50 Best Sanibel Island Vacation rentals on Holiday Lettings - Cottages

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355 Vacation rentals

(8) Excellent 

24

Sanibel Island 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

$1200 - $1500 / week

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from $150 / night

(3) Excellent 

24

Vacation condo rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
'' SEAS THE DAY '' condo is right on the beach , on the Gulf of Mexico , you just can't get away from the beach , you can't get closer . This beautiful 1300 SQ.FT. 3rd floor CORNER UNIT condo with 2 verandas wrapping around it, giving it a great sense of space and ope …see more

from $213 / night

$1488 - $3338 / week

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from $213 / night

24

Home rental in Sanibel Island with golf nearby

Southwest Gulf Coast / Sanibel Island

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Lea by the Sea is a luxurious 5 BEDROOM beach house with its own private beach and large panoramic windows overlooking San Carlos Bay . The house was completely remodeled in 2010. It has flat screen televisions in all bedrooms and a 48 inch tv in the great room. It ha …see more

from $856 / night

$5988 - $6999 / week

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from $856 / night

(1) Excellent 

17

Vacation condo in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
29 steps to the beach Just a few steps from our English owned luxury apartment and you are on the beach, a short walk from Sanibel's famous fishing pier. You will see small boats, pelicans and dolphins in the bay. Sanibel is famous for its beautiful white sandy shelli …see more

from $272 / night

$1900 - $2068 / week

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from $272 / night

(1) Excellent 

24

Vacation condo with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
'' A STEP AWAY FROM THE BEACH '' is right on the beach , on the Gulf of Mexico , you step out the door and on to the beach , you can't get closer. This beautiful 1250 SQ.FT. ground floor , corner unit condo is well furnished with a light, bright and sunny ambiance. T …see more

from $213 / night

$1488 - $2838 / week

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from $213 / night

18

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Spacious apartment with 2 bedrooms and 2 bathrooms. Fully equipped kitchen with washer and dryer. Large living and dining area and balcony. Beach towels and chairs available. Free WiFi. Free Use of bicycles and tennis courts. Large pool with Jacuzzi. Complex on the …see more

from $202 / night

$1413 / week

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from $202 / night

24

Vacation condo with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
''DAYDREAMING'' BEACHFRONT condo is right on the Gulf of Mexico , you just can't get away from the beach . This beautiful one bedroom beach condo is tastefully furnished with a light , bright and sunny ambiance .The moment you walk through the door and see the beach you …see more

from $185 / night

$1288 - $1989 / week

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from $185 / night

24

Vacation villa with golf nearby in Sanibel Island

Southwest Gulf Coast / Sanibel Island

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This recently redecorated south facing villa is situated in a quite but central part of Sanibel called Lake Murex . It is a spacious 4 bedroom, 3 full bath villa with a large open plan living area. The veranda overlooks the lake , the pool and the garden. There's a la …see more

from $356 / night

$2488 - $2789 / week

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from $356 / night

9

Apartment accommodation in Sanibel Island

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 $195 / night

$975 / week

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from $195 / night

19

Vacation home with swimming pool in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Location, location, location! A very, conveniently located 3 bedroom, 2 bathroom pool home just steps from West Gulf Drive's Beach Access #4! "Beach Time" is located in the most tranquil and desirable neighborhood on Sanibel directly off West Gulf Drive. The beach ac …see more

from $150 / night

$1050 - $2300 / week

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from $150 / night

(2) Excellent 

18

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Welcome to our B23 family!!!!! When you stay at our condo, we like to think you’ve become a part of our family. Relax and enjoy our home as much as we do and learn why Sanibel Island is a true treasure. The condo itself offers a true home away from home experience thr …see more

from $221 / night

$1547 - $2400 / week

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from $221 / night

(4) Very Good 

40

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
If you love water views, the warm Florida sunshine, watching dolphins at play and manatees meandering this is the place for you! This Mariner Pointe ground level suite is a true water lover’s paradise. Amenities galore including tennis, fishing, swimming, boating (doc …see more

from $157 / night

$1095 - $2295 / week

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from $157 / night

(8) Excellent 

29

Vacation home in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This island vacation property has 23 residences and is located on Middle Gulf Drive directly across the street from the Gulf of Mexico. Sandpepple sits on a canal where you may see many of the island tropical birds and other wildlife. You can enjoy watching them from th …see more

from $150 / night

$850 - $1800 / week

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from $150 / night

(8) Excellent 

10

Home rental in Sanibel Island with shared pool

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy the spectacular views from this direct Gulf front condo overlooking beautiful natural native vegetation of seagrapes, sea oats, and palm trees then out to the beach where warm waters wash up on Sanibel's 15 miles of beautiful uninterrupted shell filled beaches. As …see more

from $250 / night

$1300 - $3101 / week

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from $250 / night

19

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Ask about children
You’ll appropriately feel just like royalty in this light and spacious 3-bedroom/2-bath unit located in Kings Crown on West Gulf Drive. The unit features an open floor plan, remodeled kitchen and spacious lanai overlooking one of the island’s best shelling beaches. All …see more

from $182 / night

$1274 - $2674 / week

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from $182 / night

(16) Excellent 

22

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This beautiful 2 bedroom/2 bathroom third floor condo has a gorgeous angel view of the Gulf of Mexico. It offers an additional cozy den which closes off for a third sleeping area. This den has a pull out twin size sleeper sofa and remote TV. The newly remodeled kitchen …see more

from $200 / night

$1400 - $2650 / week

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from $200 / night

(3) Excellent 

10

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
54 residences make up this mid-size complex and you may choose from 2 bedrooms/ 2 bathrooms floor plan with approximately 1566 total sq. ft. Please Note: All King's Crown units require two-week minimum rental from November 15 -May 1. One week rentals are available May - …see more

from $175 / night

$1200 - $2400 / week

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from $175 / night

25

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This unit is located at the Sundial Beach Resort and is a spacious 3 bedroom, 2 bathroom condo that sits on the Gulf of Mexico with water views from the lanai. This condo offers over 1500 square feet of comfortable living space with a fully stocked kitchen and an open …see more

from $220 / night

$1540 - $2920 / week

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from $220 / night

35

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
One of the most unique condominium units on Sanibel. Owner completely remodeled October/November 2015. Photos to follow. Located on Middle Gulf Drive, this 5 bedroom 4 bath unit has 3 separate living levels all attached by elevator or spiral staircase within the u …see more

from $630 / night

$4410 - $6417 / week

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from $630 / night

(4) Excellent 

20

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Enjoy the gorgeous views of San Carlos Bay in this 2 bedroom/2 bathroom condominium! You can watch the dolphins and manatees play, the fish jumping and the birds diving right from your private screened balcony! This condo is decorated in splashes of seafoam greens and f …see more

from $150 / night

$850 - $1850 / week

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from $150 / night

35

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

4 12 28 nights min

  • 4 bedrooms
  • Sleeps 12
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
An absolutely outstanding 4 bedroom, 3 bath pool home located in the highly sought after Butterknife Community off West Gulf Drive! Come and see this beauty for yourself!! The main living area of the house features a bright and sunny living and dining room area with an …see more

from $296 / night

$2069 / week

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from $296 / night

23

Vacation apartment with tennis court in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Beautifully decorated 4th floor unit with 2 bedrooms, 2 baths and queen sleeper sofa (sleeps 6). Bonus room with bumper pool and additional seating creates extra living space! Fully equipped eat-in kitchen, washer/dryer, screened-in lanai and a private penthouse sundec …see more

from $200 / night

$1400 / week

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from $200 / night

13

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
On a clear day you can see forever! That's what can be said about the Gulf front location of this 2 bedroom 2 bath unit. You just can't get a better view on Sanibel than from this unit. Island Beach Club is a 75 unit complex centrally located off West Gulf Dri …see more

from $248 / night

$1737 - $3525 / week

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from $248 / night

20

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Pine Cove is located on West Gulf Drive. A wonderful, tropical hideaway just a boardwalk stroll from the Gulf of Mexico.This nice 2 bedroom 2 bath with den, gulf front unit offers a third floor view of the Gulf of Mexico. Has 1 flat screen TV. If you desire a quiet vac …see more

from $248 / night

$1737 - $3647 / week

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from $248 / night

(5) Excellent 

18

Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Unit #563: This bright, sunny condo features vaulted ceilings & skylights in the Living Room & Master Bedroom. There is a king sized bed in the Master bedroom and white wicker double beds with blue accents are in the Guest bedroom. The living room is spacious, with a co …see more

from $200 / night

$1100 - $2300 / week

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from $200 / night

(19) Very Good 

20

Vacation villa in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Each of our four spacious Villas is fully equipped to make your vacation stay comfortable and effortless. Each Villa offers over 1200 square feet of air conditioned living area and features two bedrooms and 1 & 1/2; baths, fully appointed kitchens, separate living and d …see more

from $170 / night

$1050 - $1610 / week

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from $170 / night

(4) Excellent 

38

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0.25 mi
  • Swimming pool
  • Child friendly
Enjoy your Sanibel vacation at the relaxing and quiet Breakers West complex in a unit that has seen many upgrades in the past year. This is a very spacious unit with 1,150 sq ft for you to relax in. The complex has a very private feel with only 18 units in the buildin …see more

from $205 / night

$1295 - $2705 / week

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from $205 / night

(2) Excellent 

20

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This condo is top of the line! A vaulted ceiling with skylights in the Living Room & Master Bedroom, brings all the natural light into this beautiful unit. The master bedroom has a king sized bed in a seashore motif. There are twin beds in the colorful Guest bedroom. Th …see more

from $200 / night

$1100 - $2400 / week

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from $200 / night

25

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Sandpiper Beach 302 has it all !! This two bedroom two bath condo is being totally remodeled with top of the line materials and furnishings. It's very private and convenient first floor living level with direct expansive Gulf Front views cannot be beat and will make t …see more

from $165 / night

$1155 - $2641 / week

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from $165 / night

18

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
If you’re looking for a quiet, relaxing location away from the crowds to unwind from the daily grind – you’ve found it! Ibis at the Sanctuary is an exclusive condo development located on the picturesque west side of Sanibel close to Blind Pass and Captiva Island. The Ib …see more

from $143 / night

$1000 - $1775 / week

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from $143 / night

32

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Shorewood is a quiet 13 unit complex centrally located off of Middle Gulf Drive. This nice, spacious 3 bedroom 3 bath unit is just the place for that perfect island vacation. Direct Gulf front view with pool and tennis. Wireless internet connection is now available …see more

from $248 / night

$1737 - $4497 / week

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from $248 / night

28

Apartment rental in Sanibel Island with shared pool

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Condo ammenities include: 2 bedrooms/2 bathrooms -- 1 King bed & 2 twin beds (sleeps 4), 3 TVs & DVD player, free WIFI & cable, fully equipped kitchen, heated shared pool, in suite washer & dryer, public BBQ gas grills, shuffleboard, community tennis courts, elevator ac …see more

from $163 / night

$1135 - $2535 / week

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from $163 / night

27

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Sanibel Surfside offers one of the best vacation locations on Sanibel Island and is one of closest complexes within just steps to the sandy beach and the Gulf of Mexico! This 2 Bedroom 2 Bathroom condo is fully equipped and offers wireless internet. If you enjoy golfi …see more

from $145 / night

$1010 - $2360 / week

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from $145 / night

(5) Good 

7

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Located within short walk to beach and facing pool. A first floor unit steps from the pool deck with large living room, dining area and above average closet space. Large 60" wall TV for your down time enjoyment. Beach chairs/umbrella's included. Complex has heated pool …see more

from $143 / night

$1000 - $1700 / week

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from $143 / night

25

Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
This spectacular 1 bedroom condo is located at the Sundial Beach Resort and is the perfect spot to call home while vacationing in paradise. This unit has been totally updated and dressed with all new furniture to compliment the beachy setting of Sanibel Island. The sh …see more

from $191 / night

$915 - $1920 / week

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from $191 / night

18

Apartment accommodation in Sanibel Island

Southwest Gulf Coast / Sanibel Island

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
This comfortable 2 bedroom, 2 bath unit looks out over the lush grounds with views of the lagoon and gulf. It is located on the 2nd floor. Pointe Santo is a 140 unit community located on West Gulf Drive. Amenities include 2 tennis courts, a swimming pool, whirlpool …see more

from $157 / night

$1099 - $2674 / week

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from $157 / night

15

Sanibel Island Vacation apartment rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This is a nice, 2 bedroom, 2 bath unit! Decorated in fun island decor, this unit is just what you need to put you in that island state of mind. Courtyard view, 3 flat screen TV's. The porch has been glass enclosed for extra room. You gotta see this one! ****** …see more

from $137 / night

$956 - $2188 / week

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from $137 / night

14

Sanibel Island Vacation cottage rental

Southwest Gulf Coast / Sanibel Island

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Suitable for children age 5+
Fully equipped beach cottage to make your vacation stay comfortable and effortless. Sanibel City ordinances permit a minimum stay of 28 days. Nerita Beach Cottage is just a short stroll to the beach. The home is just 12 houses to the beach. It features 2 bedrooms, one …see more

from $150 / night

$1050 / week

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from $150 / night

(6) Excellent 

23

Sanibel Island Vacation home rental

Southwest Gulf Coast / Sanibel Island

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Come relax and enjoy paradise in this stylishly updated condominium in one of Sanibel's best locations. Professionally decorated in charming island style, this is the ideal tropical retreat to make your vacation getaway perfect. Open the doors on the lanai, and you will …see more

from $250 / night

$1700 - $3301 / week

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from $250 / night

13

Vacation apartment in Sanibel Island

Southwest Gulf Coast / Sanibel Island

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Ask about children
This is one of just a few one bedroom units at Pointe Santo. Very nice ground floor walk out with a view of the lagoon. Perfect for that honeymoon couple or small family. 2 flat screen TV's. This beautiful 140 unit community is located on West Gulf Drive. Amenitie …see more

from $157 / night

$1099 - $2310 / week

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from $157 / night

1