50 Best Naples Vacation rentals on Holiday Lettings - Apartments

Close

View larger map

Also consider

Naples Beach
8 properties
Vanderbilt Beach Area
6 properties

Naples

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,408 Vacation rentals

(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

Book View

from $179 / night

(17) 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

Inquire View

from $179 / night

(10) 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
  • Nearest beach 4 mi
  • Swimming pool
As new luxury villa in a quiet dream location in the small freshwater lake in naturally grown residential area of ​​Naples, 5 minutes on one of the most beautiful beaches in the US = Vanderbilt Beach. At a dead end, furnished with all the bells and whistles, heated pool …see more

Certificate of Excellence

from $204 / night

$1,427 / week

Book View

from $204 / night

(4) Excellent 

25

Vacation villa rental

Southwest Gulf Coast / Naples

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
SEASON 2019 - CASA NAPOLETANA Lovely detached villa 4/3 with pool, spa & lake view in a secure community of Artesia, Naples. The house with its 4 bedrooms and 3 bathrooms easily accommodates 8 people There will be more images of this brand new home in the summer of 20 …see more

from $160 / night

$2,050 / week

Book View

from $160 / 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

Book View

from $100 / night

(6) Very Good 

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

Book View

from $179 / 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 $198 / night

$1,381 / week

Book View

from $198 / 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 $92 / night

$639 - $895 / week

Book View

from $92 / 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 $158 / night

$1,101 / week

Book View

from $158 / night

21

Vacation villa in Naples

Southwest Gulf Coast / Naples

2 4 120 nights min

  • 2 bedrooms
  • Sleeps 4
  • 120 nights min
Come visit Naples, Florida, the jewel of Southwest Florida known for its expansive pristine white sand beaches, fine dining and high end shopping. Our home is located at the end of a quiet cul de sac in the gated community of Village Walk of Naples. You will be greete …see more

from $120 / night

$840 / week

Book View

from $120 / night

(1) Excellent 

31

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 $215 / night

$1,430 - $1,716 / week

Book View

from $215 / 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 $193 / night

$1,349 - $1,704 / week

Book View

from $193 / 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

Book View

from $315 / 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

Book View

from $130 / 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 $205 / night

$1,430 / week

Book View

from $205 / 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 $199 / night

$1,999 / week

Book View

from $199 / night

(3) Very Good 

10

Naples Vacation apartment rental

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

$1,081 / week

Book View

Responds fast!
avg. 3 hours 24 minutes

from $155 / 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 $179 / night

$1,252 - $1,967 / week

Book View

from $179 / 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 $182 / night

$1,271 - $1,967 / week

Book View

from $182 / night

33

Villa rental in Lely Resort with golf nearby

Naples / Lely Resort

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 $236 / night

$1,650 / week

Book View

from $236 / 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

Book View

from $77 / night

(9) 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

Inquire View

Pricing unknown

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

Book View

from $54 / 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 $267 / night

$1,867 / week

Book View

from $267 / 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

Book View

from $200 / 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 $142 / night

$994 - $1,413 / week

Book View

from $142 / night

(10) Excellent 

13

Vacation home in Naples

Southwest Gulf Coast / Naples

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
This three bedroom, three bath home features sunlit rooms and lush landscaping, with brick driveways and paths connecting the outdoor areas with the pool and lanai. In addition to the sunny living room, there is a spacious enclosed lanai family room adjacent the pool an …see more

from $170 / night

$1,200 - $1,650 / week

Book View

from $170 / night

24

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
  • Air conditioning
Fully Renovated and very modern second floor townhouse/condo design with ultra comfortable brand new furnishings. Remodeled kitchen with granite counter-tops, fully equipped, brand new stainless steel appliances and all new flooring. Minutes to the beach with shopping, …see more

from $77 / night

$539 / week

Book View

Responds fast!
avg. 1 hour 9 minutes

from $77 / night

(1) Excellent 

26

Home rental in Naples

Southwest Gulf Coast / Naples

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • 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 $460 / night

$3,220 / week

Book View

Responds fast!
avg. 1 hour 21 minutes

from $460 / night

28

Vacation apartment with shared pool in Naples

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
Park Shore Resort, 1st Floor, End Unit, Bldg.I Park Shore Resorts prime location west of Hwy.41 (Tamiami Trail) is within close proximity to restaurants, shopping, and famous downtown Naples. There's even a local supermarket, pharmacy, and post office just across the s …see more

from $106 / night

$1,575 - $1,589 / week

Book View

Responds fast!
avg. 4 minutes

from $106 / night

(7) Very Good 

19

Vacation villa in Naples

Southwest Gulf Coast / Naples

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
This nicely furnished, three bedrooms, two baths; single family home of 2200 square feet with a garage, is situated on a quiet cul-de-sac in the upscale Lely Resort of Naples, Florida. Sleeps 4 - 6 . The villa includes a master bedroom with king-size bed, walk in clos …see more

from $108 / night

$750 / week

Book View

from $108 / night

18

Vacation apartment in Naples

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
Gorgeously renovated 2-bedroom, 2-bath, condo located less than 10 minutes from Marco Island. The kitchen and bathrooms are complete with granite countertops and brand-new stainless steel appliances. The living room and both bedrooms boast updated flat-screen television …see more

from $50 / night

$350 / week

Inquire View

from $50 / night

15

Vacation houseboat in Naples

Southwest Gulf Coast / Naples

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
Captain's Cruiser is a fully equipped house boat that comfortably accommodates 3 or 4 people. It is docked at Port of the Islands Marina in Naples, Florida close to Everglades City and Marco Island. Our floating oasis has all the comforts of home. In addition to a ful …see more

from $99 / night

$693 / week

Book View

from $99 / night

18

Naples Vacation home rental

Southwest Gulf Coast / Naples

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 16 mi
  • Swimming pool
  • Child friendly
4 Bedroom, 3 Bathroom Lakefront - easy walk to Amenities incl tennis/beach club. There is a discount for multiple month rentals. Your family and friends deserve the perfect Southwest Florida vacation. You can pamper yourself at the resort-style pool area and enjoy th …see more

from $236 / night

$1,650 - $2,000 / week

Book View

from $236 / night

(5) 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

Book View

from $58 / night

24

Vacation apartment with shared pool in Naples

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A sunny Florida getaway awaits at this 2-bedroom, 2-bathroom Naples condo with enough room to easily accommodate 4 guests. Offering fantastic amenities, including a community pool, and an excellent location close to everything Naples has to offer, this incredible vacati …see more

from $115 / night

$805 - $1,260 / week

Book View

Responds fast!
avg. 21 minutes

from $115 / night

21

Naples Vacation home rental

Southwest Gulf Coast / Naples

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Wonderful 3 bedroom/ 2 bathroom home in a lovely neighborhood. Unwind in your very own private swimming pool or take a walk on the winding trails provided. The gated community of Briarwood is located close to Naples beaches, Fifth Ave South & the Third Street South sho …see more

from $157 / night

$1,100 / week

Book View

from $157 / night

(18) Excellent 

83

Home rental in Naples

Southwest Gulf Coast / Naples

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Charming home with open floor plan! Soaring ceilings and lots of windows make this home bright and cheerful. Perfect for your Florida Vacation!! Enjoying basking in the sun at beautiful Delnor Wiggins Pass park with gorgeous beaches or if you prefer, a quiet day in your …see more

from $200 / night

$1,300 - $2,100 / week

Book View

from $200 / 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 $138 / night

$966 / week

Book View

Responds fast!
avg. 38 minutes

from $138 / night

(9) Excellent 

33

Vacation apartment in Naples

Southwest Gulf Coast / Naples

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This beautiful, luxurious, upscale condominium, is located at Regatta II. It is a large unit, with 2100 square feet and a dramatic view of the bay. Wireless internet is available in the unit. It is a light, airy unit with three bedrooms and three full baths. The lar …see more

from $129 / night

$900 - $1,950 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

from $129 / night