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Beachfront vacation rentals in Little Gasparilla Island

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Popular amenities for Little Gasparilla Island beachfront rentals

Pet-friendly beachfront home rentals

Top guest favorite
A bright and airy living space features a neutral sofa, an accent table, and a coffee table, all set against light wood flooring. A ceiling fan aids ventilation, while a large window allows natural light to fill the area. The open kitchen displays modern appliances and bar seating.
Apartment in Venice
4.98 out of 5 average rating, 66 reviews

Venice Island Pool Casita with 2Bedrooms/2 Baths

SabrinaRating, 5 stars2 weeks ago
We had an amazing time at this beautiful vacation rental! The pool was great and the kids had a blast! The beach is wonderful and close by. Corinna and Tim are responsive and generous hosts. They were accomodating and flexible. The place was increadibly clean and comfortable. We would love the opportunity to come back!
Top guest favorite
The exterior of the home is illuminated at dusk, highlighting a welcoming entrance with decorative stone pathways. Lush greenery surrounds the property, and two palm trees add a tropical element. A soft glow from the porch light enhances the inviting atmosphere.
Home in Bokeelia
4.96 out of 5 average rating, 23 reviews

Fishing and Nature Paradise

JasonRating, 5 stars1 month ago
This place is perfect for Boaters/Fishermen! Boat ramp is within walking distance. Nice new dock with water hose to clean boat. Jug Creek Marina is one canal over, fuel, ice, live bait, live music and food! The house is just as described! Very clean and everything you would need for a stay. Wonderfull screened in patio.
Guest favorite
A private patio is furnished with turquoise cushions on a wicker sofa and chair, overlooking a serene waterway. Palm trees are visible in the background, enhancing the tranquil environment. A ceiling fan is mounted above, providing comfort during warm days.
Home in Bokeelia
4.93 out of 5 average rating, 40 reviews

Shell House

KarlaRating, 5 stars1 week ago
We had a wonderful stay! The house was exactly as described clean, comfortable, and perfect for a relaxing getaway. One of the highlights was how easy it was to access our boat; the location made everything so convenient, from docking to getting out on the water quickly. The host was responsive. We would definitely stay here again!
Top guest favorite
A two-story duplex is framed by lush palm trees and landscaping. The property features a welcoming front porch with white railings and ample outdoor seating. A gravel driveway leads to two designated parking spaces in front, enhancing accessibility to the entrance.
Home in Englewood
4.87 out of 5 average rating, 62 reviews

Turtle Nest Retreat - Manasota Key (upper unit)

BenjaminRating, 5 stars1 month ago
Dana was an amazing host. The space was beautiful and magical. We can’t wait to return again. Thank you for everything.
Superhost
A hammock is seen suspended between two palm trees, featuring a purple striped fabric and two soft pillows. This peaceful spot is surrounded by sandy terrain and lush green foliage, creating a serene outdoor relaxation area near the beach.
Condo in Nokomis
4.89 out of 5 average rating, 19 reviews

Jetties Pointe Cottage # 6 - 408

EvelynRating, 5 stars2 weeks ago
Had a great stay and beautiful peaceful private beach! I will say make sure you bring your own beach chair and umbrella. It’s stated they have some but I think other guested used them all.
Guest favorite
An outdoor pool area features a thatched-roof structure providing shade. A spacious swimming pool reflects sunlight, while a person enjoys a swim. Surrounding seating areas include lounge furniture and a dining area, all set against a backdrop of palm trees and greenery.
Home in Bokeelia
5 out of 5 average rating, 20 reviews

Boater’s Paradise in Bokeelia!

JenniferRating, 5 stars3 weeks ago
I cannot say enough about how responsive Wendy is. We had a few hiccups with our stay that had to do with a leak that occurred with the AC. Unfortunately, I had to call Wendy at almost 11 PM on our day of arrival and she picked up immediately! She worked to get the issue resolved as quickly as possible and stayed in communication with me the entire time. We visit this area often and I will definitely reach back out to Wendy for another stay :)
Guest favorite
A screened-in patio is featured with comfortable seating made of woven material. A low table sits in the center with decorative items. The backdrop includes soft purple hues from the sunset and surrounded by tropical plants, offering a serene outdoor setting.
Home in Nokomis
4.98 out of 5 average rating, 42 reviews

Summer sunset. 3 minutes away from beach!

CaseyRating, 5 stars1 week ago
Very responsive and accommodating host! The house is very close to the beach and other local attractions. We enjoyed our short stay. Great value.
Guest favorite
A cozy studio features a spacious bed with a plaid coverlet, complemented by a contemporary kitchen area. Two stools are positioned at a small countertop, and seating is provided by two dark armchairs. Natural light fills the room from the doorway leading outdoors.
Home in Englewood
4.97 out of 5 average rating, 30 reviews

Cottage By the Sea B

TinaRating, 5 stars1 month ago
This place was excellent! I would definitely stay again. Within walking distance of the beach, the bars and the restaurants. We had a wonderful time. It is definitely a 10 out of 10. Summer was an excellent host and allowed me to check in an hour early in order to give me time to get to the airport to pick up my boyfriend. I highly recommend staying here. It is perfect for a couple.

Beachfront home rentals with a pool

Top guest favorite
A heated pool is surrounded by a spacious deck with lounge chairs. The building's design features an elevated structure with multiple outdoor staircases leading to individual units. A white fence encloses the pool area, providing privacy, while trees and landscaping add greenery to the surroundings.
Condo in Englewood
4.99 out of 5 average rating, 72 reviews

On Manasota Key w direct access to our Beach! (A)

BenRating, 5 stars1 month ago
Great condo just like the pictures and description. Across the street from the beach and a very short walk to restaurants. Car isn’t needed if you wanted to come by boat (there’s multiple slips)
Superhost
An aerial view captures the beachfront property surrounded by palm trees and lush greenery. The ocean is visible in the distance, framed by clear blue skies. A sandy path leads from the building to the beach, emphasizing the proximity to the water.
Condo in Englewood
4.79 out of 5 average rating, 122 reviews

Entire Beachside Condo! Don’t worry Beach Happy!

TanyaRating, 5 stars1 month ago
This is the third time we’ve stayed at this location and it does not disappoint! The place has been renovated and looks great! The host is clear and we had no issues getting into the condo. I used the laundry room and that was straight forward. The location is so close to the beach. We enjoyed our time and plan to come back!
Guest favorite
Villa in Englewood
4.95 out of 5 average rating, 98 reviews

STUNNING 3/2 beach+pool property! 2 kings/2 bunks!

JenniferRating, 5 stars10 months ago
We loved staying here especially having the beach just a few feet away! Although there was construction taking place in the development, it did not interfere with our stay at all! We didn’t even notice the workers on site. If you get a chance to book this home, do it. April is an amazing host and has thought of every amenity possible! We look forward to booking again soon!
Top guest favorite
A private pool is surrounded by a stone patio, featuring turquoise lounge chairs. The fenced yard meets the canal's edge, offering a view of the calm water and landscaping. The sun shines brightly overhead, illuminating the peaceful outdoor space.
Home in Englewood
5 out of 5 average rating, 40 reviews

Cape Haze Cottage

AnnieRating, 5 stars1 month ago
House is lovely, exactly as depicted in photos. It’s super well appointed and Nicole was responsive and helpful.
Top guest favorite
Cottage in Bokeelia
4.99 out of 5 average rating, 140 reviews

Romantic Getaway “Waterside” Dockage~Canal front

DustinRating, 5 stars3 weeks ago
The house was very quaint with great access to Charlotte Harbor. Jugg Creek is quite the place these days. Restaurant, Bar, and Fuel dock/Bait shop nearby.
Guest favorite
A spacious community pool is surrounded by a paved deck and overlooks palm tree greenery. The clear blue water reflects a partly cloudy sky, offering a refreshing atmosphere for relaxation. Nearby lounge chairs are arranged along the poolside.
Condo in Venice
4.96 out of 5 average rating, 101 reviews

Vintage Villa, Thirty-Five

MarleneRating, 5 stars9 months ago
This is our second year staying here. It was wonderfully peaceful this last weekend, just like last year. The beach is less than two minutes walk from the door. The kitchen had everything we needed in it. Plenty of beach items for use in the closet. The bathroom had more than enough towels and TP. We also used the pullout couch for our children, and they were very comfortable. we hope to book again soon, thank you!
Top guest favorite
A modern single-story home is presented with a well-maintained exterior, featuring large windows and a stylish garage door. A sprawling oak tree provides shade, while lush greenery surrounds the entrance. The driveway leads up to the front door, enhancing the welcoming atmosphere.
Home in Englewood
5 out of 5 average rating, 14 reviews

The Windsor @ Englewood Beach

EveretteRating, 5 stars2 weeks ago
The house was very open & inviting, easy to find with ample parking. It had easy access to the waterway and very convenient to grocery stores , restaurants and the beach. It’s located near the end of a canal but limited space for boat storage which we brought. But overall it was well worth the stay
Guest favorite
A modern bathroom features a double vanity with a white marble countertop and two sleek undermount sinks. Above, three circular mirrors are mounted on a light grey wall. A shower area is enclosed by a curtain, and neutral-colored towels are neatly arranged.
Home in Port Charlotte
4.89 out of 5 average rating, 19 reviews

Charming Home w/ Pool & Dock - 5 Min to Downtown

CharlesRating, 5 stars1 month ago
Amazing stay. Will definitely be coming back. Perfect for if you’re looking for somewhere on the water to keep your boat with easy ocean access.

Private beachfront home rentals

Top guest favorite
Large windows invite natural light into the space, offering a view of palm trees and the exterior of nearby buildings. A small white table is positioned near the window, enhancing the open and airy feel of the room.
Condo in Englewood
4.91 out of 5 average rating, 65 reviews

Key Condo located on Manasota Key

MistyRating, 5 stars3 weeks ago
Great location! Beach was steps away. Wish we could have stayed longer. Would definitely stay here again.
Home in Placida
4.88 out of 5 average rating, 25 reviews

Island Beachfront Cottage. Secluded! Lux! Extras!

BradRating, 5 stars18 months ago
Had a great time at the Beach Cottage. It is truly a hidden gem! Well appointed, very comfortable and extremely clean. Very quiet, secluded and peaceful setting. Had the beautiful beach basically to ourselves the entire week. The gulf views from the cottage are incredible, as were the sunsets each evening. Andy and Rebecca are wonderful people and incredible host. Their hospitality was second to none! Look forward to our next stay at this incredible property.
Top guest favorite
The image captures a serene waterfront view, showcasing a vibrant sunset with colorful streaks across the sky. Gentle ripples are observed on the water's surface, reflecting the warm hues of the evening light, creating a tranquil ambiance.
Townhouse in Englewood
5 out of 5 average rating, 13 reviews

Architect's waterfront home is a fisherman's dream

FrankRating, 5 stars2 months ago
This is was our second year at Brian's place and felt like home away from home. A real treat were the sight if Manatees swimming in the canal, right outside deck. Although there is an obvious amount of residual hurricane damage in this part of Florida, it was great to see most of favorite restaurants had reopened. In short it was good to be back and we enjoyed our stay!
An aerial view showcases the serene neighborhood with waterways and the Gulf of America visible in the distance. Houses are nestled along the coast, surrounded by lush greenery and palm trees, creating a tranquil atmosphere. The layout highlights convenient access to boating and nearby beaches.
Home in Placida
5 out of 5 average rating, 3 reviews

Canal Cottage 2 min to big water

LisaRating, 5 stars2 weeks ago
Our stay was great! The house was beautiful and very well stocked. The location is close to a grocery store and some local restaurants. We brought our boat and the dock out back was perfect. There is a boat ramp nearby so it’s very convenient but you need to make arrangements for your trailer. It cannot be parked at the house due to deed restrictions. You can park it at the boat ramp for a fee. The host Michelle was super helpful and responded very quickly every time! We would absolutely rent this place again.
Guesthouse in Englewood
4.91 out of 5 average rating, 266 reviews

Gulf front romantic cottage in paradise

ElizabethRating, 5 stars2 weeks ago
Lovely and romantic , exquisote botanical garden setting on a beautiful beach! What more you ask for in a Florida getaway package !! We will be back ! Thank you !!
A charming bayfront house with a vibrant blue exterior is depicted. A spacious deck with white railings is accessed by a set of outdoor stairs. Tropical greenery surrounds the home, while colorful murals are painted on the walls, adding character to the inviting entrance.
Home in Placida
5 out of 5 average rating, 4 reviews

Poseiden House on Little Gasparilla Is

AlishaRating, 5 stars2 months ago
We had a wonderful stay! It was peaceful and relaxing, with beautifully decorated interiors. The private dock was a fantastic bonus. We loved exploring the surrounding islands. Multiple beach access spots nearby to walk to or ride the golf cart to. The furniture and beds were comfortable. The kitchen cabinets were well-stocked. Even though the north end is still recovering from the hurricane, the roads are cleared and it was easy to get around on the golf cart. Highly recommend! Can’t wait to book again!
Top guest favorite
Home in Placida
5 out of 5 average rating, 5 reviews

Private Island Beach Getaway

AnnaRating, 5 stars2 months ago
This is our second time staying at this lovely home. It is well stocked and beautifully decorated. We love having the dock right across the street and the beach a short golf cart ride away. We will be back! Lauran was always responsive, easy to work with and kind.
A spacious screened porch features comfortable seating arrangements with patterned cushions and a wooden coffee table. Overhead, soft lighting adds ambiance. The view beyond showcases the beach and lush greenery, with the ocean visible in the distance under clear blue skies.
Home in Placida
5 out of 5 average rating, 5 reviews

"Salt of the Sea" - beachfront and pet friendly!

SamuelRating, 5 stars1 month ago
This place was incredible! It is right on the beautiful beach, and we saw dolphins, manatees and a sea turtle laying her eggs! The weather was perfect and we basically had the entire 7 miles of beach to ourselves the whole week. Make sure you carefully plan what food you are going to bring because you can't go back and forth to the mainland easily. If you can, pack some insulated grocery bags to bring your frozen food on the boat ride. The island is still recovering from the hurricanes last year, but it didn't affect our experience at Tasha's. We hope to come back again!

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