Southwest Florida Vacation Rentals
Florida's south west offers old fashioned Florida villages of Anna Maria Island to the beachcombers and boaters delights of Fort Myers, Marco Island, Sanibel and Captiva Islands. From sun soaked beaches to nature preserves and the everglades. This diverse region has something for everyone. Great for beach combers and shelling!
Cities in South West FL
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Featured
Anna Maria Island Paradise❤️Close to beach, shops&restaurants, heated pool, private lanai!
2/BR
2/BA
SLEEPS 6
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Featured
The Veranda on Jacaranda - Luxury Home, North Anna Maria Island across from Bean Point
4/BR
3.5/BA
SLEEPS 8
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Meehan - sleeps 6 with heated pool, downtown Port Charlotte from $112nt
3/BR
2/BA
SLEEPS 6
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Featured
A Lazy River Day and Night 4 Bedroom Custom Pool home on Anna Maria Island
4/BR
3.5/BA
SLEEPS 8
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COCOA CABANA! LUXURY AND BEAUTY AWAIT YOU! Anna Maria Island Vacation Rental!!
3/BR
3/BA
SLEEPS 7
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Featured
SUPER CLEAN-STEPS TO BEACH-WALK TO SHOPS, RESTAURANTS, NIGHT SPOTS - SEE REVIEWS
4/BR
3/BA
SLEEPS 10
Marco Island on the Water Newly renovated 3 bedroom 2 bath with beautiful waterviews
3/BR
2/BA
SLEEPS 8
Beautiful Gulf Coast Views, Beachfront Condo Marco Island the Sea Winds
2/BR
2/BA
SLEEPS 6
North End Cottage -Steps to Beach -Tropical Landscaping Heated Jetted Pool
2/BR
2/BA
SLEEPS 4
PRIME LOCATION ON AMI ** DIRECTLY ON WHITE SUGAR SAND BEACH ** HEATED POOL
2/BR
2/BA
SLEEPS 4
Tropical Setting and Heated Lagoon Style Pool at "Your Own Oasis"
3/BR
2/BA
SLEEPS 6
One-of-a-Kind Luxury Beach House on the desirable North End of Anna Maria!
3/BR
3/BA
SLEEPS 6
Boaters Delight Canal Front Home - with Private Dock - Pool and Spa
3/BR
2/BA
SLEEPS 6
New Luxury Custom Built Home on North End - Steps to Beach - Heated Pool - Outdoor Kitchen
3/BR
2/BA
SLEEPS 6
Highlighted
Elevator! Large Luxury Home w Elevator! Heated Pool & Spa. 3 min walk to Beach!!
5/BR
5/BA
SLEEPS 12
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Sirenia Cove - Htd Pool Waterfront Dock Ping Pong Outdoor Bar Backyard Beach
4/BR
3/BA
SLEEPS 10
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Sirenia By The Sea - Waterfront Pool Hot Tub Dock Sauna - Steps to the Beach
5/BR
5/BA
SLEEPS 12
Alecassandra Vacation Villas - Family Vacation Location, Villa4 & Villa5, 4B4B
4/BR
4/BA
SLEEPS 12
Anna Belle - Waterfront Luxury Home: North End wDock, Pool, Spa, Screened Lanai, Free WiFi
3/BR
2/BA
SLEEPS 8
Luxury Cottage Steps to Bean Point Beach Heated Pool and Outdoor Living Area
2/BR
2/BA
SLEEPS 4
Penthouse Condo in One Particular Harbour Near Anna Maria Island Marina Access
2/BR
2/BA
SLEEPS 5
Beach Cottage only steps to the white sandy beaches of Anna Maria Island!
2/BR
2/BA
SLEEPS 6
The Anna Maria Island Beach Breeze - Anna Maria Island Vacation Rentals
2/BR
1/BA
SLEEPS 6
Blue Heron Luxury Private Waterfront Oasis on Bimini Bay - Walk to the Beach
4/BR
3.5/BA
SLEEPS 8
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Sunkissed & Salty: Dreamy Amenities. Prime Location. Steps to Beach
4/BR
4/BA
SLEEPS 8
Sept Gap Deal! - Resort Style Luxury Backyard Beach Waterfront Dock Pool Spa
4/BR
3/BA
SLEEPS 10
Sea Mist - Gorgeous Coastal Home! Walk to Beach, Pine Ave Shops, Pool
3/BR
2/BA
SLEEPS 6
Satsang Blue - A Sacred Gathering Place Adorable Bungalow on AMI, Walk to Beach!
3/BR
1.5/BA
SLEEPS 6
Sand Trap- 4bed beach view *heated pool *Golf Cart * Hot Tub*Elevator*Putt Putt Course
4/BR
4/BA
SLEEPS 8
SIESTA KEY CONDO-DIRECT OCEAN FRONT, 8TH FLOOR, LUXURY, SPACIOUS, BEST VIEW
2/BR
2/BA
SLEEPS 4
NEW Renovated Luxury Canalfront Home w Water Views, Pool Spa, Bikes, Kayak, SUP!
4/BR
3/BA
SLEEPS 11
Coastal Updated Home, Steps to Beach!, Peek at Gulf, Heated Pool, Elevator
3/BR
3/BA
SLEEPS 8
Luxury Condo, Pool, Beach Gear, Bikes, Just 5 Mins to Anna Maria Gulf Beaches!
2/BR
2/BA
SLEEPS 5
GORGEOUS Newly Renovated wPvt. Pool, Backyard Oasis, Walk to Beach w Beach Gear!
2/BR
2/BA
SLEEPS 6
The Bella Siesta: Walking distance to Siesta Village; 5 minutes to Siesta Key Beach
3/BR
2/BA
SLEEPS 8
Sea Glass on Park - Premier Luxury on Beautiful Park Ave! Steps to Beach, Pool, Spa
4/BR
3/BA
SLEEPS 8
Second To None Spacious Waterfront Luxury! Dock, Pool, Spa, Rooftop Water Views!
4/BR
5/BA
SLEEPS 10
Waterfront Stunning New Luxury Home wPool, Spa, Dock, Elevator, Close to Pine
4/BR
4.5/BA
SLEEPS 8
New Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point & Pine Ave
4/BR
4/BA
SLEEPS 8
Beautiful Island Home wRooftop Water Views on Bean Point! Pool, Bar, Foosball!
3/BR
3/BA
SLEEPS 8
Stunning Luxury Home! Huge Sunny Private Pool, Block to Pine 8 Min Walk to Beach
2/BR
2/BA
SLEEPS 4
So Close to Beach You Hear the Waves! Updated Clean Beach Cottage, Start $180n
2/BR
1/BA
SLEEPS 6
Luxury Canalfront Home w Pvt. Boat Dock, PoolSpa, Bikes, Kayaks, SUP!
4/BR
3/BA
SLEEPS 8
Gorgeous 4 Bedroom Island Home! Heated Pool, Walk to Beach and Pine Avenue Shops!
6/BR
2.5/BA
SLEEPS 8
Serendipity Deux-BeachFront/4/4.5/Elevator/Heated Pool/Golf Cart/Bikes/SUP/Kayak
4/BR
4.5/BA
SLEEPS 8
New Luxury Renovated Home! Heated Pool, Cabana, Hammock, Walk to Beach
3/BR
3/BA
SLEEPS 8
cabAnna Maria Beach Block 4 bedroom4.5 Bathroom Private PoolSpa
4/BR
4.5/BA
SLEEPS 8
BEACHFRONT 1 & 2 Bedroom Condos - Olympic Pool, FREE Wi-Fi, Low Discounted Rates
1/BR
1/BA
SLEEPS 6
Sunny Getaway |Newly Remodeled1-Level Villa w South facing Lanai & Pool
3/BR
2/BA
SLEEPS 6
Enjoy Stunning Sunsets at this Luxurious Gulf Front Condo on Siesta Key
2/BR
2/BA
SLEEPS 6
Luxury 2400 sq ft 6th floor condo with private access to Crescent Beach
3/BR
2.5/BA
SLEEPS 6
Couples and Family Friendly. Some pet friendly units are available too.
1/BR
1/BA
SLEEPS 4
Dans Florida Condos - 1 bedroom 1 bath (Private Beach Access across the street; free WIFI)
1/BR
1/BA
SLEEPS 4
Private heated salt pool at OHasis Getaway and only 200 steps from the Beach!
2/BR
1/BA
SLEEPS 6
Areca Cove On Beautiful Anna Maria Island! 3 Min Walk To Beach!
4/BR
3.5/BA
SLEEPS 8
Private heated salt pool at OHasis Getaway II and only 210 steps from the Beach!
2/BR
2/BA
SLEEPS 6
Dans Florida Condos - 2 bedroom 2 bath (Private Beach Access across the street; free WIFI)
2/BR
2/BA
SLEEPS 6
MI Oasis Getaway! Just 200 Steps to the Beach on a very quiet street
2/BR
1/BA
SLEEPS 6
Chardonnay Bay ~ Magnificent Sunset Views! 5 bedroom WATERFRONT home w/Heated Pool and Boat Dock
5/BR
3.5/BA
SLEEPS 10
Mermaid's Landing - Stunning 6 bed 4 bath home heated pool and spa rooftop deck + more!
6/BR
4/BA
SLEEPS 12
Only 10 min to the Beach! New and modern Poolvilla with lots of privacy
3/BR
2/BA
SLEEPS 6
Sunset Villa -Close to Beach and Shamrock Park - Ferry Pass Included - Fenced
2/BR
2/BA
SLEEPS 6
STUNNING 5 BEDROOM 4 BATHROOM DREAM HOUSE WITH BACKYARD OASIS, STEPS TO THE BEACH
5/BR
4/BA
SLEEPS 10
Villa Desirade - perfect pool vacation for familys & golfers - spring rates avilable
3/BR
2/BA
SLEEPS 6
Pirates Bay- Beachfront with pool, kayaks and and more for your perfect escape!
2/BR
2/BA
SLEEPS 4
Beautiful Condo in the Luxurious Esplanade Resort Style Community - Monthly rental
2/BR
2/BA
SLEEPS 4
Amazing waterfront property, walking distance to beach! Private heated pool!
2/BR
1/BA
SLEEPS 6
Style of the Isle -walking distance to white beaches on Anna Maria Island
2/BR
2/BA
SLEEPS 4
AVAIL JULY 25th BEAUTIFUL 3 BED-2 BATH OPEN CONCEPT, HUGE POOL, WiFi
3/BR
2/BA
SLEEPS 6
Spacious waterfront Villa with gorgeous views, 1 mile to Siesta Beach
4/BR
3/BA
SLEEPS 6
Spacious Villa - Fenced Yard - Private Beach Access - Ferry Pass - Bikes - WiFi
2/BR
2/BA
SLEEPS 6
NEW IN 2021! Two Bedroom plus Den condo in high demand Naples, Florida!
2/BR
2/BA
SLEEPS 6
Private Pool Home, Steps from the Beach and SPECTACULAR Sunsets from the Porch
3/BR
2/BA
SLEEPS 7
Shady Retreat - Private Beach Access - Screened Patio - Fenced Yard - Pets OK
2/BR
2/BA
SLEEPS 4
3 bedroom 3 bath Anna Maria Island Paradise with Private Pool + stroll to Beach!
3/BR
3/BA
SLEEPS 6
BEAUTIFUL RENOVATED VILLA, LAKE VIEW, HEATED POOL, CLOSE TO BEACH
3/BR
2/BA
SLEEPS 5
Villa Palm Tree-Beautiful Poolvilla-SPECIAL PRICES!! Please Ask!!!
4/BR
2/BA
SLEEPS 6
Welcome to the Jungalow! Luxury 3 bedroom Tropical Paradise with Private Pool
3/BR
3/BA
SLEEPS 8
LOCATION SIESTA & DT SARASOTA Coastal Elegant House West of the Trail Family Fun
3/BR
2.5/BA
SLEEPS 6
Enjoy island life--surfer chic bungalow, private beach path, kayak
3/BR
2/BA
SLEEPS 6
Beautiful, 4 Bed, 3 bath, 2 King Beds, SW Facing Large Pool on the Golf Course. LOOK!!
4/BR
3/BA
SLEEPS 8
St. Armand's Canal-front Pool Home ~ freshly remodeled and steps to the beach!
4/BR
4/BA
SLEEPS 8
Private Pool Home, SPECTACULAR Sunsets And Only Steps from the Beaches
3/BR
2.5/BA
SLEEPS 7
Paradise Found 6 bed 6.5 bath Heated Pool & Hot TUB Bikes Free Wifi
6/BR
6.5/BA
SLEEPS 14
A SW Florida coastal "Cream Puff" with heated pool! 5 miles to Manasota Key Beach!
3/BR
2/BA
SLEEPS 6
Gone Coastal: Beautiful Pet-Friendly Home w Heated Saltwater Pool
2/BR
2/BA
SLEEPS 4
Marriott Beach Front Apartment - Amazing memories - Luxury beach front Resort
2/BR
2/BA
SLEEPS 8
Unique beach house near Bean Point, heated pool and just 2 min to beach.
3/BR
2/BA
SLEEPS 6
Grandezza Beautiful and Relaxing Fully Furnished - Monthly Rentals
3/BR
2/BA
SLEEPS 6
Comfortable, cozy home with spacious pool area in walking distance to the beach
3/BR
3/BA
SLEEPS 5
Surfside Club - 2BD-2BA Condo - 800 Steps to South Beach Entrance - South End-Marco Island
2/BR
2/BA
SLEEPS 4
Gulf Views on Beautiful Sanibel Island at PointeSanto Corner Unit
2/BR
2/BA
SLEEPS 6
RIVIERA CLUB LUXURY FROM $850 per WEEK - DIRECT BEACHFRONT - GREAT AMENITIES!
2/BR
2/BA
SLEEPS 4
Relax at Private Sandy Beach Aqua Pool House with FREE Bikes & Kayaks for Two!
3/BR
2/BA
SLEEPS 7
Chasing Waves - Steps from the beach, no roads to cross . AMI Perfect Beach House
2/BR
2/BA
SLEEPS 6
Monthly Stays from $2,890* Royal Harbor Condo on Canal, Pool, Lanai, Near Beach
2/BR
2/BA
SLEEPS 6
Gulf Breeze Villa - Lakefront, private pool and dock to fish or relax!
4/BR
2.5/BA
SLEEPS 8
“Tiki Time!” Luxury 4 bedroom with backyard oasis + pool near Anna Maria Island!!
4/BR
2.5/BA
SLEEPS 12
Beautiful, Gulf-Front Home - Halcyon House - Anna Maria Island Vacation Rentals
4/BR
3.5/BA
SLEEPS 8
Vacation Home on Marco Island with Pool+SPA+Waterfront and walking distance to Tigertail Beach
3/BR
2.5/BA
SLEEPS 6
Casa Bonita II - Sun Kissed Days. Spectacular Sunsets. Sand Between Your Toes.
2/BR
2/BA
SLEEPS 6
West Bay Point and Moorings Condo with Prime Deck Views of AMI Sound! jan thru march deal
2/BR
2/BA
SLEEPS 4
Spacious 3 bedroom, 2 bath pool home in North West Bradenton, Pet Friendly
3/BR
2/BA
SLEEPS 6
New Listing! Steps to the Beach, Amazing Covered Outdoor Area with 2 Pools!
4/BR
4/BA
SLEEPS 12
Vitamin Sea has everything! Heated pool & spa, elevator, rooftop deck, water views +++
5/BR
5/BA
SLEEPS 12
Crosswind Cottages - Sprawling 3 bed 2.5 bath heated pool elevator FREE WIFI Sleeps 9
3/BR
2.5/BA
SLEEPS 9
4 Bed 3 Bath with beautiful private backyard, 2 car garage, bikes, beach gear, heated pool
4/BR
3/BA
SLEEPS 8
Perfect Anna Maria Island Location, GROUND FLOOR UNIT, Runaway Bay Condo135
2/BR
2/BA
SLEEPS 6
Naples Happy Place! 3 BR2 BA; 2 Pets Any Size; Gated Community & Loads of Amenities!
3/BR
2/BA
SLEEPS 6
307 65th St Brand new 5 bed, 4 bath island beauty Heated pool & spa, free WiFi, sleeps 12
5/BR
4/BA
SLEEPS 10
Tropical Palm Villa- Screened Patio - Fenced Yard - Private Beach with Ferry Access
2/BR
2/BA
SLEEPS 6
EMERALD BAY 3 KING BEDROOMS & bunk room - COMES WITH BEACH GEAR AND BIKES
4/BR
3.5/BA
SLEEPS 8
Ocean View 6 bed 5.5 bath LUXURY rental heated pool, spa, waterslide roof top deck + more
6/BR
5/BA
SLEEPS 12
Villa Ocala Premiere Luxury Vacation Destination with Amenities Beyond Compare
3/BR
2/BA
SLEEPS 6