Little Gasparilla Vacation Rentals                                                                             
Your source for the most beautiful vacation rentals on Little Gasparilla Island!

  

Bud and Laurie Gaines    •   LittleGasparilla.com LLC         

Terry Simms, On-Island Guest Services

Louisa Mahoney, Booking Manager                                                                                                              

   

 

 

 

 

Our Vacation Rental Homes on Little Gasparilla Island         


                                                                                                                                                                                    

 

Seahorse Hideaway

2 BD 1 BA ; Sleeps 4

The Seahorse Hideaway is a well-maintained family home that has been immaculately cared for and well loved by the same family for years.  It is located close to the dock for ease of unloading luggage and groceries, yet it is just a 2-minute walk to the beach.  It has been updated with fresh new bed linens and new furniture but it retains the rustic charm of a much-loved beach cottage.  The master has a king bed and the second bedroom has two twins.  This cottage includes use of a golf cart for exploring the island, a brand new grill, a downstairs outdoor shower, a spacious screened porch overlooking the island roadway, and a comfortable porch swing for relaxing in the cooling island breezes.  For more photos and availability, check our VRBO site.

Rents for $195/night, $995/week, $100 pet fee


Flip Flop Bungalow

2 BD 1 BA;  Sleeps 4

The Flip Flop Bungalow is a charming small cottage nestled in the woods just a short walk from both the beach and the dock.  It is clean and cozy, simple and unpretentious and represents a great value for the couple or small family looking for a base from which to enjoy the charms of Little Gasparilla Island.  AND,  there are even kayaks included with your rental!  There is a queen in the master, two twins in the second bedroom, a fully equipped kitchen with a large pantry and a spacious family room.  The large front porch has a dining table for outdoor dining and there is an outdoor shower downstairs.  The beach is an easy one-minute stroll across the grassy front yard. For more photos and availability, check our VRBO site!

Rents for $125/night, $200/weekend nights, $795/week;  $100 pet fee; surcharge for holiday weeks


Sophie's Beach House

3 BD, 2 BA, Sleeps 6

Sophie's Beach House sits right on the beach for easy access to the best of the beachfront lifestyle!  The large open deck overlooks the beach so you can keep an eye on the family while still keeping an eye on dinner!  There is an enclosed sun porch that is warm and comfortable even during the chilly winter months.  The interior is cozy and rustic with warm knotty pine paneling and a fully equipped kitchen.  The home features 3 bedrooms, each with a spacious king size bed and there are two full bathrooms in addition to the open air outdoor shower downstairs.  (Please note that the downstairs room is not included with your rental...it is for storage only.)

For more photos and availability, check our VRBO site.

Rents for $300/night, $1950-$2000/week; Pets not permitted.


Hibiscus House

2 BD, 2 BA; sleeps 6

Hibiscus House offers wi-fi, satellite TV, a king bed in the master bedroom, queen in the second bedroom and a sleeping loft with two twins and a double.  It boasts a
fully equipped kitchen, a washer and dryer, and a fabulous private sunning balcony overlooking the Gulf. For more photos and an availability calendar, check out
our VRBO site:

Rents for $2400 per week; $100 pet fee.  Surcharge for holiday weeks.


Sand Dollar Cottage

2 BD, 1 BA, Sleeps 4

Sand Dollar Cottage is a charming gulf front cottage at the south end of the island, tucked away behind the dunes with spectacular views of the Gulf.  It is cozy and rustic, with knotty pine paneling, high ceilings and a warm and welcoming ambiance.  It is perfect for a couple or small family.  It features a queen in the master and two twins in the second bedroom,  It also inludes a golf cart for exploring the island and a private dock for excellent fishing and Gulf access. 

For more photos and availability, check out our VRBO site.

Rents for $275/night, $1400 per week  $100 pet fee, surcharge for holiday weeks.


Sea Star Beach House

2 BD/ loft, 1-1/2 BA; sleeps 7

Sea Star Beach House offers wi-fi, satellite TV, a queen bed in the master bedroom, double in the second bedroom and a sleeping loft with two twins and a trundle. The home also has a washer and dryer, and a fabulous screened front porch overlooking the Gulf.  It is in a perfect spot right ON the beach, with a decked area downstairs for grilling, a large outdoor shower and a private dunewalk leading directly to the beach. 

 For more photos and an availability calendar, check out  our VRBO site:

Rents for $300/night,  $1800-$2000 per week;  $100 pet fee.  Surcharge for holiday weeks.


Driftwood Cottage

2 BD 1 BA; sleeps 4

Driftwood Cottage is a charming and eclectic cottage sitting right in the dunes at the edge of the beach near the north end of the island.  It is one of the island's original beach cottages and it has been lovingly restored with a new kitchen yet it retains the charm and heart pine interior of the original cottage.  It is cozy and comfortable with dramatic views from every room in the house.  And you are literally just 10 steps from the beach.  The screened porch offers cooling breezes day and night and there is a new electric grill and table on the porch for al fresco dining.   It is a bit rustic, but this cottage truly transports you back to "old Florida"!

For more photos and availability, check out our VRBO site

Rents for $225/night, $1200-$1350/week; $100 pet fee, surcharge for holiday weeks.


Rosemary's Beach House

2 BD, 1 BA; sleeps 4

Rosemary's Beach House sits as close to the beach as you can get!  It is a gem of a cottage, with designer furnishings, a spacious open-plan living area and elegant appointments. It offers two queen beds, satellite TV, wi-fi, an electric grill, outdoor shower, a shady deck under the house, and an unbeatable location right ON the beach! 

For more photos and an availability calendar,
check out our VRBO site:

Rents for $1950 per week; $100 pet fee. 
 Surcharge for holidays.


The May House

2 Bd, 2 Ba Sleeps up to 10

This large family friendly home can expand to accommodate a large group of family or friends.  The master features a king bed and en suite bathroom and the bunk room offers two sets of twins.  And additional queen bed and two twin beds are available for overflow guests.  There is another newly remodeled bathroom off the living room and a washer-dryer upstairs.  The large living-dining area opens to a spacious screened porch.  The house is mid-island, just a short walk to both the beach and the dock and a golf cart is also available to facilitate exploring the island.

For more information, check out our VRBO site!

From $200/nt;  $1200-1500/wk; $100 pet fee


Serenity Cottage

2 BD, 2 BA; sleeps 4

Serenity Cottage is a cozy and charming cottage located midway between the beach and the bay...perfect for fishermen AND beach goers.  It is very peaceful and quiet, tucked amidst the palm trees and sea grapes, off the main road for lots of privacy.  It has a spacious screened and open air porch and an electric grill; a golf cart is also available for rent*.  The master has a king bed and the guest room has a double.   This home represents a tremendous value and for stays of one month or more, we can often include use of the golf cart at no charge. For more photos and availability calendar, check out our VRBO site:

 $995-$1200 per week, $100 pet fee.


Flamingo Treehouse

2 BD, 2 BA, Sleeps 4-6

This cottage is nestled amidst tropical foliage including a lush fig tree, sea grapes and palm trees that provide lots of privacy and keep the house cool and shady during the summer months.  The house is close to the bay for easy access to the water taxi or your boat, and just a 2 minute walk to the beach.  It has a comfortable screened porch and also includes a golf cart for exploring the island.  This home represents a tremendous value and a great way for a family to enjoy the charms of Little Gasparilla Island.  For more photos and available check our VRBO site.

Rents for $200/night and $995/week, $100 pet fee, surcharge for holiday weeks.


Tradewinds Cottage

2 Bd, 2 Ba Sleeps 5

Tradewinds is a charming cottage overlooking the bay with a lush tropically landscaped yard.  It boasts a new, modern kitchen, spacious screened porch offering views of the bay, a queen bed in the master and two bunks  plus an additional twin in the guest bedroom.  The spacious living area also features a wet bar perfect for entertaining.  The downstairs is fully decked with a comfortable hammock for relaxing, a fire pit and a large outdoor shower.  This home is just steps from the bay and just a short stroll to the beach.

For more photos, check out our VRBO site!

Rents for $1400 per week; $100 pet fee. Additional surcharge for holiday weeks.


Surf's Up!

3BD, 2-1/2 BA; sleeps 6-8

This striking gulf-front home overlooks the beach and the beautiful Gulf of Mexico.  It features a stunning master suite with a king bed and jetted tub, two additional bedrooms upstairs and a private downstairs room with bunk beds perfect for teenagers who want some extra privacy.  It also has paddle boards, a modern kitchen, a spacious screened porch and stunning sunset views.  This is a perfect family vacation home just steps from the beautiful beaches of Little Gasparilla.

For more photos and availability calendar, check out our VRBO site!

Rents for $2200 per week; $100 pet fee.  Surcharge for holiday weeks.


The Round House

2BD, 1 BA; sleeps 4-6

This unique house is an island original!  This home has been newly remodeled, yet it retains the charm of one of the island's original cottages.  Its location right on the beach cannot be beat.  Its views are to die for!  From the living room and kitchen you feel like you are living on the deck of a ship!  All the furnishings are fresh and new.  The breakfast bar faces south toward Boca Grande, brand new French doors face northwest for dramatic sunsets and the spacious porch provides bright sunshine and cooling breezes no matter what time of year you are here! 

For more photos check out our VRBO site.

Rents for $300/night or $1600-1700/wk; $100 pet fee, surcharge for holiday weeks.


Redfish Retreat

3 BD, 3 BA; Sleeps 6-8

This luxurious home is beautifully appointed with modern amenities, granite countertops and new stainless appliances.  It sits on a large lot near the north end of the island, very close to the bay with some exciting extras...it includes a paddle boat and a small jon boat perfect for fishing in the bay.  A golf cart is also available for a small additional fee.  It has two master suites with beautifully appointed bathrooms and access to the private sun deck.  There is also a spacious downstairs deck,  a large open air outdoor shower and a fire pit perfect for s'mores.  This home is spacious and perfect for large family gatherings.  It is just a short 4-5 minute walk to the beach.

For more photos check out our VRBO site

Rents for $325/night or $1800/week, $100 pet fee, surcharge for holiday weeks


Coconut Palm Cottage

2 BD, 1 BA,  Sleeps 4

Coconut Palm Cottage is a cozy cottage nestled amidst lush tropical foliage on a large, beautifully landscaped yard. Beautiful blooming frangipani, avocado trees, birds of paradise, orchids and other tropical palms surround the house which offers lots of peace and privacy! Inside, a spacious sun porch provides warmth in the winter months, and a large screened downstairs room provides a cool family room in the summer months. The home is located halfway between the bay and the beach so just a one minute walk will take you to the dock for some fishing or to the beach for shelling. The home offers two bedrooms and one bath with a king bed in one bedroom and a queen in the other.

For more photos, check out our VRBO site:

Rents for $225/night or $995/$1200/week  $100 pet fee, surcharge for holiday weeks.


Beachview Bungalow

3 BD, 3 BA, Sleeps 7

This unique cottage is a charming "old Florida" bungalow on Little Gasparilla Island.  The original cottage features a fireplace, knotty pine walls and a cozy and comfortable living and dining area plus two bedrooms and two bathrooms.  The newer upstairs addition features a large and spacious third bedroom with a double and another twin, and a large and breezy screened porch with views of the beach.  The upstairs bedroom has its own entrance so it is perfect if you have two families sharing the cottage.  The bungalow also features a large, grassy yard for family games and it is just a short walk out the front door to the sandy Little Gasparilla beach.

For more photos and an availability calendar, check out our VRBO site!

Rents for $1500 per week.  Sorry, pets are not permitted in this cottage.


Dream House

3 BD/Loft, 2-1/2 BA, Sleeps 10*

This spacious island home is the perfect home for family and friends to congegrate.   Downstairs there is a large covered deck area with a porch swing, seating area, a fire pit and a grill.   The modern kitchen has every appliance you could need and is conveniently located close to the living room and porch.   Two bedrooms are located downstairs and each is adjacent to a bathroom.  Upstairs the master has  its own wing and another bathroom for lots of peace and privacy.  And, a spacious loft offers a TV for videos and a place for the kids to be by themselves.   The home is just steps to the dock and just a short one-minute walk to the lovely beaches of Little Gasparilla.

For more photos, check out our VRBO site.

Rents for $1800/week; $100 pet fee

*rates are based on 6 guests; $100/week per person above 6


Seagrape Escape

3 BD, 2 BA, Sleeps 6

Seagrape Escape is a new home situated very close to the dock, perfect for fishing and kayaking. It offers views of the bay, yet it is just a short 3-minute stroll to the beach down SeaGrape Lane. This home features the ultimate in privacy with a south-facing porch overlooking both a small pond and  Placida Bay.  A private screened porch, beautiful modern kitchen with stainless appliances, gas grill, wi-fi and the use of four kayaks and fishing gear are all included with your rental.  There is also an open-air downstairs shower and the owners will include their golf cart with a monthly rental.


For more photos, check out our VRBO site:

Rents for $1500 per week, $100 pet fee


Knee Deep Beach House

3 BD, 2 BA Sleeps 6-8

Knee Deep Beach House is a spacious Gulf-front home
located right on the beach with some of the most
dramatic views of the waves.  It offers a large
beachside deck dowstairs perfect for grilling,
supervising the kids, resting in the shade or
relaxing in the hammock.  Upstairs, the master
bedroom has dramatic Gulf views as well.  The
second and third bedrooms each offer twin beds and there is a sofabed in the living room.  The large open living/dining/kitchen area offers unparalleled views of the waves and makes you feel like you are relaxing on the deck of a cruise ship!

For more photos, check out our VRBO site.

Rents for $2300/week; $100 pet fee


Island Breeze

3 BD, 2 BA; Sleeps 7

This beach house is situated at the south end of the Island, on Rum Runner Road.  It is just a short two-minute walk to the beach, and this house comes equipped with stand up paddle boards so you can explore the sand bar at your leisure and make friends with friendly manatees!  The owners also provide beach bikes.  Newly redecorated, Island Breeze features a breezy screened porch with a brand new grill and comfortable lounge furniture, brand new appliances in the kitchen, a king bed in the master (with Gulf views!) and three twins in the downstairs second bedroom.  The upstairs third bedroom has two additional twins.  Even the yard has new landscaping!

For additional photos, check our VRBO site! 

 $1195-$1400 per week; $100 pet fee


Bonefish Bungalow

2 BD, 1 BA, Sleeps 4-5

The Bonefish Bungalow sits right on the beach with dramatic views from every room in the house!  It combines "Old Florida" charm and character with modern sophistication and style:  brand new appliances, a new kitchen, new fixtures, new flooring, new bath, new doors and windows mixed with antique furniture and vintage accessories for a truly one-of-a-kind beach experience!  A king bed in the master bedroom overlooks the Gulf, and the living and dining areas also have sweeping beach views.  This cottage offers you an authentic "old Florida" beach experience with modern comfort and style!

For more photos and information, check out our VRBO site

Rents for $300/night,  $1700/week; $100 pet fee


Island Paradise

2 BD, 2 BA, Sleeps 5-9

This fabulous Gulf-to-Bay property is located at the far southern end of Little Gasparilla Island with a private dock and white sandy beach on the bay plus the beautiful white sandy beach on the Gulf of Mexico.  Truly the best of both worlds!  The home is charming and cozy, with a screened porch overlooking the bay and a small porch on the front with views of the Gulf.  The master bedroom has a king bed and the second bedroom has 3 twins.  Downstairs, a bonus room is also available with a queen sleeper sofa, a bunk bed and another bathroom and small kitchenette.  The downstairs sleeps another 4 so the home can accommodate 9 comfortably.  Kayaks are included with your rental.

For more photos and availability visit our VRBO site!

 $1800/week;  $100 pet fee


Chateau La Mer 

3 BD, 2 BA Sleeps 6-7

This spacious home offers elegant beachfront living for the sophisticated vacationer.  Colorful stained glass windows, leather furniture, oriental carpets and unique designer furnishings complement the stunning views from each room.  Tthe two upstairs bedrooms each have queen beds and access to a private balcony and some of the best views on the island. There are dual zone air-conditioners so both the upstairs and downstairs stay cool and comfortable year round.  Downstairs, another bedroom just off the living room also has Gulf views and its own en suite bathroom.  A screened porch offers a relaxing place to read or dine while enjoying the gulf breezes and a private dune walk means you don't have to trudge over hot sand to access the beach.  This home is for the truly discerning beachgoer who wants a relaxing beach vacation in elegant surroundings.

For more photos check out our VRBO site

Rents for $2250 per week; $100 pet fee


Coquina Round up

1BD, 2 BA, Sleeps 2-3

This charming "treehouse" in the woods is just steps from the beach and offers a rustic ambiance reminiscent of the northwoods.  A private screened porch has a luxurious hot tub and the loft bedroom has a private balcony overlooking the tropical foliage. There is a downstairs outdoor shower, and the owners include a gas grill and a kayak for your use.  The kitchen is fully equipped with all basic appliances and there are beach chairs and an umbrella.  The home is decorated in eclectic painted furniture and has gleaming hardwood floors.  It is a charming home perfect for a couple and small pets are also welcome. 

For more information, check out our VRBO site!

Rents for $1250-$1400 per week; $100 pet fee


Pelican Place

3 BD, 2 BA, sleeps 6

Pelican Place is a beautiful new home that has been beautifully maintained.  It features a king bedroom, a queen bedroom and a double bedroom and sleeps 6 comfortably.  The open plan living/dining/kitchen area is one of the newest and nicest on the island and offers a very comfortable home from which to enjoy the charms of Little Gasparilla Island.  It also offers a fire pit downstairs, a large decked area, and a spacious open air shower.  The large porch has comfortable seating and a gas grill.  Your rental includes lots of extras including paddleboards and kayaks and lots of beach toys.  The home is close to both the dock and the beach for easy access to great dock fishing and beach sunbathing. This is truly one of the nicest and best maintained homes on the island and the kitchen comes with everything you could need to prepare your favorite beach meal!

For more photos,  check our VRBO site!

Rents for $1800 per week; $100 pet fee


Coconut Hideaway

3 BD, 1 BA;  Sleeps 6

Coconut Hideaway offers three bedrooms...two
with king beds and a cozy sleeping porch
with two twins.  It also includes satellite TV,
wi-fi, a piano, a fully-stocked pantry, a library,
an outdoor shower and a tropical tiki hut
nestled in the dunes.  It features hardwood
floors and warm cedar paneling,  soaring
high ceilings, antiques and oriental carpets
and an eclectic ambiance.

For more photos, check out our VRBO site:

 

Rents for $2200 per week  $100 pet fee.  Surcharge for holiday weeks.


For more information on booking or availability of any of these
Little Gasparilla Island Vacation homes, e-mail us today!


We are pleased to offer this beautiful selection of vacation rental homes on Little Gasparilla Island!

Our homes have been carefully selected to offer the best value for your vacation dollar and to offer you a memorable vacation experience.We pride ourselves on the cleanliness of each of our homes and the attention to detail that makes your vacation more trouble-free.

Our homes include the following amenities:

• washer and dryer

• use of a dock slip (21-24 ft. maximum at most docks)

• easy beach access

• beach chairs

• the services of our island concierge

In addition, many of our houses are pet-friendly but we do request a $100 pet fee to help offset additional cleaning costs.

Many of our homes rent for one-week minimums, but several do offer 3 or 4-day rentals. If you cannot stay for a full week, ask us which homes can accommodate stays of less than a week.

We accept all major credit cards, personal checks, or Paypal for your rental payments. 

All homes are self-catering; no meals are provided.  Each home is cleaned prior to your arrival and inspected following your departure. 

You are expected to perform routine housekeeping services during your stay and leave the home neat and tidy upon your departure. 

*Please note if golf carts are included with your rental, they are included as a courtesy only.  The owners do not guarantee their golf carts and are under no obligation to provide a replacement cart should their cart break during your stay or if it is not working upon your arrival.  If a golf cart is extremely important to you, we suggest you rent one from LGI carts:  941-697-3820.

AND IF YOU HAVE ANY QUESTIONS ABOUT ANY OF OUR PROPERTIES, DON'T HESITATE TO GIVE US A CALL!

LITTLE GASPARILLA VACATION RENTALS

Bud and Laurie Gaines, Rental Managers  941-697-6766, 815-440-0000 or 0001

Louisa Mahoney, Booking Manager

Terry Simms, On-Island Guest Services Manager  813-310-0902