Hot-tub & Pool , Pet & Family friendly Resort
Hot-tub & Pool , Pet & Family friendly Resort
Hot-tub & Pool , Pet & Family friendly Resort
Hot-tub & Pool , Pet & Family friendly Resort
Hot-tub & Pool , Pet & Family friendly Resort

Hot-tub & Pool , Pet & Family friendly Resort

2 bedrooms·1 bath
Arcadia • Florida
5(25 reviews)

$424.00 USD total for 3 nights

Oct 17 – 20, 2026

Bedroom
House from front
Pool on back of the house
Guest unit entrance from right side
Shower

Peaceful private unit with own entrance and pool

1 bedroom·1 bath
Punta Gorda • Florida
5(1 review)

$290.00 USD total for 3 nights

Oct 25 – 28, 2026

Amazing Deep Creek Golf Course
Amazing Deep Creek Golf Course
Amazing Deep Creek Golf Course
Amazing Deep Creek Golf Course
Amazing Deep Creek Golf Course

Amazing Deep Creek Golf Course

2 bedrooms·2 baths
Punta Gorda • Florida

$775.00 USD total for 3 nights

Oct 17 – 20, 2026

2+ Acres 3BR/2BA 2200 Sq.ft Salt Heated Pool
2+ Acres 3BR/2BA 2200 Sq.ft Salt Heated Pool
2+ Acres 3BR/2BA 2200 Sq.ft Salt Heated Pool
2+ Acres 3BR/2BA 2200 Sq.ft Salt Heated Pool
2+ Acres 3BR/2BA 2200 Sq.ft Salt Heated Pool

2+ Acres 3BR/2BA 2200 Sq.ft Salt Heated Pool

3 bedrooms·2 baths
North Port • Florida
4.44(18 reviews)

$692.00 USD total for 3 nights

Oct 17 – 20, 2026

3BR Waterfront Home w/ Dock & Canal Access
3BR Waterfront Home w/ Dock & Canal Access
3BR Waterfront Home w/ Dock & Canal Access
3BR Waterfront Home w/ Dock & Canal Access
3BR Waterfront Home w/ Dock & Canal Access

3BR Waterfront Home w/ Dock & Canal Access

3 bedrooms·2 baths
Punta Gorda • Florida

$11,766.00 USD total for 3 nights

Aug 14 – 17, 2027

Enjoy the outdoor oasis with a dip in relaxation heaven, surrounded by the lush botanical of Florida!
Enjoy the light and airy space for chilling, sleeping, or hanging out!
This space offers ample room for relaxation with the family for a TV night or sleeping arrangements with a pullout extra bed.
Living room image 3
Living room image 4

Pineapple Paradise SWFL

2 bedrooms·2 baths
Port Charlotte • Florida
5(3 reviews)

$762.00 USD total for 3 nights

Oct 17 – 20, 2026

Modern, elegant, and luxurious. image 1
Modern, elegant, and luxurious. image 2
Modern, elegant, and luxurious. image 3
Modern, elegant, and luxurious. image 4
Modern, elegant, and luxurious. image 5

Southwest Florida Modern Retreat

3 bedrooms·2 baths
Port Charlotte • Florida
5(9 reviews)

$819.84 USD total for 3 nights

Oct 17 – 20, 2026

3BR Home with Pool & Parking, Solar Power
3BR Home with Pool & Parking, Solar Power
3BR Home with Pool & Parking, Solar Power
3BR Home with Pool & Parking, Solar Power
3BR Home with Pool & Parking, Solar Power

3BR Home with Pool & Parking, Solar Power

3 bedrooms·2 baths
Venice • Florida

$737.89 USD total for 3 nights

Oct 17 – 20, 2026

4BR - Heated Pool and Lanai
4BR - Heated Pool and Lanai
4BR - Heated Pool and Lanai
4BR - Heated Pool and Lanai
4BR - Heated Pool and Lanai

4BR - Heated Pool and Lanai

4 bedrooms·2 baths
North Port • Florida

$1,200.19 USD total for 3 nights

Oct 17 – 20, 2026

Dockside and Waterfront with Pool in Charlotte Harbor
Dockside and Waterfront with Pool in Charlotte Harbor
Dockside and Waterfront with Pool in Charlotte Harbor
Dockside and Waterfront with Pool in Charlotte Harbor
Dockside and Waterfront with Pool in Charlotte Harbor

Dockside and Waterfront with Pool in Charlotte Harbor

2 bedrooms·2 baths
Port Charlotte • Florida

$794.08 USD total for 4 nights

Oct 17 – 21, 2026

3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops
3BR Coastal Escape Near Beaches, Golf & Shops

3BR Coastal Escape Near Beaches, Golf & Shops

3 bedrooms·2 baths
North Port • Florida

$840.00 USD total for 3 nights

Oct 17 – 20, 2026

Salt Water Heated Pool- No Additional Charge
Pool View- Master Bedroom Sliding Glass Door
Sunset at the pool
Walkway to the private dock and boat lift
Pets welcome at Villa Hibiscus!

Dog Friendly | Walk to Fishermen’s Village • Pool

3 bedrooms·3 baths
Punta Gorda • Florida
5(55 reviews)

$1,433.15 USD total for 3 nights

Oct 19 – 22, 2026

Waterfront • Canal View • Games • King Bed
Waterfront • Canal View • Games • King Bed
Waterfront • Canal View • Games • King Bed
Waterfront • Canal View • Games • King Bed
Waterfront • Canal View • Games • King Bed

Waterfront • Canal View • Games • King Bed

2 bedrooms·2 baths
Port Charlotte • Florida

$543.90 USD total for 3 nights

Oct 17 – 20, 2026

3BR Coastal Oasis: Waterfront Home with Pool
3BR Coastal Oasis: Waterfront Home with Pool
3BR Coastal Oasis: Waterfront Home with Pool
3BR Coastal Oasis: Waterfront Home with Pool
3BR Coastal Oasis: Waterfront Home with Pool

3BR Coastal Oasis: Waterfront Home with Pool

3 bedrooms·2 baths
Port Charlotte • Florida

$1,267.22 USD total for 3 nights

Jan 2 – 5, 2027

Heated Salt Water Pool/Spa/Canal
Outdoor Seating by pool/spa-overlooking canal
Outdoor lanai with heated, saltwater pool and hot tub
Outdoor seating and dining on the lanai
Outdoor lanai with heated, saltwater pool and hot tub

Villa Tropical | Waterfront Luxury Retreat • Panoramic Water Views, Pool & Spa

3 bedrooms·2 baths
Punta Gorda • Florida
4.95(21 reviews)

$2,014.62 USD total for 3 nights

Nov 15 – 18, 2026

Screened Lanai - Heated Saltwater Pool - Hot Tub - Canal
Furnished outdoor lanai with TV, pool, hot tub, grill
Enjoy your stay at stunning Villa Tranquility!
26 270 Delido Court-13
Relaxing by the pool

Villa Tranquility | Waterfront Pool & Spa Retreat Near Fishermen’s Village

3 bedrooms·2 baths
Punta Gorda • Florida
4.83(23 reviews)

$1,338.11 USD total for 3 nights

Oct 25 – 28, 2026

Pool and Sun Loungers
Open Concept Living Room - Dining - Kitchen
Enjoy your stay at Villa Capri!
Relaxing by the heated, saltwater pool
Enjoy your stay at stunning Villa Capri!

Villa Capri | Waterfront Escape • Heated Saltwater Pool & Private Dock

3 bedrooms·2 baths
Punta Gorda • Florida
4.84(45 reviews)

$1,282.20 USD total for 3 nights

Oct 17 – 20, 2026

Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool
Canalfront Punta Gorda Retreat w/ Private Pool

Canalfront Punta Gorda Retreat w/ Private Pool

4 bedrooms·3 baths
Punta Gorda • Florida

$26,107.80 USD total for 3 nights

Oct 17 – 20, 2026

Bright, cozy living room with stylish decor and plenty of natural light
Bright modern living room with cozy seating and open kitchen pass-through
Cozy modern living room with stylish decor and open kitchen connection
Bright, stylish living room with TV and open flow to the kitchen
Bright, stylish living room with large windows and cozy seating

Skelatal Listing: Rebecca Drost - 3705 Toulouse Ct, Punta Gorda, Florida 33950

4 bedrooms·3 baths
Punta Gorda • Florida

$30,897.00 USD total for 3 nights

Oct 17 – 20, 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

Nov 1 – 4, 2026

Entire home in North Port, Florida
Entire home in North Port, Florida
Entire home in North Port, Florida
Entire home in North Port, Florida
Entire home in North Port, Florida

Entire home in North Port, Florida

4 bedrooms·1 bath
North Port • Florida
5(25 reviews)

$560.00 USD total for 3 nights

Oct 17 – 20, 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

Oct 17 – 20, 2026

Lakefront Estate • Sleeps 25+ • Game Room
Lakefront Estate • Sleeps 25+ • Game Room
Lakefront Estate • Sleeps 25+ • Game Room
Lakefront Estate • Sleeps 25+ • Game Room
Lakefront Estate • Sleeps 25+ • Game Room

Lakefront Estate • Sleeps 25+ • Game Room

9 bedrooms·4 baths
Highlands County • Florida
$875 – $2,000/ night(excl. fees & taxes)