Title: Keewaydin Island Vacation Rentals from $317: Search Short-Term Rentals | Expedia.com

[Keewaydin Island Travel Guide](https://expedia.com/Keewaydin-Island.dx6337231)[Hotels in Keewaydin Island](https://expedia.com/Keewaydin-Island-Hotels.d6337231.Travel-Guide-Hotels)[Flights to Keewaydin Island](https://expedia.com/Cheap-Flights-To-Keewaydin-Island.d6337231.Travel-Guide-Flights)[Car Rentals in Keewaydin Island](https://expedia.com/Car-Rentals-In-Keewaydin-Island.d6337231.Car-Rental-Guide)[Keewaydin Island Vacation Packages](https://expedia.com/Keewaydin-Island.d6337231.Destination-Travel-Guides)

![Keewaydin Island beach aerial](https://images.trvl-media.com/place/6337231/0b8ef5b6-2083-4cdb-97c8-d4b5fcbc1cee.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/6337231/0b8ef5b6-2083-4cdb-97c8-d4b5fcbc1cee.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6337231&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6337231&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6337231&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 19 - Jun 21](https://www.expedia.com/Hotel-Search?regionId=6337231&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Keewaydin Island vacation rentals

![House, Accessible, Private Bathroom (1902 Della Dr) | Lobby](https://images.trvl-media.com/lodging/115000000/114840000/114839100/114839050/0010e309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Accessible, Private Bathroom (1902 Della Dr) | Interior](https://images.trvl-media.com/lodging/115000000/114840000/114839100/114839050/c6a9291c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Accessible, Private Bathroom (1902 Della Dr) | Shared kitchen](https://images.trvl-media.com/lodging/115000000/114840000/114839100/114839050/a2e73b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Accessible, Private Bathroom (1902 Della Dr) | Bathroom](https://images.trvl-media.com/lodging/115000000/114840000/114839100/114839050/589dec57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 1902 Della Dr

[](https://www.expedia.com/Naples-Hotels-1902-Della-Dr.h114839050.Hotel-Information)

Rural Estates

$542 nightly

$580 total

Mar 1 - Mar 2

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-1902-Della-Dr.h114839050.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536624/659e79f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536624/659b1cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536624/3f8dbb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536624/4df69462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### House w/ Heated Pool & Grill - Walk to Beach!

[](https://www.expedia.com/Marco-Island-Hotels-House-W-Heated-Pool-Grill-Walk-To-Beach.h93536624.Hotel-Information)

South End

$640 nightly

$707 total

Mar 16 - Mar 17

Total with taxes and fees

[](https://www.expedia.com/Marco-Island-Hotels-House-W-Heated-Pool-Grill-Walk-To-Beach.h93536624.Hotel-Information)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/0dfad72d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/7402b07f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/c509def8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Breakfast, lunch, dinner served; seafood ](https://images.trvl-media.com/lodging/1000000/10000/4800/4760/014de562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bellasera Resort

[](https://www.expedia.com/Naples-Hotels-Bellasera-Resort.h4760.Hotel-Information)

Old Naples

9.6/10

Exceptional

(2,244 reviews)

"We love everything about this property and stay here whenever we're in Naples."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah

$565 nightly

$628 total

Mar 19 - Mar 20

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-Bellasera-Resort.h4760.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472247/622bc3ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472247/cae62deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472247/03d9b64c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472247/f571d4ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Naples Paradise Grill Hottub Close to Beach

[](https://www.expedia.com/Naples-Hotels-Naples-Paradise-Grill-Hottub-Close-To-Beach.h126472247.Hotel-Information)

Naples Park

$613 nightly

$681 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-Naples-Paradise-Grill-Hottub-Close-To-Beach.h126472247.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/59000000/58120000/58115200/58115199/d32fc7b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/59000000/58120000/58115200/58115199/1ed4ba95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Presidential Suite | Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/59000000/58120000/58115200/58115199/aeda482c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/59000000/58120000/58115200/58115199/w2254h1500x320y0-f08f1fd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wiggins Pass Chalet

[](https://www.expedia.com/Naples-Hotels-Wiggins-Pass-Chalet.h58115199.Hotel-Information)

Naples

9.6/10

Exceptional

(261 reviews)

"Excellent stay! Highly recommend!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

margarita

$286 nightly

$317 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-Wiggins-Pass-Chalet.h58115199.Hotel-Information)

![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/910000/908600/908559/4bd5848d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/1000000/910000/908600/908559/b5959fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from room](https://images.trvl-media.com/lodging/1000000/910000/908600/908559/083f97a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/1000000/910000/908600/908559/bc71e12f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### GreenLinks Golf Villas at Lely Resort

[](https://www.expedia.com/Naples-Hotels-GreenLinks-Golf-Villas-At-Lely-Resort.h908559.Hotel-Information)

Naples

9.4/10

Exceptional

(548 reviews)

"Clean and staff was helpful. Beautiful views"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rebecca

$582 nightly

$635 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-GreenLinks-Golf-Villas-At-Lely-Resort.h908559.Hotel-Information)

![Villa, 2 Bedrooms, Balcony | Premium bedding, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/25100/25055/618b7049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Villa, 2 Bedrooms, Balcony | Living area | 55-inch flat-screen TV with cable channels, foosball, table tennis](https://images.trvl-media.com/lodging/1000000/30000/25100/25055/0da14ffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/25100/25055/9fe38a19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/1000000/30000/25100/25055/501c1080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Marriott's Crystal Shores

[](https://www.expedia.com/Naples-Hotels-Marriotts-Crystal-Shores.h25055.Hotel-Information)

South End

9.2/10

Wonderful

(225 reviews)

"Hotel is well maintained and has beautiful grounds and beach"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Chris

$1,170 nightly

$1,299 total

Feb 28 - Mar 1

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-Marriotts-Crystal-Shores.h25055.Hotel-Information)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536686/f6fd8e04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536686/aff2e9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536686/934b7980.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment (2 Bedrooms) | Interior](https://images.trvl-media.com/lodging/94000000/93540000/93536700/93536686/b424aecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Naples Condo w/ Golf View & Resort-style Amenities

[](https://www.expedia.com/Naples-Hotels-Naples-Condo-W-Golf-View-Resort-Style-Amenities.h93536686.Hotel-Information)

Naples

10/10

Exceptional

(1 review)

"We spent a weekend here while visiting family in the area. Great location for us. Super friendly and helpful. Nice sunset view over the golf course. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mark

$394 nightly

$434 total

Mar 7 - Mar 8

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-Naples-Condo-W-Golf-View-Resort-Style-Amenities.h93536686.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472289/5e9bd8fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472289/5a3f7ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472289/ab007da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/127000000/126480000/126472300/126472289/5eda7b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Coastal Paradise

[](https://www.expedia.com/Naples-Hotels-Coastal-Paradise.h126472289.Hotel-Information)

Old Naples

$878 nightly

$975 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Naples-Hotels-Coastal-Paradise.h126472289.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-13&endDate=2026-03-14&regionId=6337231&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_6337231)

## Find vacation rentals that suit your style

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VACATION_HOME)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CONDO)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APART_HOTEL)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VILLA)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=COTTAGE)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APARTMENT)

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CABIN)

Houseboats

[](https://www.expedia.com/Hotel-Search?destination=Keewaydin+Island%2C+Florida%2C+United+States+of+America&regionId=6337231&latLong=26.070364%2C-81.786903&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=HOUSE_BOAT)

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## Top Keewaydin Island Hotel Reviews

![Fairways Inn of Naples](https://images.trvl-media.com/lodging/1000000/60000/55500/55415/9ba98d99_y.jpg)

### Fairways Inn of Naples

10/10 Excellent

"The grounds are lovely and the staff was outstanding."

[](https://expedia.com/Naples-Hotels-Fairways-Inn-Of-Naples.h55415.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Naples Downtown](https://images.trvl-media.com/lodging/1000000/30000/24700/24612/1d33d843_y.jpg)

### La Quinta Inn & Suites by Wyndham Naples Downtown

10/10 Excellent

"nice staff—easy access to paradise sports complex."

[](https://expedia.com/Naples-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Naples-Downtown.h24612.Hotel-Information)

![Baymont by Wyndham Bonita Springs Naples North](https://images.trvl-media.com/lodging/1000000/20000/19100/19063/907bbde1_y.jpg)

### Baymont by Wyndham Bonita Springs Naples North

10/10 Excellent

"It was very nice"

[](https://expedia.com/Naples-Hotels-Baymont-By-Wyndham-Bonita-Springs-Naples-North.h19063.Hotel-Information)

![Naples Grande Beach Resort](https://images.trvl-media.com/lodging/1000000/20000/15900/15898/65da812e_y.jpg)

### Naples Grande Beach Resort

10/10 Excellent

"Place was very clean for how many people were at the hotel. Hotel staff is friendly and accommodating."

[](https://expedia.com/Naples-Hotels-Naples-Grande-Beach-Resort.h15898.Hotel-Information)

![Staybridge Suites Naples – Marco Island by IHG](https://images.trvl-media.com/lodging/32000000/31910000/31900500/31900412/bc6f0696_y.jpg)

### Staybridge Suites Naples – Marco Island by IHG

10/10 Excellent

"Great staff and very nice rooms, pool and facility!"

[](https://expedia.com/Naples-Hotels-Staybridge-Suites-Naples-Marco-Island.h31900412.Hotel-Information)

![Marco Beach Ocean Suites](https://images.trvl-media.com/lodging/93000000/92930000/92927500/92927422/eeea5841_y.jpg)

### Marco Beach Ocean Suites

10/10 Excellent

"Everything was great except pool was under construction, but we that in advance."

[](https://expedia.com/Marco-Island-Hotels-Marco-Beach-Ocean-Resort.h92927422.Hotel-Information)

![Hilton Marco Island Beach Resort and Spa](https://images.trvl-media.com/lodging/1000000/20000/17600/17575/65dd4041_y.jpg)

### Hilton Marco Island Beach Resort and Spa

10/10 Excellent

"Beautiful room, comfortable beds. Wonderful amenities, Staff was very helpful! I’m definitely coming back!’ "

[](https://expedia.com/Naples-Hotels-Hilton-Marco-Island-Beach-Resort.h17575.Hotel-Information)

![Great Wolf Lodge Naples](https://images.trvl-media.com/lodging/113000000/112020000/112014600/112014521/8165046f_y.jpg)

### Great Wolf Lodge Naples

10/10 Excellent

"Bed was super comfy. Towels were great. Many things for the family to do. "

[](https://expedia.com/Naples-Hotels-Great-Wolf-Lodge-Naples.h112014521.Hotel-Information)

![Compass by Margaritaville Hotel Naples](https://images.trvl-media.com/lodging/1000000/550000/543700/543614/16d35331_y.jpg)

### Compass by Margaritaville Hotel Naples

10/10 Excellent

"Room clean lovely pool atmosphere and excellent breakfast!"

[](https://expedia.com/Naples-Hotels-Compass-By-Margaritaville-Naples.h543614.Hotel-Information)

## Find out more about Keewaydin Island

**Everything you need to know about Keewaydin Island vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Keewaydin Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Keewaydin Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Keewaydin Island vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Keewaydin Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Keewaydin Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $317 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Keewaydin Island rentals**

At Expedia, we put the best Keewaydin Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Keewaydin Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Keewaydin Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Keewaydin Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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### Trending destinations on Expedia.com

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### Expedia's Latest Trends

Hotels

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Cars

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Packages

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- [South Naples Vacation](https://expedia.com/South-Naples.d6337318.Destination-Travel-Guides)
- [Naples Botanical Garden](https://expedia.com/Naples-Botanical-Garden-East-Naples.d6177501.Vacation-Attraction)
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- [Brookside Marina](https://expedia.com/Brookside-Marina-East-Naples.d553248621557934747.Vacation-Attraction)
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Vacation Rentals

- [South Naples Vacation Rentals](https://expedia.com/South-Naples-Vacation-Rentals.d6337318.Travel-Guide-VacationRentals)

General

- [Visit South Naples](https://expedia.com/South-Naples.dx6337318)

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