Location

Dates

Guests

Vacation rentals in Little Gasparilla Island, Florida, United States

Down by the Bay

Down by the Bay

Down by the Bay

Down by the Bay

Down by the Bay

Down by the Bay

2 bedrooms·2 baths

Englewood • Florida

$175 – $225/ night(excl. fees & taxes)

Waterfront Retreat with Private Pool | Spacious 3BR, Sleeps 10

Waterfront Retreat with Private Pool | Spacious 3BR, Sleeps 10

3 bedrooms·3 baths

Rotonda West • Florida

Sunshine and blue skies as far as the eye can see

Open concept living area with sliders to the lanai and a 55" smart TV

The kitchen is fully stocked!

Plenty of outdoor seating on our lanai

Paradise awaits!

Flip Flops and Tank Tops

3 bedrooms·2 baths

Rotonda West • Florida

5(19 reviews)

$1,561.28 USD $1,427.56 USD total for 6 nights

Sep 23 – 29, 2026

Master king bedroom with en suite bathroom

Home with hot tub, 5 miles to Englewood beach image 2

Home with hot tub, 5 miles to Englewood beach image 3

Home with hot tub, 5 miles to Englewood beach image 4

Home with hot tub, 5 miles to Englewood beach image 5

Home with hot tub, 5 miles to Englewood beach

2 bedrooms·2 baths

Englewood • Florida

4.98(54 reviews)

$80 – $149/ night(excl. fees & taxes)

Secluded sunset views

Large stainless sink with disposal

Fully renovated with large custom island

Luxury Condo on Little Gasparilla Island-Family Friendly, ferry included

2 bedrooms·2 baths

Little Gasparilla Island • Florida

5(40 reviews)

$215/ night(excl. fees & taxes)

Beautiful, Clean, Open Floor plan, pool faces SW

Beautiful, Clean, Open Floor plan, pool faces SW

Beautiful, Clean, Open Floor plan, pool faces SW

Beautiful, Clean, Open Floor plan, pool faces SW

Beautiful, Clean, Open Floor plan, pool faces SW

Beautiful, Clean, Open Floor plan, pool faces SW

3 bedrooms·3 baths

Rotonda West • Florida

$930.00 USD total for 4 nights

Sep 23 – 27, 2026

Simple Old Florida Style Home image 1

Simple Old Florida Style Home image 2

Simple Old Florida Style Home image 3

Simple Old Florida Style Home image 4

Simple Old Florida Style Home image 5

Bring your motorboat:Simple Old Florida Style Home

2 bedrooms·2 baths

Englewood • Florida

$43 – $106/ night(excl. fees & taxes)

Villa Happy Gator 2 - Tropical Retreat near Beach

Villa Happy Gator 2 - Tropical Retreat near Beach

Villa Happy Gator 2 - Tropical Retreat near Beach

Villa Happy Gator 2 - Tropical Retreat near Beach

Villa Happy Gator 2 - Tropical Retreat near Beach

Villa Happy Gator 2 - Tropical Retreat near Beach

3 bedrooms·2 baths

Englewood • Florida

5(3 reviews)

$1,008.00 USD total for 5 nights

Sep 23 – 28, 2026

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

Englewood Escape: 3BR Water-Front with Pool

3 bedrooms·2 baths

Englewood • Florida

$832.50 USD total for 3 nights

Sep 23 – 26, 2026

Coral cottage 2 miles to the beach bring your boat image 1

Coral cottage 2 miles to the beach bring your boat image 2

Coral cottage 2 miles to the beach bring your boat image 3

Coral cottage 2 miles to the beach bring your boat image 4

Coral cottage 2 miles to the beach bring your boat image 5

Coral cottage 2 miles to the beach bring your boat

2 bedrooms·1 bath

Englewood • Florida

$76 – $138/ night(excl. fees & taxes)

Sunset from the condo

Walkway to public beach

Start your morning w/ a homemade latte or espresso, French press or just coffee!

Large dining table for dinner or a family game night.

Waterfront Island Condo on Boca Grande-Pure Bliss

2 bedrooms·2 baths

Boca Grande • Florida

$1,968.00 USD $1,878.60 USD total for 4 nights

Sep 23 – 27, 2026

5 minutes to the beaches of Boca grande

PLACIDA: 2/2 Villa A, private pool SOUTH GULF COVE

PLACIDA: 2/2 Villa A, private pool SOUTH GULF COVE

PLACIDA: 2/2 Villa A, private pool SOUTH GULF COVE

PLACIDA: 2/2 Villa A, private pool SOUTH GULF COVE

PLACIDA: 2/2 Villa A, private pool SOUTH GULF COVE

2 bedrooms·2 baths

Port Charlotte • Florida

5(29 reviews)

$1,473.00 USD $1,274.55 USD total for 7 nights

Sep 23 – 30, 2026

3 BR Pool Home, Near the Beach & Golf Courses!

3 BR Pool Home, Near the Beach & Golf Courses!

3 BR Pool Home, Near the Beach & Golf Courses!

3 BR Pool Home, Near the Beach & Golf Courses!

3 BR Pool Home, Near the Beach & Golf Courses!

3 BR Pool Home, Near the Beach & Golf Courses!

3 bedrooms·2 baths

Port Charlotte • Florida

$730.24 USD total for 3 nights

Sep 23 – 26, 2026

Pool/Waterfront View

Outdoor Patio Living Space & Outdoor BBQ

Tiki Hut/Dock view

Queen Bedroom, access to lanai

2nd bathroom with tub & shower

Florida's Sunshine Paradise

4 bedrooms·2 baths

Florida

5(3 reviews)

$3.15 USD total for 3 nights

Sep 23 – 26, 2026

Front of the house tucked away in Florida greens

New heated pool

1 of 2 seating areas by the pool

New hotel style lounge chairs

Manasota Beach Vacation Villa

3 bedrooms·3 baths

Englewood • Florida

5(12 reviews)

$1,912.37 USD total for 7 nights

Sep 23 – 30, 2026

Waterfront Paradise image 1

Waterfront Paradise image 2

Waterfront Paradise image 3

Waterfront Paradise image 4

Waterfront Paradise image 5

Waterfront Paradise

2 bedrooms·2 baths

Port Charlotte • Florida

5(5 reviews)

$648.00 USD total for 3 nights

Sep 27 – 30, 2026

Relaxing and inviting private pool

Relaxing and inviting private pool

Relaxing and inviting private pool

Grill for guest use right outside the pool patio area

Sit back and relax on a newly added Leather sofa set watching a new 55” smart TV

Pool Villa by the Beach

2 bedrooms·2 baths

Venice • Florida

$595.00 USD total for 3 nights

Sep 29 – Oct 2, 2026

sit back and relax on this cozy porch

bright ,cheerful open floor plan

cozy wraparound porch

updated fully equipped kitchen with new large sitting island

Tree house by the beach

1 bedroom·1 bath

Venice • Florida

$609.28 USD total for 4 nights

Sep 23 – 27, 2026

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

Abigial's Cottage Snowbird & pet friendly

2 bedrooms·2 baths

North Port • Florida

$866.00 USD total for 3 nights

Sep 23 – 26, 2026

Eclectic painted house

Plush furniture

Easy Access Living Area

Plenty of Seating

356 Azure

3 bedrooms·2 baths

Venice • Florida

$740.15 USD total for 7 nights

Dec 1 – 8, 2026

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 2

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 1

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 3

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 4

Quiet 3BD/2BA Home near Warm Mineral Springs Park image 5

Quiet 3BD/2BA Home near Warm Mineral Springs Park

3 bedrooms·2 baths

North Port • Florida

4.92(12 reviews)

$126/ night(excl. fees & taxes)

Unit 379

2 bedrooms·2 baths

Venice • Florida

4.6(30 reviews)

$5,508.75 USD total for 30 nights

Mar 31 – Apr 30, 2027

Unit 171

2 bedrooms·2 baths

Venice • Florida

4.67(9 reviews)

$5,593.50 USD total for 30 nights

Mar 31 – Apr 30, 2027

Unit 270

2 bedrooms·2 baths

Venice • Florida

$3,096.20 USD total for 29 nights

Apr 30 – May 29, 2027