50 Best Naples Vacation rentals on Holiday Lettings - Apartments

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1,625 Vacation rentals

(4) Excellent 

25

Vacation villa rental

Naples / Briarwood

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
SEASON 2018 GUEST WHO BOOK THE SEASON OF 2018 WILL RECEIVE A DISCOUNT OF 10% OF THE RENTAL BUT THEY SHOULD ALLOW THE POSSIBLE SHOWINGS ON SUNDAYS AND THURSDAYS FROM 11am to 3 pm. DURING THE SHOWINGS NO NEED TO LEAVE THE HOUSE. Lovely detached villa vith large pool in a …see more

from $185 / night

$1,300 - $1,500 / week

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from $185 / night

(14) Very Good 

28

Villa rental in Naples with golf nearby

Naples / Lely Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
This beautiful, three bedroom home is both spacious and well-designed. Built in 2003, it provides all the modern amenities you would expect in a family home. It also has a large heated private pool and spa with screened lanai overlooking a tranquil lake. Both pool and l …see more

from $179 / night

$1,250 - $1,850 / week

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from $179 / night

21

Vacation villa with golf nearby in Naples

Naples / Lely Resort

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This is a stunning home that is furnished and decorated to a very high standard and in a wonderful location - you will not be disappointed. Our villa is a beautiful lakeside home in the prestigious Lely Resort. It is set in a quiet cul-de-sac of only three house …see more

from $200 / night

$1,400 - $1,800 / week

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from $200 / night

14

Vacation villa with golf nearby in Naples

Naples / Naples Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Westlake Villa offers guests a lovely comfortable vacation home full of old Naples charm. It has 3 bedrooms, the master suite with king sized bed is en-suite and has a flat screen TV. The queen has a flat screen tv and twin room has a dvd flat screen tv, there is a 2nd …see more

from $130 / night

$1,000 - $1,400 / week

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from $130 / night

(1) Excellent 

17

Vacation villa rental

Southwest Gulf Coast / Naples

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
The Briarwood villa, yet another beautiful, well kept home in the heart of Naples offers both superb accommodation, great south facing views, privacy, security and close proximity to heart of Old Naples. This spacious 4 bed 3 bath home is within the community of Briar …see more

from $179 / night

$1,253 - $1,939 / week

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from $179 / night

14

Vacation home in Naples

Southwest Gulf Coast / Naples

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Home is located in a residential neighborhood 0.5 miles from private park (for owners and their guests ) adjacent to the beautiful Naples beach. We are also 0.5 miles from shopping, grocery store and restaurants. This home has been recently renovated with all new air-co …see more

from $315 / night

$2,200 / week

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from $315 / night

(1) Excellent 

11

Home rental in Naples with golf nearby

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
We overlook the beautiful Hibiscus Golf Course in the famous Lely Area. Our single family pool home has three bedrooms and open plan living space of 2000 square feet. A magnificent chefs kitchen area should you want to wine and dine. It boasts 1800 of outdoor living sp …see more

from $210 / night

$1,400 - $1,680 / week

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from $210 / night

(9) Very Good 

Certificate of Excellence

28

Vacation home with golf nearby in Naples

Naples / Vanderbilt Beach Area

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Absolutely mint condition luxury villa dream peacefully on small freshwater lake, in natural, residential area of Naples, 5 minutes to one of the most beautiful beaches in the United States = Vanderbilt beach. At the end of a cul-de-sac, set up with all imaginable Extra …see more

Certificate of Excellence

from $205 / night

$1,431 / week

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from $205 / night

22

Vacation apartment with golf nearby in Naples

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
A beautiful 2 bedroom plus den 2 bathroom condominium on Falling Waters, Amelia Lake ,Davis Boulevard, Naples - a stunning, world class gated resort complex themed around tropical gardens and waterfalls with one of the largest and most photogenic swimming pools in SW Fl …see more

from $155 / night

$1,085 / week

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from $155 / night

(2) Excellent 

15

Vacation home in Naples

Southwest Gulf Coast / Naples

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Be one of the first people to live in this beautiful, brand new luxury home in the community of Hawthorne. The home was finished in December 2013 and comes fully furnished and designed by Pottery Barn. The master bedroom features a king size bed and two walk-in clos …see more

from $140 / night

$1,999 / week

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from $140 / night

22

Villa rental in Lely Resort with golf nearby

Naples / Lely Resort

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
DEAL ALERT!! This property very rarely has peak season availability...however I have a last minute cancellation for the first two and a half weeks of December 2015. As an incentive I am offering a 20% discount for booking these dates (1 - 19 December 2015). ****** …see more

from $279 / night

$1,950 - $2,300 / week

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from $279 / night

(5) Excellent 

36

Naples Vacation home rental

Southwest Gulf Coast / Naples

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This gorgeous high spec 2000 sq ft 2 bedroom, 2 bathroom house in East Naples has been completely remodeled in 2015. Situated in the exclusive Woodlands development in Kings Lake, Naples, this bright, beautiful Florida home is available for rental from October 2015. The …see more

from $179 / night

$1,250 / week

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from $179 / night

14

Vacation home with golf nearby in Naples

Southwest Gulf Coast / Naples

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Our Villa is a luxury home, with full air conditioning set in the small-gated community situated within Lely Resort Golf and Country Club, Just minutes from beautiful beaches, Fifth Avenue shops, Naples Pier, Marco Island, World Class Golf Courses, and numerous fine din …see more

from $190 / night

$1,330 - $1,680 / week

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from $190 / night

25

Vacation apartment in Vanderbilt Beach Area

Naples / Vanderbilt Beach Area

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Apartment Florida style for a relaxing and active holiday. 2 bedrooms, living room with dining room and open kitchen, bar, 2 walk-in closets, large balcony with views of the West Wigginspass and jetties. Elevator to the third floor, storage room on the ground floor. In …see more

from $100 / night

$700 / week

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from $100 / night

24

Vacation villa rental

Naples / Naples Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Villa, 3 bedroom, 5-6 Personen, Privater Strand- und Seezugang, beheizbarer Pool, Die Lage ist perfekt, fußläufig vom Strand entfernt (privater Strandzugang mit Parkplatz) eigner Zugang zum wunderbaren und idyllisch gelegenen See, ideale Sonnen- und Lichtverhälnisse. I …see more

from $199 / night

$1,388 / week

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from $199 / night

43

Vacation apartment in Naples

Southwest Gulf Coast / Naples

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Our condo at the World Tennis Club in Naples, Florida, is spacious and luxurious with a large lounge/diner with comfortable sofas and dining for 6. Patio doors give access to a screened balcony/lanai with views over a lake. Herons, egrets, Ibis, ducks and otters inhabit …see more

from $90 / night

$630 - $1,190 / week

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from $90 / night

20

Naples Vacation villa rental

Southwest Gulf Coast / Naples

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Child friendly
Our Villa is a lovely luxury villa set in the small gated community of Masters Reserve situated within Lely Resort Golf and Country Club. The villa has 3 good-sized bedrooms and 2 bathrooms. Apart from the high specifications of the property it benefits from being in a …see more

from $200 / night

$1,400 / week

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from $200 / night

(16) Excellent 

26

Vacation villa in Naples

Southwest Gulf Coast / Naples

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Conway House is a fantastic family holiday home situated in a private location in old Naples. Whilst the house is central (only 5 mins drive to the beach and to the Coastland shopping centre) it is in a very quiet residential area and backs onto a lagoon. The villa is …see more

from $179 / night

$1,250 - $2,000 / week

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from $179 / night

18

Villa rental in Naples with golf nearby

Southwest Gulf Coast / Naples

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Augusta Falls could not be better located in Naples as it is short walk of a large shopping centre, less than a mile from an interstate junction, very much in the centre of Naples, yet on one of Naples most well known sought after secure gated golf communities. Thus pea …see more

from $175 / night

$1,225 / week

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from $175 / night

(3) Very Good 

10

Naples Vacation apartment rental

Southwest Gulf Coast / Naples

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning
Our child-friendly non-smoking apartment is situated in a beautiful, tranquil tropical landscaped, 'gated', so closed, community, In the Naples bath and tennis club. The condo is about 120 square meters, was largely new and lovingly furnished and decorated, and off …see more

from $155 / night

$1,084 / week

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Responds fast!
avg. 3 hours 52 minutes

from $155 / night

44

Vacation apartment with golf nearby in Naples

Naples / Naples Beach

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
SPECIAL RATES starting MAY!!! This property is only for non-smokers. Pets are not allowed. Holiday period normally requires a minimum of 30 days, however a 14 day may apply according to booking. Please ask! The apartment is located in a residence that is part of one of …see more

from $77 / night

$537 / week

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from $77 / night

20

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Beautiful lake view, safe gated community, comfortable for seniors, ground floor with walkout from lanai, kind neighbours, walking distance from groceries / drug store, 10 minutes from beautiful Gulf beaches. Tons of fabulous restaurants and fun things to do. (1.5 Hou …see more

from $54 / night

$374 / week

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from $54 / night

20

Naples Vacation villa accommodation

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
Westlake Villa offers guests a lovely comfortable vacation home full of old Naples charm. It has 3 bedrooms, the master suite with king sized bed is en-suite and has a flat screen TV. The queen has a flat screen tv and twin room has a dvd flat screen tv, there is a 2nd …see more

from $150 / night

$1,050 / week

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from $150 / night

12

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
Abaco Bay is a Key West inspired community in an ideal central Naples location. Less than 5 minutes from the Gulf of Mexico and its pristine beaches and shopping and fine dining nearby off 5th Avenue (the heart of Historic Downtown Naples) and 3rd Street South. Abaco B …see more

from $54 / night

$374 / week

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from $54 / night

(8) Very Good 

10

Vacation home in Naples

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
This is a 2 bedroom, 2 bath, private pool home in Southwest Florida, located in a quiet residential neighborhood called Bonita Shores, West of Hwy. 41. Within walking distance to the beach. Just a few miles north of Naples in Collier county, this home (house) is within …see more

Pricing unknown

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Pricing unknown

5

Home rental in Naples

Southwest Gulf Coast / Naples

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
Please note this home was rented in Jan 2016 for for the January 2017season and has just come back on the market. It is available from Jan 2 2017 for the season. The perfect winter getaway in Fiddler’s Creek awaits you in this outstanding single family, former show hom …see more

from $267 / night

$1,867 / week

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from $267 / night

11

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 4 21 nights min

  • 2 bedrooms
  • Sleeps 4
  • 21 nights min
  • Swimming pool
  • Air conditioning
Beautiful top floor condo in two story building, south facing, lake view. At just less than 1500 square feet this two bedroom, two bathroom condo will feel like home as soon as you enter. Minutes from the beaches, shopping and dining of North Naples, anything you want …see more

from $62 / night

$434 / week

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Responds fast!
avg. 2 hours 12 minutes

from $62 / night

10

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Suitable for children age 5+
WOW.....SIMPLY AMAZING!!...."LAST MINUTE"... 4-5* STAR "MARCH VACATION SPECIALS" FROM MAR.3,2018 - APRIL 30,2018! PLEASE ONLY "CALL US" FIRST... AFTER YOU READ “OUR ENTIRE AD" & PLEASE DO NOT SEND US AN EMAIL!!! JUST ‘TEXT’ OR ‘CALL US’ “ONLY” WITH YOUR "BEST CONT …see more

from $69 / night

$489 - $979 / week

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from $69 / night

(4) Excellent 

20

Vacation apartment with shared pool in Naples

Southwest Gulf Coast / Naples

1 2 14 nights min

  • 1 bedroom
  • Sleeps 2
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
Spacious one bedroom-one bath condo on the SECOND floor with a screened-in terrace. Living room, dining area, and walk-in closet. Washer and dryer in the unit. Very clean, fully furnished, all electric appliances, central air conditioning, wire-less internet access. Ki …see more

from $58 / night

$400 / week

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from $58 / night

27

Vacation home with swimming pool in Naples

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
*Please note that seasonal reservations for this home must be 120 days in length in order to be approved. Please contact Island Escapes directly for more information.* GOLF COURSE COMMUNITY Tee off in your own backyard! This home has it all!!! The home is on the secon …see more

from $171 / night

$1,200 - $2,900 / week

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from $171 / night

28

Vacation condo in Naples

Southwest Gulf Coast / Naples

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This luxurious and spacious 3 bedroom Coach Home located in Fiddler Creek's Village of Serena is the perfect family retreat. Enjoy breakfast or dinner on the lanai overlooking the lake and lush, tropical landscaping. The home looks brand new and is tastefully furnishe …see more

from $110 / night

$825 / week

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from $110 / night

19

Naples Vacation apartment rental

Southwest Gulf Coast / Naples

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
THESE SUITES HAVE EVERYTHING : UNIQUE LOCATION PARK SHORE RESORT CLOSE TO BEACH one mile Our suites in the only ones in the resort with Complimentary pass to privat …see more

from $100 / night

$700 / week

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from $100 / night

(9) Excellent 

38

Naples Vacation home rental

Southwest Gulf Coast / Naples

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
Come escape into a cute cottage near the beach for your Florida vacation! Enjoy soaking up the sun at Delnor Wiggins Pass Park (1.2 miles away) or Vanderbilt Beach (1.9 miles away), both so close to you that it's tempting to go everyday for the spectacular sunsets! Ri …see more

from $130 / night

$520 - $1,000 / week

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from $130 / night

13

Home accommodation in Naples with shared pool

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
This delightful first floor Beachwalk is located within walking distance to the pristine Vanderbilt Beach in North Naples. Conveniently located, Beachwalk is also a short distance to shopping, dining, the theater, a public library and park. The community offers 2 comm …see more

from $150 / night

$1,050 / week

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from $150 / night

(11) Excellent 

62

Cottage rental in Naples

Southwest Gulf Coast / Naples

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Come escape to Naples and enjoy this bright and airy 2nd floor coastal cottage! Beautifully decorated in relaxing ocean blues, this quaint cottage immediately sets you at ease and invites you in to stay. Enjoy the relaxing breeze on the 2nd floor screened back porch, n …see more

from $75 / night

$600 - $1,175 / week

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from $75 / night

24

Vacation home in Naples

Southwest Gulf Coast / Naples

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Prepare for a perfect Florida getaway with this amazing home in Naples! Enjoy an enclosed private pool and the privacy of a gated community. Securely nestled in the gated community of Briarwood, your new home away from home is east of shopping and dining at Third Stree …see more

from $143 / night

$1,001 / week

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Responds fast!
avg. 3 hours 6 minutes

from $143 / night

28

Vacation apartment rental

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Vanderbilt Landings on Gulf Shore Drive, located on the north end of Gulf Shore Drive at the intersection with Bluebill Ave. This is as close to beach front rental as you can get without the high rates! Vanderbilt Landings gated community with secured lobby & …see more

from $217 / night

$952 - $1,981 / week

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Responds fast!
avg. 11 minutes

from $217 / night

19

Apartment rental in Naples with shared pool

Southwest Gulf Coast / Naples

2 4 28 nights min

  • 2 bedrooms
  • Sleeps 4
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Totally Renovated 2/2 in Tropic Schooner. All new tile, granite, walk-in showers. Luxurious! Brand new furnishings throughout. Queen bed in Master bedroom-Twins Beds in Guest Bedroom....New appliances...Fresh and welcome place for you! Flat Screen TVS-DVD-WiFi Beautifu …see more

from $90 / night

$630 / week

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from $90 / night

18

Vacation home with shared pool in Naples

Southwest Gulf Coast / Naples

2 6 27 nights min

  • 2 bedrooms
  • Sleeps 6
  • 27 nights min
  • Swimming pool
  • Ask about children
Lovely second floor unit in the North Naples community of Tarpon Cove. Owner has decorated in soft pastel colors. Light, bright and airy. Very private, peaceful view of Preserve from lanai. Parking for residence is able to accommodate two vehicles as well as ample guest …see more

from $117 / night

$819 / week

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from $117 / night

(2) Excellent 

18

Home rental in Naples

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Walk or Bike to the Beaches. This lovely two bedroom is absolutely adorable and charming, and part of a larger estate. This home doesn't disappoint, it has an incredible setup! The home has a wonderful lanai and front porch, leading into a large fenced backyard. The ho …see more

from $119 / night

$783 - $2,250 / week

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Responds fast!
avg. 34 minutes

from $119 / night