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Beachfront holiday rentals in Little Gasparilla Island

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Top-rated beachfront rentals in Little Gasparilla Island

Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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Guest house in Englewood

4.92 out of 5 average rating, 237 reviews

Gulf front romantic cottage in paradise

Gated and surrounded by lush scenery you will feel like you have suddenly escaped to the caribbean! The pressures of the world melt away as you get your first glimpse of the Gulf of Mexico. Eclectic design with mostly Caribbean influences. Marble floors, tile counter tops and a large shower with a sit down bench. Walk the custom pathways which reveal beautiful orchids and exotic plants. Go kayaking, fish off the beach or look for sharks teeth. Take a swim in the pool or work on your tan.

Guest favourite

Island in Sarasota

4.97 out of 5 average rating, 305 reviews

NEW NEXT 4 DAYS CX 30% OFF Sarasota #1 Lux Villa

Check our nearby sister properties for 2024 dates by clicking our host picture, then click picture again or "contact host". Or BOOK 2024 NOW, stay in Style magazines exclusive beachfront gem! This property OWNS THE BEACH!! UNIQUE PRIVATE POOL & BEACH combo is HEAVEN! Private ELEVATOR! 32,000/gl FREEFORM POOL, with 4 WATERFALLS, HOT GROTTO with HOT falls! NEW BBQ PIT AREA, BIKES, KAYAKS, and PADDLEBOARDS! WRAPAROUND BALCONY, CHEF kitchen. Hosted CELEBS! SHOPPING, FINE DINING, watch our VIDEOS!

Apartment in Venice

4.83 out of 5 average rating, 178 reviews

Venice Beach Studio 71

This is a studio second floor apartment, only 50’ from the oversized pool and approximately 300 steps to the beach! Quick bike ride, or 20-25 min walk to all of what downtown Venice has to offer. About the same to Sharky’s and Fishing Pier. Inside you will find all you would expect from a very nicely appointed studio. Efficiency kitchen new appliances, and everything you need to prepare simple meals. Lots of pillows and a super comfy brand new queen bed will ensure a restful night’s sleep.

Guest favourite

Cottage in Bokeelia

4.99 out of 5 average rating, 112 reviews

Romantic Getaway “Waterside” Dockage~Canal front

Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. The dock is shared, but there is plenty of room! Lots of history on this beautiful island, with fishing you’ll be amazed with! Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources!

Guest favourite

Apartment in Siesta Key

4.96 out of 5 average rating, 277 reviews

On the Beach; Siesta Key SunBum Studio

STEPS TO YOUR OWN PRIVATE BEACH!! NO TRICKS or GIMMICKS LIKE OTHER LISTINGS on the KEY. This is the only studio in the Palm Bay Club tower on ground level with breathtaking views of the white sand and gulf waters. The Palm Bay Club offers 2 pools, hot tub, new gym, boat docks, fishing pier, outdoor grills, tennis/pickle ball courts; not to mention FREE parking+ beach lounge chairs. Enjoy 2 free bikes day rental with booking! You are sure to enjoy your time here on the #1 U.S. Beach.

Guest favourite

Home in Captiva

4.97 out of 5 average rating, 108 reviews

The Pearl Beach House, North Captiva Island,FL

This water-front property offers designer furniture and panoramic views of the Gulf of Mexico throughout the home. Experience unprecedented privacy with direct walking access to the beach, and a very secluded location suitable for couples, friends or families. The property has a Main House and Guest Cottage, both with expansive decking and panoramic windows and doors providing spectacular views of the water and sunsets. StarLink WiFi and Samsung QLED smart TV. We allow dogs up to 50 lbs

Guest favourite

Home in Captiva

4.91 out of 5 average rating, 102 reviews

Blue Laguna - Vacation in paradise!

Beautiful and welcoming are just two words to describe this magnificent, 4 story home with heated private pool and sweeping 360 degree water views from the observation deck. Blue Laguna features 3 bedrooms and 3 full baths allowing this home to sleep up to 6 people. Two screened in lanai's so you can sit and enjoy the island breeze and leave the sliding doors open for a true island nature experience during the colder seasons. A golf cart for 4 persons is also included in the rental.

Guest favourite

Apartment in Venice

4.82 out of 5 average rating, 223 reviews

Updated beachy condo - ready for you!

Conveniently located on Venice Island. This recently renovated, cozy, light an bright beachside condo has everything you need for your vacation. We have beach chairs, umbrella, towels and cooler. The efficiency unit has a full size frige, stovetop, microwave and convection oven. Comfy queen bed, Xfinity cable TV & Wifi in the condo. Park right in front of your unit, 1st floor - no stairs! Kayak rentals at the beach, bike rentals nearby. Bring your flip flops and sun tan lotion!

Guest favourite

Apartment in Englewood

4.94 out of 5 average rating, 117 reviews

Gulf Side Condo Englewood Florida

A cozy 2 bed 2 bath condo with a full kitchen, dining area, living room, a king size master bedroom and a small 2nd bedroom. The coastal decor and furnishings create the ambiance of an island home. The condo opens onto a wide porch which has beautiful views of the Gulf of Mexico. Wander down the sandy path to a private beach and the turquoise waters of the Gulf. Enjoy sunsets from the porch or the beach. Unwind and let all of your cares float away on the Gulf breezes.

Guest favourite

Flat in Englewood

4.9 out of 5 average rating, 115 reviews

Gulf front, Shoreview Beach House, Unit C

Relax at our Manasota Key beachfront getaway, while you enjoy the magnificent gulf and sunset views. This lovely triplex is GULF FRONT on a laid back stretch of beautiful Manasota Key, between Englewood Public Beach and Stump Pass. Our units have a beach cottage feel, and have beachfront views from the living areas. Enjoy your morning breakfast, while watching dolphins pass you by or a dinner watching the sunset from the upper deck. BBQ right on the beach.

Guest favourite

Loft in Boca Grande

4.97 out of 5 average rating, 102 reviews

The Loft on Park Ave--Boca Grande FL

We survived Ian and are ready to host you! A unique loft in the heart of Boca Grande. Grab dinner and drinks and simply walk home. The loft apartment has great views of the main drag in Boca Grande. The timber framed interior and high end appliances assure you will have a comfortable stay. This is a great place to park your car-grab a golf cart- and enjoy the Boca Grande lifestyle.

Guest favourite

Apartment in Siesta Key

4.93 out of 5 average rating, 181 reviews

Siesta key getaway!

perfect and very comfortable 4th floor condo with elevator, screened in lanai, fully stocked kitchen and full bath. laundry facilities on the premises, a tennis court. We supply beach chairs, umbrellas, a rolling cooler and big beach bag. There is a beautiful dock on the intercoastal side of us with picnic chairs, grills, and you may even see dolphins playing !

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for beachfront rentals in Little Gasparilla Island

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Guest favourite

Home in Punta Gorda

4.93 out of 5 average rating, 123 reviews

Tropical themed Island style home!

Guest favourite

Guest suite in Siesta Key

4.93 out of 5 average rating, 136 reviews

Cozy Studio - 5 min walk to #1 Siesta Key Beach!

Guest favourite

Villa in Siesta Key

4.91 out of 5 average rating, 142 reviews

Mermaid Villa Ocean Front!

Guest favourite

Apartment in Nokomis

4.83 out of 5 average rating, 146 reviews

Private Beachside Kitchenette

Guest favourite

Home in Placida

5.0 out of 5 average rating, 54 reviews

Little Gasparilla Island Beachfront Oasis

Guest favourite

Home in Englewood

4.91 out of 5 average rating, 11 reviews

Quaint Surf Cottage on Beach

Cottage in Englewood

4.83 out of 5 average rating, 81 reviews

Free Kayaks/bikes/walk to beach/pet friendly #3

Guest favourite

Flat in Englewood

5.0 out of 5 average rating, 16 reviews

Bungalow across from the Beach!

Beachfront home rentals with a pool

Guest favourite

Flat in Siesta Key

4.99 out of 5 average rating, 145 reviews

Siesta Key #1 Beach, pickle ball & tennis paradise

Cottage in Siesta Key

4.84 out of 5 average rating, 134 reviews

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Guest favourite

Home in Placida

5.0 out of 5 average rating, 24 reviews

Close to beaches, canal view, golf, fishing

Guest favourite

Cottage in Englewood

5.0 out of 5 average rating, 39 reviews

Waterfront! Sunset Deck, Pier & FREE Boat Docking!

Guest favourite

Home in Englewood

5.0 out of 5 average rating, 15 reviews

Vacation Condo- Beach Access!

Guest favourite

Apartment in Englewood

5.0 out of 5 average rating, 22 reviews

A little slice of paradise

Guest favourite

Home in Englewood

5.0 out of 5 average rating, 19 reviews

Cape Haze Cottage

Guest favourite

Apartment in Englewood

4.88 out of 5 average rating, 96 reviews

Beach Front Englewood Beach Condo

Private beachfront home rentals

Guest favourite

Home in Placida

5.0 out of 5 average rating, 7 reviews

Just listed! BRAND NEW Coastal Sol on Palm Island!

Home in Placida

4.95 out of 5 average rating, 39 reviews

CocoHut~Tub

Guest favourite

Home in Placida

5.0 out of 5 average rating, 14 reviews

Salty Mermaid on LGI / Island Beach Retreat

Guest favourite

Home in Englewood

5.0 out of 5 average rating, 25 reviews

Clean & Comfy Beach Cottage super-close to Gulf!

Guest favourite

Cottage in Englewood

5.0 out of 5 average rating, 57 reviews

Private Cottage on Manasota Key

Home in Placida

4.91 out of 5 average rating, 11 reviews

Dolphin Watch

Guest favourite

Cottage in Englewood

5.0 out of 5 average rating, 45 reviews

Casa Tortuga - Beachfront Oasis

Guest favourite

Apartment in Nokomis

5.0 out of 5 average rating, 17 reviews

Private Studio (entire space)

Destinations to explore