50 Best Naples Vacation rentals on Holiday Lettings - Apartments

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14 properties
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701 Vacation rentals

(13) 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

$1250 - $1851 / week

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from $179 / night

(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 $97 / night

$719 - $1700 / week

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from $97 / night

4

Vacation apartment in Naples

Southwest Gulf Coast / Naples

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
On the bay in Olde Naples within easy walking distance of the excellent shops and restaurants of Fifth Avenue and Third Street, as well as the beach and pier, famous for viewing the sunset. Adjacent small park with larger park close by with bandshell for regular concert …see more

from $250 / night

$1750 / week

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from $250 / 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

(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 $168 / night

$1173 - $2031 / week

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from $168 / 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 $197 / night

$1310 - $1572 / week

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from $197 / 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 $93 / night

$649 - $1114 / week

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from $93 / night

(8) Excellent 

Certificate of Excellence

29

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 $179 / night

$1247 / week

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Responds fast!
avg. 3 hours 39 minutes

from $179 / night

19

Vacation apartment with indoor pool in Naples

Southwest Gulf Coast / Naples

2 6 4 nights min

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
LAST MINUTE AVAILABILITY XMAS & NY!!! ALSO LONG TERM RENTAL POSSIBLE. PLEASE INQUIRE ABOUT DISCOUNTED RATES FOR LONGER STAYS AND SPECIAL PRICES FOR OFF-PEAK DATES If you want LUXURY pure this is the one for you! Many people rent this one for special occasions as it is …see more

from $459 / night

$3210 / week

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from $459 / night

21

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

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 $164 / night

$1147 - $1304 / week

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from $164 / 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 $265 / night

$1851 - $2300 / week

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from $265 / night

(2) Excellent 

15

Vacation home in Naples

Southwest Gulf Coast / Naples

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $200 / night

$1900 / week

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from $200 / night

44

Vacation apartment with golf nearby in Naples

Naples / Naples Beach

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $229 / night

$1600 / week

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from $229 / night

35

Vacation apartment with golf nearby in Naples

Southwest Gulf Coast / Naples

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hotel. If you have many people in your party, or want to have some privacy from your …see more

from $209 / night

$1463 / week

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Responds fast!
avg. 1 hour 12 minutes

from $209 / night

(15) Excellent 

26

Vacation villa in Naples

Southwest Gulf Coast / Naples

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • 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 $172 / night

$1200 - $1880 / week

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from $172 / 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

$2200 / week

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from $315 / 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 $50 / night

$350 / week

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from $50 / night

(2) 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 $144 / night

$1006 / week

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from $144 / 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

$1250 / 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 $178 / night

$1245 - $1441 / week

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from $178 / night

38

Naples Vacation apartment rental

Southwest Gulf Coast / Naples

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
HOUSEKEEPING, SHUTTLE SERVICE AROUND THE AREA, 5 HEATED SWIMMING POOLS, JACUZZI, SPA AND HEALTH CENTER, TENNIS COURTS Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel …see more

from $232 / night

$1618 / week

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Responds fast!
avg. 1 hour 12 minutes

from $232 / 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

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 $141 / night

$983 - $1245 / week

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from $141 / 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 $150 / night

$1046 / week

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from $150 / 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 $188 / night

$1310 / week

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from $188 / 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 $131 / night

$1153 - $1441 / week

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from $131 / night

24

Apartment rental in Naples with golf nearby

Southwest Gulf Coast / Naples

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Air conditioning
Unique chance to stay at a gorgeous luxury apartment with a touch of elegance and impressive water & city views of Miami's upscale Brickell and the Atlantic Ocean. Enjoy the quality of a 5 star hotel in a luxurious, impeccable and comfortable condo, with Italian design …see more

from $172 / night

$1200 / week

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from $172 / night

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 $200 / night

$1400 / week

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from $200 / night

33

Vacation apartment with golf nearby in Naples

Southwest Gulf Coast / Naples

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
SHUTTLE SERVICE AROUND THE AREA, 5 HEATED SWIMMING POOLS, JACUZZI, SPA AND HEALTH CENTER, TENNIS COURTS Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like …see more

from $236 / night

$1652 / week

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Responds fast!
avg. 1 hour 12 minutes

from $236 / night

29

Naples Vacation apartment accommodation

Southwest Gulf Coast / Naples

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
This beautiful 500sf Studio is located in a luxury building that has several swimming pools, bars, restaurants, gym, full service front desk, 24/7 security and so on. The Studio features a large 90ft balcony, contemporary Italian furniture, floor-to-ceiling windows, TV, …see more

from $179 / night

$1253 / week

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Responds fast!
avg. 1 hour 12 minutes

from $179 / 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 Street …see more

from $130 / night

$910 / week

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Responds fast!
avg. 3 hours 13 minutes

from $130 / night

(4) Very Good 

19

Vacation apartment in Naples

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 

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

$550 - $1175 / week

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from $75 / night

(1) Excellent 

19

Home rental in Naples

Southwest Gulf Coast / Naples

4 11 1 night min

  • 4 bedrooms
  • Sleeps 11
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Fantastic wide canal views from this newly redesigned and professionally decorated Vanderbilt Beach gem. You will love this very light, cozy and spring-2012 newly redone executive style waterfront home in walking distance to famous uptown Vanderbilt Beach. Mercato and …see more

from $400 / night

$2800 - $3535 / week

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Responds fast!
avg. 3 hours 35 minutes

from $400 / night

(1) Excellent 

17

Vacation home rental

Southwest Gulf Coast / Naples

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
This newly remodeled house has 3 bedrooms and 2 bathrooms. A cot (Graco pack ’n play) is also available. The heated swimming pool and spa are located in the backyard enclosed by a lanai. There is a gas grill, outdoor shower and patio table and chairs also in the lanai …see more

from $215 / night

$1500 - $2500 / week

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from $215 / night

(9) Excellent 

20

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Park Shore Resort is the quintessential tropical paradise nestled in the most fantastic city of SouthWest, non other than Naples. Park Shore, the surrounding area, elegantly welcomes walkers in the sunny mornings and at night for a stroll, run or bicycle ride across the …see more

from $90 / night

$580 - $1800 / week

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Responds fast!
avg. 3 hours 4 minutes

from $90 / night

(1) Excellent 

22

Naples Vacation home rental

Southwest Gulf Coast / Naples

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Beautiful newly remodeled, coastal contemporary home on a double lot. Kitchen features new stainless steel appliances, and bathrooms showcase a luxurious finish out with marble tile. Relax on brand new, stylish furniture, throughout the home. Watch TV from all rooms on …see more

from $100 / night

$700 / week

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from $100 / night

(16) Excellent 

15

Naples Vacation apartment rental

Southwest Gulf Coast / Naples

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.32 mi
  • Swimming pool
  • Child friendly
This 3B/2B condo is located in The Regatta, a beautifully landscaped, gated and guarded community just a block and a half from the beach and across the street from the Ritz Carlton. The Regatta has all of the features of a resort! Enjoy the beautiful lagoon style pool …see more

from $172 / night

$1200 - $2000 / week

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from $172 / night

(1) Excellent 

12

Vacation villa in Naples

Southwest Gulf Coast / Naples

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our beautiful home which has lake views to the rear has two master en-suite bedrooms, both with king size beds and which open onto the pool and sun-terrace. The lounge and dining room is open-plan with a large four section sliding door which opens onto the pool and lana …see more

from $222 / night

$1550 - $2355 / week

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from $222 / night