15 Best Little Gasparilla Island Vacation rentals on Holiday Lettings - House rentals

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Little Gasparilla Island

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19 Vacation rentals

26

Condo rental in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
AKA the "Green Roof Condos", we are a 1000 sq ft end unit with no one above or below. South facing and perched 20 feet above the ground with palm trees in all views. There is a second floor loft (fixed ladder) that sleeps 2. We have a freshwater pool right on the island …see more

from $140 / night

$1000 - $1300 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from $140 / night

16

Home rental in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Sea Star Beach House is a glorious beach-front house overlooking the beautiful Gulf of Mexico. It comes fully stocked with everything you need for a great beach vacation, including a kayak, beach floats, fishing gear and beach toys. Please note that this house is on L …see more

from $258 / night

$1800 - $2200 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $258 / night

(12) Excellent 

Certificate of Excellence

38

Condo rental in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Gulf Front Beach Condo located on Little Gasparilla Island ,Placida, Florida. Right near Placida Property is a Publix grocery store, post office, gas station and a couple of restaurants. Park your car at Placida Property (the mainland) and enjoy a quick ferry ride (co …see more

Certificate of Excellence

from $189 / night

$1323 / week

Book View

from $189 / night

(1) Excellent 

25

Vacation cottage in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Coconut Palm Cottage is brand new to the rental market! This charming home has been lovingly maintained by one owner for years. The lovely tropical foliage and well maintained yard attests to the care and love lavished on this little cottage. Now it is available for …see more

from $300 / night

$1100 - $1300 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $300 / night

(5) Excellent 

28

Vacation home in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Casa Contenta of LGI is a key west style island home ideally situated 500 feet from the Gulf of Mexico and 300 feet from Lemon Bay. Its garden overflows with tropical foliage including palms, hibiscus, bird of paradise, sea grapes, and bougainvillea. The main floor is …see more

from $143 / night

$999 - $1200 / week

Book View

Responds fast!
avg. 2 hours 29 minutes

from $143 / night

(13) Excellent 

33

Little Gasparilla Island Vacation cottage rental

Southwest Gulf Coast / Little Gasparilla Island

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Hibiscus House is a sparkling clean cottage in one of the most superb locations in Florida. It features fresh, beachy decor, dramatic Gulf views, bright, sunshine-filled rooms, a nearly deserted beach and it includes everything to make your beach vacation memorable.... …see more

from $343 / night

$2400 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $343 / night

(1) Excellent 

22

Vacation home in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
RoseMary's Beach House is a small jewel of a beach house! It is located directly on the beach, with unparalled views and access to the water. Your front deck literally sits right on the beach! Inside, this home is a gem....designer furnishings with tropical flair, hi …see more

from $375 / night

$1950 - $2200 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $375 / night

(2) Very Good 

38

Cottage rental in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This classic island house has been a fixture on Little Gasparilla Island for over 30 years. The new owners have lovingly redecorated and renovated the interior while keeping the quaint charm of the original "round" design. Everything has been updated, with new steps a …see more

from $300 / night

$1700 - $2100 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $300 / night

21

Vacation cottage in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Angler's Paradise is located on beautiful Little Gasparilla Island, one of the most pristine barrier islands in Florida. This island has no bridge and can only be reached via private boat or water taxi, which means that your stay here will be one of peace and tranquili …see more

from $275 / night

$1100 - $1400 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $275 / night

(2) Very Good 

24

Vacation home in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Sunset Beach house is a spacious and sunny four-bedroom home located directly on the Gulf of Mexico. It is has one of the most spacious gulf-front porches on the island, with both a large outdoor sunning porch, a covered, screened porch for dining and a private porch u …see more

from $315 / night

$2200 - $2696 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $315 / night

(5) Excellent 

45

Vacation cottage in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This villa, located on beautiful Little Gasparilla Island, features peace and privacy in a serene tropical setting. Located just a short stroll from the beach, it offers dramatic Gulf views, bright sun-filled rooms and luxurious and elegant furnishings. The master be …see more

from $258 / night

$1800 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $258 / night

14

Vacation home in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
The 'La Te Da' house is a two story key west style home located directly on the Gulf of Mexico. The backyard is a private beach, you are simply foot steps away from beautiful turquoise water and sandy beach. We are next to Boca Grande, which is known for the world famou …see more

from $315 / night

$2200 / week

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from $315 / night

13

Vacation home in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
View of The Bay from the front porch.. 1200 square foot living area. Creatively decorated very comfortable. All the conveniences of home yet surrounded by the pristine natural elements of a remote island community. Spacious kitchen, dining and living room, cathedral cei …see more

from $195 / night

$1575 - $1785 / week

Book View

Responds fast!
avg. 2 hours 2 minutes

from $195 / night

22

Vacation cottage in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Serenity Cottage is an oasis of peace and privacy located on one of Florida's most beautiful barrier islands. This lovely cottage is a respite from the hustle and bustle and is just a short walk to the beach or the bay....for the best of both worlds when it comes to is …see more

from $250 / night

$995 - $1400 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $250 / night

20

Vacation home in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
This beautiful beach home is the perfect place to stay at this amazing island getaway! The open floor plan is filled with fun and cheerful decorations and comfortable furnishings. This 3 bedroom 2.5 bath, plus loft can sleep 10 comfortably and has something fun for ever …see more

from $300 / night

$1800 - $2620 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $300 / night

(2) Excellent 

39

Vacation cottage in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
SeaGrape Escape is a brand new beach cottage on charming SeaGrape Lane...just steps from the bay for easy fishing and kayaking! Plus, seven miles of beautiful, pristine beach is just a short stroll down SeaGrape Lane. This cottage is perfectly situated to offer you th …see more

from $215 / night

$1500 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $215 / night

(10) Very Good 

46

Little Gasparilla Island Vacation villa rental

Southwest Gulf Coast / Little Gasparilla Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
COCONUT HIDEAWAY is one of the most charming and unique homes on the island. This is our private home -- not a 'rental unit' -- and we have decorated it with antiques, oriental carpets, original artwork and many collections from our travels abroad. Our Caribbean-inspir …see more

from $315 / night

$2200 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $315 / night

(1) Excellent 

13

Vacation home rental

Southwest Gulf Coast / Little Gasparilla Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Looking for that perfect getaway beach home? No noise, luxurious solitude of the island, a deck to watch the magic of the sun setting again and again...and rising the next morning....a spectacular setting to experience Gulf-front living. Best Sunsets, Best Beach Waves, …see more

from $286 / night

$2000 / week

Book View

from $286 / night

(1) Excellent 

42

Vacation home in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This lovely 2 story home is situated right on the Bay. Arrive at your own private dock Walk past new outdoor shower, to front porch to enjoy serene view of bay. Lucky Me is tiled thru-out, and features spacious master bedroom with king size bed, large walk-in closet, c …see more

from $230 / night

$1500 / week

Book View

Responds fast!
avg. 3 hours 30 minutes

from $230 / night