50 Best Naples Vacation rentals on Holiday Lettings - Apartments

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1,639 Vacation rentals

(14) Very Good 

28

Villa rental in Naples with golf nearby

Naples / Lely Resort

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • 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 $215 / night

$1,500 / week

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from $215 / night

(4) Excellent 

16

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, hot tub & lake view in a secure community of Artesia, Naples. The house with its 4 bedrooms and 3 bathrooms easily accommodates 8 people New furniture in the lounge: sofa, love seat, fautauill , coffe …see more

from $175 / night

$1,350 - $2,050 / week

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from $175 / 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 $86 / night

$598 - $837 / week

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Responds fast!
avg. 2 hours 48 minutes

from $86 / night

(6) Very Good 

36

Naples Vacation home rental

Southwest Gulf Coast / Naples

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 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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Responds fast!
avg. 2 hours 43 minutes

from $179 / 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 $250 / night

$1,750 / week

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from $250 / 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

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from $179 / 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 $200 / night

$1,329 - $1,595 / week

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from $200 / 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

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from $199 / 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

(10) Very Good 

31

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

from $192 / night

$1,339 / week

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from $192 / 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 $103 / night

$720 - $750 / week

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from $103 / 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

(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 $170 / night

$1,189 - $1,841 / week

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from $170 / 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

21

Vacation villa in Naples

Southwest Gulf Coast / Naples

2 4 120 nights min

  • 2 bedrooms
  • Sleeps 4
  • 120 nights min
We are seeking a retired individual/couple who would like to escape to our home in North Naples for the 2018/2019 rental season. Our home is located at the end of a quiet cul de sac in the gated community of Village Walk of Naples. Newly painted and tastefully decorat …see more

from $120 / night

$840 / week

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from $120 / 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

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 $147 / night

$1,030 / week

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from $147 / 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 $181 / night

$1,263 - $1,595 / week

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from $181 / 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

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from $267 / 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

(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 $145 / night

$1,015 / week

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Responds fast!
avg. 2 hours 20 minutes

from $145 / 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 $166 / night

$1,163 - $1,827 / week

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from $166 / 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

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Pricing unknown

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 $200 / night

$1,400 / week

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from $200 / 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 $190 / night

$1,329 / week

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from $190 / 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 $133 / night

$929 - $1,321 / week

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from $133 / night

28

Naples Vacation apartment rental

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
My place is located in Naples, Florida, in the beautiful and quiet neighborhood of Coral Falls Resort - this is the perfect choice for visitors wanting a relaxing home away from home. Peaceful, but a hop in the car away from the splendid Marco Island beach, entertainmen …see more

from $65 / night

$455 / week

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from $65 / night

(4) Excellent 

8

Vacation apartment in Naples

Southwest Gulf Coast / Naples

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Two Bedroom Condo at Coral Falls Resort. Perfect location. 10 mintues from both Marco Island and Downtown Naples. Located within walking distance to shopping, and minutes from Gulf beaches. Onsite amenities include tropical waterfall pool and spa, two 18 hole champions …see more

from $125 / night

$700 / week

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Responds fast!
avg. 3 hours 59 minutes

from $125 / night

(11) Excellent 

13

Vacation home in Naples

Southwest Gulf Coast / Naples

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • 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 / week

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from $170 / night

18

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Minutes from Old Naples, Tin City, the famous seven miles of pure white sand Naples Beaches and a short drive to Marco Island, this two-bedroom condo is nestled in the middle of an 18-hole golf course. The Par 5 group of condominiums has its own heated pool, and is a s …see more

from $70 / night

$490 / week

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from $70 / night

14

Naples Vacation condo rental

Southwest Gulf Coast / Naples

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Car not necessary
A perfect condo on Vanderbilt Bay, A breath taking view of the Bay, walk to white sandy Vanderbilt Beach, your own fishing pier, Boat Dock and Boat Lift, Electronic Gated Entry, Elevator, Heated Pool, Spa. Just the other side of Ritz Carlton Hotel. Turtle Club, La Playa …see more

from $149 / night

$1,600 - $2,300 / week

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from $149 / night

(5) Excellent 

30

Apartment rental in Naples with golf nearby

Southwest Gulf Coast / Naples

2 6 14 nights min

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Welcome to our beautiful lake-front home, located in North Naples, at Heritage Bay Golf & Country Club, famous for its 27-hole Championship Golf Course. It is elegant yet cozy, relaxing, bright and sunny, and offers breathtaking views of the lake. A haven of serenity an …see more

from $120 / night

$840 / week

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from $120 / night

11

Vacation condo with shared pool in Naples

Southwest Gulf Coast / Naples

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Swimming pool
  • Air conditioning
Beautiful 2 bedroom condo on the second floor overlooking golf course and association pool. Fully stocked kitchen, all new mattresses, bedding, and linens. Newer leather sectional in living room with flatscreen TV, WIFI, Cable, dvd player, and newer Lanai furniture. Co …see more

from $104 / night

$725 / week

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from $104 / night

(2) Excellent 

36

Vacation condo in Naples

Southwest Gulf Coast / Naples

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
* PLEASE SEND AN INQUIRY FIRST PRIOR TO REQUESTING A RESERVATION. VIEWS, VIEWS, VIEWS! The view alone from this unit should do it, but there’s more. This unit is in an most desirable location, in the famed Park Shore Resort in Naples. It is a AAA-3-Diamond resort with …see more

from $140 / night

$973 - $1,650 / week

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Responds fast!
avg. 27 minutes

from $140 / night

24

Naples Vacation home rental

Southwest Gulf Coast / Naples

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Our house is located in Naples park, in walking distance to the beach. It has 3 bedrooms and 2 bathrooms. We also have 2 sofa beds in the living area that are converted to queen size beds. The house is nicely decorated and will impress by comfy space and cozy atmospher …see more

from $100 / night

$700 / week

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from $100 / night

(4) Very Good 

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

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Responds fast!
avg. 2 hours 44 minutes

from $460 / night

18

Vacation condo rental

Southwest Gulf Coast / Naples

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
Treviso Bay is an absolutely stunning TPC course with incredible conditions; well-designed and challenging for players of all skill levels. The best part, all you pay for unlimited play is the $26 cart fee. Our 3 year old, 2 bedroom unit fronts on the course with the la …see more

from $200 / night

$1,500 / week

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from $200 / 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
****Spring & Summer Special: 10% OFF Base Rental Rate 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 s …see more

from $106 / night

$1,575 - $1,589 / week

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Responds fast!
avg. 9 minutes

from $106 / night

14

Vacation condo rental

Southwest Gulf Coast / Naples

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Enjoy the Florida sun while watching golfers approach the tenth green of the Championship Flamingo Golf Course, birds gathering by the lake, or a turtle walk by as you relax on your lanai. Spend a day poolside swimming or lying on a chaise lounge or unwind in the spa a …see more

from $100 / night

$700 / week

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from $100 / night

(17) 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

$1,200 - $2,100 / week

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from $172 / night