Featured
Exterior
Pool
Interior
Living area
Private kitchen

Villa Brillante: Cape Coral Waterfront Villa, Sleeps 6

3 bedrooms·2 baths
Cape Coral • Florida
5(2 reviews)

$2,657.95 USD total for 6 nights

Oct 22 – 28, 2026

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

Oct 22 – 26, 2026

Secluded sunset views
Large island for dining or entertainment
Centrally located
Guest Registry
Fully equipped kitchen

Herda Hideaway on Little Gasparilla Island

2 bedrooms·2 baths
Little Gasparilla Island • Florida
5(40 reviews)

$931.00 USD $817.60 USD total for 3 nights

Oct 22 – 25, 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)

$1,568.00 USD $1,500.80 USD total for 6 nights

Oct 22 – 28, 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

Dec 16 – 20, 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)

$4,235.43 USD total for 5 nights

Nov 1 – 6, 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(16 reviews)

$5,114.70 USD total for 5 nights

Dec 6 – 11, 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)

$3,124.94 USD $2,880.77 USD total for 5 nights

Oct 26 – 31, 2026

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

Oct 22 – 25, 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)

$6,132.04 USD total for 7 nights

Oct 22 – 29, 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

Oct 22 – 29, 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)

$2,886.06 USD $2,665.78 USD total for 5 nights

Oct 22 – 27, 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)

$9,765.00 USD total for 30 nights

Apr 1 – May 1, 2027

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

Oct 22 – Nov 19, 2026

HEATED SALT WATER POOL! This beautiful modern pool gets up to 5ft in depth, and has enough room for all the friends and family. With a stunning background, a fully enclosed screened in lanai, and fountains, escape into the tranquility of luxury.
Raised Ceilings, Room darkening shades, and a modern, cozy feel with seating for up to 6! Fan has remote control with 3 settings & lights
Large area to prepare meals, double door refrigerator and freezer, reverse mount sink with dish washer, oven, plenty of storage space and remote soap dispenser
A Large, king mattress is provided for the main bedroom. This very large room also has 2 night stands, overhead remote control fan, LED streaming TV, darkening shades and blinds, and your own private bathroom.
Our beautiful pool has fountains and sprayers with LED lights and 2 sun loungers to really enjoy your stay in privacy. The lush foliage around the entire pool deck allows complete tranquility!

Modern Villa Heated Saltwater Pool 10 Min to Beach

3 bedrooms·2 baths
Rotonda West • Florida

$679.10 USD total for 3 nights

Oct 25 – 28, 2026

Your private saltwater pool, with complimentary heating included in every stay. Heating target: 85°F (29°C), weather permitting. Enjoy tropical surroundings, lounge chairs, and your own screened lanai.
Spacious living area with vaulted ceiling detail, ceiling fan, large TV, tropical accent chairs, and easy access to the nearby bedroom.
Bright, open kitchen with white cabinetry, stainless steel appliances, a large stone island with bar seating, and easy access to the dining area and screened patio.
This inviting primary bedroom offers a king bed, elegant tray ceiling, ceiling fan, dresser storage, and direct access to the ensuite bathroom. Soft coastal decor, bright lighting, and plenty of open floor space make the room feel airy and clean!
Enjoy evenings by your private saltwater pool, with complimentary pool heating included in every stay. Heating target: 85°F (29°C), weather permitting. Pool and enclosure lighting make the lanai especially inviting after sunset.

Heated Saltwater Pool | Near Beach | Pets Welcome!

3 bedrooms·2 baths
Rotonda West • Florida

$588.80 USD total for 3 nights

Oct 22 – 25, 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

$2,100.00 USD total for 7 nights

Oct 22 – 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)

$445.00 USD total for 3 nights

Oct 22 – 25, 2026

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

Oct 30 – Nov 4, 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)

$4,124.82 USD total for 7 nights

Oct 22 – 29, 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

$888.00 USD total for 3 nights

Dec 2 – 5, 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

$460.86 USD total for 4 nights

Nov 26 – 30, 2026