3 separate patios.

Private Beach-Luxury 4BR+SUPs&Kayaks-Pets-BBQ

Charming 4 Bed Cottage (sleeps 9), Private Beach to Gulf Across Street, with Large Screened Porch, Super Shark Tooth Hunting, Free use of 2 Kayaks and SUPs, Restaurants, Live Music, Golf, and Tennis . Uber Eats & Grocery delivery, 50 Minutes from Sarasota Airport (75 minutes from Fort Myers airport). Lush tropical rainforest in the "Old Florida" region on the Gulf surrounds this cute cottage. *Please note small extra $50 pp nightly fee for guests 7-9.