50 Best Vacation Rentals in Southwest Gulf Coast - Holiday Lettings - Cabins

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Southwest Gulf Coast

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5,265 Vacation rentals

(15) Excellent 

25

Vacation home accommodation

Fort Myers Beach / Estero Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
Bay Front Dream Home. If the water is your passion, come stay in this beautiful bayfront home. Bring your morning cup of coffee to the screen-enclosed pool and lanai to watch the sunrise over Estero Bay. Enjoy fishing from the boat dock, watch the dolphins or its just …see more

from $291 / night

$2,033 - $3,409 / week

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from $291 / night

(29) Excellent 

24

Vacation villa in Fort Myers Beach

Southwest Gulf Coast / Fort Myers Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Island setting. 4 Bed, 2.5 Bath Villa, 8 minutes stroll from the lovely Fort Myers Beach. 33 Foot Infinity Pool with massage jets giving onto canal (dolphin+manatee visits). Extensive south facing Patio/Deck/Pool area with barbecue.Sleeps up to 8. Beach Equipment + Cadd …see more

from $277 / night

$1,595 - $2,445 / week

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from $277 / night

(20) Excellent 

22

Vacation villa with golf nearby in Southwest Gulf Coast

Rotonda West / Broadmoor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This privately own Villa is rented directly from its U.K. owners with no agents or commissions. It is maintained in lovely condition by the owners and their local professional management company who are always available should you need help or advice. This …see more

from $100 / night

$700 - $1,127 / week

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Responds fast!
avg. 1 hour 50 minutes

from $100 / night

17

Southwest Gulf Coast Vacation villa rental

Southwest Gulf Coast / Sarasota

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
A 3 bedroom/2 bathroom villa situated in a quiet residential location only minutes from downtown Sarasota.It has a private and secluded south facing garden with its own caged, solar heated private pool which catches the sun throughout the day.(electric pool heater is av …see more

from $108 / night

$756 / week

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from $108 / night

(2) Excellent 

12

Vacation villa rental

Rotonda West / Long Meadow

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 7 mi
  • Swimming pool
WOW, this really is one of the loveliest homes on the whole of Rotonda, in fact, in my humble opinion probably most of Florida! Fantastic outlook to the rear overlooking the lovely lake and golf course, private yet not secluded. Stunning inside and exceptionally well m …see more

from $257 / night

$735 - $1,610 / week

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Responds fast!
avg. 1 hour 26 minutes

from $257 / night

9

Apartment accommodation in Southwest Gulf Coast

Southwest Gulf Coast / Sanibel Island

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This excellent Timeshare waterfront resort is set on a west coast island that is world-renowned for its shelling beaches. This ground floor condo is located in Lighthouse Resort and Club --a luxury waterfront resort on the world top rated Sanibel Island, Florida . The s …see more

from $210 / night

$1,050 / week

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from $210 / night

(4) Excellent 

24

Vacation villa with indoor pool in Southwest Gulf Coast

Southwest Gulf Coast / Bradenton

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Spacious Villa 4 bed, 2 bath, front lake view, BBQ Grill, Lanai, up to 8 people Relax at your pool and admire at the same time the lake view with herons !!! Great location just a short drive to amazing beaches, great restaurants and shopping, 15 minutes from downtown …see more

from $117 / night

$819 / week

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from $117 / night

(2) Excellent 

19

Vacation apartment in Southwest Gulf Coast

Southwest Gulf Coast / Sarasota

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
An air conditioned 3 bedroom/2 bathroom villa with private solar heated pool. The villa is conveniently located in a residential area, close to all amenities including stunning beaches, golf courses, restaurants and shopping malls. Fully equipped kitchen and dining room …see more

from $89 / night

$616 / week

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from $89 / night

29

Vacation home with swimming pool in Englewood

Southwest Gulf Coast / Englewood

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Nearest beach 7 mi
  • Swimming pool
  • Child friendly
Open and bright split floor plan. Large lanai featuring a pool that is accessible from kitchen, living and master bedroom. Property located in the quiet Pine Lake community. Minutes to Englewood & Manasota beaches, shopping, dining and downtown in Englewood. Large mast …see more

from $125 / night

$1,000 / week

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from $125 / night

6

Vacation condo in Fort Myers Beach

Southwest Gulf Coast / Fort Myers Beach

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Child friendly
EVERYTHING new in this 2 bedroom, 2 bathroom condo!! Features a full size and fully equipped kitchen. Open floor plan to dining and living room. Washer and dryer conveniently located in unit. Beautiful view of beach and sunsets off of the 4th floor screened in lanai. Re …see more

from $100 / night

$700 / week

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Responds fast!
avg. 6 minutes

from $100 / night

(22) Excellent 

28

Vacation villa with golf nearby in Southwest Gulf Coast

Southwest Gulf Coast / Cape Coral

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
An elegant and luxuriously appointed waterfront home situated in the exclusive up-market South West region of Cape Coral. Built in 2002 and one of only six houses of its kind, this charming home offers over 2400 sq ft of stylish,air conditioned living accommodation. One …see more

from $138 / night

$961 - $1,470 / week

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from $138 / night

(15) Very Good 

30

Vacation villa in Southwest Gulf Coast

Southwest Gulf Coast / Cape Coral

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool
Our newly remodeled Villa has about 2,000 sq.ft. Living area with 1,100 sq.ft. Generous pool area. You will be love the heated pool with the separate Scandinavian style SPA (Jacuzzi). Within only 3 minutes by boat you’ll reach the high-speed areas on Caloosahatchee Rive …see more

from $140 / night

$980 - $1,275 / week

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from $140 / night

(17) Excellent 

24

Home rental in Fort Myers with golf nearby

Fort Myers / South Fort Myers

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 25 mi
  • Swimming pool
2200 square feet fully air conditioned living space. Further 800 square feet non air conditioned garage and covered lanai. Beautiful private rear views onto Federal Preserve area. Full electric heated swimming pool with hot tub. Purchased for owners own use as a second …see more

from $110 / night

$770 - $1,106 / week

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from $110 / night

(1) Excellent 

11

Lido Key Vacation bungalow rental

Sarasota / Lido Key

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
We are the happy owners of a cozy and charming cottage on the coast of Florida. Since we do not live permanently and fun - we live in this beautiful area and our wonderful holiday - gladly give to others, we rent the cottage to anyone who is in need of a holiday paradis …see more

from $248 / night

$1,735 / week

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from $248 / night

(2) Excellent 

22

Southwest Gulf Coast Vacation villa rental

Southwest Gulf Coast / Rotonda West

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
"Broad Key Villa" - Enjoy this luxurious, private villa located in a deed restricted community of Rotonda West on Florida's Gulf Coast, renowned for its numerous championship golf courses and beautiful soft, white, sandy beaches. Rotonda is the perfect location to sati …see more

from $253 / night

$1,767 / week

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from $253 / night

(6) Excellent 

Certificate of Excellence

26

Vacation villa with swimming pool, golf nearby in Southwest Gulf Coast

Southwest Gulf Coast / Port Charlotte

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 25 mi
  • Swimming pool
Very quietly located pool Vila between Port Charlotte and North port. In five minutes, one is with the bike at supermarkets and restaurants. This approx. 185 m² House offers all the amenities and has the great advantage that the neighbouring plots include free or to the …see more

Certificate of Excellence

from $86 / night

$600 / week

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from $86 / night

(4) Excellent 

24

Vacation apartment in Bradenton

Southwest Gulf Coast / Bradenton

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This is a brand new coach home (built 2013) 2,515 Sq. Ft. Including a two car garage of 376 Sq. Ft. It has a private entrance and is located on the ground floor. Once you enter the Foyer you overlook a beautiful Living Room mostly furnished with dark brown le …see more

from $122 / night

$850 / week

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from $122 / night

(13) Excellent 

Certificate of Excellence

26

Vacation home with golf nearby in Fort Myers

Fort Myers / South Fort Myers

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
Fort Myers is situated in the south west of Florida on the beautiful Gulf Coast, renowned for its long stretches of white sand and the warm waters of the Gulf Stream.Our modern two-storey house (2700 sq feet) is only 3 miles from Fort Myers Beach and 4 miles from the be …see more

Certificate of Excellence

from $133 / night

$973 - $1,119 / week

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Responds fast!
avg. 2 hours 35 minutes

from $133 / night

(20) Excellent 

25

Vacation villa in Southwest Gulf Coast

Southwest Gulf Coast / Cape Coral

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
This beautiful Floridian home provides accommodation for up to 9 people in four bedrooms. Extending to 2400sq ft under air. With 2 lounges and an outside seating and dining area plus a bar with outside TV, an indoor formal dining room and breakfast bar give relaxed conv …see more

from $100 / night

$650 - $797 / week

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from $100 / night

19

Rotonda West Vacation villa rental

Southwest Gulf Coast / Rotonda West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Green Acres" - If you are looking for a luxurious retreat to spend a relaxed and fun-filled holiday with your family or friends then Green Acres, a vacation rental in Rotonda, FL is perfect for you. Beautifully appointed with a multitude of amenities, this splendid retr …see more

from $130 / night

$1,148 - $1,344 / week

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from $130 / night

(14) Excellent 

16

Vacation apartment in Southwest Gulf Coast

Southwest Gulf Coast / Bradenton

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
Our light, spacious, open-plan apartment is in the Shorewalk complex, situated on the beautiful central Gulf Coast of Florida.  Shorewalk comprises 2-story buildings on 30 acre grounds with mature trees.  Paths, well-lit at night, meander around 6 stocked lakes to lead …see more

from $88 / night

$596 - $881 / week

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from $88 / night

12

Home rental in Englewood

Southwest Gulf Coast / Englewood

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Our house is right on the boat slip, has an inflatable canoe and two bicycles. The residential area is quiet, the beach is about 2 miles. It is fully equipped to local stations can be received, WiFi via a router with prepaid access. We offer the possibility to clean the …see more

from $65 / night

$451 - $902 / week

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from $65 / night

(14) Very Good 

28

Villa rental in Southwest Gulf Coast 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

(2) Excellent 

17

Vacation villa in Southwest Gulf Coast

Southwest Gulf Coast / Cape Coral

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
TREAT YOURSELF TO RELAX & DE-STRESS IN YOUR OWN PRIVATE VILLA COMPLETE WITH DUAL HEATED SALT WATER IN GROUND POOL, PALM TREES, AND YOUR PERSONAL PRIVATE DOCK LOCATED ON A SALT WATER CANAL, ONLY MOMENTS TO OPEN WATER AND THE GULF OF MEXICO! Hi! We are Pat & Trudy, and …see more

from $139 / night

$910 - $1,200 / week

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from $139 / night

(2) Excellent 

34

Vacation villa in Southwest Gulf Coast

Fort Myers / South Fort Myers

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Located in the ever popular South Fort Myers area of Florida, the home is ideally situated close to all local amenities, outlet malls, restaurants shops and recreational activities are a short jog away. The Islands of Sanibel and Captiva, and the beautiful beaches of Fo …see more

from $140 / night

$980 - $1,260 / week

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from $140 / night

(2) Excellent 

15

Vacation home in Southwest Gulf Coast

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

(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

(18) Excellent 

24

Villa rental in Punta Gorda with indoor pool, golf nearby

Southwest Gulf Coast / Punta Gorda

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our villa is a 3700 square foot villa with three bedrooms and three bathrooms.!You will stop your search after a look at this unique property. This piece of property is one of the most sought after lots in Florida, it is called a (point) lot, sun all day and three sid …see more

from $200 / night

$1,650 / week

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Responds fast!
avg. 3 hours 10 minutes

from $200 / night

(8) Excellent 

24

Southwest Gulf Coast Vacation home rental

Southwest Gulf Coast / Sanibel Island

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Surfsound home is tucked away off Rabbit Road and is just a 5 minute walk to deeded beach access. This beautiful spacious home offers 3 bedrooms (1 US king, 1 queen and one twin), 3 ½ bathrooms, fully equipped kitchen private screened heated pool and beautiful décor. Su …see more

from $150 / night

$1,500 / week

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from $150 / night

26

Condo rental in Little Gasparilla Island

Southwest Gulf Coast / Little Gasparilla Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
AKA the "Green Roof Condos", we are a 1000 sq ft end unit with no one above or below. South facing and perched 20 feet above the ground with palm trees in all views. There is a second floor loft (fixed ladder) that sleeps 2. We have a freshwater pool right on the island …see more

from $140 / night

$1,000 - $1,300 / week

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Responds fast!
avg. 2 hours 34 minutes

from $140 / night

(7) Excellent 

21

Bradenton Vacation villa rental

Southwest Gulf Coast / Bradenton

4 8 14 nights min

  • 4 bedrooms
  • Sleeps 8
  • 14 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
This home is regarded as a ‘Premier Property’ by local agents, owing to it’s size and very high standard of finish. Its delightful rear aspect overlooking the lake and exceptional furnishings makes this home extremely desirable. It has floor space in excess of 2,400 squ …see more

from $160 / night

$1,119 / week

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from $160 / night

29

Southwest Gulf Coast Vacation home rental

Southwest Gulf Coast / Bonita Springs

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 7 mi
  • Swimming pool
  • Child friendly
Gorgeous new home with awesome amenities.12 foot coffered ceilings Large shower and bidet in Master bathroom High speed internet with WiFi (WLAN) extender so that you maintain a strong signal even in the lanai/pool area. 65" 4K TV's in Master Bedroom and Great Room Cage …see more

from $130 / night

$910 / week

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from $130 / night

16

Vacation villa in Fort Myers

Fort Myers / South Fort Myers

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
Luxury 3 bedroom detached villa with private pool, 2 bathrooms, 2 lounges The villa has 3 bedrooms, 1 twin bedded rooms and 2 with queen sized beds. The master bedroom has a large walk in closet and is en-suite with large Roman bath, two washbasins, cupboards un …see more

from $154 / night

$1,260 - $2,240 / week

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from $154 / night

19

Vacation townhouse in Southwest Gulf Coast

Fort Myers / Paseo

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This is a brand new, non-smoking condo. It is a single family home with a two car garage second floor features a beautifully decorated master bedroom with king size bed and walk-in closet. The en suite master bathroom features a glass-enclosed, stand-alone shower …see more

from $115 / night

$800 / week

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from $115 / night

(5) Excellent 

12

Vacation villa in Southwest Gulf Coast

Port Charlotte / South Gulf Cove

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
A stunning 4-5 bed home with 2 amazing master en suites. South facing pool & spa overlooking woodland. A perfect, quiet, restful setting to enjoy the delights of the South West cost of Florida in what really is a perfect home. Everything you could wish for is here read …see more

from $115 / night

$1,393 - $1,610 / week

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Responds fast!
avg. 1 hour 26 minutes

from $115 / night

(1) Excellent 

11

Home rental in Southwest Gulf Coast 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

(1) Excellent 

25

Vacation home rental

Rotonda West / Broadmoor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This beautiful fully air conditioned three en-suite bedroom villa is situated in Rotonda West, an area of unspoiled natural beauty and tranquility. Beautiful white sandy beaches provide sunbathing, swimming and beachcombing. There are championship golf courses on Rotond …see more

from $145 / night

$1,015 / week

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from $145 / night

(1) Excellent 

22

Vacation home rental

Southwest Gulf Coast / Port Charlotte

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Chaves - Vacation home near beach und golf course Approx. 1205 sqft under air, 1 living room, 2 bed rooms with built-in closets, 1 study, 2 bath rooms (thereof one with shower, one with shower & tub combination), 1 kitchen, 1 garage (approx. 215 sqft)., lanai (roofed) …see more

from $110 / night

$660 - $900 / week

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from $110 / night

(11) Very Good 

Certificate of Excellence

17

Vacation home in Southwest Gulf Coast

Bradenton / Sabal Harbour

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sabal Harbour house description This beautiful 2,550 Sq.Ft, four-bedroom, two-bathroom villa enjoys an enviable, south-facing position overlooking a picturesque lake. It is situated in the Sabal Harbour area in Bradenton, Florida. It offers the opportunit …see more

Certificate of Excellence

from $168 / night

$1,050 / week

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Responds fast!
avg. 1 hour 40 minutes

from $168 / night

(17) Excellent 

27

Vacation villa with golf nearby in Rotonda West

Southwest Gulf Coast / Rotonda West

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Luxury South West facing 4 Bed 4 Bath villa overlooking Lake and Golf Course on Rotonda, West. Very private and furnished to a high standard. Everything you could want for that special holiday. Heated pool and spa (not solar). This high quality villa offers a private …see more

from $190 / night

$1,330 / week

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Responds fast!
avg. 2 hours 3 minutes

from $190 / night