Keewaydin Island Vacation Rentals

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Our top choices for Keewaydin Island vacation rentals

Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River

Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
Bonita Shores
9.6 out of 10, Exceptional, (5 reviews)
"Is good , and Beauty"
United States
Jorge T.
The price is CA $208
CA $409 total
includes taxes & fees
Feb 11 - Feb 12
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River

Nuevo y Confortable Estudio

Nuevo y Confortable Estudio
Naples
8.8 out of 10, Excellent, (10 reviews)
"Great stay for a solo trip! This location was very close to the beaches and pickleball courts. Definitely recommend this place! "
United States
Esosa
The price is CA $130
CA $209 total
includes taxes & fees
Mar 4 - Mar 5
Nuevo y Confortable Estudio

Naples Marina Getaway Studio DIRECT WATER VIEWS!

Naples Marina Getaway Studio DIRECT WATER VIEWS!
Naples
9.8 out of 10, Exceptional, (17 reviews)
"Best stay I've had in a very long time. The place is awesome, great restaurant, nice and quiet, and close to everything. Will visit again!! "
United States
Rodney
The price is CA $206
CA $426 total
includes taxes & fees
Feb 9 - Feb 10
Naples Marina Getaway Studio DIRECT WATER VIEWS!

Cozy Apartment in Naples

Cozy Apartment in Naples
Rural Estates
9.2 out of 10, Wonderful, (15 reviews)
"The place was off the grid from the busyness of the downtown/beach area but close enough to go there and the other areas too! "
United States
Robyn S.
The price is CA $149
CA $443 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Apartment in Naples

Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4

Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4
Bonita Shores
10.0 out of 10, Exceptional, (9 reviews)
"The home & location were both excellent. The surroundings were very quiet.We enjoyed our stay immensely and would definitely stay again.Thank you for a great experience!"
United States
debbra f.
The price is CA $211
CA $412 total
includes taxes & fees
Feb 9 - Feb 10
Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4

Amazing Private Suite Large Bathroom 3.3mi to Beach Close 2 Everything Updated

Amazing Private Suite Large Bathroom 3.3mi to Beach Close 2 Everything Updated
Bonita Shores
9.8 out of 10, Exceptional, (13 reviews)
"Excellent place to stay. "
United States
Barb
The price is CA $144
CA $291 total
includes taxes & fees
Feb 8 - Feb 9
Amazing Private Suite Large Bathroom 3.3mi to Beach Close 2 Everything Updated

Old Florida Fishing Cottage See The Water From Living Room on Imperial River

Old Florida Fishing Cottage See The Water From Living Room on Imperial River
Bonita Shores
10.0 out of 10, Exceptional, (11 reviews)
"Lovely old Florida area!! Quiet, charming area.Close to great restaurants, beaches, sunset!We will be back"
United States
Anonymous traveller
The price is CA $280
CA $524 total
includes taxes & fees
Mar 3 - Mar 4
Old Florida Fishing Cottage See The Water From Living Room on Imperial River

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!
Naples
9.6 out of 10, Exceptional, (10 reviews)
"Perfect location. "
United States
Jennifer E.
The price is CA $205
CA $429 total
includes taxes & fees
Mar 4 - Mar 5
Marina Fish- Boat and Relax in this Paradise newly remodeled in Naples, Florida!

The Gulfstream Place 2

The Gulfstream Place 2
East Naples
9.0 out of 10, Wonderful, (16 reviews)
"Great place for quiet relaxation "
United States
Richard
The price is CA $203
CA $416 total
includes taxes & fees
Feb 7 - Feb 8
The Gulfstream Place 2

Florida style home walking distance to Barefoot Beach

Florida style home walking distance to Barefoot Beach
Bonita Shores
9.0 out of 10, Wonderful, (29 reviews)
"Easy in and out"
United States
Theresa
The price is CA $204
CA $515 total
includes taxes & fees
Feb 28 - Mar 1
Florida style home walking distance to Barefoot Beach

Private Suite near the Beach

Private Suite near the Beach
Naples Park
9.8 out of 10, Exceptional, (15 reviews)
"Perfect location. Exactly what we're were looking for. Great for adult couple."
United States
douglas e
The price is CA $191
CA $357 total
includes taxes & fees
Feb 20 - Feb 21
Private Suite near the Beach

Cute Cottage 1.5Mi 2 Beach Duplex Has Dock on Gulf Access Imperial River

Cute Cottage 1.5Mi 2 Beach Duplex Has Dock on Gulf Access Imperial River
Bonita Shores
9.8 out of 10, Exceptional, (6 reviews)
"Great little beach cottage in a peaceful neighborhood near the beaches!"
United States
HOLLY M.
The price is CA $270
CA $469 total
includes taxes & fees
Mar 3 - Mar 4
Cute Cottage 1.5Mi 2 Beach Duplex Has Dock on Gulf Access Imperial River

Tiny Home Renovated 2023 1.5 Mi, 2 Beach Kit W & D Regular Bed on Imperial River

Tiny Home Renovated 2023 1.5 Mi, 2 Beach Kit W & D Regular Bed on Imperial River
Bonita Shores
9.8 out of 10, Exceptional, (6 reviews)
"Cute little home! Enjoyed our stay. Thank you for your hospitality "
United States
Robin S.
The price is CA $182
CA $341 total
includes taxes & fees
Feb 9 - Feb 10
Tiny Home Renovated 2023 1.5 Mi, 2 Beach Kit W & D Regular Bed on Imperial River

Swimming pool, lake view, minutes to Naple's downtown and beach.

Swimming pool, lake view, minutes to Naple's downtown and beach.
East Naples
9.2 out of 10, Wonderful, (31 reviews)
"Beautiful spot! Enjoyed our stay. Very calm, quiet peaceful location. Quick 15 minute drive to the beach. Beautiful pool and backyard"
United States
Karissa S.
The price is CA $306
CA $383 total
includes taxes & fees
Feb 18 - Feb 19
Swimming pool, lake view, minutes to Naple's downtown and beach.

* * Endless Summer * * Beach, Unique & Comfort

* * Endless Summer * * Beach, Unique & Comfort
Naples Park
9.4 out of 10, Exceptional, (16 reviews)
"A beautiful property with attention to detail. Nice beach towels and beach chairs provided as well as bikes.Perfect location for beach time and many options for night life -- restaurants, shopping, cocktails.Would definitely recommend this place for your next getaway."
United States
Terry W.
The price is CA $249
CA $529 total
includes taxes & fees
Feb 8 - Feb 9
* * Endless Summer * * Beach, Unique & Comfort

5 O'Clock Somewhere getaway-Walk/Bike to Beach,Shops ,Fenced private doggie area

5 O'Clock Somewhere getaway-Walk/Bike to Beach,Shops ,Fenced private doggie area
Naples Park
9.0 out of 10, Wonderful, (32 reviews)
"We enjoyed our stay at this property and loved how convenient it was to one of the nearby beaches!"
United States
Laura
The price is CA $409
CA $756 total
includes taxes & fees
Mar 4 - Mar 5
5 O'Clock Somewhere getaway-Walk/Bike to Beach,Shops ,Fenced private doggie area

Wiggins Pass Chalet

Wiggins Pass Chalet
4.0 star property
Naples
9.6 out of 10, Exceptional, (257 reviews)
"Excellent stay! Highly recommend!"
United States
margarita
Wiggins Pass Chalet

Marco Island Florida Family Vacation Home-heated pool, beach, Pet friendly

Marco Island Florida Family Vacation Home-heated pool, beach, Pet friendly
Marco Island
9.8 out of 10, Exceptional, (36 reviews)
"We had a great time staying at this quiet property with a beautiful pool."
United States
Tara B.
The price is CA $370
CA $1,022 total
includes taxes & fees
Feb 28 - Mar 1
Marco Island Florida Family Vacation Home-heated pool, beach, Pet friendly

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

House w/ Heated Pool & Grill - Walk to Beach!
3.0 star property
South End
The price is CA $403
CA $969 total
includes taxes & fees
Feb 12 - Feb 13
House w/ Heated Pool & Grill - Walk to Beach!

STARFISH PARADISE,FENCED YARD-ONLY 1/2MILE TO OCEAN-SLEEPS 4-1BED/1.5BATH, 2 TVs

STARFISH PARADISE,FENCED YARD-ONLY 1/2MILE TO OCEAN-SLEEPS 4-1BED/1.5BATH, 2 TVs
Naples Park
9.4 out of 10, Exceptional, (22 reviews)
"Absolutely amazing location! The bikes were fabulous to have on site! The host was very responsive. Would definitely come back."
United States
Trisha S.
The price is CA $274
CA $629 total
includes taxes & fees
Feb 7 - Feb 8
STARFISH PARADISE,FENCED YARD-ONLY 1/2MILE TO OCEAN-SLEEPS 4-1BED/1.5BATH, 2 TVs
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.
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Top Keewaydin Island Hotel Reviews

Find out more about Keewaydin Island

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Keewaydin Island. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.