Front of building
one of the community pools
Serene First-Level Condo with Pool Access
Serene First-Level Condo with Pool Access
Dining room

Serene First-Level Condo with Pool Access

2 bedrooms·2 baths
Naples • Florida

$4,020.00 USD total for 30 nights

Oct 30 – Nov 29, 2026

Superb location 3bed/2bath ~ 1.5 mile to the beach
Welcome to Casa Capri
Family room
Living room
Superb location 3bed/2bath ~ 1.5 mile to the beach

Superb location 3bed/2bath ~ 1.5 mile to the beach

3 bedrooms·2 baths
Naples • Florida
5(180 reviews)

$666.40 USD total for 3 nights

Oct 30 – Nov 2, 2026

Morningside Luxury Escape - New Build-Pool & Spa
Morningside Luxury Escape - New Build-Pool & Spa
Morningside Luxury Escape - New Build-Pool & Spa
Morningside Luxury Escape - New Build-Pool & Spa
Morningside Luxury Escape - New Build-Pool & Spa

Morningside Luxury Escape - New Build-Pool & Spa

4 bedrooms·4 baths
Naples • Florida

$2,759.80 USD total for 3 nights

Oct 30 – Nov 2, 2026

Community Pool/Restaurant
Community Hot Tub
Front Entrance 1st Floor Unit
Entrance/family room
Remodeled Kitchen

Naples Florida - World Tennis Club

2 bedrooms·2 baths
Naples • Florida

$14,255.00 USD total for 90 nights

Oct 30, 2026 – Jan 28, 2027

Naples Winter Escape at Positano Place
Swimming pool
Naples Winter Escape at Positano Place
Naples Winter Escape at Positano Place
Naples Winter Escape at Positano Place

Naples Winter Escape at Positano Place

2 bedrooms·2 baths
Naples • Florida

$4,975.00 USD total for 30 nights

Oct 30 – Nov 29, 2026

4 Private Suites in a New Ultra Luxury Residence
4 Private Suites in a New Ultra Luxury Residence
4 Private Suites in a New Ultra Luxury Residence
4 Private Suites in a New Ultra Luxury Residence
4 Private Suites in a New Ultra Luxury Residence

4 Private Suites in a New Ultra Luxury Residence

4 bedrooms·4 baths
Naples • Florida
5(2 reviews)

$3,000.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

NEAR BEACH/ FENCED DOGGIE AREA! COZY BEACH HOME!
NEAR BEACH/ FENCED DOGGIE AREA! COZY BEACH HOME!
NEAR BEACH/ FENCED DOGGIE AREA! COZY BEACH HOME!
Queen bed with Twin bed on top
Queen bed with Twin bed on top

NEAR BEACH/ FENCED DOGGIE AREA! COZY BEACH HOME!

2 bedrooms·1 bath
Naples • Florida
4.58(72 reviews)

$665.08 USD total for 3 nights

Oct 30 – Nov 2, 2026

The Fitz
The Fitz
Kitchen and Breakfast Bar
Master Bedroom
Master Bathroom

The Fitz

3 bedrooms·2 baths
North Naples • Florida
5(30 reviews)

$4,429.84 USD total for 7 nights

Nov 17 – 24, 2026

Starfruit Beach House - Heated Pool Near Beach
Island with seating for three
The primary bedroom with king bed
Second king bedroom
A gorgeous private pool awaits you in lovely Naples, FL. Bike to Vanderbilt Beach!

Starfruit Beach House - Heated Pool Near Beach

3 bedrooms·2 baths
Naples • Florida
5(4 reviews)

$1,165.50 USD total for 3 nights

Mar 8 – 11, 2027

Closest 1/1 to Vanderbilt Bch, full kitchen +more!
Closest 1/1 to Vanderbilt Bch, full kitchen +more!
Closest 1/1 to Vanderbilt Bch, full kitchen +more!
Closest 1/1 to Vanderbilt Bch, full kitchen +more!
Closest 1/1 to Vanderbilt Bch, full kitchen +more!

Closest 1/1 to Vanderbilt Bch, full kitchen +more!

1 bedroom·1 bath
North Naples • Florida

$1,780.00 USD total for 5 nights

Oct 30 – Nov 4, 2026

Studio closest to Bch, yard, everything, & extras!
Studio closest to Bch, yard, everything, & extras!
Studio closest to Bch, yard, everything, & extras!
Studio closest to Bch, yard, everything, & extras!
Studio closest to Bch, yard, everything, & extras!

Studio closest to Bch, yard, everything, & extras!

0 bedrooms·1 bath
North Naples • Florida
5(2 reviews)

$1,500.00 USD total for 5 nights

Oct 30 – Nov 4, 2026

Starfruit - Vanderbilt Beach House
Starfruit - Vanderbilt Beach House
Starfruit - Vanderbilt Beach House
A gorgeous private pool awaits you in lovely Naples, FL. Bike to Vanderbilt Beach!
With 8 sets of loungers, choose between sun and shade at all times of day.

Starfruit - Vanderbilt Beach House

3 bedrooms·2 baths
Naples • Florida

$902.43 USD total for 3 nights

Nov 7 – 10, 2026

Seas The Day
Seas The Day
Seas The Day
Seas The Day
Seas The Day

Seas The Day

3 bedrooms·2 baths
Naples • Florida

$1,743.53 USD total for 5 nights

Oct 30 – Nov 4, 2026

BEACHSIDE GETAWAY *FENCED AREA*-Walk/Bike to beach
BEACHSIDE GETAWAY *FENCED AREA*-Walk/Bike to beach
BEACHSIDE GETAWAY *FENCED AREA*-Walk/Bike to beach
BEACHSIDE GETAWAY *FENCED AREA*-Walk/Bike to beach
BEACHSIDE GETAWAY *FENCED AREA*-Walk/Bike to beach

BEACHSIDE GETAWAY *FENCED AREA*-Walk/Bike to beach

1 bedroom·1 bath
Naples • Florida
4.66(64 reviews)

$856.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

Aerial view of backyard
Living Room
Living Room
Living Room
Fully equipped kitchen

The Oasis

3 bedrooms·2 baths
North Naples • Florida
4.96(50 reviews)

$1,513.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

The Sun-kissed Retreat • Near Vanderbilt Beach
The Sun-kissed Retreat • Near Vanderbilt Beach
LIVING ROOM | Spacious and comfortable pullout sectional
KITCHEN | Fully equipped with all the cooking essentials
PRIMARY | Spacious room with king bed and workspace area

The Sun-kissed Retreat • Near Vanderbilt Beach

3 bedrooms·2 baths
Naples • Florida
5(50 reviews)
$350/ night(excl. fees & taxes)
Heated Pool & Hot Tub, Walk to Beach, Free Bikes
Heated Pool & Hot Tub, Walk to Beach, Free Bikes
Heated Pool & Hot Tub, Walk to Beach, Free Bikes
Heated Pool & Hot Tub, Walk to Beach, Free Bikes
Heated Pool & Hot Tub, Walk to Beach, Free Bikes

Heated Pool & Hot Tub, Walk to Beach, Free Bikes

3 bedrooms·2 baths
Naples • Florida
5(2 reviews)

$1,843.52 USD $1,647.54 USD total for 4 nights

Oct 30 – Nov 3, 2026

mit gemeinschaftlichem Pool
mit gemeinschaftlichem Pool
mit gemeinschaftlichem Pool
mit gemeinschaftlichem Pool
mit gemeinschaftlichem Pool

mit gemeinschaftlichem Pool

2 bedrooms·2 baths
Naples • Florida
Multiple views
Aerial view. 0.9 mile walk to beach.
Living Room
Front door
Spacious Living room with 55" smart TV

Naples Beach house retreat, just 3 min. to beach

2 bedrooms·1 bath
North Naples • Florida
5(1 review)

$1,234.00 USD total for 3 nights

Oct 30 – Nov 2, 2026

Welcome to Eagles Nest Florida
Take a deep breath and unwind as you enjoy this Naples home.
Surround yourself with beauty, comfort and the serenity of nature.
The natural Florida sunshine pours in every room. Come and enjoy your very own Florida vacation, in your home away from home.
Relax and feel right at home, with a glass of wine after a long day of exploring Naples. Spend time together and indulge yourself if this tropical retreat.

Eagles Nest Florida

2 bedrooms·2 baths
Naples • Florida
5(47 reviews)

$650.63 USD total for 3 nights

Oct 30 – Nov 2, 2026

Beach 🏝 Life
Beach 🏝 Life
Beach 🏝 Life
Beach 🏝 Life
Beach 🏝 Life

Beach 🏝 Life

3 bedrooms·2 baths
Naples • Florida
4.92(24 reviews)

$911.60 USD total for 4 nights

Nov 3 – 7, 2026

Emerald Oasis Naples • Luxury Stay by 5th Ave
Emerald Oasis Naples • Luxury Stay by 5th Ave
Emerald Oasis Naples • Luxury Stay by 5th Ave
Emerald Oasis Naples • Luxury Stay by 5th Ave
Emerald Oasis Naples • Luxury Stay by 5th Ave

Emerald Oasis Naples • Luxury Stay by 5th Ave

2 bedrooms·1 bath
Naples • Florida
4.5(10 reviews)

$868.16 USD total for 3 nights

Oct 30 – Nov 2, 2026

Naples Luxe Coral Oasis - Walk to the beach and 5th Ave
Naples Luxe Coral Oasis - Walk to the beach and 5th Ave
Naples Luxe Coral Oasis - Walk to the beach and 5th Ave
Naples Luxe Coral Oasis - Walk to the beach and 5th Ave
Naples Luxe Coral Oasis - Walk to the beach and 5th Ave

Naples Luxe Coral Oasis - Walk to the beach and 5th Ave

2 bedrooms·1 bath
Naples • Florida
4.2(5 reviews)

$797.02 USD total for 3 nights

Oct 30 – Nov 2, 2026

Minimalist Haven Naples • Walk to Beach & 5th Ave
Minimalist Haven Naples • Walk to Beach & 5th Ave
Minimalist Haven Naples • Walk to Beach & 5th Ave
Minimalist Haven Naples • Walk to Beach & 5th Ave
Minimalist Haven Naples • Walk to Beach & 5th Ave

Minimalist Haven Naples • Walk to Beach & 5th Ave

2 bedrooms·1 bath
Naples • Florida
4.33(9 reviews)

$908.54 USD total for 3 nights

Oct 30 – Nov 2, 2026