Vacation Rentals in Florida South West

Find the perfect Cheap Vacation Rentals, Vacation Rental Deals and Luxury Villas in Florida, Colorado, California, Hawaii, South Carolina, Outerbanks and more! Get Last Minute Deals on Beach Houses, Ski cabins, Family Vacation Rentals and Pet Friendly Vacation Rentals now at How2Vacation.com!

Vacation Rentals in Florida South West

309 Marquesas

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • You will enjoy this brand new home with heated pool. Lovely furnishings and professional decorating. Private office and sitting room.…
  • from
  • $1500
    weekend

 

Seawinds Condominium

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • You will enjoy this condo on the beach. Fully furnished 2 bedroom 2 bath condo with pool, tennis, and the…
  • from
  • $800
    weekend

 

Down By the Riverside

  • 1 Bedroom, 1 Bathroom, Sleeps 3
  • Watch the sunrise and the boats drift by for your vacation. Lovely one bedroom condo just 1 mile from the…
  • from
  • $400
    weekend

 

Essex Condominium

  • 2 Bedrooms, 2 Bathrooms, Sleeps 5
  • Ideally located - one block's walk to the beach, close to shopping. The Essex complex comes with a pool and…
  • from
  • $550
    weekend

 

1570 Buccaneer Court

  • 3 Bedrooms, 2 Bathrooms, Sleeps 8
  • Treat your family to a perfect vacation. This home offers the ultimate experience in relaxation. It is ideally located off…
  • from
  • $1200
    weekend

 

Seawinds Condominium

  • 0 Bedroom, 0 Bathroom, Sleeps 0
  • Vacation in a beautifully appointed beachfront condo with accommodations for six. Each Seawinds apartment is comprised of approximately 1,000 square…
  • from
  • $800
    weekend

 

Apollo Condominium

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • The Apollo complex is situated on the beach and offers you the most amenities: Pool, tennis, sauna, jacuzzi, exercise room…
  • from
  • $700
    weekend

 

Somerset Condominium

  • 2 Bedrooms, 2 Bathrooms, Sleeps 5
  • Treat your family to an oceanfront vacation! The Somerset condominium is one of the most requested buildings on Marco Island.…
  • from
  • $1200
    weekend

 

South Seas Condo

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • This condo is located right on the beach at Marco Island. Tigertail Beach is a 32 acre state park and…
  • from
  • $800
    weekend

 

Hyacinth Ct

  • 4 Bedrooms, 2 Bathrooms, Sleeps 8
  • Wake up to the sunshine from the master bedroom private balcony overlooking a private bay. This home is casual and…
  • from
  • $2500
    weekend

 

Century 21 First Southern Trust

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Century 21 First Southern Trust is a vacation rental company on Marco Island. We help owners find quality rentals weekly,…
  • from
  • $650
    weekend

 

'My Florida Paradise' 2 Bedroom Vacation Condo at Bonita Village…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • This 2-Bedroom residence is perfectly located within Bonita Village Resort. You will appreciate the casual upscale living combined with this…
  • from
  • $795
    weekly

 

Sterling Oaks Villa 3 Bedroom Vacation Home Rental in Naples…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • Enjoy this delightful attached villa with a private preserve view! This community is very social and has a marvelous club…
  • from
  • Contact Owner

 

4 Bedroom Family Vacation Rental Home with Heated Pool and…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 10
  • The Features of this Marco Island Vacation Rental Home Private Lanai Private dock 2400 square feet under air conditioning Private…
  • from
  • $1355
    weekly

 

Century 21 First Southern Trust

  • 0 Bedroom, 0 Bathroom, Sleeps 0
  • We manage condos and homes for owners. We do the work for you providing 24 hour service. Professional staff and…
  • from
  • Contact Owner

 

Pet Friendly 3 Bedroom Vacation Home Rental with Private Pool…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 6
  • Naples is one of America's most desirable places to live. Selected as a favorite place among top executives and professionals…
  • from
  • $90
    nightly

 

Elegant 3 Bedroom Vacation Home with Private Pool -1063 Tivoli…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • The elegant town of Naples is sited on Florida's Gulf Coast, famous for miles of beautiful, white sandy beaches and…
  • from
  • $90
    nightly

 

3 Bedroom Vacation Condo Rental - 326 Dover Place J…

  • 3 Bedrooms, 2 Bathrooms, Sleeps 6
  • This beautiful 3 bedroom 2 bath condo is located in the most requested Sub division in Naples, Briarwood. Located close…
  • from
  • $60
    nightly

 

Pet Friendly 1 and 2 Bedroom Vacation Rental Triplex -…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • 3311 29th Ave SW Unit B- This adorable country cottage is located just 10 miles east of the beach, yet…
  • from
  • $25
    nightly

 

Pet Friendly 4 Bedroom Family Vacation Home with Pool &…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • This elegant Briarwood home exemplifies the Florida lifestyle at its best. Luxuriously decorated to an exceptional standard with comfort and…
  • from
  • $80
    nightly

 

4 Bedroom Vacation Home Rental with Private Pool & Spa…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • The property has been tastefully furnished to the highest standard to ensure your total comfort and piece of mind. Situated…
  • from
  • $100
    nightly

 

Elegant 4 Bedroom Family Vacation Home with Private Pool |…

  • 4 Bedrooms, 3 Bathrooms, Sleeps 8
  • This elegant Briarwood home exemplifies the Florida lifestyle at its best. Luxuriously decorated to an exceptional standard with comfort and…
  • from
  • $100
    nightly

 

Sea Breeze at Bonita Village Resort! 2 Bedroom Delightful Vacation…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • You'll enjoy the refreshing interior of "Sea Breeze". The open living areas and delightful Lanai offer perfect vacation living and…
  • from
  • Contact Owner

 

Spanish Wells Luxury 3 Bedroom Golf Course Vacation Home in…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 8
  • Enjoy a panoramic view of the fairway and green along with a marvelous SW Exposure. The pictures do not reflect…
  • from
  • Contact Owner

 

Waterfront 2 Bedroom Vacation Rental Home with Boat Dock- 4818…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Cute 2 bedroom, 1 bath waterfront location with dock and lift. Residence is small but well-designed and in excellent condition.…
  • from
  • Contact Owner

 

Vanderbilt Beach 2 Bedroom Oceanfront Vacation Condo in Naples Florida

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • This North Naples 2 bedroom is within walking distance of Vanderbilt Beach and Delnor-Wiggins Pass State Park. The gated community…
  • from
  • Contact Owner

 

'My Penthouse Paradise' - The Nicest 1 Bedroom Vacation Rental…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • My Penthouse Paradise may be the nicest one bedroom in the Bonita Beach area! Plus, it is hard to beat…
  • from
  • Contact Owner

 

Angels Vacation Rentals SPECIAL book 7 nts get 8th night…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Welcome: SPECIAL book 7 nights get 8th night free OVERLOOKING BEACH OCT 15 TO NOV 15 ONLY To Angel's Longboat…
  • from
  • $903
    weekly

 

Longboat Key 1 Bedroom vacation condo with beach views- Turtle…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • If you want to enjoy the beach but do not want to pay the high prices check out this Garden…
  • from
  • $138
    nightly

 

Newly Remodeled Oceanview Vacation Rental Studio in Longboat Key FL-…

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • Great vacation getaway or short term rental. Newly remodeled large studio with modern furniture in a beachfront building with direct…
  • from
  • $155
    nightly

 

Only Steps to the Beach! Vacation Studio Rental in Longboat…

  • 1 Bedroom, 1 Bathroom, Sleeps 4
  • This Villa rental is located across the street from Club Bamboo South which is steps away from the beach.Take a…
  • from
  • $115
    nightly

 

1 Bedroom Private Honeymoon Villa in Longboat Key FL -…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Our Cabana, that we loving refer to as our Honeymoon Villa is elevated above the pool and is very private.…
  • from
  • $168
    nightly

 

Longboat Key Private 2 Bedroom Vacation Villa- Turtle Crawl Hibiscus…

  • 2 Bedrooms, 1.5 Bathrooms, Sleeps 0
  • This two bedroom one and a half baths makes this Villa ideal for the family that prefers some privacy. Surrounded…
  • from
  • $213
    nightly

 

Romantic Honeymoon 2 Bedroom Vacation Villa with Beach Views! Longboat…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • This is a perfect home away from home for the romantic honeymoon or plenty of room for the whole family.…
  • from
  • $1500
    weekly

 

Longboat Key Beachfront Studio Vacation Rental- Club Bamboo South Studio…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • This Beach front studio rental has a king size bed and 2 single pull out beds -1 from the couch…
  • from
  • $135
    nightly

 

Longboat Key Beach Vacation Rental w/ Fully Equipped Kitchen- Club…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • This Beach front studio rental has a king size bed and 2 single pull out beds -1 from the couch…
  • from
  • $135
    nightly

 

Longboat Key Beachfront Vacation Rental Studio - Club Bamboo South…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • This Beach front studio rental has a king size bed and 2 single pull out beds -1 from the couch…
  • from
  • $135
    nightly

 

Longboat Key Beachfront Studio Vacation Rental- Club Bamboo South Studio…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • This Beach front studio rental has a king size bed and 1 single pull out bed and a pull out…
  • from
  • $135
    nightly

 

Beachfront Studio Vacation Rental - Club Bamboo South Studio 117

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • This Beach front studio rental has a king size bed and 2 single pull out beds -1 from the couch…
  • from
  • $135
    nightly

 

Cute Longboat Key 2 Bedroom Vacation Duplex- Perfect for small…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • This cute 2/2 duplex is located just as you go over the Longboat Key Bridge. This home is ideal for…
  • from
  • $600
    weekly

 

"Our Beach Haven by the Sea" - 2 Bedroom Pet…

  • 2 Bedrooms, 1 Bathroom, Sleeps 6
  • This Beautiful old style single family home located on the canal, has 2 bedrooms ( with bonus queen sofa in…
  • from
  • $205
    nightly

 

Longboat Arms - 2 Bedroom Bayfront Vacation Condo- 1 Block…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Beautiful bay front view with all of the amenities. 1 block walk to gulf beach. Great location for shopping, site-seeing,…
  • from
  • Contact Owner

 

Heron House, Longboat Key 3 Bedroom Vacation Home with Private…

  • 3 Bedrooms, 3 Bathrooms, Sleeps 10
  • This newly remodeled 3 bedroom 3 bath house on the canal has a roomy mother in law apartment on the…
  • from
  • $1250
    weekly

 

Bradenton Beach 2 Bedroom Vacation Condo across from the Beach!…

  • 2 Bedrooms, 1 Bathroom, Sleeps 4
  • Quaint 2/1 Across the street from public beach access The unit pictured here is an upstairs unit, it is located…
  • from
  • $1050
    weekly

 

Runaway Bay 2 Bedroom Vacation Condo- Short Walk to Beach-…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • This beautiful 2 bedroom 2 bath 2nd floor walk up overlooks one of the small lagoons located throughout the complex.…
  • from
  • $145
    nightly

 

Waterfront 2 Bedroom Vacation Condo- Runaway Bay 2 Bedroom 2…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 6
  • Beautiful Waterfront Condo This beautiful 2 bedroom 2 bath 2nd floor walk up overlooks the bay. Enjoy watching dolphins, birds…
  • from
  • $165
    nightly

 

Stay at this Oceanfront 2 Bedroom Vacation Condo at The…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • The Island Beach Club is directly on Big Carlos Pass and Estero Bay. Enjoy 240 degree views of Bonita Springs…
  • from
  • Contact Owner

 

Siesta Key Two Bedroom Vacation Condo- Monthly Rentals!

  • 2 Bedrooms, 2 Bathrooms, Sleeps 2
  • Address: 8710 Midnight Pass Road, Suite 405B, Siesta Key, FL 34242 Professionally decorated 2 bedroom condo, has just been renovated.…
  • from
  • $2000
    monthly

 

Modern 2 Bedroom Longboat Key Vacation Beach Condo- Cabana Beach…

  • 2 Bedrooms, 2 Bathrooms, Sleeps 4
  • Come and enjoy Old Florida. This modern 2 bedroom 2 bath Condo located in a stilt house with the pool…
  • from
  • $195
    nightly

 

Longboat Key Beach Vacation Rental- Club Bamboo South Studio Condo…

  • 1 Bedroom, 1 Bathroom, Sleeps 2
  • Look at where you should be right now! Go ahead and click on the pictures! This clean, fresh studio condo…
  • from
  • $135
    nightly

 
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