Vacation rentals with a patio in Gasparilla Island

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Top-rated patio rentals in Gasparilla Island

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Guest favorite

Cottage in Englewood

5.0 out of 5 average rating, 36 reviews

Waterfront! Sunset Deck, Pier & FREE Boat Docking!

Welcome to Tiki In Paradise! Enjoy the tropical setting in this restored fishing cottage with direct Lemon Bay front cottage views! Sit back & relax and enjoy Lemon Bay water views from every window in our cottage! All the comforts you want and deserve. You will never find another property with the character, views & cleanliness like this special place. Completely remodeled. We are moments from Gulf front beaches, Historic Dearborn Street & fantastic restaurants! Private, Unique & Special!

Sep 9 – 16

G$30,233 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 15 reviews

Vacation Condo- Beach Access!

DIRECT GULF FRONT, SPECTACULAR VIEWS, ONLY STEPS TO THE BEACH! Enjoy the Gulf Coast lifestyle with direct beach access. Manasota Key is famous for its old Florida charm, and relaxed, comfortable pace. This meticulously maintained, second-floor residence has been updated with a contemporary, coastal feel. Relax on your private balcony with views of dolphin, manatee, plus the seasonal turtle nesting and tarpon run. Lounge by the heated pool or walk to local shops, restaurants, and seafood market!

Dec 7 – 14

G$77,813 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 25 reviews

"Lost Loon" Oceanfront Cottage by Roxy Rentals

Located right on the Gulf, our renovated beach cottage is equipped with everything you need for a relaxing getaway. With private beach access and outdoor dining area, take in the views and enjoy with your family, friends or a solo trip to reset with a little R&R. This 2-bedroom, 2-bath bungalow has all the accoutrements for your a home-away-from-home, complete with beach chairs, boogie boards, beach games and of course, sun tan lotion. Come for some fun in the sun, your beachfront oasis awaits!

Jan 21 – 28

G$144,252 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 12 reviews

Breathtaking 250' Bayfront home w/ private pool

PRIVATE AND PRISTINE! This stunning 5 bedroom home with views you must see to believe. 250' of unobstructed Bay views neighboring the Lemon Bay Environmental Park. Your slice of paradise sits at the end of a cul-de-sac surrounded by water, with a large private pool. Wake up to Dolphins splashing, manatees playing, and various kinds of exotic birds on the property. Relax in luxury in this 3200 SF completely updated home that was meticulously decorated. Think "Ralph Lauren" beach vibes!!

Aug 17 – 24

G$192,266 GYD per night

Guest favorite

Condo in Englewood

5.0 out of 5 average rating, 40 reviews

Sunrise Over the Bay

Watch the sunrise on Manasota Key in Englewood Florida and dolphins & birds from your balcony. PRIVATE BEACH ACCESS directly across the street! Beach chairs, & umbrella provided for your use. Find restaurants or jet ski rentals near by. This condo has 2 bedrooms, 1 bath and a kitchen. Boat slips available upon request & availability. You must arrange off site trailer parking. A community heated pool & grills are right outside your condo. It’s time for some spring and summer fun!

Jun 16 – 23

G$26,627 GYD per night

Guest favorite

Home in Captiva

5.0 out of 5 average rating, 25 reviews

Private Island Luxury * Pool * Dock * Club Access

🏠 Exquisite interior design & curated coastal furnishings 🏖️ Stroll to beach: chairs, umbrellas, wagon provided 🛥️ Shared boat dock - ask about availability. 🏊 Private pool 🍹 Screened-in pool bar 🏓 FUN! Ping pong, cornhole, PlayStation, bikes, games ✅ Fully stocked kitchen 🧴 Plush bedding, luxurious linens & bath amenities 💻 Starlink internet 🐶 Pet-friendly 🌴 Breathtaking views; luxury treehouse experience ⭐ Dedicated guest concierge to help you plan your perfect vacation

Sep 29 – Oct 6

G$134,498 GYD per night

Superhost

Home in Englewood

4.89 out of 5 average rating, 9 reviews

Quaint Surf Cottage on Beach

This quaint surf cottage sits right on the beach, and it has all the amenities necessary for a comfortable extended stay. Situated right on the ocean, you will fall asleep every night to the sound of the waves. Enjoy time in your screen-porch with tables and chairs or a patio with chaise lounges where you can soak up the sun and witness some of the most spectacular sunsets on the Gulf coast. The Surf Cottage generally see repeat customers who love its convenience and privacy.

Apr 27 – May 4

G$75,756 GYD per night

Guest favorite

Home in Englewood

5.0 out of 5 average rating, 28 reviews

Relax at La Perla Pool Home - Heated Pool

Welcome to our beautiful, 2bed 2 bath house in Englewood, Florida! Immerse yourself in style & comfort as you step into La Perla. With its modern decor, this house offers the perfect blend of relaxation and style. The bedrooms are furnished to provide a peaceful haven after a day at the beach. Just a quick 10-minute drive from the beach. Whether you're enjoying the pool or exploring the pristine beaches of Manasota Keys, our house offers a delightful escape from the everyday.

Jun 17 – 24

G$29,166 GYD per night

Guest favorite

Cottage in Placida

4.97 out of 5 average rating, 38 reviews

Simply Adrift Island Cottage

Take it easy at this unique and tranquil getaway only accessible by boat. Little Gasparilla Island is a bridge-less barrier island off FL's West Coast in the Gulf of Mexico. Access is for residents and renters only, you will arrive by your private boat or jump aboard the water taxi for a 10 minute ride to our dock. No cars, shops, or restaurants on the island. The 7 mile beach is private and uncrowded. Get around LGI by renting a golf cart or explore by foot-you decide.

Oct 9 – 16

G$67,109 GYD per night

Guest favorite

Home in Placida

5.0 out of 5 average rating, 7 reviews

Just listed! BRAND NEW Coastal Sol on Palm Island!

Escape to the Coastal Sol retreat and be one of the first guests to enjoy this newly built home! This brand new 3 bedroom, 2.5 bathroom sanctuary is located on the exclusive Don Pedro-Knight-Palm Island, accessible only by private boat or a 5 minute car ferry ride. Coastal Sol offers a perfect blend of seclusion and accessibility. Enjoy 'old Florida' island life pursuits, complete with spectacular sunsets and leisurely strolls on uncrowded beaches.

Jul 20 – 27

G$81,607 GYD per night

Guest favorite

Apartment in Englewood

4.97 out of 5 average rating, 32 reviews

Your Englewood Beach Retreat!

Escape to your dream beach home in Englewood's hidden gem! This fully furnished 2-bed, 1-bath unit spells convenience and comfort. With 900 sq ft, a washer-dryer, central AC, and a private lanai, it's your seaside sanctuary. Just minutes from the stunning Englewood beach, and surrounded by vibrant restaurants and entertainment. Your beachy paradise awaits – book now for a hassle-free coastal living experience! and centrally located place.

May 16 – 23

G$16,246 GYD per night

Guest favorite

Home in Captiva

5.0 out of 5 average rating, 6 reviews

Beach Paradise: Oceanfront, Sleeps 10, Pool, Games

Discover the allure of Beach Paradise, a brand-new listing boasting unparalleled luxury. This recently furnished 4-bedroom rental property rests directly on the pristine Gulf of Mexico shores, nestled amidst lush tropical surroundings adorned with swaying coconut palms and pristine white sands adorned with exquisite seashells.

Apr 16 – 23

G$241,017 GYD per night