Location

Dates

Guests

Vacation rentals in Naples

Downtown Naples Retreat - Walk to 5th Ave & Beach

Downtown Naples Retreat - Walk to 5th Ave & Beach

Downtown Naples Retreat - Walk to 5th Ave & Beach

Downtown Naples Retreat - Walk to 5th Ave & Beach

Downtown Naples Retreat - Walk to 5th Ave & Beach

Downtown Naples Retreat - Walk to 5th Ave & Beach

2 bedrooms·1 bath

Naples • Florida

4.85(13 reviews)

$836.34 USD total for 3 nights

Sep 22 – 25, 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)

$824.63 USD total for 3 nights

Sep 22 – 25, 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)

$915.89 USD total for 3 nights

Sep 22 – 25, 2026

We love swimming at sunset and watching the sky change colors right before our eyes!

So much to enjoy at our Costa Bella Retreat in Naples, FL! We have bikes, chairs, umbrella, toys and much more just waiting for you to visit!

Heated Pool*2 Kings*2 miles to Beaches*Spa*Bikes image 3

Come stay with us and experience Naples sunsets from the privacy of our backyard hot tub!

Plenty of room in the fenced backyard to relax and enjoy the Florida sun!

Heated Pool2 Kings2 miles to BeachesSpaBikes

3 bedrooms·3 baths

Naples • Florida

4.98(48 reviews)

$1,020.00 USD total for 3 nights

Sep 22 – 25, 2026

Enjoy your privat pool space

Fun and Love at VILLA BELLY

VILLA BELLY view from the shady dining place

Masterbedroom Kingbed

VILLA BELLY - Poolhome in Naples - enjoy privacy

3 bedrooms·2 baths

Naples • Florida

4.96(28 reviews)

$4,793.60 USD total for 14 nights

Jan 1 – 15, 2027

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

Sep 22 – 25, 2026

Dining area leading to kitchen & front door

Queen Room showing vanity

Paradise Coast Townhome - Heated Pool

2 bedrooms·1½ baths

Naples • Florida

$1,400.00 USD total for 28 nights

Oct 31 – Nov 28, 2026

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

Welcome to Casa Capri

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)

$652.96 USD total for 3 nights

Oct 17 – 20, 2026

Front of building

one of the community pools

Serene First-Level Condo with Pool Access

Serene First-Level Condo with Pool Access

Serene First-Level Condo with Pool Access

2 bedrooms·2 baths

Naples • Florida

$134/ night(excl. fees & taxes)

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

Sep 22 – Dec 21, 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)

$635.63 USD total for 3 nights

Sep 22 – 25, 2026

Naples Ground Floor Fabulous Falling Waters Davis

Naples Ground Floor Fabulous Falling Waters Davis

Naples Ground Floor Fabulous Falling Waters Davis

Naples Ground Floor Fabulous Falling Waters Davis

Naples Ground Floor Fabulous Falling Waters Davis

Naples Ground Floor Fabulous Falling Waters Davis

2 bedrooms·2 baths

Naples • Florida

$5,400.00 USD total for 30 nights

Sep 22 – Oct 22, 2026

First-Floor Lakeview 2BR/2BA Condo in Naples

First-Floor Lakeview 2BR/2BA Condo in Naples

First-Floor Lakeview 2BR/2BA Condo in Naples

First-Floor Lakeview 2BR/2BA Condo in Naples

First-Floor Lakeview 2BR/2BA Condo in Naples

First-Floor Lakeview 2BR/2BA Condo in Naples

2 bedrooms·2 baths

Collier County • Florida

$4,772.67 USD total for 28 nights

Oct 1 – 29, 2026

Beach 🏝 Life

3 bedrooms·2 baths

Naples • Florida

4.92(24 reviews)

$150 – $300/ night(excl. fees & taxes)

Primary bedroom-King bed

Ascot in Lely Resort

3 bedrooms·2 baths

Naples • Florida

$7,500/ night(excl. fees & taxes)

Bird' s eye view of the property

Free Golf May 15-October 15

Bird's eye view of the golf course

Bird's eye view of the property and amenities

Balcony with seating area overlooking the water

GreenLinks Retreat - Pool, Hot Tub, Tennis, Golf

2 bedrooms·2 baths

Naples • Florida

$660.74 USD total for 3 nights

Sep 22 – 25, 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

$826.95 USD total for 3 nights

Sep 22 – 25, 2026

Seas The Day

3 bedrooms·2 baths

Naples • Florida

$249 – $649/ night(excl. fees & taxes)

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)

$602.68 USD total for 3 nights

Sep 22 – 25, 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)

Naples Park Beach House

Naples Park Beach House

Naples Park Beach House

Naples Park Beach House

Naples Park Beach House

0 bedrooms·2 baths

Naples • Florida

$153 – $477/ night(excl. fees & taxes)

Aerial view. 0.9 mile walk to beach.

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)

$358/ 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)

$1,282.40 USD $1,159.37 USD total for 3 nights

Sep 22 – 25, 2026

Sports Ranch Luxe Estate

Sports Ranch Luxe Estate

Sports Ranch Luxe Estate

Sports Ranch Luxe Estate

Sports Ranch Luxe Estate

Sports Ranch Luxe Estate

3 bedrooms·3 baths

Naples • Florida

$2,172.77 USD total for 3 nights

Sep 22 – 25, 2026