Sunset from the condo
Walkway to public beach
Brand new kitchen w/ spices, plenty of plates, pots, pans and utensils.
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 7 – 11, 2026

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 7 – 13, 2026

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 7 – 11, 2026

Waterfront Retreat with Private Pool | Spacious 3BR, Sleeps 10
Living Area
Outdoor Dining
Pool
King Bed

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

3 bedrooms·3 baths
Rotonda West • Florida
Latitude Adjustment on North Captiva- Beachfront
Eastern view provides and amazing sunrise and shade in the hot afternoon. Check out the manatee visiting the dock!
Latitude Adjustment on North Captiva- Beachfront
Latitude Adjustment on North Captiva- Beachfront
There are 5 miles of beautiful beaches to walk on North Captiva, two-thirds of which border a 700-acre state land preserve.

Latitude Adjustment on North Captiva- Beachfront

4 bedrooms·4 baths
Captiva • Florida
5(72 reviews)

$4,776.20 USD total for 5 nights

Sep 7 – 12, 2026

Large private heated pool with expansive lounging space to soak up Florida rays
Water View from Balcony after New House
View of the pool and Gulf of Mexico from the upstairs lanai
Water View from Screened Lanai after New House
Near beachfront, great views of the Gulf of Mexico before New House

Captiva Isles on North Captiva

3 bedrooms·2½ baths
Lee County • Florida
4.93(15 reviews)
$600/ night(excl. fees & taxes)
2 full screened in decks for peaceful relaxation
Play a game in the screened in porch with a million dollar view!
Enjoy the sunset hour from atop!
Fresh breeze while cooking island eats
Pool complete with outdoor shower and foot washers near both steps

Isle Escape

5 bedrooms·5 baths
Inlet Beach • Florida
5(15 reviews)

$4,081.20 USD total for 5 nights

Sep 7 – 12, 2026

Welcome to Tortuga Sunset—your island home awaits 🏡🌴
“Open spaces, cozy places—your perfect beachside retreat 🌊🛋️”
“Gather ‘round—meals taste better with a side of island vibes 🍽️🌴”
Master Bedroom-King bed
Spacious, inviting, and ready to welcome all. Our home offers room for everyone, ensuring that every gathering is filled with laughter, warmth, and shared moments. Create memories that resonate in every corner

Tortuga Sunset

3 bedrooms·3½ baths
Captiva • Florida
5(1 review)
$362 – $1,986/ night(excl. fees & taxes)
Exterior detail
Outdoor dining
Exterior
Outdoor dining
Terrace/patio

Island Oasis/Hidden Beach House-Private pool

3 bedrooms·2 baths
Captiva • Florida
5(75 reviews)

$1,338.00 USD $1,070.40 USD total for 3 nights

Sep 7 – 10, 2026

Stella Maris on North Captiva-Beachfront Paradise
Stella Maris on North Captiva-Beachfront Paradise
Stella Maris on North Captiva-Beachfront Paradise
Stella Maris on North Captiva-Beachfront Paradise
Hot tub with a view

Stella Maris on North Captiva-Beachfront Paradise

3 bedrooms·4 baths
Captiva • Florida
5(42 reviews)

$5,749.60 USD total for 7 nights

Sep 7 – 14, 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 7 – 14, 2026

Dive into pure bliss in our outdoor paradise. Immerse yourself in the warmth of luxury with an inviting heated pool and spa that redefine relaxation. Let the tranquil waters and tropical surroundings transport you to a haven of serenity
“Pulling up to paradise… and the fun starts now! 🏝️✨”
Experience the seamless flow of space in our open floor plan, where each room gracefully transitions into the next. A design that fosters connection, natural light, and an expansive sense of freedom. Welcome to a living space that feels as open as the poss
“4 bed, 3 bath, 100% island vibes 💚🏝️”
“Grillin’ and chillin’ island style 🔥🌴”

Green Tortuga

4 bedrooms·3 baths
Captiva • Florida
5(4 reviews)
$350 – $1,601/ night(excl. fees & taxes)
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 7 – 10, 2026

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

$5,480.00 USD total for 28 nights

Sep 7 – Oct 5, 2026

Quiet one bedroom in Bokeelia
Quiet one bedroom in Bokeelia
Quiet one bedroom in Bokeelia
Quiet one bedroom in Bokeelia
Quiet one bedroom in Bokeelia

Quiet one bedroom in Bokeelia

1 bedroom·1 bath
Bokeelia • Florida
$300/ night(excl. fees & taxes)
Heated pool
Entrance
Entrance
Living room
Living room

Sandi Villa

3 bedrooms·2 baths
Cape Coral • Florida

$1,312.78 USD total for 5 nights

Sep 7 – 12, 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)
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 7 – 12, 2026

Serenity’s Edge Reflections
Serenity’s Edge saltwater infinity edge private pool
Serenity’s Edge
Front Entry
Interior Entry hallway looking in

Serenity’s Edge

4 bedrooms·4 baths
Cape Coral • Florida
5(1 review)

$2,679.74 USD total for 4 nights

Sep 7 – 11, 2026

Casa Champion
Casa Champion
Casa Champion
Casa Champion
Casa Champion

Casa Champion

4 bedrooms·3 baths
Cape Coral • Florida

$1,549.85 USD total for 4 nights

Sep 7 – 11, 2026

Gulf Coast Retreat: 3BR Waterfront | Heated Pool
Gulf Coast Retreat: 3BR Waterfront | Heated Pool
Gulf Coast Retreat: 3BR Waterfront | Heated Pool
Gulf Coast Retreat: 3BR Waterfront | Heated Pool
Gulf Coast Retreat: 3BR Waterfront | Heated Pool

Gulf Coast Retreat: 3BR Waterfront | Heated Pool

3 bedrooms·3 baths
Cape Coral • Florida
$129 – $1,000/ night(excl. fees & taxes)
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

$405.57 USD total for 4 nights

Sep 7 – 11, 2026

Villa Kokopelli Leben Sie den Traum - es ist Ihre Zeit.
Villa Kokopelli Leben Sie den Traum - es ist Ihre Zeit.
Villa Kokopelli Leben Sie den Traum - es ist Ihre Zeit.
Villa Kokopelli Leben Sie den Traum - es ist Ihre Zeit.
Villa Kokopelli Leben Sie den Traum - es ist Ihre Zeit.

Villa Kokopelli Leben Sie den Traum - es ist Ihre Zeit.

5 bedrooms·3 baths
Cape Coral • Florida
$579 – $610/ night(excl. fees & taxes)
3BR Cape Coral Waterfront Home | Pool & Lanai
3BR Cape Coral Waterfront Home | Pool & Lanai
3BR Cape Coral Waterfront Home | Pool & Lanai
3BR Cape Coral Waterfront Home | Pool & Lanai
3BR Cape Coral Waterfront Home | Pool & Lanai

3BR Cape Coral Waterfront Home | Pool & Lanai

3 bedrooms·2 baths
Cape Coral • Florida

$882.51 USD total for 3 nights

Sep 7 – 10, 2026